This Flipping the Script Podcast features a discussion between C&F CEO Marc Adee and Jack Ryan, Solutions Architect, A&H Digital Transformation. The conversation focuses on C&F’s decentralization model, why Marc moved away from a centralized corporate structure, and how that shift changed accountability, leadership and resource decisions. Marc also connects the discussion to a theme from his Checking in - 164: in a decentralized structure, the strongest ideas often come through “demand pull,” bubbling up from the businesses rather than being pushed down as top-down mandates.

Main Topic Summary

0:19: Introductions

Marc introduces Jack Ryan, who shares his role in A&H Digital Transformation and his path from intern to full-time employee at C&F.

1:21: Why Decentralize

Marc explains that the old centralized model created resource bottlenecks and slow support for divisions. Decentralization moved resources and accountability closer to the business units.

8:19: Pushback & Accountability

Marc discusses resistance from corporate and divisions, noting that decentralization reduced excuses and increased accountability for results.

14:36: Trusting the Model

Marc explains that true decentralization depends on strong leaders, trust and effective corporate controls. 

18:53: Leadership Gears

Marc reflects on how leadership style changes depending on the company’s phase, such as cleanup, rebuilding or growth. 

20:42: Making the Change

Marc says he had little hesitation once he believed decentralization was the right path, even though it was not easy or universally popular. 

24:12: Demand Pull

Marc contrasts top-down “supply push” decisions with division-driven “demand pull” investments that better match business needs.

30:07: Efficiency & Collaboration

Marc notes that decentralization may seem less efficient on paper, but forced consolidation can hurt culture and results. He favors voluntary collaboration and shared expertise over mandates.

35:09: Success & Takeaways

Marc says decentralization’s success is reflected in C&F’s results, speed and clear accountability. He closes by emphasizing that the model is intentional, culturally embedded and valuable for employees.

This Flipping the Script Podcast features a career-focused conversation between C&F CEO Marc Adee and Brianne Banasiak, Senior Underwriter in Accident & Health, Special Risk. The discussion centers on career development, leadership readiness and relationship-building. The conversation emphasizes taking ownership of one’s career, embracing uncomfortable opportunities, and intentionally developing the broader skills and connections needed for future leadership.

Here's a summary of what Marc and Brianne discuss:

Weekly Check-in Referenced: #189

0:42: Brianne's Career Path 

Brianne explains that her father started a travel MGU. She initially considered accounting, interned at C&F, briefly explored the brokerage side, and ultimately returned to underwriting at C&F in 2023. 

2:35: Industry Age Gap

Brianne raises the issue of the insurance industry’s age gap and the wave of retirements creating leadership openings.

5:03: Readiness for Leadership

Marc talks about the importance of being both technically and psychologically ready when opportunities appear. He notes that many people are qualified for leadership roles before they feel comfortable.

7:29: Pushing Beyond Comfort Zones

Marc explains that senior leaders should actively push rising talent into stretch opportunities. He argues that growth rarely happens by staying comfortable, and unfamiliar situations help build the confidence needed for bigger roles.

9:00: Excellence in Current Role

Marc stresses that the best foundation for advancement is mastering your current responsibilities, while also observing what additional skills future roles require.

11:09: Broadening Career Options 

Marc highlights the value of exploring different functions, reading broader company materials, and considering rotations or pivots before career paths become more fixed over time.  

17:12: Discussing Career Moves

Brianne asks how employees can approach managers when they want to explore a different role. Marc says those conversations are easiest when someone has already built credibility, and he encourages employees to seek feedback on which skills they need to develop next.

21:55: Path to CEO

Brianne asks when Marc first realized he could become a CEO. Marc reflects that he always had confidence, but recognized that leadership required a different set of skills, which he built by taking on difficult assignments.

28:05: Building Relationships

Marc and Brianne emphasize the value of high-density office days, Brand Ambassador Programs, conferences, and peer networking as ways to build long-term connections with future leaders in the industry.

34:04: Motivation & Leadership Lessons

Marc stresses that challenge creates growth, motivation must be partly self-generated, and true leadership is ultimately about people, not just technical excellence.

In this podcast conversation, C&F CEO Marc Adee and Alex Morales, Chief Actuary, discuss Alex’s path into actuarial science, the professional experiences that shaped his leadership perspective, and how the actuarial function has evolved at C&F. They also explore decentralization, communication as a leadership skill, and the growing role of data science and AI in actuarial work.

Main Topics Summary:

0:53: Entering actuarial science

During his senior year of college, Alex was deciding between teaching, grad school, and actuarial science. Taking an early actuarial exam led him to begin his career at ISO, despite actuarial science not being a common path at MIT.

5:02: Early career and AIG

Alex discusses his early years at ISO, where he built technical skills and progressed through the actuarial exams. He then reflects on his brief but memorable time at AIG during the 2008 financial crisis.

8:26: Wisconsin roles and leadership growth

After moving to Wisconsin, Alex joined CUNA Mutual Group and later American Family. These roles gave him deeper experience in commercial lines pricing.

14:00: Joining C&F and becoming Chief Actuary

Alex explains that C&F was a company he had long wanted to join and that he came aboard in 2018; becoming Chief Actuary in 2020.

18:01: Decentralization at C&F

Marc and Alex discuss decentralization as one of the biggest changes at C&F during Alex’s tenure. They describe how it improved accountability, gave divisions more ownership over decisions, and strengthened the role of embedded actuarial support within the business units.

23:48: Reserve discipline and communication

Alex notes that C&F has become better at saying no to business that does not fit, and Marc connects that to stronger accountability and reserve discipline. They also discuss Alex’s writing in the President’s Report and the importance of explaining technical actuarial concepts clearly to a broad audience.

29:14: Actuarial vs. data science

The discussion turns to career paths and whether actuarial science or data science is the better choice for quantitatively minded professionals. Alex believes that the future is not one versus the other, but a combination of the two.

38:54: Soft markets, modeling, and AI

Alex talks about C&F’s strong reserve position and previews work on how modeling can help navigate a soft market. He and Marc also discuss AI as a force multiplier that can enhance actuarial work.

46:12: Future of the profession

Alex predicts that actuaries will increasingly move into broader leadership roles across the business. He ends on an optimistic note about the actuarial profession and the professional opportunities available at C&F.

This podcast episode features a conversation between C&F CEO Marc Adee and Mike McTigue, Chief Legal Officer & Secretary, covering Mike's career journey from accounting to law, and ultimately insurance. The discussion explores the realities of legal practice, the broad responsibilities of Corporate Legal — including regulatory compliance, governance, transactions, policies, and litigation oversight — and how the legal team supports the business. The episode also examines the importance of regulatory and trade association relationships, industry reputation and advocacy, and the value of legal professionals serving as practical business partners.

1:54: An Unplanned Path to Insurance

From accounting at Liberty Mutual to practicing law and joining AIG, Mike's financial background unexpectedly helped shape his insurance career.

8:45: Building a Career Beyond the Courtroom

The conversation explores the realities of legal practice, the business skills attorneys need to succeed, and Mike's transition from litigation to transactional insurance work.

14:00: Corporate Legal as the Company's Goalkeeper

A look at the many responsibilities of Corporate Legal, from regulatory compliance and governance to contracts, policy development, and business risk management.

19:08: Managing Transactions and Deals

An inside look at how Corporate Legal manages transactions, works with Fairfax on major acquisitions, and leverages outside counsel when specialized expertise is needed.

22:48: Why Company Policies Matter

Company policies serve as both a resource for employees and a safeguard for the business — acting as both a sword and shield. This means that awareness, compliance, and early reporting are essential for success.

27:13: Navigating the Regulatory Landscape

The discussion turns to the challenges of operating in a highly-regulated industry and the importance of relationships with regulators across the country.

33:46: The Role of Trade Associations

Trade groups like APCIA help insurers monitor legislation, influence policy discussions, and stay ahead of emerging regulatory issues.

41:45: Improving the Industry's Reputation

Insurance affordability, public perception, and industry advocacy take center stage as the conversation examines how insurers communicate their value to consumers.

48:29: Legal as a Business Partner

The episode closes with a reminder that Corporate Legal is a business partner, helping teams navigate challenges and achieve their goals.

In this episode, C&F CEO Marc Adee and Lauren Train, VP & Actuary, Commercial Lines, discuss key themes from the second quarter President’s Report, focusing on how to interpret production, underwriting results, earned premium, reserve development, and market conditions. The conversation balances technical actuarial and insurance topics with broader points about underwriting discipline, long-term thinking, and C&F’s culture.

Here’s a summary of what Marc and Lauren discuss:

0:35: Award and Opening

Marc opens by congratulating Lauren on winning Zywave’s Cyber Risk Person of the Year award in the actuary/modeler category.

4:20: Top Line vs. Plan

Lauren asks why production is slightly up year over year but behind plan. Marc explains that top-line numbers can be misleading on their own.

10:20: Soft Market Discipline

Marc discusses how competitive pressure, aggressive pricing, and cash-flow-style underwriting can distort growth. He emphasizes that some growth is unhealthy, while disciplined shrinkage can be the better long-term outcome.

12:34: Written vs. Earned Premium

Lauren asks how underwriting income and combined ratio can still be on plan when net written premium is below plan. Marc explains that earned premium reflects prior writings and timing effects, so current written premium shortfalls do not immediately translate into weaker earned results.

20:19: A&H Accounting and Structure

The conversation turns to A&H, where Lauren notes that premium often earns immediately. Marc explains that this reflects product design and accounting conventions.

27:20: Medical Stop Loss Market

Lauren references Tanya Arrowsmith’s article on stop loss and asks about competitors exiting the market. Marc says these exits often reflect companies entering a specialized line without enough expertise.

35:25: Profitability Over Size

Lauren discusses both A&H and Seneca, noting that a smaller business can still generate similar underwriting income. Marc uses this to reinforce that bottom-line profitability and discipline matter more than simple premium size.

36:55: Reserve Development and Combined Ratio

Marc explains that prior-year reserve development affects divisions differently and can materially shape reported results.

51:52: Talent and Charitable Impact

Marc closes by encouraging employees to read beyond the financial sections of the report. He highlights talent development, career guidance, and charitable initiatives as important parts of C&F’s long-term culture and success.

President's Report Page Numbers Mentioned & Time Stamps:

04:33: President's Report Page 3, Start of metrics discussion, gross premium written, underwriting result

13:22: Appendix 1 Pages 3 & 4, How C&F is able to earn premium in line with plan, despite a shortfall in written premium

23:24: Appendix 1 Page 9, Net Premiums Earned

24:01: Appendix 4 Pages 54 and 55, A&H Net Premiums Written and Earned

35:50: President's Report Page 4, Recap by C&F

41:50: Appendix 5 Page 110, C&F Property and the unique nature of its claims

This Flipping the Script podcast episode features C&F CEO Marc Adee and Andy Crocker, Regional Underwriting Director in Surety, discussing Andy’s career path and several themes from Marc’s Weekly Check-In #311. Andy asks about C&F’s growth, Fairfax’s capital strategy, and the value of long-term thinking. The conversation blends financial and strategic discussion with culture, talent development, and the practical realities of hybrid work.

Flipping the Script: Friday Check-In Deep Dive episodes feature employees taking a closer look at topics from Marc’s Weekly Check-Ins, asking follow-up questions and gaining deeper insight into his perspective on the issues that matter most.

Main Topics Summary:

01:12: Andy’s path into surety

Andy describes how he entered surety through networking after majoring in economics. Marc and Andy reflect on how people often “fall into” insurance and surety from versatile academic backgrounds.

03:54: C&F growth and Fairfax

Andy asks about Marc’s Check-In #311, which noted that C&F’s Q4 growth outpaced the rest of Fairfax combined. Marc explains that C&F’s diversified business mix is similar to Fairfax’s approach – the diversity smooths the natural seasonality and cyclical nature of the industry.

08:21: C&F’s standing within Fairfax

Andy asks the perception of C&F in Fairfax’s eyes today. Marc says C&F is still sometimes viewed through an outdated lens, and sees storytelling as important to changing that perception, including his book, The Once and Future C&F.

10:32: Fairfax share buybacks

Andy raises Fairfax’s share buyback strategy and asks why repurchasing shares above book value can still make sense.

18:42: Long-term leadership mindset

Andy asks how long-term thinking influences Marc’s daily decision-making as CEO. Marc says it shapes how he develops people, manages the business, and avoids short-term decisions.

25:55: Career growth and culture

Marc expands on how leaders must shift from focusing on themselves to thinking about the company and its people with a long-term view.

27:11: Brand Ambassador program and C&F culture

When asked about the C&F Brand Ambassador Program, Andy says it has helped raise C&F’s visibility externally while connecting employees internally. Andy links C&F’s strong culture to leadership focus and employee-centered initiatives.

29:00: Hybrid work and local presence

Marc and Andy discuss how hybrid work functions in Surety, where in-person producer and agent relationships still matter.

31:49: C&F’s Future

Andy closes by stressing that C&F’s culture is a major differentiator, especially compared with other workplaces.

This podcast episode between C&F CEO Marc Adee and Alex Morrone, CFO of Commercial Lines, centers on how AI is reshaping insurance work at C&F, from small productivity gains to broader underwriting and claims transformation. They discuss Alex’s background, his team’s innovation practices, an internally-built prediction market, and a forward-looking view of how AI, documentation, and human judgment may define competitive advantage in insurance over the next decade.

00:47: Alex's Path into Insurance

Alex explains that he originally expected to become a math teacher or professor. His path changed when he discovered actuarial science in college, and began building a career in insurance from there.

3:25: Building a Prediction Market with AI

Marc and Alex explore how an internal prediction market could become both fun and operationally useful. They also discuss needed improvements, such as bet-closing rules, admin controls, broader participation, and guardrails around insider knowledge. Visit C&F Signal to learn more.

12:20: AI Experimentation in Daily Work

Alex describes how his team uses AI to handle time-consuming analytical tasks. He emphasizes that these tools can save substantial time, but still require human review and validation to catch errors.

14:51: Industry AI Momentum and C&F's Positioning

Marc notes that C&F’s bubble-up innovation seems to be keeping us on pace with the industry.

16:13: Silver Platter and Underwriting Support

Alex outlines the Commercial Lines initiative called Silver Platter, which aims to surface key underwriting and claims insights more efficiently. The goal is to reduce administrative burden to focus more on judgment and decision-making.

18:43: Deterministic systems vs evolving AI Insights

Marc raises the challenge of consistency in AI-driven underwriting, especially when models can produce changing answers over time.

20:49: Growth Through More Underwriting Capacity

Alex explains that by reducing the time spent on document review, comparisons, and administrative analysis, underwriters could potentially quote significantly more business with the same resources.

22:46: Claims and Service Efficiency

Marc extends the AI discussion to claims and customer service, describing how AI can prepare information in advance so employees can respond faster and more effectively.

24:41: Innovation Day as a Team Practice

Alex explains how his team’s quarterly Innovation Day has evolved into a forum for experimentation, sharing ideas, and learning what new tools make possible.

28:01: Insurance in 2035

Alex shares his view that the future of insurance will depend heavily on how well companies capture and structure institutional knowledge, documentation, and context for AI-assisted decision-making.

34:49: Future Distribution and Quoting Dynamics

Alex notes that both carriers and producers are building more automation, which could lead to faster, more direct quote requests. They recognize that long-standing distribution relationships will still matter.

37:48: Encouraging Employees to Explore Better Tools

Alex closes by encouraging employees to reach out if they have repetitive or labor-intensive processes that may be improved through automation or AI.

In this installment of Flipping the Script: Friday Check-In Deep Dive, Michael Guerriero, Senior Manager of Data & Analytics, Commercial Lines, joins C&F CEO Marc Adee to explore questions drawn from Marc’s Weekly Check-Ins. The discussion examines how people interpret large numbers and the real-world implications for insurance — particularly in areas like claims, pricing, and decision-making. Marc also breaks down key concepts such as float, combined ratio, and underwriting discipline, emphasizing their role in driving performance and investment value. The conversation closes with reflections on C&F’s culture, growth, and the importance of continuous learning.

Here’s a summary of what Marc and Michael discuss:

00:46: Michael’s Path to Insurance

Michael shares how he moved from banking to C&F and now supports Commercial Lines through data and analytics.

02:32: MarcBot

Marc and Michael briefly discuss how Michael used MarcBot to shape interview questions, with both highlighting its practicality and helpfulness.

02:49: Making Sense of Big Numbers

Referencing Check-In #300, Michael and Marc discuss how examples like SpaceX, AI data centers, and billion-dollar claims can distort perspective when massive numbers become normalized and influence decision-making.

9:14: The Compounding Impact of Insurance Trends

Marc explains how compounding trends and soft-market rate expectations can erode insurance profitability over time.

12:44: Float Explained

Referencing Check-In #201, Marc defines float as money insurers hold before paying claims and explains why it matters in P&C insurance.

18:58: Float, Return on Equity (ROE), and the Discipline of 95%

Michael and Marc discuss how float can support investment income and ROE, but Fairfax’s practical performance focus remains clear: deliver a disciplined 95% combined ratio.

29:15: Growth, Deals, and Acquisitions

Marc discusses how C&F evaluates new opportunities, using the pet sale and potential acquisitions as examples.

33:01: Culture & Continuous Learning

Michael reflects on C&F’s positive culture, flexibility, leadership support, and the value of continuous learning.

In the first installment of our new series, Flipping the Script: Friday Check-In Deep Dive, featured employees take a closer look at topics from C&F CEO Marc Adee’s Weekly Check-In, asking follow-up questions and gaining deeper insight into Marc’s perspective on the issues that matter most.

Marc and Sara Iuzzolino, Associate Underwriter Trainee in Surety, discuss Sara’s entry into insurance, lessons for early-career professionals, and how young employees can build toward leadership over time. The conversation centers on career ownership, confidence, networking, intern and trainee development, and the role C&F’s culture plays in making work meaningful and motivating.

Here’s a summary of what Marc and Sara discuss:

00:32: Entering Surety

Sara shares that she has just reached her C&F one-year anniversary, and explains how a marketing background and an internship led her into insurance, and ultimately to a Surety trainee role at C&F.

03:20: Revisiting Check-In 189

Sara introduces Marc’s earlier thoughts and asks whether he always intended to pursue senior leadership. Marc explains that leadership became clearer over time and emphasizes intentionally building skills, experiences, and readiness for future roles.

08:54: Getting Exposure Early

Marc explains how focusing on being useful and adding value gave him early access to senior-level conversations.

16:41: Being Young in Senior Executive Meetings

Sara asks about feeling intimidated as a younger professional, and Marc says confidence comes from knowing why you were invited.

22:51: Networking and Building a Cohort: Check-In 156

They discuss how networks expand over time and why building relationships with peers and future leaders matters early on.

27:12: Interns, Trainees, and Choosing Insurance

Marc shares his personal path to insurance. He notes that most people do not study specifically for insurance careers and that curiosity and willingness to learn matter more.

39:01: Advice and Perspective of the Next Generation

Sara challenges stereotypes about Gen Z and says she feels energized by C&F’s supportive culture and work environment.

40:12: In-Person Connection and Culture

Sara describes the strong sense of support among Surety trainees, including shared study efforts and daily walks. Marc emphasizes the value of office interaction, informal relationship-building, and the importance of not taking strong company culture for granted.