Head of Commercial Sales

At Talkspace, we are committed to fostering a diverse, equitable, inclusive, and belonging-centered workplace where everyone can thrive while making a difference in mental health. Want to help over two million people receive quality mental healthcare? Come join our mission of getting therapy in the hands of everyone! We are looking for a Head of Commercial Sales to join our team. The Head of Commercial Sales is responsible for building, executing, and iterating on a scalable go-to-market strategy for our new AI Business. This individual will be able to come in and quickly close flagship enterprise buyers that will serve as a foundational jumping off point for commercial strategy and sales playbook. This role requires a highly entrepreneurial and execution-oriented business development leader who is comfortable operating in ambiguity and building from 0 to 1. The ideal candidate combines strategic thinking with a hands-on approach, and can independently build pipeline, create sales materials, engage prospective partners, and close flagship enterprise opportunities. The role is heavily cross-functional, working across Product, Clinical, Marketing, and Executive Leadership to shape market positioning, refine buyer strategy, and scale new partnership channels. To work at Talkspace, you need to be as passionate as we are about our work, and excited to partner with us on delivering quality mental healthcare. What You’ll Do Business Development & GTM Strategy Champion immediate foundational wins: closing several high-value flagship enterprise buyers. Develop and execute a scalable go-to-market and partnership strategy for emerging AI-enabled behavioral health solutions. Identify, prioritize, and penetrate key market segments and partnership channels, including enterprise and strategic partnership opportunities. Build and own a targeted pipeline of prospective enterprise customers, strategic partners, brokers, consultants, and channel relationships. Drive prospect opportunities through the full sales lifecycle, from initial outreach and positioning through negotiation and close. Create and refine repeatable sales playbooks, messaging, outreach strategies, and commercialization frameworks for new product offerings. Develop compelling presentations, decks, proposals, and partnership materials tailored to executive and enterprise stakeholders. Represent Talkspace and its products in a professional and compelling manner aligned with company branding and messaging. Relationship Building Build relationships with enterprise buyers, consultants, benefits stakeholders, and emerging AI ecosystem partners. Identify and establish strategic partnerships that accelerate adoption, credibility, and market expansion. Maintain executive-level relationships with key clients and partners over time. Attend industry events, conferences, and networking opportunities relevant to behavioral health, AI, benefits, and workforce productivity. Internal Collaboration Partner closely with Product, Clinical, Marketing, Implementation, and Executive teams to align market feedback with product strategy and commercialization efforts. Collaborate with internal stakeholders to refine positioning around employee productivity, resilience, workforce wellbeing, and organizational impact. Support the transition of prospects into successful long-term partnerships and client relationships. Performs other related duties as assigned. About You 8 - 10+ years of experience in business development, strategic partnerships, enterprise sales, or go-to-market leadership within a high-growth, startup, SaaS, healthcare, AI, or benefits-related environment. Demonstrated experience building pipeline and commercial strategies for new or emerging products in ambiguous or greenfield environments. Strong executive presence, communication skills, and relationship-building abilities. Existing network or familiarity with enterprise buyers, broker channels, consultants, or strategic partnerships w…