Head of Benefits Strategy

Sword Health

91d • $169,467 - $266,305

About The Position

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.

Requirements

• 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).

Responsibilities

• 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.
• 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.
• 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.
• 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.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Number of Employees: 1,001-5,000 employees