Senior Manager, Enterprise Sales

For our client, we are seeking a Senior Manager, Enterprise Sales to join the team of a leader in the Healthcare space. This role will own enterprise new-business bookings for an assigned territory, with a strong focus on building pipeline, developing territory strategy, and advancing complex sales cycles. The position will work closely with employers, non-profits, and government agencies to understand their needs and deliver tailored solutions that support meaningful outcomes. Success will require a relationship-driven approach, strong cross-functional coordination, and the ability to create opportunities from scratch in a competitive B2B environment. Location: Remote - US based candidates only, no visa sponsorship available Compensation: $150,000+ annually Responsibilities Own and achieve individual new-business bookings quota for the assigned territory Develop and implement a territory strategy targeting priority accounts and market opportunities Build and maintain a robust sales pipeline through multiple channels Engage with diverse clients, including employers, non-profits, and government agencies Lead the sales process from initial engagement through contract signing Conduct discovery conversations to understand client needs and decision-making processes Deliver tailored presentations and proposals aligned with client needs Qualifications Bachelor's degree in Business, Marketing, Communications, or a related field, or equivalent experience 8+ years of B2B sales experience, particularly in SMB and Mid-Market segments Proven track record in Direct-to-Employer (D2E) sales and the HR and Benefits market Experience managing complex sales cycles with multiple stakeholders Strong prospecting and business development skills, with the ability to create opportunities from scratch Excellent project management and organizational skills, including CRM management Genuine curiosity about clients and a relationship-driven sales approach Benefits Remote work with regular in-person bonding experiences sponsored by the company Holistic perks program, including free therapy and employee wellness initiatives Excellent health, dental, and vision coverage 401k benefits with employer matching contributions Access to hardware or software that enhances productivity An opportunity to contribute to a mission that changes lives and is well-received by users A supportive and engaging community of co-workers Our client is an equal opportunity employer. We encourage you to apply even if you don’t meet every qualification—your background could be exactly what this team needs.