Director of Enablement

At Sword, we’re building AI to heal billions and unlock humanity’s full potential. In doing so, we’re pioneering AI Care, a fundamentally new approach to healthcare built for medical reasoning, safety, and real-time treatment, not generic technology applied after the fact. As both a clinical-centric frontier AI lab and an applied AI platform, Sword is reimagining how care is delivered at scale, removing traditional barriers like appointments, waiting rooms, and stigma so more people can access the care they need—and ultimately get back to lives lived in full.

Since 2020, Sword has expanded across physical therapy, women’s health, cardiometabolic, and mental health, and is now moving beyond the session to a fully AI-native, 24/7 care program that brings physical activity, therapeutic exercise, psychotherapy, nutrition, and behavior change into one connected experience. More than 700,000 members across three continents have completed over 10 million AI sessions, helping 1,000+ enterprise clients avoid more than $1 billion in unnecessary healthcare costs. Backed by 42 clinical studies, 44+ patents, and more than $500 million raised from leading investors including Khosla Ventures, General Catalyst, and Founders Fund, Sword is defining a new standard for healthcare.

AI Proficiency at Sword

AI fluency is a core expectation at Sword. Every candidate is assessed against our three-level framework — be ready to share real examples of how AI is already part of how you work.

• Explorer (Level 1) — Uses AI daily to boost personal productivity
• Builder (Level 2) — Creates workflows and tools that elevate the whole team
• Integrator (Level 3) — Embeds AI into products and processes at scale

Every hire must demonstrate at least Level 1. The expected level will vary depending on the seniority of the role.

Role

Sword 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.

…