Director of B2B Sales - West Coast (Remote)

Director Of B2B Sales

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.

This role requires a proven ability to close high-impact enterprise partnerships and influence go-to-market motions. You'll operate as both a revenue leader and strategic operator: owning pipeline and outcomes, navigating health plan and employer dynamics, and partnering across teams to remove blockers and scale what works into durable, company-level impact.

Required Qualifications

• 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. Must have 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 (816+ 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

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

We're serious about your well-being! As part of our team, full-time employees receive:

• 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): Supporting your mental and physical health

• Quarterly department stipend: Fun team-building activities or in-person gatherings

• Community and employee resource groups: Participate in groups that celebrate employee identity and lived experiences, fostering a sense of community and belonging for all

• Home office stipend: New hire home office stipend & $50 monthly stipend to help cover internet or cell phone expenses

• Wellness at Rula program: Year-round wellness initiatives and a $50/month wellness stipend

Our team

We believe that diversity, equity, and inclusion are fundamental to our mission of making mental healthcare work for everyone. We are dedicated to having a culture of inclusion that will support our employees in feeling safe, seen, heard, and valued.