Full-Time

Assistant Vice President, Head of Benefits

Posted on 9/10/2026

The Hartford

The Hartford

10,001+ employees

Insurance provider for individuals and businesses

Compensation Overview

$184k - $276k/yr

+ Bonus + Long-term incentives

Chicago, IL, USA + 1 more

More locations: Hartford, CT, USA

Hybrid

Hybrid work is available in Hartford or Chicago; up to 10% travel is required, with heavier first-year travel for candidates outside Hartford.

Bachelor's

Category
People & HR (1)
Required Skills
Data Visualization
Mergers & Acquisitions (M&A)
Data Analysis

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Requirements
  • 15+ years of progressive benefits leadership experience at a public company or large organization with 10,000 or more employees, including responsibility for health, welfare, and retirement programs.
  • Demonstrated success developing and executing enterprise-wide benefits strategies.
  • Proven ability to lead large-scale benefits transformations, technology implementations, and vendor management initiatives.
  • Track record of leading benefits programs within a large, complex organization; international benefits experience is a plus.
  • Demonstrated experience leading benefits due diligence, integration planning, and workforce transition activities in mergers, acquisitions, divestitures, or other corporate transactions.
  • Deep knowledge of employee benefits regulations, compliance requirements, and governance practices.
  • Proven success managing significant budgets and complex vendor relationships.
  • Demonstrated ability to leverage artificial intelligence, automation, analytics, and digital technologies within Human Resources or Benefits functions.
  • Background supporting a publicly traded organization or other large, complex employer and operating within a complex governance environment.
  • Track record of partnering with Human Resources technology, Information Technology, data, privacy, and vendors to evaluate and implement emerging technologies and artificial intelligence that improve employee support, decision-making, personalization, and operational efficiency.
  • Bachelor's degree or equivalent work experience.
  • Willingness to travel up to 10%.
Responsibilities
  • Develop and execute a forward-looking global benefits strategy aligned with business priorities, workforce needs, and Total Rewards objectives, anticipating emerging workforce trends and evolving employee expectations to create innovative and differentiated offerings.
  • Lead benefits-related due diligence, risk assessment, integration planning, and employee transition activities for mergers, acquisitions, divestitures, and other strategic transactions.
  • Lead a high-performing team, clarify priorities, align resources to the work, and cultivate accountability, innovation, inclusion, and continuous development.
  • Champion a consumer-grade employee experience through communications and training that makes benefits easy to understand, access, and use.
  • Leverage employee feedback, analytics, and market insights to continuously enhance program effectiveness and keep stakeholders well-informed.
  • Drive innovative benefits-delivery approaches, including artificial intelligence and emerging technologies, to strengthen employee experience, attraction, retention, and workforce performance.
  • Ensure compliance with all applicable federal, state, and local regulations.
  • Serve as a fiduciary leader overseeing plan governance, audits, filings, vendor compliance, and regulatory reporting.
  • Lead or support governance committees, prepare committee materials, and ensure benefit plans are administered according to plan documents and regulatory requirements.
  • Maintain strong controls and operational discipline while balancing innovation and employee experience objectives.
  • Manage multimillion-dollar benefits budgets and ensure effective stewardship of company and employee investments.
  • Develop long-term strategies to improve cost effectiveness while maintaining competitive and meaningful benefits offerings.
  • Lead vendor strategy, selection, negotiation, performance management, and governance processes.
  • Establish metrics and dashboards to measure program effectiveness, employee engagement, vendor performance, and financial outcomes.
  • Translate complex data into actionable recommendations for executive leadership and governance committees.
  • Monitor market trends and benchmark practices to maintain a competitive benefits portfolio.
Desired Qualifications
  • International benefits experience.
  • Heavier travel during the first year is expected for candidates not based in the Hartford home office.

The Hartford provides insurance protection for individuals and businesses and extends its role beyond policy terms to make a positive impact. It underwrites and issues risk coverage, including assessing risk, pricing premiums, and handling claims to help people recover from losses and manage uncertainty. The company differentiates itself by pursuing social impact and practical help that goes beyond a standard insurance contract—focusing on human achievement and community support as part of its mission. Its goal is to protect people and organizations and to improve lives through responsible risk management and community involvement, not just by selling insurance but by contributing to broader well-being.

Company Size

10,001+

Company Stage

IPO

Headquarters

Hartford, Connecticut

Founded

1810

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Simplify Jobs

Simplify's Take

What believers are saying

  • July 23, 2026 Q2 revenue hit $7.26 billion and EPS reached $3.42.
  • Management expanded Columbus technology hiring and deployed AWS customer-experience tools on Sept. 10, 2026.
  • UConn and Berkeley partnerships target heat losses and data-center risks, opening niche insurance demand.

What critics are saying

  • Beth Bombara added reserve strength in general liability and commercial auto on Sept. 10, 2026.
  • Goldman Sachs and BofA flag soft P&C pricing; capital supply now pressures growth.
  • Long-tail asbestos and social inflation can trigger a reserve hit that crushes 2027 earnings.

What makes The Hartford unique

  • AI-driven underwriting cuts small-business quotes without humans, per Beth Bombara on Sept. 10, 2026.
  • Employee Benefits ranks number one in fully insured disability and paid family leave.
  • Business Insurance delivered 8% growth with an 88.5% underlying margin in 2025.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

Paid Vacation

Paid Holidays

Hybrid Work Options

Remote Work Options

Tuition Reimbursement

Company News

Associated Press
Jul 15th, 2026
The Hartford appoints former AssuredPartners CEO Randy Larsen to board

The Hartford has appointed Randy Larsen to its board of directors, effective 1 September. He will serve on the Finance, Investment and Risk Management Committee and the Nominating and Corporate Governance Committee. Larsen spent 13 years with AssuredPartners, a large insurance brokerage firm, serving as chief executive officer from 2023 until Gallagher acquired the company in 2025. During his tenure, he oversaw significant business growth through organic initiatives and acquisitions whilst leading operational transformation efforts. Prior to AssuredPartners, Larsen spent 14 years with insurance brokerage Schifman Remley & Associates, which AssuredPartners acquired in 2012. He earned a bachelor's degree in finance from Nebraska Wesleyan University.

Yahoo Finance
May 16th, 2026
Hartford beats revenue estimates by 40% but shares drop 2.6% on disappointing earnings

Hartford reported Q1 revenues of $7.23 billion, up 6.1% year on year, exceeding analyst expectations by 40%. Despite the top-line beat, the multi-line insurance company missed analysts' book value per share and earnings per share estimates. The Hartford, recognisable by its stag logo dating to 1810, provides property and casualty insurance, group benefits and investment products across the United States. The company delivered the largest analyst estimate beat among multi-line insurance stocks tracked this quarter. However, investors appeared dissatisfied with the results. Hartford's stock has declined 2.6% since reporting and currently trades at $132.15. The multi-line insurance sector overall saw revenues beat consensus estimates by 8.6%, though share prices have declined an average of 2.8% following earnings.

Business Wire
Apr 14th, 2026
The Hartford and UConn partner on worker safety and energy innovation research

The Hartford and the University of Connecticut have launched a collaboration focused on business resiliency, worker safety and energy innovation. The partnership includes two key initiatives: The Hartford Laborer Safety Fund and The Hartford Sustainability Research Fellowship. The Hartford will invest in UConn's Korey Stringer Institute to research how extreme heat affects workers across industries, examining both short- and long-term impacts on health and productivity. The companies plan to pilot heat-management programmes with select business customers. The Hartford Sustainability Research Fellowship, established within UConn's College of Engineering, will examine evolving energy needs of data centres and emerging risks related to onsite generation, battery storage and renewable energy. The research aims to provide insights into future insurance and risk-management needs for emerging technologies.

Yahoo Finance
Mar 23rd, 2026
Hartford Insurance targets cluster around $150 amid underwriting strength and P&C cycle concerns

Hartford Insurance Group has drawn price targets from several research firms clustering around US$150, aligning with a model fair value estimate of US$150.85. Goldman Sachs, Keefe Bruyette, Wells Fargo, Cantor Fitzgerald, Citi, Morgan Stanley and UBS have raised targets to the US$150-160 range, citing confidence in Hartford's underwriting and pricing execution. However, concerns remain about softening property and casualty market conditions. Goldman Sachs and BofA flag increased capital supply and competition pressuring growth, whilst BofA notes loss costs may be rising faster than prices in some lines. Hartford recently joined Centro Benefits' digital quoting ecosystem, opened a technology hub in Columbus, Ohio, and repurchased 3 million shares for US$400 million between October and December 2025.

Yahoo Finance
Feb 1st, 2026
Hartford Insurance reports Q4 core earnings of $1.1B, plans to boost quarterly buybacks to $450M

The Hartford Insurance Group reported fourth-quarter core earnings of $1.1 billion ($4.06 per share) and a full-year core earnings return on equity of 19.4%. Business insurance written premium grew 8%, whilst personal insurance showed improved combined ratios and employee benefits maintained solid margins. Net investment income rose 17% to $832 million in the fourth quarter. The company repurchased approximately $400 million of stock and plans to increase quarterly buybacks to $450 million. It also boosted catastrophe protection coverage to $1.9 billion and expects roughly $2.9 billion in net dividends from operating companies in 2026. Management is pursuing an "AI-first" strategy across claims, underwriting and operations. The company is rolling out its Prevail platform across agency and direct channels, with 10 states currently live and approximately 30 launches planned by early 2027.