Director of B2B Sales - West Coast (Remote)

About the role

We’re hiring a Director of B2B Sales to own and evolve our enterprise employer growth strategy, leading complex, multi-stakeholder deals with enterprise organizations. This is a high-impact individual contributor role driving full-cycle enterprise sales while shaping how Rula wins in this segment, refining positioning, influencing cross-functional partners, and building repeatable systems that accelerate growth.

Responsibilities

• Own and evolve our enterprise employer growth strategy
• Lead complex, multi-stakeholder deals with enterprise organizations
• Refine positioning and influence cross-functional partners
• Build repeatable systems that accelerate growth
• Owning pipeline and outcomes
• Navigate health plan and employer dynamics
• Partner across teams to remove blockers and scale what works into durable, company-level impact
• Close high-impact enterprise partnerships and influence go-to-market motions

Requirements

• 10+ years of enterprise sales experience within the medical, wellness, benefits or insurance sectors, with a proven track record of closing complex deals with Fortune 500 employers
• Extensive experience navigating the HR and corporate benefits ecosystem, including established relationships with major insurance carriers, brokers, and 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

Qualifications

• Proven ability to close high-impact enterprise partnerships and influence go-to-market motions
• 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

Preferred Qualifications

• 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

Benefits

• 100% remote work environment
• Attractive pay and benefits
• Comprehensive health benefits
• 401(k) plan access
• Gross time-off policies
• Paid parental leave
• Employee Assistance Program (EAP)
• Quarterly department stipend
• Fun team-building activities or in-person gatherings
• Community and employee resource groups
• Home office stipend
• Year-round wellness initiatives
• Wellness stipend