RoleSword Health is a multi-product commercial organization selling AI Care across the employer and health plan markets. The Director of Commercial Operations owns the engine behind that growth: planning, systems, deal governance, enablement, clinical pre-sales support and commercial analytics. You lead four teams (Revenue Operations, Field Enablement, Clinical Specialists and Business Analysts) and act as a strategic partner to the CRO and the commercial leaders. The right person has scaled a commercial org through hypergrowth, is equally at ease in a pipeline review and a board deck, and builds operating systems that make sellers faster.
What you'll be doing- Lead and develop the Commercial Operations org (Revenue Operations, Field Enablement, Clinical Specialists, Business Analysts): set direction, hire and develop leaders, and hold each team accountable for its impact on revenue
- Set the commercial operating rhythm and be accountable for its outcomes: annual and quarterly planning, capacity and quota strategy, and business reviews with the CRO and executive team
- Be the single source of truth on commercial performance: pipeline health, conversion, win/loss, deal economics and rep productivity. Turn the data into decisions, not dashboards
- Set deal governance policy: pricing guardrails, approval authority and contracting standards across employer, health plan and channel deals, carried out through the RevOps and Deal Desk teams
- Make sure Enablement and Clinical Specialists are deployed where they move revenue, so sellers walk into every meeting with the right narrative, proof and clinical credibility
- Drive the GTM systems roadmap (Salesforce, CPQ/CLM, Gong and the data stack) and bring in AI and automation to remove manual work from the commercial process
- Partner with Finance, Legal, Product, Marketing and Account Management on pricing, packaging, new product launches and cross-sell motions
What you need to have- 10+ years in Revenue/Commercial Operations, Strategy & Ops or consulting, with 5+ years leading multi-function teams (RevOps plus at least one of Enablement, Sales Strategy or Analytics)
- Track record of scaling a B2B commercial org through hypergrowth, ideally in US digital health, health benefits or enterprise SaaS
- Hands-on ownership of planning, forecasting, quota and compensation design at the company level
- Fluency in long, complex enterprise sales cycles with multiple buyers (employers, health plans, consultants, channel partners)
- Executive presence: you can push back on a CRO, present to the board, and coach a first-time manager in the same week
Nice to have- Experience with multi-product or platform pricing and packaging
- Experience bringing AI tooling into GTM workflows (forecasting, deal review, rep coaching)
*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
$203,000-$319,000 USD
Country-specific benefits may vary and will be detailed separately.
