RoleSword Health is a multi-product commercial organization selling across employer health and health plan markets. The Field Enablement Lead builds the content, training, and deal support that keep sellers effective across a growing portfolio, including hands-on deal preparation: dry runs, objection handling sessions, and rep coaching on high-value opportunities. The right person has carried a bag, knows what a rep needs in the room, and builds enablement that reflects how deals actually happen.
What you'll be doing- Partner with reps on high-value deal preparation: run practice sessions, lead objection handling workshops, coach multi-threading and outreach strategy, help build account-specific narratives and presentation prep
- Build field-grade sales content across a multi-product portfolio: talk tracks, objection handling playbooks, discovery frameworks, conversation starters, competitive battlecards, curated call recordings
- Own the commercial training cadence: bi-weekly enablement sessions and recurring calls covering product positioning, win/loss insights, and competitive intelligence. You set the agenda and run the room
- Design and deliver quarterly skill-based training aligned to the selling cycle (negotiation, discovery, executive presence) in partnership with product and clinical leaders
- Map the sales journey across commercial teams: interview reps, ride along on deals, document where sellers get stuck and what's missing
- Own content governance: audit, organize, retire stale materials, build a system where reps find the right content without digging
What you need to have- 7+ years in B2B sales, sales enablement, or revenue-facing roles with direct experience carrying a quota or supporting quota-carrying teams in US health benefits, employer wellness, or digital health
- Track record building field-grade sales content (not marketing collateral) that reps voluntarily reach for
- Experience designing and delivering live training to commercial teams
- Fluency in US employer health benefits sales: buyer personas, procurement cycles, competitive landscape, and how large employers and health plans evaluate vendors
Nice to have:
- Comfort with sales intelligence tools (Gong or equivalent) and content management platforms
- Multi-product portfolio enablement, interest in just in time enablement
*The range below reflects base, variable, and equity for this role.
This is a starting point, not a ceiling - once someone joins and proves they're outlier talent, we adjust quickly to make sure their compensation matches their impact.
Job titles may span more than one career level, so actual pay depends on skills, qualifications, experience, location, and market demand, among other factors. The range reflects base salary plus any variable, bonus, or sales incentives, and our estimate of the value of private company stock options where applicable. It's subject to change, and future stock value isn't guaranteed. Sword also offers additional benefits beyond total compensation.
Total Compensation Range
$140,000-$220,000 USD
Country-specific benefits may vary and will be detailed separately.
