A

Ascot

Global specialty insurer and reinsurer.

Director, HR Business Partner

Full-TimeUpdated on 10/23/2026
$160k - $175k/yr+ Annual cash bonus + Discretionary compensation
Expert
Bachelor's
Chicago, IL, USA+1 moreMore locations: Atlanta, GA, USA
HybridHybrid role requiring at least 3 days in the office; travel as needed.
People & HRHR Generalist & Employee Relations

About the job

Requirements
  • A minimum of 10 years of progressive human resources experience, including at least 5 years serving in an HR Business Partner role.
  • Prior property and casualty insurance industry experience is required.
  • Strong foundational HR expertise across talent acquisition, talent development, performance management, compensation, employee relations, and workforce planning.
  • Demonstrated ability to partner with senior leaders, align HR strategies to business objectives, and influence decision-making across all levels of the organization.
  • Interpersonal, communication, presentation, facilitation, and relationship management skills, with the ability to navigate sensitive matters with discretion and professionalism.
  • Strong judgment, problem-solving capability, and initiative, with the ability to manage complex, evolving situations and maintain confidentiality.
  • Analytical mindset with the ability to interpret HR data and workforce trends to inform decisions, identify opportunities, and improve business performance.
  • Demonstrated ability to manage multiple priorities independently, execute with strong attention to detail, and deliver high-quality work in a fast-paced environment.
  • Strong results orientation, sound execution skills, and a hands-on approach to supporting the business and delivering HR solutions.
  • Proficiency in Microsoft PowerPoint and Excel.
  • A bachelor's degree is required.
  • Ability to travel as needed.
Responsibilities
  • Partner with managers and business leaders to implement HR strategies that support business goals, organizational priorities, and operational objectives.
  • Serve as a strategic partner and trusted advisor by providing expert guidance on HR matters, including policy interpretation, employee relations, performance management, talent planning, and organizational effectiveness.
  • Provide day-to-day performance management support to leaders, including coaching, counseling, career development guidance, and disciplinary actions, while promoting a high-performance and accountable culture.
  • Partner with talent acquisition to ensure alignment throughout the process, including creating and validating job descriptions, evaluation, and the offer process.
  • Collaborate with business leaders to identify and address workforce needs, ensuring the right talent, structure, and capabilities are in place to meet current and future business demands.
  • Lead and support initiatives as part of the broader HR team and strategic plan to enhance employee engagement, retention, development, and overall employee experience.
  • Manage and resolve complex employee relations issues with sound judgment, ensuring compliance with company policies, employment laws, and regulatory requirements.
  • Analyze HR metrics, trends, and workforce insights to inform decision-making, identify opportunities for continuous improvement, and strengthen business and talent outcomes in partnership with the broader HR team.
  • Lead change management initiatives, emphasizing the integration of AI technologies and continuous process improvement to enhance organizational effectiveness.
  • Support the implementation and execution of HR programs, systems, practices, and policies to ensure consistency, effectiveness, and alignment with business objectives.
  • Mentor and develop HR team members, fostering a culture of collaboration, continuous learning, and professional growth across the function.
  • Model integrity, collaboration, inclusivity, and accountability in daily interactions and in support of colleague engagement and development.
Desired Qualifications
  • Experience supporting underwriting teams is strongly preferred.

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

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.