Head of Benefits Strategy

The Head of Benefits Strategy role is designed for experienced former employee benefits leaders who join Sword to help power the 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, help build Sword’s platform within the broader HR and benefits ecosystem, elevating the company as a category leader. Participate in shaping product development by providing market insights and strategic feedback. Partner closely with Account Executives to create opportunities. Provide strategic guidance in top pursuits. Represent Sword in prospect conversations. Act as a trusted advisor to buyers. Support enterprise deals by offering peer-to-peer credibility. Actively participate in the broader benefits ecosystem through conferences. Provide critical input on messaging. Serve as an integral member of the selling team, especially in enterprise pursuits.