Head of Commercial
$500,000–$500,000 year
RemoteUnited States
Job Summary
Shape WellTheory's go-to-market strategy and lead the commercial engine to drive predictable revenue with employer and health plan partners. Build and scale a sales team from zero to 20+ members over 12–18 months, developing the playbook, refining messaging, and coaching pitches directly. Close your first deal by generating pipeline, crafting outreach, running calls, and executing contracts. Report to the CEO on revenue targets while navigating complex, multi-stakeholder sales cycles. This player-coach role requires hands-on execution in building the sales infrastructure, conducting RFPs, and documenting deal progress in a fully remote environment.
Required Qualifications
- 12-18+ years of experience in sales roles with progressively increased scope
- Proven commercial leadership
- Experience leading sales or commercial teams in digital health, value-based care, or benefits innovation
- Experience building and scaling revenue functions from early traction through growth
- Ability to move from founder-led sales to a high-performing, repeatable engine
- Experience managing complex, multi-stakeholder sales cycles with employers, payers, and channel partners from initial engagement through contracting and launch
- Adeptness at navigating RFPs, procurement, and financial modeling
- Fluency in GTM design, revenue forecasting, and pipeline strategy
- Ability to connect the dots across marketing, sales, partnerships, and retention to build alignment across stakeholders
- Experience building a category, not just selling in one
- Ability to educate the market rather than just compete in it
- Comfortability introducing new models of care
- Ability to create urgency where there isn't yet awareness
- Ability to get decision-makers to see problems and possibilities in a new light
- Thrive on pioneering a category that doesn't yet exist
- Ability to shape the narrative as well as close the deal
- Experience leading high-performing teams with empathy and accountability
- Ability to hire exceptional talent
- Ability to foster collaboration and create a culture of ownership and momentum
- Ability to set a high bar and bring out the best in others
- Comfortability getting into the weeds to figure out unsexy or complex tasks
- Comfortability building commercial infrastructure rather than inheriting it
- Ability to iterate fast, refine based on feedback, and adjust the playbook as the company scales
- Strong verbal and written communication skills
- Expertise in storytelling rather than traditional sales
- Strong presentation skills and ability to be in front of an audience
- Ability to craft effective written communication (emails, proposals, etc.)
- Ability to act as an editor for the team to weigh in on emails, slide titles, and decks
- Consultative approach to sales as a partnership rather than a transaction
- Ability to ask thoughtful questions and uncover unspoken needs
- Ability to guide clients toward new perspectives
- Ability to challenge assumptions when it helps clients make smarter decisions
- Ability to effectively read a prospect on a call and adjust the pitch as needed
- Ability to meet partners where they are and figure out when to push and when not to
- Ability to build systems for clarity
- Ability to use data to inform decisions and forecast with accuracy
- Valuing precision and process as much as creativity and adaptability
- Ability to spot risks early
- Ability to keep forecasts rooted in reality rather than wishful thinking
- Ability to ensure teams operate with clarity, honesty, and alignment
- Ability to keep the main thing the main thing while juggling multiple tasks
- Comfortability working for a company that values documentation and process
- Ability to keep CRM up to date
- Ability to document deal progress clearly
- Ability to share written context so others can plug in without needing a meeting
- Ability to work in a fully remote setting
- Ability to partner closely with the CEO on commercial efforts
- Ability to spend significant time on the ground generating pipeline, crafting emails, scheduling meetings, attending conferences, and using sales tools
- Comfortability in a build-and-learn model where refining product, pitch, and positioning based on real-time feedback is required
- Comfortability creating the playbook as much as executing it
- Comfortability with ambiguity and taking initiative without a roadmap
- Proactivity, resourcefulness, and willingness to make judgment calls rather than waiting for permission
- Deep empathy for the lived experience of autoimmune patients
- Ability to effectively convey empathy for the lived experience of autoimmune patients to potential customers
- A love of learning and ability to solve problems from the ground up
- Curiosity and ability to embrace the opportunity to explore unfamiliar aspects of the role
- Ability to ask questions and seek understanding without fear of judgment
- Openness to admit mistakes and be open-minded when it comes to new approaches of problem-solving
- Relentlessness and persistence
- Ability to do something most people wouldn't (e.g., ran a marathon, started a company, got a degree while working full-time, and/or overcame difficult adversities)
Desired Qualifications
- Experience in environments where the solution didn't fit neatly into an existing box
- Comfortability introducing new models of care
- Ability to create urgency where there isn't yet awareness
- Ability to get decision-makers to see problems and possibilities in a new light
- Thrive on pioneering a category that doesn't yet exist
- Ability to shape the narrative as well as close the deal
- Experience leading high-performing teams with empathy and accountability
- Ability to hire exceptional talent
- Ability to foster collaboration and create a culture of ownership and momentum
- Ability to set a high bar and bring out the best in others
- Comfortability getting into the weeds to figure out unsexy or complex tasks
- Comfortability building commercial infrastructure rather than inheriting it
- Ability to iterate fast, refine based on feedback, and adjust the playbook as the company scales
- Strong verbal and written communication skills
- Expertise in storytelling rather than traditional sales
- Strong presentation skills and ability to be in front of an audience
- Ability to craft effective written communication (emails, proposals, etc.)
- Ability to act as an editor for the team to weigh in on emails, slide titles, and decks
- Consultative approach to sales as a partnership rather than a transaction
- Ability to ask thoughtful questions and uncover unspoken needs
- Ability to guide clients toward new perspectives
- Ability to challenge assumptions when it helps clients make smarter decisions
- Ability to effectively read a prospect on a call and adjust the pitch as needed
- Ability to meet partners where they are and figure out when to push and when not to
- Ability to build systems for clarity
- Ability to use data to inform decisions and forecast with accuracy
- Valuing precision and process as much as creativity and adaptability
- Ability to spot risks early
- Ability to keep forecasts rooted in reality rather than wishful thinking
- Ability to ensure teams operate with clarity, honesty, and alignment
- Ability to keep the main thing the main thing while juggling multiple tasks
- Comfortability working for a company that values documentation and process
- Ability to keep CRM up to date
- Ability to document deal progress clearly
- Ability to share written context so others can plug in without needing a meeting
- Ability to work in a fully remote setting
- Ability to partner closely with the CEO on commercial efforts
- Ability to spend significant time on the ground generating pipeline, crafting emails, scheduling meetings, attending conferences, and using sales tools
- Comfortability in a build-and-learn model where refining product, pitch, and positioning based on real-time feedback is required
- Comfortability creating the playbook as much as executing it
- Comfortability with ambiguity and taking initiative without a roadmap
- Proactivity, resourcefulness, and willingness to make judgment calls rather than waiting for permission
- Deep empathy for the lived experience of autoimmune patients
- Ability to effectively convey empathy for the lived experience of autoimmune patients to potential customers
- A love of learning and ability to solve problems from the ground up
- Curiosity and ability to embrace the opportunity to explore unfamiliar aspects of the role
- Ability to ask questions and seek understanding without fear of judgment
- Openness to admit mistakes and be open-minded when it comes to new approaches of problem-solving
- Relentlessness and persistence
- Ability to do something most people wouldn't (e.g., ran a marathon, started a company, got a degree while working full-time, and/or overcame difficult adversities)
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