Into the Breach

Hosted by Seyfarth Shaw LLP

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Mar 2026

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About the show

The first law firm podcast exclusively devoted to reps and warranties insurance and the transactional risk markets. Hosted by Seyfarth partners Bryan M. O’Keefe and Gena B. Usenheimer, each week the hosts in their unique, buoyant style, interview leaders from the industry, and explore the latest developments, market trends, and news impacting RWI and transactional risk insurance.

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44 recent

March 23, 202633 min

Episode 44: Covering More Than Title

On the latest episode of Into the Breach, Bryan and Gena welcome back return guest A.J. Kritzman, for a discussion about his new role as Vice President, Transaction Risk Solutions, at First American. Topics discussed include: • The intersection of title insurance and transactional risk insurance • How A.J. and his team can help provide unique solutions in commercial real estate transactions • Rates, retention, and scope of coverage issues • What is meant by “commercial real estate” and what types of real estate are best fits • How real estate attorneys can better represent their clients through the proper utilization of transactional risk insurance • AI’s continued role in the underwriting process • A.J.’s favorite type of commercial real estate Read the full transcript here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Into-The-Breach-Episode-44.pdf

October 8, 202543 min

Episode 43: Welcome to the Aon Claims Team!

On this episode of ITB, Bryan and Gena are joined by the wonderful Aon team of Stephen Davidson, Jennifer Drake and Anthony Dragone. Topics discussed include: • ITB’s award-winning status! Thank you to Million Podcasts for ranking us as one of the Top 60 M&A Podcasts! • Key takeaways from the Aon Claims Report, including: • Frequency and severity of claims and record high recoveries • How the high multiples from 2021 are driving claims severity • Financial statement and material contract claims continue to drive claim frequency • No single industry stands out as an outlier when it comes to claims • Stephen’s hope for the next 12 months and his career advice for someone interested in the space • What tropical and exotic locale should host the Aon conference next year? Read the full transcript of the episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/IntoTheBreach_Episode43.pdf

June 10, 202533 min

Episode 42: Oil Strike – Utilizing RWI on Oil and Gas Transactions

On this episode of ITB, Bryan and Gena are joined by Paige Brewin, Senior Vice President and Head of Transactional Liability QBE North America, to talk about the benefits of using representations and warranties insurance in oil and gas transactions. Topics discussed include: • Paige and Gena’s axe throwing skills • How Paige’s background serving as underwriting counsel prepared her for her current role • The unique structure of the QBE oil and gas team • How QBE’s dedicated group of oil and gas underwriters benefit insureds in the underwriting process • The type of due diligence QBE requires for oil and gas deals and the timing of these reports • An overview of pricing these transactions • Claims activity • What gas octane Paige uses for her car Read the full transcript of the episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/IntoTheBreach_Episode42.pdf

May 1, 202533 min

Episode 41: Use of RWI in Healthcare Deals

On this episode of ITB, Bryan and Gena are joined by Philip Z. Glorieux, Managing Director – Healthcare, Ambridge Partners LLC to discuss his career underwriting in the healthcare space and how the market has changed with respect to the availability of coverage for these deals Topics discussed include: • Gena’s experience at Othello and her horror at the lack of cell phone access (for the whole show!!) • Ambridge’s appetite for different healthcare risks and what kind of deals fall into its “sweet spot” for underwriting • What keeps Phil up at night (other than his kids!) • Quality of the diligence and how we regularly get comfortable in this highly regulated space • Overview of claim activity • Everyone’s favorite TV medical drama Read the full transcript of the episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/IntoTheBreach_Episode41.pdf

March 25, 202529 min

Episode 40: Making the Change – Transitioning from Big Law Associate to RWI Underwriter

In another career oriented episode of Into the Breach, Bryan and Gena are joined by Caroline Barry, Assistant Vice President & Counsel at Ryan Transactional Risk, for a discussion of how she transitioned from big law associate to RWI underwriter. Topics discussed include: • Gena’s early morning encounter with a canine friend • Caroline’s background as a corporate associate working in big law • How Caroline made the career transition from corporate associate to RWI underwriter • Why working as a RWI underwriter allows you to be more entrepreneurial in your career • How the RWI career is a hybrid opportunity, combining the best of big law and in-house work • The biggest challenges that Caroline has encountered as a RWI underwriter • The importance of broker relationships • More information about the wonderful team at Ryan Transactional Risk • Caroline and Gena reminiscence about attending a Madonna concert together (while Bryan names his favorite Madonna song) Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/IntoTheBreach_Episode40.pdf

March 6, 202533 min

Episode 39: Forensic Accounting – Not Just For CSI

On this episode of ITB, Bryan and Gena are joined by Ephraim Stulberg, Partner, MDD Forensic Accountants, for a discussion on the resolution of financial statement claims on RWI policies. Topics discussed include: • Bryan and Gena’s shared history of forensics/debate in high school! (Hi Miss Esslinger at Syosset High School!) • Ephraim’s studies at The University of Toronto and his career trajectory • Plus, his near-miss with television celebrity • Common pitfalls and pain points in financial statement claims • The philosophical application of accounting to deal valuation • How economic uncertainty might impact RWI • Keys to success in the RWI industry • Gena and Ephraim’s shared love of musical theater and Come From Away’s successful pro-Canadian propaganda

February 25, 202536 min

Episode 38: Underwriting Real Estate Transactions (Who Doesn’t Love an Easement!?)

On this episode of ITB, Bryan and Gena are joined by Simon Wood, Head of Real Estate, CFC Underwriting, to discuss utilizing RWI on real estate transactions. Topics discussed include: • Bryan and Gena’s favorite activities at the 2025 Aon M&A and Transactional Solutions Symposium • How Gena invited herself to CFC’s “puppy day” • Simon’s status as a “real estate nerd” • The Growth of CFC’s real estate practice and “sweet spots” for real estate transactions • Pricing and scope of coverage • What we can expect to see in terms of diligence on a true “real estate” deal • Simon’s favorite piece of real estate in the world • Gena’s next career as a goat promoter

December 12, 202434 min

Episode 37: Point Man: An Interview with Dennis Kearns, Chief Executive Officer, Sands Point Risk

Bryan and Gena welcome back the only two-time insurer guest on Into the Breach with a return visit from Dennis Kearns, Chief Executive Officer of Sands Point Risk. Topics discussed include: • The launch of Sands Point Risk • How Sands Point Risk will utilize transactional risk insurance as a flagship offering for a new full-service MGA • How Dennis came up with the name “Sands Point Risk” and the company’s brand identity • Why the Sands Point Risk team makes this MGA a special place to work • The backing that Sands Point Risk receives from Avesi Partners, a global private equity firm • Other lines of insurance that Sands Point Risk will offer in the near future • The “sweet spot” deals that Sands Point Risk is pursuing in the current market • Dennis’s favorite wine spot in Napa Valley

December 2, 202429 min

Episode 36: The Role of Underwriting Counsel in the RWI Process

In the latest episode of Into the Breach, Bryan and Gena tackle a topic near and dear to their hearts: the critical role that underwriting counsel play in the RWI process. For this enlightening discussion, our hosts are joined by Sara Josselyn, a Partner at Gowling WLG, who frequently serves as underwriting counsel to RWI insurers in Canada. Topics discussed include: • How Sara’s work as a corporate attorney prepared her to serve as underwriting counsel for insurers • The launch of Sara’s underwriting counsel practice at Gowling WLG • What Sara is seeing in the M&A markets now in her role as underwriting counsel • How Sara tailors her process to meet the needs of individual insurers • The continued growth of RWI in Canada and emerging trends in the Canadian market • The movement towards shorter underwriting calls and a more efficient underwriting process • How Sara works with her subject matter specialists to deliver positive client outcomes • Sara’s favorite “secret” destination in Canada to visit

September 16, 202431 min

Episode 35: RWI Claims: Everything You Want To Know

In a first for the podcast, Bryan and Gena are joined by special guest co-host Christine Kim, Counsel, Seyfarth Shaw, for a discussion with Phil Casper, Principal at Euclid Transactional, on RWI claims. Topics discussed include: • How Phil’s prior work as an underwriter helped prepare him for his current role in managing Euclid’s claims • Background on Euclid’s claims team and how they are able to provide superior client service • Why claims are the crux of the RWI product • Phil’s “least favorite” type of claim • The interplay between RWI premiums and claims paid, especially in the current rate environment • Whether claim trends are impacting RWI underwriting • Why buyers should continue to use RWI considering the amount of claims that have been paid • Phil’s favorite podcast other than “Into the Breach”