Head of Benefits Strategy
Sword Health
Accounting & Finance
United States
USD 229,565-360,745 / year + Equity
Posted on Oct 17, 2025
Sword Health is shifting healthcare from human-first to AI-first through its AI Care platform, making world-class healthcare available anytime, anywhere, while significantly reducing costs for payers, self-insured employers, national health systems, and other healthcare organizations. Sword began by reinventing pain care with AI at its core, and has since expanded into women’s health, movement health, and more recently mental health. Since 2020, more than 700,000 members across three continents have completed 10 million AI sessions, helping Sword's 1,000+ enterprise clients avoid over $1 billion in unnecessary healthcare costs. Backed by 42 clinical studies and over 44 patents, Sword Health has raised more than $500 million from leading investors, including Khosla Ventures, General Catalyst, Transformation Capital, and Founders Fund. Learn more at www.swordhealth.com.
The Head of Benefits Strategy role is designed for experienced former employee benefits leaders who join Sword to help power our commercial engine. This role is embedded within the sales organization, serving as both a market-facing thought leader and an internal strategic partner to our Account Executives. The position combines sales strategy, prospect engagement, and industry advocacy to accelerate Sword’s impact in the enterprise benefits space.
In this role, you’ll help build Sword’s platform within the broader HR and benefits ecosystem, elevating the company as a category leader in digital MSK and holistic employee health. You’ll also participate in shaping product development by providing market insights and strategic feedback that ensure Sword’s offerings align with the evolving needs of enterprise buyers.
What you’ll be doing:
- Commercial Support & Sales Enablement
- Partner closely with Account Executives (AEs) to create opportunities, leveraging industry knowledge and personal networks to open doors with benefits leaders.
- Align to a hybrid model of named accounts and territory, with deep integration into AE workflows.
- Provide strategic guidance in top pursuits, particularly within Sword’s Top 100 accounts and competitive Hinge Health steals.
- Client & Prospect Engagement
- Represent Sword in prospect conversations, both in formal client meetings and breakout discussions with key decision-makers.
- Act as a trusted advisor to buyers, drawing on first-hand experience as a benefits leader to validate Sword’s value proposition.
- Consult with clients on implementation and utilization strategies to drive adoption and maximize program impact.
- Support enterprise deals by offering peer-to-peer credibility that complements the sales team’s expertise.
- Market Thought Leadership
- Actively participate in the broader benefits ecosystem through conferences, speaking engagements, and panels.
- Position Sword as an innovator in digital MSK and employee health benefits by sharing perspectives shaped by lived benefits leadership experience.
- Provide leadership in building, managing, and strategically leveraging an advisory council to open doors and amplify Sword’s market presence.
- Sales Strategy & Internal Impact
- Collaborate with sales leadership to shape go-to-market strategies and deal positioning.
- Provide critical input on messaging, objection handling, and competitive differentiation from the perspective of a former buyer.
- Manage and strategically leverage a team of fractional advisors organized by client segment to expand reach within the Consultant and Broker community and influence Payers.
- Serve as an integral member of the selling team, especially in enterprise pursuits.
What you need to have:
- Former Head of Benefits, VP of Total Rewards, or similar benefits leadership role.
- Extensive network of benefits decision-makers and influencers across Fortune 500/enterprise organizations.
- Proven ability to communicate with executive buyers and shape large-scale benefits strategies.
- Background in holistic benefits and wellness strategy, with experience in implementation, risk, and compliance strongly preferred.
- Former consulting and client-facing experience is a plus.
- Comfortable operating in both external-facing roles (speaking circuit, client engagements) and internal strategic roles (sales strategy, account planning).
Performance & Incentives:
- While traditional quota may not apply, success in this role is measured by influence on closed-won deals—with particular weight on:
- Top 100 strategic accounts
- Competitive displacements
- High-impact enterprise opportunities
- Example Metrics:
- Executive meetings influenced or attended (e.g., quarterly target of X+).
- Opportunities created or sourced via network.
- Percentage of Top 100 accounts engaged in a cycle with their direct involvement.
- Speaking engagements or thought leadership events per quarter.
- Closed-won revenue influenced, with higher weighting for enterprise and competitive wins.
US - Sword Benefits & Perks:
• Comprehensive health, dental and vision insurance*
• Life and AD&D Insurance*
• Financial advisory services*
• Supplemental Insurance Benefits (Accident, Hospital and Critical Illness)*
• Health Savings Account*
• Equity shares*
• Discretionary PTO plan*
• Parental leave*
• 401(k)
• Flexible working hours
• Remote-first company
• Paid company holidays
• Free digital therapist for you and your family
*Eligibility: Full-time employees regularly working 25+ hours per week
Note: Applicants must have a legal right to work in the United States, and immigration or work visa sponsorship will not be provided.
SWORD Health, which includes SWORD Health, Inc. and Sword Health Professionals (consisting of Sword Health Care Providers, P.A., SWORD Health Care Providers of NJ, P.C., SWORD Health Care Physical Therapy Providers of CA, P.C.*) complies with applicable Federal and State civil rights laws and does not discriminate on the basis of Age, Ancestry, Color, Citizenship, Gender, Gender expression, Gender identity, Gender information, Marital status, Medical condition, National origin, Physical or mental disability, Pregnancy, Race, Religion, Caste, Sexual orientation, and Veteran status.
229565 - 360745 USD a year
*This range includes base, variable and equity
These compensation bands are just the starting point. Once someone joins and proves they’re outlier talent, we adjust quickly to ensure their compensation aligns with their impact.
Our job titles may span more than one career level. Actual pay is determined by skills, qualifications, experience, location, market demand, and other factors. Compensation details listed in this posting reflect the base salary and any potential variable, bonus or sales incentives, and the Company’s estimation of the value of private company stock options, if applicable. The pay range is subject to change, future value of company stock options is not guaranteed, and compensation may be modified in the future. In addition to our total compensation, Sword offers a number of benefits as listed below.