Vice President - Actuary, Head of Reserving
Ascot Group
Listing collected from Ascot Group's career site. NextChapter is independent of Ascot Group.
CHICAGO, IL · Posted November 6, 2026
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Where CHICAGO, IL ranks
Where CHICAGO, IL placed in our monthly rankings, month by month. Each month stays online at its own address.
November 2026
- #1Best cities for government pay after cost of living$146k · of 18
- #1Cities with the most jobs that do not need a four-year degree in the Midwest684 jobs · of 51
- #1Cities with the most jobs that do not need a four-year degree in the Great Lakes684 jobs · of 36
- #1Best cities for software and engineering jobs in the Midwest1,140 openings · of 59
- #1Best cities for software and engineering jobs in the Great Lakes1,140 openings · of 48
- #1Best all-round cities for mid-career professionals in the Midwest80 / 100 · of 20
Rankings about finance jobs
- Best cities for finance jobs #1 New York (1,932 openings)
- Best cities for finance pay after cost of living #1 San Mateo ($162k)
- Most requested AI skills in finance jobs #1 AI tools in daily work (4.3%)
- AI tools named most often in finance jobs #1 Claude (0.55%)
- Employers with the most finance jobs #1 Amazon (475 roles)
How AI is used in this kind of work
AI use among actuaries is little observed so far. Measured exposure for actuaries: 5% (little observed).
Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.
About the job
This is an opportunity to join Ascot Group - one of the world’s preeminent specialty risk underwriting organizations.
Designed as a modern-era company operating through an ecosystem of interconnected global operating platforms, we’re bound by a common mission and purpose: One Ascot. Our greatest strength is a talented team who flourish in a collaborative, inclusive, and entrepreneurial culture, steeped in underwriting excellence, integrity, and a passion to find a better way, The Ascot Way.
The Ascot Way guides our people and our organization. Our underwriting platforms collaborate to find creative ways to deploy our capital in a true cross-product and cross-platform approach. These platforms work as one, deploying our capital creatively through our unique Fusion Model: Client Centric, Risk Centric, Technology Centric.
Built to be resilient, Ascot maximizes client financial security while delivering bespoke products and world class service — both pre- and post-claims. Ascot exists to solve for our clients’ brightest tomorrow, through agility, collaboration, resilience, and discipline.
Ascot is embedding artificial intelligence (AI) and automation across the organization to enhance decision making, efficiency, and quality of outcomes. In this role, you will be expected to work confidently alongside AI-enabled tools, apply sound judgment when interpreting insights, and adapt as technology continues to evolve. We value curiosity, critical thinking, and a willingness to embrace change as part of how we work.
Responsibilities :
Lead and oversee the execution of the quarterly reserving process including initial reconciliations, ACE selections, peer review, management reporting, controls and documentation
Present ACE recommendations to the quarterly US Reserve Committee in a way that goes beyond the numbers, effectively communicating the underlying story and findings
Oversee the selection of actuarial assumptions including initial expected loss ratios, loss development curves, default method weights, and other key inputs
Support legal entity and corporate reporting requirements.
Oversee performance of regularly scheduled and ad-hoc deep dive analyses on LOBs and reserving areas of focus
Continually enhance processes, data flows, and help improve reserving analytics.
Lead the US Reserving team, ensuring the company recruits, retains and develops staff to enable a high-performance reserving function
Provide recommendations of management’s best estimate of reserves based on key uncertainties and risks
Effectively maintain, and create or improve where necessary, best practice reserving practices and policies
Enhance data and capabilities to improve reserving analytics and diagnostics
Peer review segment calculation of pricing loss ratios and pricing model assumptions
Partner with UK and Bermuda reserving leads to enhance group reserving capabilities and consistency
Commitment to The Ascot Way: As a senior member of the actuarial team, the Vice President - Actuary, Head of Reserving will embody The Ascot Way in their daily interaction with colleagues, fostering colleague engagement and development, collaboration, inclusivity, and individual accountability
Requirements:
Proven math and analytical skills, as normally acquired through the pursuit of a Bachelor's degree in Mathematics, Statistics, Economics, Actuarial Science, or related field
A minimum 15 years of relevant actuarial experience, including at least 5 years of reserving experience in a leadership role
Proven managerial experience, and demonstrated ability to train and develop junior level people managers on team to be effective managers and coaches
Proven track record of hiring, developing, and retaining high performing teams
FCAS designation for at least 7 years
Prior extensive experience and knowledge of advanced actuarial techniques and standards and insurance operations
Excellent verbal and written communication skills, with the executive presence and confidence to present findings effectively to stakeholders
Ability to exercise discretion and apply independent judgment and critical thinking skills in execution of assignments
Ability to balance multiple projects with minimal direction
Experience using Arius reserving software preferred
High attention to detail and a strong ability and desire to collaborate across the organization
Compensation
For Actual base pay could vary and may be above or below the listed range based on factors including but not limited to experience, subject matter expertise, and skills. The base pay is just one component of Ascot’s total compensation package for employees. Other rewards may include an annual cash bonus, and other forms of discretionary compensation awarded by the Company.
Salary Range: $250,000 - $280,000
Company Benefits
The Company provides a competitive benefits package that includes the following (eligibility requirements apply):
Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health Savings Account, Commuter Account, Health Care and Dependent Care Flexible Spending Accounts, Life Insurance, AD&D, Work/Life Resources (including Employee Assistance Program), and more
Leave Benefits: Paid holidays, annual Paid Time Off (includes paid state /local paid leave where required), Short-term Disability, Long-term Disability, Other leaves (e.g., Bereavement, FMLA, Adoption, Maternity, Military, Primary & Non-Primary Caregiver)
Retirement Benefits: Contributory Savings Plan (401k)
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