Director of Enablement

Sword

6h • $140,000 - $220,000

About The Position

Sword Health is seeking a Director of Enablement to build the content, training, and deal support that help sellers succeed across its multi-product commercial organization, selling in employer health and health plan markets. The role combines field enablement with hands-on support for high-value deals, including practice sessions, objection handling, and coaching. The ideal candidate has carried a sales quota, understands what representatives need in customer conversations, and creates enablement that reflects how deals are actually conducted.

The Director will partner with sales representatives on deal preparation; develop practical sales content across a multi-product portfolio; own recurring commercial training; design quarterly skills training with product and clinical leaders; map the sales journey by gathering input from representatives and observing deals; and maintain a governed content library so sellers can readily find current materials.

AI fluency is a core expectation at Sword. Candidates are assessed using the company’s three-level framework and must demonstrate at least Level 1, which is using AI daily to improve personal productivity. The expected level varies by role seniority.

The stated total compensation range is $140,000–$220,000 USD, reflecting base salary, variable compensation, and equity. Actual compensation depends on factors including skills, qualifications, experience, location, and market demand. Sword notes that additional benefits are offered and that country-specific benefits may vary and will be detailed separately.

Requirements

• At least 7 years in B2B sales, sales enablement, or revenue-facing roles.
• Direct experience carrying a quota or supporting quota-carrying teams in US health benefits, employer wellness, or digital health.
• A track record of building field-grade sales content that representatives voluntarily use, rather than marketing collateral.
• Experience designing and delivering live training to commercial teams.
• Fluency in US employer health benefits sales, including buyer personas, procurement cycles, the competitive landscape, and how large employers and health plans evaluate vendors.
• Demonstrate at least Level 1 AI proficiency under Sword’s framework: use AI daily to improve personal productivity.

Nice To Haves

• Comfort with sales intelligence tools such as Gong or equivalent and content management platforms.
• Experience with multi-product portfolio enablement.
• Interest in just-in-time enablement.

Responsibilities

• Partner with representatives on high-value deal preparation, including practice sessions, objection-handling workshops, multi-threading and outreach strategy, account-specific narratives, and presentation preparation.
• Build field-grade sales content across the product portfolio, including talk tracks, objection-handling playbooks, discovery frameworks, conversation starters, competitive battlecards, and curated call recordings.
• Own the commercial training cadence, including bi-weekly enablement sessions and recurring calls on product positioning, win/loss insights, and competitive intelligence; set agendas and facilitate sessions.
• Design and deliver quarterly skill-based training aligned to the selling cycle, including negotiation, discovery, and executive presence, in partnership with product and clinical leaders.
• Map the sales journey across commercial teams by interviewing representatives, observing deals, and documenting seller challenges and missing resources.
• Own content governance by auditing, organizing, and retiring outdated materials and creating a system that helps representatives find the right content.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed