Top Remote Senior Level Sales Leadership Jobs in Boston, MA

The Senior Director will lead Affirm's retail sales organization, ensuring strategic partnerships, managing teams, and driving revenue through key merchant relationships.

Lead and grow a distributed team of Solutions Architects for the East enterprise territory. Coach and hire, engage as a hands-on architect on key deals, drive consistent technical evaluations, collaborate with Sales, Product, and Engineering, and track team KPIs to ensure adoption of GitLab Enterprise Edition.

Lead and scale a high-performing enterprise sales team to exceed targets through account-based execution, forecasting discipline, and coaching. Drive strategic cross-functional initiatives with Marketing, Product, RevOps, and Solutions Engineering to improve win rates, ACVs, and deal velocity. Act as a senior thought leader, manage performance, mentor AEs, and influence GTM strategy and product direction.

Lead and develop a national B2B sales organization: manage quota-carrying AEs, coach through complex deals, drive pipeline/forecasting discipline, enablement, cross-functional alignment, participate in customer meetings and negotiations, and scale sales processes and playbooks.

Lead and grow a Central-region mid-market sales organization targeting employers (50–9,999 lives). Manage Regional Directors and AEs, set and execute sales strategy, develop broker/partner relationships, hit revenue targets, collaborate cross-functionally, and ensure compliance. Coach and scale a high-performing team focused on measurable impact and adoption of AI-enabled tools.

Lead and coach a virtual network of independent, licensed Medicare insurance agents to drive revenue growth, monitor performance, ensure CMS compliance, collaborate with cross-functional teams, and improve sales processes and customer experience.

Lead and develop an enterprise sales team to acquire, grow, and retain health system customers. Build commercial strategy, coach sellers on account planning and negotiations, drive data-informed revenue growth, recruit and retain sales talent, and align cross-functional teams to scale repeatable processes and improve customer outcomes.

The Channel Leader drives Zerigo Health's channel strategy through partner relationships, facilitating sales, managing account health, and ensuring growth.

Lead and scale Strategic and Enterprise sales for large accounts: own GTM, pipeline, bookings, and deal execution; coach and recruit AEs/managers; enforce MEDDPICC and Mutual Action Plan rigor; partner with RevOps, CS, Marketing, and Product; represent segment to CRO and execs.

Serve as a trusted commercial advisor to design and negotiate customer-centric licensing and contracting solutions. Lead cross-functional sales teams to drive revenue, structure complex deals, manage risk and compliance, leverage AI and analytics to identify growth opportunities, and ensure adherence to policies and legal/regulatory requirements while coaching and enabling sellers.