Enterprise Sales Director - Majors, Healthcare
ABOUT THE HEALTHCARE TEAM
- Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
- Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
- Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
WHAT YOU'LL DO
- Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
- Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.
- Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
- Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.
- Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
- Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
- Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
WHAT YOU'LL BRING
- 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.
- Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
- Proven ability to multi-thread and build trusted relationships across customer C-suites.
- Exceptional verbal and written communication.
- Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.
EVEN BETTER...
- Familiarity with the AI landscape, key players, and emerging trends.