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Argo Group International Holdings, Ltd. (ARGO) SEC Filing 10-K Annual report for the fiscal year ending Thursday, December 31, 2020

Argo Group International Holdings, Ltd.

CIK: 1091748 Ticker: ARGO

Exhibit 99.1 Investor Update March 12, 2021Exhibit 99.1 Investor Update March 12, 2021


Disclaimer This presentation may include forward-looking statements, both with respect to Argo Group and its industry, that reflect our current views with respect to future events and financial performance. Forward-looking statements include all statements that do not relate solely to historical or current facts, and can be identified by the use of words such as expect, intend, plan, believe, “do not believe,” “aim,” project, anticipate, “seek,” will, “likely,” “assume,” “estimate,” may, “continue,” “guidance,” “objective,” “remain optimistic,” path toward, “outlook,” “trends,” “future,” “could,” “would,” “should,” “target,” “on track” and similar expressions of a future or forward-looking nature. There can be no assurance that actual developments will be those anticipated by Argo Group. Actual results may differ materially as a result of significant risks and uncertainties including but not limited to: the continuing impact of the novel coronavirus (COVID-19) pandemic and related economic matters; changes in the pricing environment including those due to the cyclical nature of the insurance and reinsurance industry; increased competition; the adequacy ofour projected loss reserves including development of claims that varies from that which was expected when loss reserves were established, adverse legal rulings which may impact the liability under insurance and reinsurance contracts beyond that which was anticipated when the reserves were established, development of new theories related to coverage which may increase liabilities under insurance and reinsurance contracts beyond that which were anticipated whenthe loss reserves were established, reinsurance coverage being other than what was anticipated when the loss reserves were established; changes to regulatory and tax conditions and legislation; natural and/or man-made disasters, including terrorist acts and civil unrest; impact of global climate change; the inability to secure reinsurance; the inability to collect reinsurance recoverables; a downgrade in our financial strength ratings; changes in interest rates; changes in the financial markets that impact investment income and the fair market values of our investments; changes in asset valuations; failure to execute information technology strategies; exposure to information security breach; failure of outsourced service providers; failure to execute expense targets; inability to successfully execute mergers or acquisitions; and costs associated with shareholder activism. For a more detailed discussion of such risks and uncertainties, see Item 1A, “Risk Factors” in Argo’s Annual Report on Form 10-K for the fiscal year ended December 31, 2019, as supplemented in Part II, Item 1A, “Risk Factors” of Argo’s subsequent Quarterly Reports on Form 10-Q and in other filings with the Securities and Exchange Commission. The inclusion of a forward-looking statement herein should not be regarded as a representation by Argo that Argo’s objectives will be achieved. Argo undertakes no obligation to publicly update forward-looking statements, whether as a result of new information, future events or otherwise. You should not place undue reliance on any such statements. Please refer to the Company’s Form 8-K filed with the Securities and Exchange Commission on March 12, 2021, disclosing that, in connection with the preparation, review and audit of the Company’s 2020 10-K, management identified and corrected certain immaterial errors in the Company’s historical financial statements. As a result of these adjustments, certain financial results vary from those furnished in our earnings press release filed with the Securities and Exchange Commission as an exhibit to the Company’s Form 8-K on February 17, 2021. This presentation includes certain corrected figures. Each variation is immaterial to the Company’s financial statements. 2Disclaimer This presentation may include forward-looking statements, both with respect to Argo Group and its industry, that reflect our current views with respect to future events and financial performance. Forward-looking statements include all statements that do not relate solely to historical or current facts, and can be identified by the use of words such as expect, intend, plan, believe, “do not believe,” “aim,” project, anticipate, “seek,” will, “likely,” “assume,” “estimate,” may, “continue,” “guidance,” “objective,” “remain optimistic,” path toward, “outlook,” “trends,” “future,” “could,” “would,” “should,” “target,” “on track” and similar expressions of a future or forward-looking nature. There can be no assurance that actual developments will be those anticipated by Argo Group. Actual results may differ materially as a result of significant risks and uncertainties including but not limited to: the continuing impact of the novel coronavirus (COVID-19) pandemic and related economic matters; changes in the pricing environment including those due to the cyclical nature of the insurance and reinsurance industry; increased competition; the adequacy ofour projected loss reserves including development of claims that varies from that which was expected when loss reserves were established, adverse legal rulings which may impact the liability under insurance and reinsurance contracts beyond that which was anticipated when the reserves were established, development of new theories related to coverage which may increase liabilities under insurance and reinsurance contracts beyond that which were anticipated whenthe loss reserves were established, reinsurance coverage being other than what was anticipated when the loss reserves were established; changes to regulatory and tax conditions and legislation; natural and/or man-made disasters, including terrorist acts and civil unrest; impact of global climate change; the inability to secure reinsurance; the inability to collect reinsurance recoverables; a downgrade in our financial strength ratings; changes in interest rates; changes in the financial markets that impact investment income and the fair market values of our investments; changes in asset valuations; failure to execute information technology strategies; exposure to information security breach; failure of outsourced service providers; failure to execute expense targets; inability to successfully execute mergers or acquisitions; and costs associated with shareholder activism. For a more detailed discussion of such risks and uncertainties, see Item 1A, “Risk Factors” in Argo’s Annual Report on Form 10-K for the fiscal year ended December 31, 2019, as supplemented in Part II, Item 1A, “Risk Factors” of Argo’s subsequent Quarterly Reports on Form 10-Q and in other filings with the Securities and Exchange Commission. The inclusion of a forward-looking statement herein should not be regarded as a representation by Argo that Argo’s objectives will be achieved. Argo undertakes no obligation to publicly update forward-looking statements, whether as a result of new information, future events or otherwise. You should not place undue reliance on any such statements. Please refer to the Company’s Form 8-K filed with the Securities and Exchange Commission on March 12, 2021, disclosing that, in connection with the preparation, review and audit of the Company’s 2020 10-K, management identified and corrected certain immaterial errors in the Company’s historical financial statements. As a result of these adjustments, certain financial results vary from those furnished in our earnings press release filed with the Securities and Exchange Commission as an exhibit to the Company’s Form 8-K on February 17, 2021. This presentation includes certain corrected figures. Each variation is immaterial to the Company’s financial statements. 2


Agenda • Overview & Vision • U.S. Business Opportunities • International Platform • Digital Tools • Financial Analysis • Execution • Q&A 3Agenda • Overview & Vision • U.S. Business Opportunities • International Platform • Digital Tools • Financial Analysis • Execution • Q&A 3


Introduction: Non-Executive Chairman of the Board • Aligned with shareholders • Engaged and supportive of the management team’s vision for Argo • Oversight and guidance to management in developing strategy • Committed to achieving financial targets and strong stewards of capital • Actively participates in shareholder outreach • Compensation and governance changes to align with shareholder interests 4Introduction: Non-Executive Chairman of the Board • Aligned with shareholders • Engaged and supportive of the management team’s vision for Argo • Oversight and guidance to management in developing strategy • Committed to achieving financial targets and strong stewards of capital • Actively participates in shareholder outreach • Compensation and governance changes to align with shareholder interests 4


Corporate Responsibility Actions We are stewards of the environment, advancing our societal impact and providing transparent corporate governance Environmental Social Governance • Objectives based on United • Established diversity and inclusion • Completed a Board refreshment Nations Sustainable Development program process in 2020, adding 9 new Goals directors with diverse backgrounds • Sponsored the Spencer • Declassified our Board, with • Climate-related disclosures Foundation’s first Diversity Directors standing for annual Scholarship • Greenhouse Gas reduction targets elections • Established paid caregiver leave • ClimateWise membership • Enhanced long-term incentive and enhanced flexible workplace program policies • Climate risk management • Extensive review and framework • Signatory of the United Nations enhancement of governance Principles for Responsible • Energy Star-certified office controls Investments locations • Engaged with shareholders to • Clean energy value chain insurer improve corporate governance and executive compensation practices 5Corporate Responsibility Actions We are stewards of the environment, advancing our societal impact and providing transparent corporate governance Environmental Social Governance • Objectives based on United • Established diversity and inclusion • Completed a Board refreshment Nations Sustainable Development program process in 2020, adding 9 new Goals directors with diverse backgrounds • Sponsored the Spencer • Declassified our Board, with • Climate-related disclosures Foundation’s first Diversity Directors standing for annual Scholarship • Greenhouse Gas reduction targets elections • Established paid caregiver leave • ClimateWise membership • Enhanced long-term incentive and enhanced flexible workplace program policies • Climate risk management • Extensive review and framework • Signatory of the United Nations enhancement of governance Principles for Responsible • Energy Star-certified office controls Investments locations • Engaged with shareholders to • Clean energy value chain insurer improve corporate governance and executive compensation practices 5


Overview & Vision 6Overview & Vision 6


Argo Overview A distinctive U.S.-focused specialty insurer with well established businesses operating in key specialty markets Financial Objectives: Margins Returns Growth Low 90% Double-Digit 10+% Return on Combined Ratio Premium Growth Common Equity Expect to reach target returns by year-end 2022 7Argo Overview A distinctive U.S.-focused specialty insurer with well established businesses operating in key specialty markets Financial Objectives: Margins Returns Growth Low 90% Double-Digit 10+% Return on Combined Ratio Premium Growth Common Equity Expect to reach target returns by year-end 2022 7


Streamlined Management Selected for Refocused Strategy Executive Officers Kevin Rehnberg Scott Kirk Tim Carter President & CEO EVP & CFO EVP & CUO Years in current role: <1 Years in current role: 1 Years in current role: 1 Years at Argo: 8 Years at Argo: <1 Years at Argo: 2 Years in the industry: 32 Years in the industry: 20 Years in the industry: 32 Matt Harris Andy Borst Allison Kiene Chief Admin. Officer SVP, General Counsel Head of International Years in current role: 1 Years in current role: <1 Years in current role: 2 Years at Argo: 4 Years at Argo: 7 Years at Argo: <1 Years in the industry: 25 Years in the industry: 14 Years in the industry: 30 Note: Scott Kirk will become the Chief Financial Officer on the first business day after the Company files the 2020 10-K with the Securities and Exchange Commission. 8Streamlined Management Selected for Refocused Strategy Executive Officers Kevin Rehnberg Scott Kirk Tim Carter President & CEO EVP & CFO EVP & CUO Years in current role: <1 Years in current role: 1 Years in current role: 1 Years at Argo: 8 Years at Argo: <1 Years at Argo: 2 Years in the industry: 32 Years in the industry: 20 Years in the industry: 32 Matt Harris Andy Borst Allison Kiene Chief Admin. Officer SVP, General Counsel Head of International Years in current role: 1 Years in current role: <1 Years in current role: 2 Years at Argo: 4 Years at Argo: 7 Years at Argo: <1 Years in the industry: 25 Years in the industry: 14 Years in the industry: 30 Note: Scott Kirk will become the Chief Financial Officer on the first business day after the Company files the 2020 10-K with the Securities and Exchange Commission. 8


Streamlined Management Selected for Refocused Strategy Executive Leadership Tony Cicio Susan Comparato Gary Grose Alex Hindson Chief Human SVP, U.S. EVP, U.S. Chief Risk & Resources Officer Sustainability Officer Years in current role: 1 Years in current role: 1 / 7 Years in current role: 2 Years in current role: 5 Years at Argo: 3 Years at Argo: 7 Years at Argo: 2 Years at Argo: 5 Years in the industry: 20 Years in the industry: 33 Years in the industry: 2 Years in the industry: 23 Michael Murphy Mark Rose Mark Wade SVP, Head of Internal Audit Chief Investment Officer Chief Claims Officer Years in current role: <1 Years in current role: 8 Years in current role: 5 Years at Argo: <1 Years at Argo: 8 Years at Argo: 5 Years in the industry: 25 Years in the industry: 26 Years in the industry: 30 9Streamlined Management Selected for Refocused Strategy Executive Leadership Tony Cicio Susan Comparato Gary Grose Alex Hindson Chief Human SVP, U.S. EVP, U.S. Chief Risk & Resources Officer Sustainability Officer Years in current role: 1 Years in current role: 1 / 7 Years in current role: 2 Years in current role: 5 Years at Argo: 3 Years at Argo: 7 Years at Argo: 2 Years at Argo: 5 Years in the industry: 20 Years in the industry: 33 Years in the industry: 2 Years in the industry: 23 Michael Murphy Mark Rose Mark Wade SVP, Head of Internal Audit Chief Investment Officer Chief Claims Officer Years in current role: <1 Years in current role: 8 Years in current role: 5 Years at Argo: <1 Years at Argo: 8 Years at Argo: 5 Years in the industry: 25 Years in the industry: 26 Years in the industry: 30 9


Argo Group: A U.S.-Focused Specialty Insurer ARGO GROUP ~90% of Companywide Premium from U.S. Domiciled Risks U.S. Operations Bermuda Insurance Syndicate 1200 • Differentiated E&S and specialty • Underwriting risks that are • Focused on U.S. non-admitted admitted platform not placed in U.S. markets in and global specialty risks casualty, professional and • Class profile narrowed following • Strong history of profitability property lines re-underwriting actions and growth • Robust historical underwriting • Reinsurance to close (RITC) • Organized into 12 business units results over 10+ year period transaction creates focused segmented by niche specialty risk profile 10Argo Group: A U.S.-Focused Specialty Insurer ARGO GROUP ~90% of Companywide Premium from U.S. Domiciled Risks U.S. Operations Bermuda Insurance Syndicate 1200 • Differentiated E&S and specialty • Underwriting risks that are • Focused on U.S. non-admitted admitted platform not placed in U.S. markets in and global specialty risks casualty, professional and • Class profile narrowed following • Strong history of profitability property lines re-underwriting actions and growth • Robust historical underwriting • Reinsurance to close (RITC) • Organized into 12 business units results over 10+ year period transaction creates focused segmented by niche specialty risk profile 10


What is Specialty Insurance? Specific coverage or coverage for an industry group in which underwriting, claims or risk management expertise is valued by the customer 11 11What is Specialty Insurance? Specific coverage or coverage for an industry group in which underwriting, claims or risk management expertise is valued by the customer 11 11


Specialty Insurance Argo’s Competitive Advantage • Deep, longstanding, multi-channel distribution relationships – retail, wholesale and managing general agents (MGA) • Responsiveness and service • Talented underwriting and claims personnel • Partner with producers by providing highly specialized counsel and industry knowledge • Innovative and customized solutions • Digital capabilities 12Specialty Insurance Argo’s Competitive Advantage • Deep, longstanding, multi-channel distribution relationships – retail, wholesale and managing general agents (MGA) • Responsiveness and service • Talented underwriting and claims personnel • Partner with producers by providing highly specialized counsel and industry knowledge • Innovative and customized solutions • Digital capabilities 12


Vision of Transformation • Business Optimization • Underwriting Focus EFFICIENCY EFFICIENCY • Reduce Volatility • Efficiency Gains UNDERWRITING UNDERWRITING • Financial Targets OPTIMIZATION OPTIMIZATION 13Vision of Transformation • Business Optimization • Underwriting Focus EFFICIENCY EFFICIENCY • Reduce Volatility • Efficiency Gains UNDERWRITING UNDERWRITING • Financial Targets OPTIMIZATION OPTIMIZATION 13


Our Business Line Optimization Process Characteristics Grow & Invest Remediate Reduce or Exit • Industry leader • Enhance talent • No product differentiation • Specialized expertise • Pricing discipline Competitive required • No discernable edge • Deep relationships Standing • Superior analytics • Large total addressable • Potential to scale with • Subscale market (TAM) the proper operational • Capital intensive improvement actions • Ability to gain high quality • Unlikely to be able to Scalable market share without grow profitably sacrificing rate or terms • Capital efficient • Rational competition • Portions of book not • Irrational pricing priced to compensate for Rate and • Responds to changes in • Poor macro environment the risk claims levels or patterns for the foreseeable future Terms • Terms and pricing need • Profitable even in soft to be realigned macro environment 14Our Business Line Optimization Process Characteristics Grow & Invest Remediate Reduce or Exit • Industry leader • Enhance talent • No product differentiation • Specialized expertise • Pricing discipline Competitive required • No discernable edge • Deep relationships Standing • Superior analytics • Large total addressable • Potential to scale with • Subscale market (TAM) the proper operational • Capital intensive improvement actions • Ability to gain high quality • Unlikely to be able to Scalable market share without grow profitably sacrificing rate or terms • Capital efficient • Rational competition • Portions of book not • Irrational pricing priced to compensate for Rate and • Responds to changes in • Poor macro environment the risk claims levels or patterns for the foreseeable future Terms • Terms and pricing need • Profitable even in soft to be realigned macro environment 14


Business Optimization • Increase capital and resource allocation to strong, defensible, scalable businesses • Return on allocated capital target of 10%+ on a sustainable basis • Remediation of underperforming businesses that show improvement potential • Exit businesses lacking scale or with an unfavorable macroeconomic environment • Operational flexibility to dial-up or dial-back to a particular business line based on rate and terms 15Business Optimization • Increase capital and resource allocation to strong, defensible, scalable businesses • Return on allocated capital target of 10%+ on a sustainable basis • Remediation of underperforming businesses that show improvement potential • Exit businesses lacking scale or with an unfavorable macroeconomic environment • Operational flexibility to dial-up or dial-back to a particular business line based on rate and terms 15


Examples: Volatility Reduction Actions 1-in-250 Year Florida and Caribbean PML • Strategic focus on reducing the volatility of property underwriting % of results common 10% 9% 7% 4% equity • Reducing exposure by deploying limited capacity for maximum return • Exiting or divesting businesses and executing focused underwriting measures • Argo will further reduce 1-in-250 year probable maximum loss (PML) by 40% in 2021 to reflect our reduced risk appetite 2018 2019 2020 2021E • Property strategy supports Argo’s specialty Insurance vision Gross PML Net PML Note: Gross and Net PMLs represent expected modeled losses. 16Examples: Volatility Reduction Actions 1-in-250 Year Florida and Caribbean PML • Strategic focus on reducing the volatility of property underwriting % of results common 10% 9% 7% 4% equity • Reducing exposure by deploying limited capacity for maximum return • Exiting or divesting businesses and executing focused underwriting measures • Argo will further reduce 1-in-250 year probable maximum loss (PML) by 40% in 2021 to reflect our reduced risk appetite 2018 2019 2020 2021E • Property strategy supports Argo’s specialty Insurance vision Gross PML Net PML Note: Gross and Net PMLs represent expected modeled losses. 16


Examples: Volatility Reduction Actions in Key Business Units Net Average Annual Loss Progression • Sale of Ariel Re reduces net average annual loss (AAL) by 25% with up to 40% reduction in the tail $75 • Decreasing average limits deployed and focusing risk appetite in U.S. property • Reduced appetite for binding $43 authority business in both the U.S. and London, including geographic limits • Modest growth expected in the attractive Bermuda Property portfolio Q4 2020 Business U.S. Property London & Retention 2022 • Robustly addressing wildfire Exits & Contract Bermuda Changes exposure and California earthquake Binding exposure $ in millions Note: AALs represent expected modeled losses. 17Examples: Volatility Reduction Actions in Key Business Units Net Average Annual Loss Progression • Sale of Ariel Re reduces net average annual loss (AAL) by 25% with up to 40% reduction in the tail $75 • Decreasing average limits deployed and focusing risk appetite in U.S. property • Reduced appetite for binding $43 authority business in both the U.S. and London, including geographic limits • Modest growth expected in the attractive Bermuda Property portfolio Q4 2020 Business U.S. Property London & Retention 2022 • Robustly addressing wildfire Exits & Contract Bermuda Changes exposure and California earthquake Binding exposure $ in millions Note: AALs represent expected modeled losses. 17


Examples: Underwriting Actions – Liability Limit Reduction Focusing on limits, terms and conditions while getting strong rate increases Historical Limit Reduction • Focus on gross vs. net • Carefully managing limits and 100% 100% 100% 95% attachment points 94% 91% 87% 77% • Significant limit reduction achieved in certain key products 64% • Average commercial D&O limits have declined ~13% from 2018 to 2020 • Average U.S. excess casualty limits have declined ~23% from 2018 to 2020 • Average Bermuda excess casualty limits 2018 2019 2020 2018 2019 2020 2018 2019 2020 Commercial U.S. Excess Bermuda Excess have declined ~36% from 2018 to 2020 D&O Casualty Casualty 18Examples: Underwriting Actions – Liability Limit Reduction Focusing on limits, terms and conditions while getting strong rate increases Historical Limit Reduction • Focus on gross vs. net • Carefully managing limits and 100% 100% 100% 95% attachment points 94% 91% 87% 77% • Significant limit reduction achieved in certain key products 64% • Average commercial D&O limits have declined ~13% from 2018 to 2020 • Average U.S. excess casualty limits have declined ~23% from 2018 to 2020 • Average Bermuda excess casualty limits 2018 2019 2020 2018 2019 2020 2018 2019 2020 Commercial U.S. Excess Bermuda Excess have declined ~36% from 2018 to 2020 D&O Casualty Casualty 18


What is Remediation? Actions taken to improve underwriting profitability in certain lines or business units not meeting our margin expectations Key Actions • Terminate portions of an existing book of business or segments of a market • Re-price portions of an existing book of business, including specific lines of coverage or geographies • Change terms or conditions on products to control claims experience • Eliminate certain distribution partners not meeting profitability or volume requirements • Bring in experienced underwriting talent to stabilize results then focus on growth potential 19What is Remediation? Actions taken to improve underwriting profitability in certain lines or business units not meeting our margin expectations Key Actions • Terminate portions of an existing book of business or segments of a market • Re-price portions of an existing book of business, including specific lines of coverage or geographies • Change terms or conditions on products to control claims experience • Eliminate certain distribution partners not meeting profitability or volume requirements • Bring in experienced underwriting talent to stabilize results then focus on growth potential 19


Remediation In Process Business units that are scalable where Argo has good competitive positioning but require proactive steps to improve profitability, including changes to pricing and terms Business Unit Action CONTRACT BINDING Terminating relationships with unprofitable distribution partners (Delegated Authority) Reducing exposure to catastrophe-prone PROPERTY geographies, offset by rate increases 20Remediation In Process Business units that are scalable where Argo has good competitive positioning but require proactive steps to improve profitability, including changes to pricing and terms Business Unit Action CONTRACT BINDING Terminating relationships with unprofitable distribution partners (Delegated Authority) Reducing exposure to catastrophe-prone PROPERTY geographies, offset by rate increases 20


Remediation Case Studies Actions are expected to result in improved business prospects over a reasonable period of time or business will be exited U.S. Specialty Programs Grocery & Restaurants • Business had been sub-scale and producing • Business had been producing an an unacceptable combined ratio of ~105% unacceptable combined ratio of +110% • Implemented leadership change • Implemented leadership change • Upgraded staff • Upgraded staff • Changed underwriting guidelines • Changed underwriting guidelines • Changed risk appetite • Changed risk appetite • Clear strategy to execute • Digital risk management tools • Rehabilitated to produce sub 90% • Business placed into run-off combined ratio business 21Remediation Case Studies Actions are expected to result in improved business prospects over a reasonable period of time or business will be exited U.S. Specialty Programs Grocery & Restaurants • Business had been sub-scale and producing • Business had been producing an an unacceptable combined ratio of ~105% unacceptable combined ratio of +110% • Implemented leadership change • Implemented leadership change • Upgraded staff • Upgraded staff • Changed underwriting guidelines • Changed underwriting guidelines • Changed risk appetite • Changed risk appetite • Clear strategy to execute • Digital risk management tools • Rehabilitated to produce sub 90% • Business placed into run-off combined ratio business 21


Business Exits – Last 18 Months International • Ariel Re • ArgoGlobal Assicurazioni S.p.A (Italy) • ArgoGlobal SE (Malta) • Syndicate 1200, London D&O • Syndicate 1200, Asia • Syndicate 1200, Hull class • Regional underwriting office for Latin America U.S. • Grocery & Restaurants • Trident (MGA Transaction) Note: Includes announced exits that are expected to close prior to year end. 22Business Exits – Last 18 Months International • Ariel Re • ArgoGlobal Assicurazioni S.p.A (Italy) • ArgoGlobal SE (Malta) • Syndicate 1200, London D&O • Syndicate 1200, Asia • Syndicate 1200, Hull class • Regional underwriting office for Latin America U.S. • Grocery & Restaurants • Trident (MGA Transaction) Note: Includes announced exits that are expected to close prior to year end. 22


Selected Business Lines Growth and investment focused on areas with best potential • Favorable rates and terms • Disciplined growth opportunities ARGO PRO CASUALTY • Competitive advantages • Expertise • Relationships CONSTRUCTION ENVIRONMENTAL • Analytics • Digital capabilities • Liability-focused risks • Businesses represent ~55% INLAND MARINE SURETY of U.S. gross written premiums (GWP) 23Selected Business Lines Growth and investment focused on areas with best potential • Favorable rates and terms • Disciplined growth opportunities ARGO PRO CASUALTY • Competitive advantages • Expertise • Relationships CONSTRUCTION ENVIRONMENTAL • Analytics • Digital capabilities • Liability-focused risks • Businesses represent ~55% INLAND MARINE SURETY of U.S. gross written premiums (GWP) 23


U.S. Business Opportunities 24U.S. Business Opportunities 24


Argo Pro Business Overview Disciplined Growth Opportunities • Management liability and professional liability • Broad based distribution, both retail and lines including lawyers, architects and wholesale engineers and miscellaneous • Focused on small to medium sized accounts • Directors & Officers (D&O): ~60% of GWP • Underwriting team organized to focus on • Primary 33% / Excess 67% specific classes of business • Errors & Omissions (E&O): ~30% of GWP • Primary 90% / Excess 10% Competitive Advantages • Programs: ~10% of GWP • Excellent underwriting and claims staff • 100% claims made business • Digital solutions that help underwriters and producers Favorable Rates and Terms • Predictive analytics tools for public company • More than $400M of GWP D&O, and being rolled out for private company D&O • 3 year GWP CAGR of ~40% • Expected to growth at strong double digits • 2 year cumulative rate change of +80% in commercial and +30% in financial institutions Note: CAGR defined as compound annual growth rate. 25 25Argo Pro Business Overview Disciplined Growth Opportunities • Management liability and professional liability • Broad based distribution, both retail and lines including lawyers, architects and wholesale engineers and miscellaneous • Focused on small to medium sized accounts • Directors & Officers (D&O): ~60% of GWP • Underwriting team organized to focus on • Primary 33% / Excess 67% specific classes of business • Errors & Omissions (E&O): ~30% of GWP • Primary 90% / Excess 10% Competitive Advantages • Programs: ~10% of GWP • Excellent underwriting and claims staff • 100% claims made business • Digital solutions that help underwriters and producers Favorable Rates and Terms • Predictive analytics tools for public company • More than $400M of GWP D&O, and being rolled out for private company D&O • 3 year GWP CAGR of ~40% • Expected to growth at strong double digits • 2 year cumulative rate change of +80% in commercial and +30% in financial institutions Note: CAGR defined as compound annual growth rate. 25 25


Casualty Business Overview Disciplined Growth Opportunities • Primary and excess casualty coverage for • Primarily wholesale distribution technology, industrial, machinery products, • Focused on small to medium sized accounts commercial real estate, hospitality and • Growing book judiciously and managing limits warehousing end markets • Addressing issues of social inflation through • Primary Casualty: ~50% of GWP limits, attachment points and account • Excess Casualty: ~50% of GWP selection • 100% occurrence business • Has been an incubator for some businesses Favorable Rates and Terms Competitive Advantages • Approaching $100M of GWP • Speed of execution within core casualty (small • 3 year GWP CAGR of ~10% account primary and excess): quote issuance <1 hour versus expectation of 1 day • Rates up +20% in 2020 • Diverse team with broad and deep experience in the marketplace 26 26Casualty Business Overview Disciplined Growth Opportunities • Primary and excess casualty coverage for • Primarily wholesale distribution technology, industrial, machinery products, • Focused on small to medium sized accounts commercial real estate, hospitality and • Growing book judiciously and managing limits warehousing end markets • Addressing issues of social inflation through • Primary Casualty: ~50% of GWP limits, attachment points and account • Excess Casualty: ~50% of GWP selection • 100% occurrence business • Has been an incubator for some businesses Favorable Rates and Terms Competitive Advantages • Approaching $100M of GWP • Speed of execution within core casualty (small • 3 year GWP CAGR of ~10% account primary and excess): quote issuance <1 hour versus expectation of 1 day • Rates up +20% in 2020 • Diverse team with broad and deep experience in the marketplace 26 26


Construction Business Overview Disciplined Growth Opportunities • Primary and excess coverage for areas of the • 100% wholesale distribution construction market with a focus on interior • Focused on small to medium sized accounts renovation and service repair contractors • Average limits of approximately $1.5M • Primary: ~80% of GWP • Addressing issues of social inflation through • Excess: ~20% of GWP (no unsupported excess) consistent monitoring of bodily injury claims • 100% occurrence business especially within NY construction Favorable Rates and Terms Competitive Advantages • More than $300M of GWP • Highly efficient operation • 3 year GWP CAGR of ~7%, with recent growth • Early adopter of digital technologies impacted by COVID-19 • Owners Edge platform issues quotes based on • Rates up +5% in 2020 built-in logic and pricing for quick response to the market • Growing book judiciously and managing limits • Strong expertise in certain markets such as New York City 27 27Construction Business Overview Disciplined Growth Opportunities • Primary and excess coverage for areas of the • 100% wholesale distribution construction market with a focus on interior • Focused on small to medium sized accounts renovation and service repair contractors • Average limits of approximately $1.5M • Primary: ~80% of GWP • Addressing issues of social inflation through • Excess: ~20% of GWP (no unsupported excess) consistent monitoring of bodily injury claims • 100% occurrence business especially within NY construction Favorable Rates and Terms Competitive Advantages • More than $300M of GWP • Highly efficient operation • 3 year GWP CAGR of ~7%, with recent growth • Early adopter of digital technologies impacted by COVID-19 • Owners Edge platform issues quotes based on • Rates up +5% in 2020 built-in logic and pricing for quick response to the market • Growing book judiciously and managing limits • Strong expertise in certain markets such as New York City 27 27


Environmental Business Overview Disciplined Growth Opportunities • Environmental liability coverage focused • Primarily wholesale distribution, with a on construction, service contractors, growing retail channel manufacturing, real estate and energy • Focused on small to medium sized accounts (clean tech & renewable) end markets • Average limits of approximately $2.3M • Primary: ~60% of GWP • Mandating rate increases of at least 3-5% • Excess: ~40% of GWP • ~80% claims made / 20% occurrence business Competitive Advantages • New leadership team with deep experience Favorable Rates and Terms in environmental casualty and site pollution • Approaching $100M of GWP • Efficient operation that leverages third party • 3 year GWP CAGR of ~10% resources and bots • 3 year average combined ratio sub 90% • Stable rates in 2020 28 28Environmental Business Overview Disciplined Growth Opportunities • Environmental liability coverage focused • Primarily wholesale distribution, with a on construction, service contractors, growing retail channel manufacturing, real estate and energy • Focused on small to medium sized accounts (clean tech & renewable) end markets • Average limits of approximately $2.3M • Primary: ~60% of GWP • Mandating rate increases of at least 3-5% • Excess: ~40% of GWP • ~80% claims made / 20% occurrence business Competitive Advantages • New leadership team with deep experience Favorable Rates and Terms in environmental casualty and site pollution • Approaching $100M of GWP • Efficient operation that leverages third party • 3 year GWP CAGR of ~10% resources and bots • 3 year average combined ratio sub 90% • Stable rates in 2020 28 28


Inland Marine Business Overview Disciplined Growth Opportunities • Broad array of products and services with • Leverages wholesale, retail and MGA admitted and non-admitted capabilities distribution channels focusing on customers in construction, • Focused on small to medium sized accounts transportation and ocean cargo end markets • Short tail business line, with average duration • Primary: ~90% of GWP <1 year • Excess: ~10% of GWP • Closely monitoring industries where fraud • 100% occurrence business is more prevalent Favorable Rates and Terms Competitive Advantages • More than $25M of GWP • Business leader with extensive history of running a larger operation at strong • 2 year GWP CAGR of ~100% profitability levels • Expect continued strong growth given size • Assembled a team of strong underwriters and market potential across the U.S. • Rates increases in the mid single digit range • Digital solutions allowing for a broader market during 2020 penetration, which creates a long-term expense advantage 29 29Inland Marine Business Overview Disciplined Growth Opportunities • Broad array of products and services with • Leverages wholesale, retail and MGA admitted and non-admitted capabilities distribution channels focusing on customers in construction, • Focused on small to medium sized accounts transportation and ocean cargo end markets • Short tail business line, with average duration • Primary: ~90% of GWP <1 year • Excess: ~10% of GWP • Closely monitoring industries where fraud • 100% occurrence business is more prevalent Favorable Rates and Terms Competitive Advantages • More than $25M of GWP • Business leader with extensive history of running a larger operation at strong • 2 year GWP CAGR of ~100% profitability levels • Expect continued strong growth given size • Assembled a team of strong underwriters and market potential across the U.S. • Rates increases in the mid single digit range • Digital solutions allowing for a broader market during 2020 penetration, which creates a long-term expense advantage 29 29


Surety Business Overview Disciplined Growth Opportunities • Commercial and contract surety bonds in • 100% retail distribution the U.S. and select international markets • Focused on medium to large sized accounts • Targeting Fortune 2000 public and private • Average bond size of $1.2M companies • Organically grown business with a strong focus on risk management Favorable Rates and Terms • Expense ratio runs in the low 50% range • More than $150M of GWP • Loss ratio run significantly lower than other • 3 year GWP CAGR of ~15% business lines • Rates down slightly in 2020 in response to strong profitability levels Competitive Advantages • Highly skilled underwriting and claims team, committed to disciplined underwriting • Expert in-house engineers provide critical evaluation on a significant portion of risks submitted • Favorable reinsurance support based on historical results 30 30Surety Business Overview Disciplined Growth Opportunities • Commercial and contract surety bonds in • 100% retail distribution the U.S. and select international markets • Focused on medium to large sized accounts • Targeting Fortune 2000 public and private • Average bond size of $1.2M companies • Organically grown business with a strong focus on risk management Favorable Rates and Terms • Expense ratio runs in the low 50% range • More than $150M of GWP • Loss ratio run significantly lower than other • 3 year GWP CAGR of ~15% business lines • Rates down slightly in 2020 in response to strong profitability levels Competitive Advantages • Highly skilled underwriting and claims team, committed to disciplined underwriting • Expert in-house engineers provide critical evaluation on a significant portion of risks submitted • Favorable reinsurance support based on historical results 30 30


U.S. Businesses Exited Dynamic and disciplined approach to exiting businesses with a clear focus on profitable growth Growth of U.S. Operations & Business Characteristics Cumulative Volume of Business Exited $1,995 • Macro issues $1,859 $1,692 • Irrational pricing $1,510 • No product differentiation $1,278 $1,145 $1,047 $1,013 • No discernable edge • Subscale • Capital Intensive • Unlikely to grow profitably 2013 2014 2015 2016 2017 2018 2019 2020 • Non-strategic Kevin Rehnberg joins Argo as Cumulative GWP Exited U.S. Operations GWP President, U.S. Operations $ in millions Note: Chart reflects cumulative gross written premium volume of businesses exited over time period. 31U.S. Businesses Exited Dynamic and disciplined approach to exiting businesses with a clear focus on profitable growth Growth of U.S. Operations & Business Characteristics Cumulative Volume of Business Exited $1,995 • Macro issues $1,859 $1,692 • Irrational pricing $1,510 • No product differentiation $1,278 $1,145 $1,047 $1,013 • No discernable edge • Subscale • Capital Intensive • Unlikely to grow profitably 2013 2014 2015 2016 2017 2018 2019 2020 • Non-strategic Kevin Rehnberg joins Argo as Cumulative GWP Exited U.S. Operations GWP President, U.S. Operations $ in millions Note: Chart reflects cumulative gross written premium volume of businesses exited over time period. 31


International Platform 32International Platform 32


Market Potential Business Focus 2019 Direct U.S. Surplus Premiums Lines Market • Focused on U.S. and global specialty and Group Written Share non-admitted risks written through Lloyd’s and Bermuda markets Lloyd’s Market $12,477 22.5% • Bermuda insurance market is ~90% U.S. domiciled risk Argo U.S. • More than half of all risks written through $949 1.7% (#12 market share) Lloyd’s are from the U.S. and Canada • Hardening market with respect to rates and terms over last 12-24 months and Top 15, ex Lloyd’s $24,207 43.6% expected to continue • Argo is focused on these risks through its Total U.S. Surplus $55,486 100% Syndicate 1200 and Bermuda Insurance Lines Market businesses $ in millions Source: A.M. Best 33Market Potential Business Focus 2019 Direct U.S. Surplus Premiums Lines Market • Focused on U.S. and global specialty and Group Written Share non-admitted risks written through Lloyd’s and Bermuda markets Lloyd’s Market $12,477 22.5% • Bermuda insurance market is ~90% U.S. domiciled risk Argo U.S. • More than half of all risks written through $949 1.7% (#12 market share) Lloyd’s are from the U.S. and Canada • Hardening market with respect to rates and terms over last 12-24 months and Top 15, ex Lloyd’s $24,207 43.6% expected to continue • Argo is focused on these risks through its Total U.S. Surplus $55,486 100% Syndicate 1200 and Bermuda Insurance Lines Market businesses $ in millions Source: A.M. Best 33


Bermuda Insurance & Syndicate 1200 Focus Areas Transitioning to portfolio optimization in certain lines, while re-underwriting actions continue where needed Bermuda Insurance: Long-standing presence and track record in the Bermuda market, 2021 focus on continuation of re-underwriting strategy across the three classes of business written • Casualty • Professional Liability • Property Syndicate 1200: Argo’s Lloyd’s platform, focusing on Property, Casualty, Marine & Energy and Specialty lines of business – extensive remediation over recent years, transitioning to portfolio optimization • Marine & Energy • Professional & Casualty • Property • Specialty Note: Bermuda Property line is reported within Syndicate 1200 results beginning in 2021. 34Bermuda Insurance & Syndicate 1200 Focus Areas Transitioning to portfolio optimization in certain lines, while re-underwriting actions continue where needed Bermuda Insurance: Long-standing presence and track record in the Bermuda market, 2021 focus on continuation of re-underwriting strategy across the three classes of business written • Casualty • Professional Liability • Property Syndicate 1200: Argo’s Lloyd’s platform, focusing on Property, Casualty, Marine & Energy and Specialty lines of business – extensive remediation over recent years, transitioning to portfolio optimization • Marine & Energy • Professional & Casualty • Property • Specialty Note: Bermuda Property line is reported within Syndicate 1200 results beginning in 2021. 34


Management Actions and Environment Taking Hold International Rate & Margin Improvement • Access to U.S. non-admitted and global specialty risks 64% 58% • Favorable rates and terms 60% 54% expected to continue in 2021 57% 52% • More focused underwriting 14.2% portfolio following recent management actions 8.6% 3.2% 2018 2019 2020 Rate Change Reported AY ex-CAT Loss Ratio Pro Forma AY ex-CAT Loss Ratio Note: AY defined as accident year; CAT defined as net catastrophe losses. Note: Pro Forma reflects historical results of Bermuda Insurance, LatAm and Syndicate 1200; excludes Ariel Re (Reinsurance), Italy and Malta Operations. 35Management Actions and Environment Taking Hold International Rate & Margin Improvement • Access to U.S. non-admitted and global specialty risks 64% 58% • Favorable rates and terms 60% 54% expected to continue in 2021 57% 52% • More focused underwriting 14.2% portfolio following recent management actions 8.6% 3.2% 2018 2019 2020 Rate Change Reported AY ex-CAT Loss Ratio Pro Forma AY ex-CAT Loss Ratio Note: AY defined as accident year; CAT defined as net catastrophe losses. Note: Pro Forma reflects historical results of Bermuda Insurance, LatAm and Syndicate 1200; excludes Ariel Re (Reinsurance), Italy and Malta Operations. 35


Digital Tools 36Digital Tools 36


Our Digital Journey Targeted investments to enhance underwriting quality and efficiency Digital Enhancements • Digital distribution – automate business that doesn’t require an underwriter to touch it • Rolling out one common rate, quote, bind (RQB) platform across all lines and integrating existing platforms • Targeting rollout across U.S. businesses Workflow Updates • Workflow process to be rolled out across the U.S. by end of 2021 Other Product Enhancements • Rolling out submission automation to streamline processes, reducing offshore costs around data input, as well as administrative work for underwriters • Underwriting analytics tools to efficiently gather data and substantially reduce the time for underwriters to review and quote 37Our Digital Journey Targeted investments to enhance underwriting quality and efficiency Digital Enhancements • Digital distribution – automate business that doesn’t require an underwriter to touch it • Rolling out one common rate, quote, bind (RQB) platform across all lines and integrating existing platforms • Targeting rollout across U.S. businesses Workflow Updates • Workflow process to be rolled out across the U.S. by end of 2021 Other Product Enhancements • Rolling out submission automation to streamline processes, reducing offshore costs around data input, as well as administrative work for underwriters • Underwriting analytics tools to efficiently gather data and substantially reduce the time for underwriters to review and quote 37


Efficiency Measures in U.S. Operations Investments in technology and operations have enabled Argo’s U.S. Operations to handle significantly more premium with only a modest increase in headcount GWP per Key Changes Employee $1.59 $1.63 $1.79 $2.13 $2.27 $2.49 $2.62 $2.81 ($m) • Increased automation $1,995 $1,859 • Better workflow systems $1,692 $1,510 • Data analytics tools driving $1,278 more efficient underwriting $1,145 $1,047 $1,013 • Enterprise solutions 710 711 680 664 644 638 640 • GWP CAGR of 10% from 2013 601 to 2020 • Average combined ratio over period of 91.4% 2013 2014 2015 2016 2017 2018 2019 2020 Kevin Rehnberg joins Argo as U.S. GWP U.S. Headcount President, U.S. Operations $ in millions 38Efficiency Measures in U.S. Operations Investments in technology and operations have enabled Argo’s U.S. Operations to handle significantly more premium with only a modest increase in headcount GWP per Key Changes Employee $1.59 $1.63 $1.79 $2.13 $2.27 $2.49 $2.62 $2.81 ($m) • Increased automation $1,995 $1,859 • Better workflow systems $1,692 $1,510 • Data analytics tools driving $1,278 more efficient underwriting $1,145 $1,047 $1,013 • Enterprise solutions 710 711 680 664 644 638 640 • GWP CAGR of 10% from 2013 601 to 2020 • Average combined ratio over period of 91.4% 2013 2014 2015 2016 2017 2018 2019 2020 Kevin Rehnberg joins Argo as U.S. GWP U.S. Headcount President, U.S. Operations $ in millions 38


Construction / Casualty Wrapper Investments designed to enhance underwriting outcomes and efficiency • Pulls data and consolidates underwriting information • Allows faster quoting • Eliminates unwanted business and tasks • Combines with workflow enhancements to produce attractive margins • Supports a $100M book of business producing 20%+ margins 39Construction / Casualty Wrapper Investments designed to enhance underwriting outcomes and efficiency • Pulls data and consolidates underwriting information • Allows faster quoting • Eliminates unwanted business and tasks • Combines with workflow enhancements to produce attractive margins • Supports a $100M book of business producing 20%+ margins 39


AI Streamlines Processes Screening tools allow underwriters to focus on high quality opportunities Submission Prioritization • Based on historical results • Auto-decline business outside of risk appetite Workflow Monitoring • Improves underwriter productivity • Improves resource allocation Efficiency Benefits • Artificial Intelligence (AI) automation reads submissions from producers and automatically populates our systems • Speed to market • Appropriate staffing 40AI Streamlines Processes Screening tools allow underwriters to focus on high quality opportunities Submission Prioritization • Based on historical results • Auto-decline business outside of risk appetite Workflow Monitoring • Improves underwriter productivity • Improves resource allocation Efficiency Benefits • Artificial Intelligence (AI) automation reads submissions from producers and automatically populates our systems • Speed to market • Appropriate staffing 40


Financial Analysis 41Financial Analysis 41


Financial Analysis Outline • Growth Outlook • Ceded Reinsurance Changes • Expense Initiative • Investment Income • Capital Management • Operating Targets 42 42Financial Analysis Outline • Growth Outlook • Ceded Reinsurance Changes • Expense Initiative • Investment Income • Capital Management • Operating Targets 42 42


Growth Outlook Impact of exited business units will mute underlying growth picture • ~90% of our gross premiums come Argo Group GWP Growth from U.S. domiciled risks High Single Digit CAGR* • U.S. Operations $3,500 4% • Growth focus areas include Argo Pro, $3,000 13% $443 15% $473 Casualty, Construction, Environmental, 30% $2,500 25% $826 Inland Marine and Surety 27% $834 $2,000 • Remediation is concentrated in Contract Binding and Property $1,500 66% $1,000 • International Operations 58% $1,822 62% $1,964 $500 • Growth is largely driven by rate increases, as well as select focus areas $0 with a track record of profitability 2019 2020 2021 U.S. International Exited Businesses $ in millions. * Growth rate excludes exited businesses including Ariel Re, Italy, Malta and U.S. grocery & restaurants. 43Growth Outlook Impact of exited business units will mute underlying growth picture • ~90% of our gross premiums come Argo Group GWP Growth from U.S. domiciled risks High Single Digit CAGR* • U.S. Operations $3,500 4% • Growth focus areas include Argo Pro, $3,000 13% $443 15% $473 Casualty, Construction, Environmental, 30% $2,500 25% $826 Inland Marine and Surety 27% $834 $2,000 • Remediation is concentrated in Contract Binding and Property $1,500 66% $1,000 • International Operations 58% $1,822 62% $1,964 $500 • Growth is largely driven by rate increases, as well as select focus areas $0 with a track record of profitability 2019 2020 2021 U.S. International Exited Businesses $ in millions. * Growth rate excludes exited businesses including Ariel Re, Italy, Malta and U.S. grocery & restaurants. 43


Ceded Reinsurance Changes Exited business impacting overall ceded reinsurance ratios • U.S. Operations U.S. NWP / GWP 70% • Ceded reinsurance levels are relatively 63% 63% stable 61% 60% • Reduced gross limits in excess casualty and D&O 50% • Reducing PMLs and exposures in 40% property lines 2019 2020 2021 • International Operations International NWP / GWP 70% • Decreasing property exposures • Exiting businesses and reducing third 57% 60% party capital 47% 50% 46% • Managing gross exposures down in casualty and property lines 40% 2019 2020 2021 Note: NWP defined as net written premiums. 44Ceded Reinsurance Changes Exited business impacting overall ceded reinsurance ratios • U.S. Operations U.S. NWP / GWP 70% • Ceded reinsurance levels are relatively 63% 63% stable 61% 60% • Reduced gross limits in excess casualty and D&O 50% • Reducing PMLs and exposures in 40% property lines 2019 2020 2021 • International Operations International NWP / GWP 70% • Decreasing property exposures • Exiting businesses and reducing third 57% 60% party capital 47% 50% 46% • Managing gross exposures down in casualty and property lines 40% 2019 2020 2021 Note: NWP defined as net written premiums. 44


U.S. Operations Net Earned Premium Financial Impact of Exits $11 $1,300 $28 $31 $1,100 U.S. 2020 Operations Financial Impact $900 $31M of GWP • Exit of the U.S. $700 Grocery & Restaurant ~80% NWP / GWP $500 business 120%+ Combined Ratio 2019 2020 2021 U.S. Operations Pro Forma Exited Business Units International Operations Net Earned Premium International 2020 $600 Operations Financial Impact $50 $162 $130 Exit of: $400 $412M of GWP • Ariel Re ~33% NWP / GWP $200 • Italian Operations 130%+ Combined Ratio • Malta $0 2019 2020 2021 Int’l. Operations Pro Forma Exited Business Units $ in millions 45U.S. Operations Net Earned Premium Financial Impact of Exits $11 $1,300 $28 $31 $1,100 U.S. 2020 Operations Financial Impact $900 $31M of GWP • Exit of the U.S. $700 Grocery & Restaurant ~80% NWP / GWP $500 business 120%+ Combined Ratio 2019 2020 2021 U.S. Operations Pro Forma Exited Business Units International Operations Net Earned Premium International 2020 $600 Operations Financial Impact $50 $162 $130 Exit of: $400 $412M of GWP • Ariel Re ~33% NWP / GWP $200 • Italian Operations 130%+ Combined Ratio • Malta $0 2019 2020 2021 Int’l. Operations Pro Forma Exited Business Units $ in millions 45


Expense Initiatives Phase 1 – 2020 to 2022 Remaining Targeted Savings • Initial phase of the expense program targeting other corporate and general expenses, in addition to benefiting Restructuring $10 from expense reductions as part of the announced business rationalizations General Expense $10 • There will also be a small component of restructuring during Business Rationalization $20 this phase • In 2020, we established an expense initiative to remove $100M of 2019 total expenses incurred – of this, circa $40M Timing of Savings were non-recurring expenses $25 • The focus is to provide detail on the targeted $60M of savings across the remaining operating expenses that $20 impact the combined ratio $15 • We made progress in 2020 and our focus in 2021 is to realize the benefits of the business rationalization that we have undertaken in 2020 in addition to reducing general expenses and benefiting from some additional restructuring 2020 2021 2022 $ in millions 46Expense Initiatives Phase 1 – 2020 to 2022 Remaining Targeted Savings • Initial phase of the expense program targeting other corporate and general expenses, in addition to benefiting Restructuring $10 from expense reductions as part of the announced business rationalizations General Expense $10 • There will also be a small component of restructuring during Business Rationalization $20 this phase • In 2020, we established an expense initiative to remove $100M of 2019 total expenses incurred – of this, circa $40M Timing of Savings were non-recurring expenses $25 • The focus is to provide detail on the targeted $60M of savings across the remaining operating expenses that $20 impact the combined ratio $15 • We made progress in 2020 and our focus in 2021 is to realize the benefits of the business rationalization that we have undertaken in 2020 in addition to reducing general expenses and benefiting from some additional restructuring 2020 2021 2022 $ in millions 46


Expense Ratio Improvement • Impact of growth initiatives, operating Expense Ratio expense reductions and reinvestment costs driving overall expense ratio reductions • Expense ratio improvement weighted toward 2022 as savings are realized and earned premium growth accelerates • 36% expense ratio expected to be achieved for full year 2022 vs. Q4 2022 target realization previously • Disciplined approach to expense management 2020 Impact of 2021 Impact of 2022 Expense Change Expense Change Expense Ratio Ratio Ratio • Improved transparency over expense reporting 47Expense Ratio Improvement • Impact of growth initiatives, operating Expense Ratio expense reductions and reinvestment costs driving overall expense ratio reductions • Expense ratio improvement weighted toward 2022 as savings are realized and earned premium growth accelerates • 36% expense ratio expected to be achieved for full year 2022 vs. Q4 2022 target realization previously • Disciplined approach to expense management 2020 Impact of 2021 Impact of 2022 Expense Change Expense Change Expense Ratio Ratio Ratio • Improved transparency over expense reporting 47


Expense Initiatives Phase 2 – Beyond 2022 • The second phase requires a deeper dive into the operating model, focusing primarily on infrastructure and systems, to identify opportunities to develop a scalable expense model for Argo to deliver run-rate savings beyond 2022 • Minimize stranded overhead during run-off period • Focus on net savings • Determine run-rate potential beyond 2022 48Expense Initiatives Phase 2 – Beyond 2022 • The second phase requires a deeper dive into the operating model, focusing primarily on infrastructure and systems, to identify opportunities to develop a scalable expense model for Argo to deliver run-rate savings beyond 2022 • Minimize stranded overhead during run-off period • Focus on net savings • Determine run-rate potential beyond 2022 48


Investment Portfolio December 31, 2020 Portfolio Mix Realignment 13% Investment Grade Debt • Reduction in capital weighting of assets to Non-Investment Grade Debt deploy into underwriting opportunities 8% Equities • Reduced risk assets – equities, non 3% investment grade debt and alternatives 7% Alternatives Short Term & Cash 69% Optimization • Investment Committee recently revised strategic asset allocation (SAA) by third party • Focus on optimizing returns and income December 31, 2018 Portfolio Mix with diverse set of asset classes while maintaining diversification and capital 13% Investment Grade Debt discipline Non-Investment Grade Debt 10% Moving Forward Equities 7% • Working on refined investment policy 60% Alternatives • Will adjust asset class weightings over 10% Short Term & Cash time based on SAA targets 49Investment Portfolio December 31, 2020 Portfolio Mix Realignment 13% Investment Grade Debt • Reduction in capital weighting of assets to Non-Investment Grade Debt deploy into underwriting opportunities 8% Equities • Reduced risk assets – equities, non 3% investment grade debt and alternatives 7% Alternatives Short Term & Cash 69% Optimization • Investment Committee recently revised strategic asset allocation (SAA) by third party • Focus on optimizing returns and income December 31, 2018 Portfolio Mix with diverse set of asset classes while maintaining diversification and capital 13% Investment Grade Debt discipline Non-Investment Grade Debt 10% Moving Forward Equities 7% • Working on refined investment policy 60% Alternatives • Will adjust asset class weightings over 10% Short Term & Cash time based on SAA targets 49


Net Investment Income • Portfolio duration 2.5 years $20 $20 • Fixed income book yield 2.2% $9 • Average credit rating of A1 / A+ $131 $112 • New money rates 1% to 1.5% $104 • Slightly higher contribution expected from alternative investments in 2021 based on 2018 2019 2020 current market trends Investment Income, ex. Alts. Alternative Investments $ in millions 50Net Investment Income • Portfolio duration 2.5 years $20 $20 • Fixed income book yield 2.2% $9 • Average credit rating of A1 / A+ $131 $112 • New money rates 1% to 1.5% $104 • Slightly higher contribution expected from alternative investments in 2021 based on 2018 2019 2020 current market trends Investment Income, ex. Alts. Alternative Investments $ in millions 50


Proactive Approach to Capital Management • Continual focus on capital stewardship: return capital to shareholders when it is financially more attractive to do so than deploying elsewhere in the business • Commitment to ensure strong levels of capital are maintained to support our regulatory and rating agency obligations • In July 2020, Argo completed a $150M preference share offering to refinance an existing term loan 51Proactive Approach to Capital Management • Continual focus on capital stewardship: return capital to shareholders when it is financially more attractive to do so than deploying elsewhere in the business • Commitment to ensure strong levels of capital are maintained to support our regulatory and rating agency obligations • In July 2020, Argo completed a $150M preference share offering to refinance an existing term loan 51


2021 Target Operating Metrics Metric 2021 6% to 9% GWP Growth (ex divestitures) 59% to 62% NWP : GWP Combined Ratio 95% to 97% Operating Return 6.5% to 8.5% on Common Equity Note: Guidance does not contemplate any material capital actions, nor does it allow for any impact on results through March 11, 2021 522021 Target Operating Metrics Metric 2021 6% to 9% GWP Growth (ex divestitures) 59% to 62% NWP : GWP Combined Ratio 95% to 97% Operating Return 6.5% to 8.5% on Common Equity Note: Guidance does not contemplate any material capital actions, nor does it allow for any impact on results through March 11, 2021 52


Operating Return on Common Equity Glidepath Key actions to deliver an 8-10% ROCE in 2022 10.0% 10% 8.5% 8% 8.0% 6% 6.5% 4% 2% 0% (1.3)% -2% 2020 COVID-19 Normalized Non-Recurring Underwriting Investment 2021 Premium Expense Underwriting Investment 2022 Operating CAT Losses CAT Losses Expenses Actions Income & Operating Growth Reductions Actions Income & Operating ROCE Other ROCE Other ROCE 53Operating Return on Common Equity Glidepath Key actions to deliver an 8-10% ROCE in 2022 10.0% 10% 8.5% 8% 8.0% 6% 6.5% 4% 2% 0% (1.3)% -2% 2020 COVID-19 Normalized Non-Recurring Underwriting Investment 2021 Premium Expense Underwriting Investment 2022 Operating CAT Losses CAT Losses Expenses Actions Income & Operating Growth Reductions Actions Income & Operating ROCE Other ROCE Other ROCE 53


Execution 54Execution 54


Execution of Strategy • Positioned for growth in attractive markets • 90%+ U.S. domiciled risks • Benefitting from improving market conditions • Dynamic and disciplined approach to business • Expense initiatives in place anticipated to remove costs and achieve a 36% expense ratio target for the full year 2022 • Investing in technology to improve operating efficiency and risk selection, while reducing overall expenses • Balanced investment portfolio to support underwriting operations • Strong balance sheet with modest financial leverage 55Execution of Strategy • Positioned for growth in attractive markets • 90%+ U.S. domiciled risks • Benefitting from improving market conditions • Dynamic and disciplined approach to business • Expense initiatives in place anticipated to remove costs and achieve a 36% expense ratio target for the full year 2022 • Investing in technology to improve operating efficiency and risk selection, while reducing overall expenses • Balanced investment portfolio to support underwriting operations • Strong balance sheet with modest financial leverage 55


Q&A Thank YouQ&A Thank You


Appendix 57Appendix 57


U.S. Segment Overview U.S. Operations 1 • Argo Construction – Offers a range of primary & excess coverage to the contractor segment GWP Mix 2 • Argo Pro: 23% • Management Liability – Provides products for commercial and financial institution risks on both a primary and excess basis • E&O – Provides Errors & Omissions coverage on a primary and excess basis for risks on both an admitted and non-admitted basis 3 • Argo Surety – Provides commercial and contract bonds to businesses that must satisfy 17% various eligibility conditions in order to conduct commerce 4 • ARS – Provides non-risk bearing fronting services 14% 5 • Casualty – Casualty insurance for hospitality, manufacturers, and premises risks and specializes in writing general liability and excess 6 • Commercial Programs – Provides administration of risk-bearing programs on Argo paper 7 • Contract Binding – Targets general liability and property accounts with premises 7% 8% driven risks 7% 8 • Environmental – Provides environmental liability insurance with coverage of businesses 5% with pollution exposures, chemicals distributors / manufacturers, industrial cleaners, storage 4% 4% 4% 4% tank manufacturing / install, contractors and other various site pollution risks 3% 9 • Inland Marine – Provides coverage of products, materials and equipment when they are transported over land, such as via truck or train, or while they are temporarily warehoused by a third party 1 2 3 4 5 6 7 8 9 10 11 12 10 • Specialty Property – E&S Property business unit predominantly writes middle market shared and layered accounts with a small number of full value accounts 11 • Rockwood – Provides workers compensation coverage to mining and select industries 12 • Transportation – Provides both admitted and non-admitted garage products designed to cover a wide range of auto dealer and auto service operations 58U.S. Segment Overview U.S. Operations 1 • Argo Construction – Offers a range of primary & excess coverage to the contractor segment GWP Mix 2 • Argo Pro: 23% • Management Liability – Provides products for commercial and financial institution risks on both a primary and excess basis • E&O – Provides Errors & Omissions coverage on a primary and excess basis for risks on both an admitted and non-admitted basis 3 • Argo Surety – Provides commercial and contract bonds to businesses that must satisfy 17% various eligibility conditions in order to conduct commerce 4 • ARS – Provides non-risk bearing fronting services 14% 5 • Casualty – Casualty insurance for hospitality, manufacturers, and premises risks and specializes in writing general liability and excess 6 • Commercial Programs – Provides administration of risk-bearing programs on Argo paper 7 • Contract Binding – Targets general liability and property accounts with premises 7% 8% driven risks 7% 8 • Environmental – Provides environmental liability insurance with coverage of businesses 5% with pollution exposures, chemicals distributors / manufacturers, industrial cleaners, storage 4% 4% 4% 4% tank manufacturing / install, contractors and other various site pollution risks 3% 9 • Inland Marine – Provides coverage of products, materials and equipment when they are transported over land, such as via truck or train, or while they are temporarily warehoused by a third party 1 2 3 4 5 6 7 8 9 10 11 12 10 • Specialty Property – E&S Property business unit predominantly writes middle market shared and layered accounts with a small number of full value accounts 11 • Rockwood – Provides workers compensation coverage to mining and select industries 12 • Transportation – Provides both admitted and non-admitted garage products designed to cover a wide range of auto dealer and auto service operations 58


International Segment Overview International Segment Syndicate 1200 (~76% of GWP) GWP Mix 1• Property – provides direct and facultative, binding authority, forced 27% placed and flood products across a wide range of property coverages 2• Liability – provides Professional Indemnity, General Liability, International 23% Casualty Treaty, Medical Malpractice and Warranty & Indemnity coverage 3• Marine & Energy – provides Marine Cargo, Marine Liability, Offshore Construction and Upstream / Offshore Energy coverage 4• Specialty – provides Accident & Health, Terrorism, Political Violence and Credit & Political Risk coverage 5• MENA – provides Professional Liability products including Annual & 14% Project PI, D&O and Banker Blanket Bond coverage 10% Bermuda Insurance (~16% of GWP) 9% 6• Casualty – provides General and Products Liability excess casualty 6% coverage of worldwide casualty risks 4% 7 • Professional – provides Excess Public Company D&O, Excess Employment 3% 3% Practices Liability, Excess Errors & Omissions, Blended Excess and Primary 1% Wage & Hour coverage Argo Seguros (~8% of GWP) 1 2 3 4 5 6 7 8 9 10 8 • Cargo Marine – provides Inland & Ocean Marine and Truckers coverage 9 • Financial Lines – provides Liability, Professional and Surety coverage Bermuda 10 • Property & Engineering – provides Property & Engineering coverage Syndicate 1200 Insurance Argo Seguros focused on writing small and medium risks 59International Segment Overview International Segment Syndicate 1200 (~76% of GWP) GWP Mix 1• Property – provides direct and facultative, binding authority, forced 27% placed and flood products across a wide range of property coverages 2• Liability – provides Professional Indemnity, General Liability, International 23% Casualty Treaty, Medical Malpractice and Warranty & Indemnity coverage 3• Marine & Energy – provides Marine Cargo, Marine Liability, Offshore Construction and Upstream / Offshore Energy coverage 4• Specialty – provides Accident & Health, Terrorism, Political Violence and Credit & Political Risk coverage 5• MENA – provides Professional Liability products including Annual & 14% Project PI, D&O and Banker Blanket Bond coverage 10% Bermuda Insurance (~16% of GWP) 9% 6• Casualty – provides General and Products Liability excess casualty 6% coverage of worldwide casualty risks 4% 7 • Professional – provides Excess Public Company D&O, Excess Employment 3% 3% Practices Liability, Excess Errors & Omissions, Blended Excess and Primary 1% Wage & Hour coverage Argo Seguros (~8% of GWP) 1 2 3 4 5 6 7 8 9 10 8 • Cargo Marine – provides Inland & Ocean Marine and Truckers coverage 9 • Financial Lines – provides Liability, Professional and Surety coverage Bermuda 10 • Property & Engineering – provides Property & Engineering coverage Syndicate 1200 Insurance Argo Seguros focused on writing small and medium risks 59


The following information was filed by Argo Group International Holdings, Ltd. (ARGO) on Friday, March 12, 2021 as an 8K 2.02 statement, which is an earnings press release pertaining to results of operations and financial condition. It may be helpful to assess the quality of management by comparing the information in the press release to the information in the accompanying 10-K Annual Report statement of earnings and operation as management may choose to highlight particular information in the press release.

View differences made from one year to another to evaluate Argo Group International Holdings, Ltd.'s financial trajectory

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Argo Group International Holdings, Ltd.'s Definitive Proxy Statement (Form DEF 14A) filed after their 2021 10-K Annual Report includes:

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Inside Argo Group International Holdings, Ltd.'s 10-K Annual Report:

Financial Statements, Disclosures and Schedules

Inside this 10-K Annual Report

Cover
Consolidated Balance Sheets
Consolidated Balance Sheets (Parenthetical)
Consolidated Statements Of Cash Flows
Consolidated Statements Of Comprehensive Income (Loss)
Consolidated Statements Of Income (Loss)
Consolidated Statements Of Shareholders' Equity
Consolidated Statements Of Shareholders' Equity (Parenthetical)
Accounting Changes And Error Corrections
Accumulated Other Comprehensive Income (Loss)
Accumulated Other Comprehensive Income (Loss) (Tables)
Accumulated Other Comprehensive Income (Loss) - Amounts Reclassified From Accumulated Other Comprehensive Income (Loss) (Detail)
Accumulated Other Comprehensive Income (Loss) - Changes In Accumulated Other Comprehensive Income (Loss) (Detail)
Allowance For Credit Losses
Allowance For Credit Losses (Tables)
Allowance For Credit Losses - Premium Receivables (Details)
Allowance For Credit Losses - Reinsurance Recoverables (Details)
Business And Significant Accounting Policies
Business And Significant Accounting Policies (Policies)
Business And Significant Accounting Policies (Tables)
Business And Significant Accounting Policies - Additional Information (Detail)
Business And Significant Accounting Policies - Intangible Assets And Accumulated Amortization (Detail)
Business And Significant Accounting Policies - Schedule Of Interest Paid (Detail)
Commitments And Contingencies
Commitments And Contingencies - Additional Information (Detail)
Disclosures About Fair Value Of Financial Instruments
Disclosures About Fair Value Of Financial Instruments (Detail)
Disclosures About Fair Value Of Financial Instruments (Tables)
Disclosures About Fair Value Of Financial Instruments - Summary Of Fair Values Measured On Recurring Basis (Details)
Income Taxes
Income Taxes (Tables)
Income Taxes - Additional Information (Detail)
Income Taxes - Income Tax (Benefit) Provision Expense (Detail)
Income Taxes - Reconciliation Of Difference Between Provision For Income Taxes And Expected Tax Provision At Weighted Average Tax Rate (Detail)
Income Taxes - Schedule Of Net Deferred Tax Liability Comprises Tax Effect Related To Assets And Liabilities (Detail)
Income Taxes - Schedule Of Net Operating Loss Carryforwards Amounts By Jurisdiction And Year Of Expiration (Detail)
Income Taxes - Schedule Of Pre-Tax Income (Loss) And Effective Income Tax Rates (Detail)
Income Taxes - Schedule Of Unrecognized Tax Benefits (Details)
Insurance Assessments
Insurance Assessments (Detail)
Investments
Investments (Tables)
Investments - Additional Information (Detail)
Investments - Allowance For Credit Losses (Detail)
Investments - Components Of Restricted Assets (Detail)
Investments - Financial Assets Measured At Fair Value On Recurring Basis (Detail)
Investments - Schedule Of Aging Of Unrealized Losses On Company's Investments In Fixed Maturities, Equity Securities And Other Investments (Detail)
Investments - Schedule Of Amortized Cost And Fair Values Of Fixed Maturity Investments, By Contractual Maturity (Detail)
Investments - Schedule Of Amortized Cost, Gross Unrealized Gains, Gross Unrealized Losses And Fair Value Of Investments (Detail)
Investments - Schedule Of Carrying Value And Unfunded Investment Commitments Of Other Invested Assets Portfolio (Detail)
Investments - Schedule Of Changes In Unrealized Appreciation (Depreciation) (Detail)
Investments - Schedule Of Company's Gross Realized Investment Gains (Losses) (Detail)
Investments - Schedule Of Fair Value Of Foreign Currency Exchange Forward Contracts (Detail)
Investments - Schedule Of Investment Income And Expenses (Detail)
Investments - Schedule Of Realized Gains And Losses Of Investment On Foreign Currency Exchange Forward Contracts (Detail)
Investments - Schedule Of Reconciliation Of Beginning And Ending Balances For Investments Categorized As Level 3 (Detail)
Leases
Leases (Tables)
Leases - Additional Information (Details)
Leases - Components Of Leases (Details)
Leases - Lease Cost (Details)
Leases - Lease Maturity (Details)
Long-Term Debt
Long-Term Debt (Tables)
Long-Term Debt - Additional Information (Detail)
Long-Term Debt - Schedule Of Floating Rate Loan Stock, Notes Outstanding (Detail)
Long-Term Debt - Schedule Of Junior Subordinated Debentures (Detail)
Long-Term Debt - Schedule Of Long-Term Debt Maturity (Details)
Long-Term Debt - Schedule Of Maybrooke Junior Subordinated Debentures (Detail)
Long-Term Debt- Schedule Of Terms And Principal Amounts Of Other Indebtedness (Detail)
Net (Loss) Income Per Common Share
Net (Loss) Income Per Common Share (Tables)
Net (Loss) Income Per Common Share - Additional Information (Detail)
Net (Loss) Income Per Common Share - Net (Loss) Income Per Common Share On Basic And Diluted Basis (Detail)
Pension Benefits And Savings Plans
Pension Benefits And Savings Plans (Detail)
Recent Acquisitions, Disposals &Amp; Other Transactions
Recent Acquisitions, Disposals &Amp; Other Transactions - Acquisitions (Details)
Recent Acquisitions, Disposals &Amp; Other Transactions - Sale Of Business Unit (Details)
Reinsurance
Reinsurance (Tables)
Reinsurance - Additional Information (Detail)
Reinsurance - Schedule Of Reinsurance Premium (Detail)
Reserves For Losses And Loss Adjustment Expenses
Reserves For Losses And Loss Adjustment Expenses (Tables)
Reserves For Losses And Loss Adjustment Expenses - Additional Information (Detail)
Reserves For Losses And Loss Adjustment Expenses - Impact From (Favorable) Unfavorable Development Of Prior Accident Years' Loss And Lae Reserves On Each Reporting Segment (Detail)
Reserves For Losses And Loss Adjustment Expenses - Reserves For Losses And Loss Adjustment Expenses (Detail)
Reserves For Losses And Loss Adjustment Expenses - Schedule Of Information About Discounted Liabilities For Unpaid Losses And Lae (Detail)
Reserves For Losses And Loss Adjustment Expenses - Schedule Of Supplementary Unaudited Information About Annual Percentage Payout Of Incurred Losses And Alae, Net Of Reinsurance (Detail)
Reserves For Losses And Loss Adjustment Expenses - Summary Of Information About Incurred And Cumulative Paid Losses And Allocated Loss Adjustment Expenses, Net Of Reinsurance (Detail)
Reserves For Losses And Loss Adjustment Expenses - Summary Of Reconciliation Of Net Incurred And Paid Development To Liability For Unpaid Losses And Lae In Consolidated Balance Sheets (Detail)
Revisions Of Previously Issued Financial Statements (Tables)
Revisions Of Previously Issued Financial Statements - Adjusted Condensed Consolidating Statement Of Income (Loss) (Details)
Revisions Of Previously Issued Financial Statements - Adjusted Consolidated Balance Sheet (Details)
Run-Off Lines
Run-Off Lines (Tables)
Run-Off Lines - Gross Reserves For Run-Off Lines (Detail)
Run-Off Lines - Total Gross Reserves For Asbestos Exposure (Detail)
Run-Off Lines - Underwriting Losses For Run-Off Lines (Detail)
Schedule Ii Condensed Financial Information Of Registrant
Schedule Ii Condensed Financial Information Of Registrant - Schedule Of Balance Sheets (Detail)
Schedule Ii Condensed Financial Information Of Registrant - Schedule Of Statements Of Cash Flows (Detail)
Schedule Ii Condensed Financial Information Of Registrant - Schedule Of Statements Of Income (Detail)
Schedule Iii Supplemental Insurance Information
Schedule Iii Supplemental Insurance Information (Detail)
Schedule V Valuation And Qualifying Accounts
Schedule V Valuation And Qualifying Accounts (Detail)
Schedule Vi Supplemental Information For Property-Casualty Insurance Companies
Schedule Vi Supplemental Information For Property-Casualty Insurance Companies (Detail)
Segment Information
Segment Information (Tables)
Segment Information - Additional Information (Detail)
Segment Information - Identifiable Assets (Detail)
Segment Information - Revenue And Income (Loss) Before Income Taxes For Each Segment (Detail)
Segment Information - Schedule Of Earned Premiums By Geographic Location (Detail)
Segment Information - Schedule Of Goodwill And Intangible Assets Net Of Accumulated Amortization (Detail)
Senior Unsecured Fixed Rate Notes
Senior Unsecured Fixed Rate Notes (Tables)
Senior Unsecured Fixed Rate Notes - Additional Information (Detail)
Senior Unsecured Fixed Rate Notes - Condensed Consolidating Balance Sheet (Detail)
Senior Unsecured Fixed Rate Notes - Condensed Consolidating Statement Of Cash Flows (Detail)
Senior Unsecured Fixed Rate Notes - Condensed Consolidating Statement Of Income (Loss) (Detail)
Senior Unsecured Fixed Rate Notes - Schedule Of Unamortized Debt Issuance Costs Deducted From Carrying Value Of Debt Liability (Detail)
Share-Based Compensation
Share-Based Compensation (Tables)
Share-Based Compensation - Additional Information (Detail)
Share-Based Compensation - Summary Of Restricted Share Activity (Detail)
Share-Based Compensation - Summary Of Stock-Settled Sars Activity (Detail)
Shareholders' Equity
Shareholders' Equity - Additional Information (Detail)
Statutory Accounting Principles
Statutory Accounting Principles (Tables)
Statutory Accounting Principles - Additional Information (Detail)
Statutory Accounting Principles - Statutory Capital And Surplus For Principal Operating Subsidiaries (Detail)
Statutory Accounting Principles - Statutory Net Income (Loss) For Principal Operating Subsidiaries (Detail)
Transactions With Related Parties
Transactions With Related Parties Transactions With Related Parties (Detail)
Underwriting, Acquisition And Insurance Expenses &Amp; Other Corporate Expenses
Underwriting, Acquisition And Insurance Expenses &Amp; Other Corporate Expenses (Detail)
Underwriting, Acquisition And Insurance Expenses &Amp; Other Corporate Expenses (Tables)
Ticker: ARGO
CIK: 1091748
Form Type: 10-K Annual Report
Accession Number: 0001628280-21-004668
Submitted to the SEC: Fri Mar 12 2021 7:18:07 PM EST
Accepted by the SEC: Mon Mar 15 2021
Period: Thursday, December 31, 2020
Industry: Title Insurance

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