10+ years of experience in healthcare or health tech sales, with a demonstrated track record of closing complex, enterprise deals with F500 employers and navigating the HR / benefits ecosystem (including health plans and / or broker / consultants).
Proven history of exceeding quota in enterprise sales roles, consistently performing in the top tier, with ownership of large, multi-threaded deals and long sales cycles (8–16+ weeks).
Deep experience selling into and influencing executive stakeholders (CHRO, Head of Benefits, CFO), with the ability to build business cases and drive alignment across complex buying committees.
Strong cross-functional leadership skills, with experience partnering across teams (e.g., product, marketing, partnerships) to remove blockers and drive outcomes in ambiguous, fast-changing environments.
Exceptional communication and executive presence, with the ability to distill complex ideas into clear, compelling narratives for both external partners and internal senior leadership.
Must be based on the West Coast to support travel requirements.

Experience operating in a high-growth, early-to-mid stage company, with a track record of building or scaling GTM motions in ambiguous environments.
Experience partnering with or selling alongside health plans, including navigating payer dynamics and joint enterprise sales motions.
Background in marketplace or two-sided platform businesses, with an understanding of supply / demand dynamics and activation challenges.
Strong operational rigor with CRM and forecasting tools (e.g., Salesforce), including building pipeline models, tracking conversion metrics, and informing strategic decisions.
Experience mentoring or informally leading others, contributing to team development and raising the performance bar.

100% remote work environment: Working hours to support a healthy work-life balance, ensuring you can meet both professional and personal commitments (must be based in United States, currently not hiring in Hawaii)
Attractive pay and benefits: Full transparency of pay ranges regardless of where you live in the United States
Comprehensive health benefits: Medical, dental, vision, life, disability, and FSA/HSA
401(k) plan access: Start saving for your future
Generous time-off policies: Including 2 company-wide shutdown weeks each year for self-care (for most employees)
Paid parental leave: Available for all parents, including birthing, non-birthing, adopting, and fostering
Employee Assistance Program (EAP): Support for your mental and physical health
New hire home office stipend: Set up your workspace for success
Quarterly department stipend: Fun team-building activities or in-person gatherings
Wellness events and lunch & learns: Explore a variety of engaging topics
Community and employee resource groups: Participate in groups that celebrate employee identity and lived experiences, fostering a sense of community and belonging for all

Rula is hiring a Director of B2B Sales (Remote)