Sales Director (100% Remote)

We asked ourselves — What if better care didn't cost more?

That's why we built Vitable: a YC-backed, Series A healthtech platform making healthcare better for employers of everyday workers. We bring accessible, high-quality care to over 85 million uninsured and underinsured Americans. Unlike traditional options, our suite of health benefits is designed with real people at the center.

Vitable empowers businesses to become better employers by making it easy to offer healthcare benefits to their teams. It's a better experience for employees and a smarter solution for employers. Simply put, we're built for better.

Vitable is seeking a disciplined, high-performance Sales Director to lead our Core Account Executive team (~20 AEs). This is a hands-on revenue leadership role — you'll own team performance across pipeline coverage, forecast accuracy, and quarterly revenue targets while building the systems and culture required to scale a high-growth B2B sales org from Series A onward.

• →Drive aggressive revenue growth and own quarterly targets for a team of ~20 quota-carrying AEs
• →Build scalable sales systems and processes in HubSpot to support a growing revenue organization
• →Maintain 2–3x pipeline coverage and strong forecast accuracy
• →Coach AEs across discovery, deal strategy, and closing at every stage
• →Develop top performers and build the next generation of sales leaders

• Buyer: SMB and mid-market employers offering healthcare benefits to hourly and frontline workers
• Motion: Full-cycle new business (pipeline → close)
• Cycle: ~30–90 days
• Team: ~20 Account Executives supported by SDRs and RevOps

• 90 days: Deep knowledge of Vitable's buyers, motion, and playbook; AE strengths assessed; forecast cadence established
• 6 months: Pipeline coverage and forecasting are predictable; coaching improves deal execution and win rates
• 12 months: AE team consistently meets or exceeds revenue targets; sales execution is disciplined and repeatable

• 7–10+ years of B2B sales experience, including 3+ years leading full-cycle Account Executives
• Proven track record managing 10+ quota-carrying AEs in a high-growth environment
• Strong forecasting, pipeline management, and CRM discipline (HubSpot preferred)
• Experience scaling a B2B sales org from Series A to Series B strongly preferred
• Startup experience required — comfortable building, not just managing