A

Ascot

Global specialty insurer and reinsurer.

Head of U.S. Treaty Reinsurance

Full-TimeUpdated on 10/23/2026
$400k - $420k+ Annual cash bonus + Discretionary compensation
Expert
Bachelor's
Stamford, CT, USA+1 moreMore locations: New York, NY, USA
HybridBased in the Stamford or New York office; frequent travel to other Ascot offices, including London and Bermuda.
InsuranceUnderwriting

About the job

Requirements
  • A bachelor's degree is required.
  • Executive experience leading a significant reinsurance operation is required.
  • A minimum of 10 years of leadership experience in the reinsurance industry is required.
  • Demonstrated success building and scaling businesses, launching products or capabilities, and identifying new avenues for profitable growth is required.
  • Ability to identify and implement operational improvements, including effective use of artificial intelligence-enabled tools, automation, and analytics to improve underwriting insight, workflow efficiency, and decision quality is required.
  • Strong financial and analytical acumen, including ability to interpret financial, actuarial, and portfolio performance data and convert findings into action, is required.
  • Superior written and verbal communication skills and ability to influence senior stakeholders internally and externally are required.
  • Ability to partner across claims, finance, actuarial, technology, operations, and marketing to deliver integrated business outcomes is required.
  • Proven experience mentoring, coaching, and developing high-performing teams while fostering accountability, engagement, and inclusion is required.
  • Recognized enterprise leadership, sound judgment, strong decision-making capability, and ability to operate effectively in a dynamic, evolving environment are required.
  • Demonstrated experience developing and executing business plans, setting performance goals, and delivering measurable underwriting and financial results is required.
Responsibilities
  • Advise the Group Executive Committee on key U.S. market reinsurance trends and conditions.
  • Ensure coordination of reinsurance strategies across North America and collaboration between the U.S. treaty team and Bermuda treaty team to avoid channel conflict and maximize reinsurance solutions for clients.
  • Leverage strong relationships with reinsurance brokers and clients.
  • Develop a U.S. reinsurance strategy to drive profitable growth and optimal return on capital while adhering to group risk appetite and tolerances.
  • In conjunction with the Group Chief Underwriting Officer, establish a treaty reinsurance business in the United States, building upon and extending established books of business in Bermuda and ensuring teams are coordinated, resourced, and trained.
  • Promote the company and its U.S., UK, and Bermuda platforms to executive leadership of relevant trading partners.
  • Provide visible, hands-on leadership to underwriting teams, fostering underwriting judgment, accountability, collaboration, colleague development, and continuous improvement.
  • Partner across underwriting, claims, actuarial, finance, information technology, data, and operations to steer the portfolio and support high-quality business decisions.
  • Partner with Human Resources leadership to set Leadership & Development direction and Talent Acquisition objectives.
  • Participate in relevant industry groups and events as a representative for Ascot Group.
  • Model The Ascot Way by fostering an inclusive, collaborative, entrepreneurial, and accountable culture grounded in excellence, integrity, resilience, and continuous improvement.

About the company

Ascot Group is a global specialty insurer and reinsurer that provides property and casualty coverage through its Lloyd’s and Bermuda platforms. It underwrites risk for clients and partners and serves small and mid-sized U.S. businesses, plus it offers underwriting services to other insurers and syndicates. The company differentiates itself with a global reach via Lloyd’s and Bermuda, a dedicated SME focus in the U.S., and its partnership-based underwriting services. Its goal is to provide a broad range of durable property and casualty solutions with strong underwriting discipline and reliable claims service for clients and partner markets.

Company Size

1,001-5,000

Company Stage

Debt Financing

Total Funding

$350M

Headquarters

Hamilton, Bermuda

Founded

2001

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Simplify's Take

What believers are saying

  • Oct. 1, 2026, Mark Pepper, Elizabeth Johnson, and Christopher Flatt deepen leadership bench.
  • Sept. 10, 2026, Ascot consolidated seven U.S. segments into five product verticals.
  • July 2026, James Lee joined Leadline, supporting global capital raising and investor engagement.

What critics are saying

  • Sept. 25, 2026, Placer County Water Agency litigation keeps Ascot in expensive California insurance disputes.
  • Jan. 2026, Ascot Specialty Insurance fought a $2.2 million Kentucky coverage claim in court.
  • A failed consumer push or treaty expansion can erode capital and trigger rating pressure.

What makes Ascot unique

  • Sept. 29, 2026, Ascot split underwriting into Specialty Insurance/Reinsurance and Consumer Solutions.
  • Ascot’s Leadline Capital Partners, expanded July 23, 2026, monetizes third-party capital and ILS.
  • Ascot operates across London, Bermuda, and the U.S., with A ratings and $16 billion assets.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • Life Insurance
  • Disability Insurance
  • Health Savings Account/Flexible Spending Account
  • Paid Holidays
  • Unlimited Paid Time Off
  • Short-term Disability
  • Long-term Disability
  • 401(k) Retirement Plan

Growth & Insights and Company News

Headcount

6 month growth

19%

1 year growth

19%

2 year growth

19%
Yahoo Finance
Oct 22nd, 2026
AM Best rates new Ascot Guernsey unit A (Excellent), affirms ratings on Ascot's core subsidiaries

AM Best has assigned Ascot Insurance Guernsey Limited a Financial Strength Rating (FSR) of A (Excellent) and a Long-Term Issuer Credit Rating of "a+" (Excellent), with a stable outlook. The Guernsey company is a 100% reinsured subsidiary of Ascot Bermuda Limited. The rating agency also affirmed the A and "a+" ratings of Ascot Bermuda and members of Ascot Insurance US Group. It affirmed a "bbb+" (Good) rating on Ascot Group Limited's $400 million 2030 notes and $350 million 2035 notes. AM Best cited Ascot's very strong balance sheet, adequate operating performance, and support from its parent, Canada Pension Plan Investment Board. Ascot reported gross written premiums of $5.2 billion in 2025, and its five-year weighted average combined ratio was 97.7%.

Business Insurance
Sep 29th, 2026
Ascot reorganizes underwriting businesses, names division presidents.

Ascot reorganizes underwriting businesses, names division presidents. * by Gavin Souter Ascot Group on Tuesday announced a reorganization that will bring its global insurance and reinsurance underwriting operations into a newly created division and establish a separate consumer lines business. The specialty insurer and reinsurer named Elizabeth Johnson president of the new specialty insurance and reinsurance division and said former American International Group executive Christopher Flatt will join Ascot as president of its new consumer solutions division. Specialty insurance and reinsurance will encompass Ascot's global specialty, Bermuda specialty and third-party capital and alternative reinsurance business, and U.S. specialty businesses, Ascot said in a statement. Ms. Johnson, currently Ascot's group chief operating officer, will take up the new role Oct. 1. She joined Ascot in 2020 as chief underwriting officer, North America, and previously held senior roles at Nationwide and AIG. The consumer solutions division will offer coverage across consumer-focused classes, including "high-net-worth" personal lines, Ascot said. Mr. Flatt, who will join Ascot in early November, was most recently global chief underwriting officer at AIG. Ascot also named Mark Pepper president, global underwriting, effective Oct. 1, with responsibilities across the company's U.K., U.S. and Bermuda operations. Mr. Pepper, Ascot's group chief underwriting officer since 2009, will work with the company's segment CEOs on growth strategies, business development and coordination across the businesses, the statement said. Ms. Johnson, Mr. Flatt and Mr. Pepper will report to Ascot Group CEO and President Jonathan Zaffino. September 29, 2026

PR Newswire
Sep 29th, 2026
Ascot Group appoints Mark Pepper president of global underwriting, reshapes leadership structure

Ascot Group, a global specialty (re)insurance company, has announced three executive leadership appointments effective October 1st. Mark Pepper has been named President of Global Underwriting, taking on an expanded role after serving as Chief Underwriting Officer since 2009. Elizabeth Johnson will become President of Specialty Insurance and Reinsurance, overseeing a newly created division combining Ascot's global insurance and reinsurance operations. Johnson joined Ascot in 2020 and most recently served as Group Chief Operating Officer. Christopher Flatt will join as President of a new Consumer Solutions division, focusing on consumer lines including high-net-worth personal insurance. Flatt brings over 30 years of experience, most recently serving as Global Chief Underwriting Officer at AIG. The restructuring aims to advance Ascot's growth strategy whilst maintaining consistency across its 25-year established business. Ascot operates globally across the US, Bermuda, and London, with $16 billion in total assets.

Advertisement Shout
Aug 19th, 2026
Ascot names O'Flynn EVP, Casualty Facultative Hybrids/Automatics.

Ascot names O'Flynn EVP, Casualty Facultative Hybrids/Automatics. Global specialty re/insurance company Ascot Group has announced the appointment of Ann Marie G. O'Flynn as Executive Vice President, Casualty Facultative Hybrids/Automatics. O'Flynn is a highly accomplished reinsurance leader with over 25 years of experience in casualty and professional lines underwriting, business development, account management, and client engagement. The executive is joining Ascot from Everest Reinsurance Company, where she most recently served as Vice President, US Head of Casualty & Professional Programs/Hybrid Solutions. Before this, she was Vice President and New Business Development Manager at Berkley Re Solutions (a Berkley Company), and served as Director, Casualty Facultative Underwriter, at Markel Re. Her career also includes roles at Lexington Insurance Company, Swiss Re, and Gen Re. At Ascot, O'Flynn will be reporting to Rory Cline, President, Ascot Re U.S., and will play a key role in advancing the company's Casualty Facultative Hybrids/Automatics platform. The post Ascot names O'Flynn EVP, Casualty Facultative Hybrids/Automatics appeared first on ReinsuranceNe.ws. Spread the love

North Somerset Council
Aug 11th, 2026
Jigsaw workspace.

Jigsaw workspace. 11th August 2026 New state-of-the-art office hub launches beside major rail link, M5, airport and Somerset coast near Weston-super-Mare A newly refurbished, high-spec office hub just seconds from a London-bound mainline railway station, motorway and close to Somerset's countryside has launched near Weston-super-Mare. The Ascot Group, a UK-leading firm, has unveiled Jigsaw, at 502 Park Way in Worle. The development sits just a 30-second walk from Worle railway station, which provides direct services to Bristol, London and beyond. The location also provides strong road and air links, around two minutes from the M5 and approximately 15 minutes from Bristol Airport. Six private offices, accommodating between four and 28 desks, are available across three floors following full refurbishment. Each has been designed to offer modern, flexible workspace for growing businesses. Surrounded by a thriving local community of cafés, pubs and shops, the hub also benefits from being near to Somerset's stunning countryside and coastline. Andrew Scott, CEO of Ascot Group, said: "This has to be one of the best state-ofthe- art office spaces around - the location is simply off the scale, with outstanding transport links and the Somerset countryside and beaches all around. "Jigsaw offers six private offices ready to move into. Businesses get their own dedicated space alongside shared facilities including a fully equipped kitchen, local EV parking and access to a bookable, modern podcast and video studio - ideal for creating professional content." Amenities at the site include: * Fully equipped kitchen and breakout area * Bookable meeting rooms * On-site bookable podcast and video studio * Free on-site parking * Super-fast broadband * Secure entry, CCTV and bike racks The launch reflects growing demand for high-quality office space in regional locations offering strong connectivity and lifestyle benefits outside major city centres. Businesses interested in viewing or renting space can contact [email protected], call 01934 906445 or visit the website for more information www.jigsaw.ws.