Head of Commercial

WellTheory

12d•$500,000•Remote

About The Position

WellTheory is a digital health company helping people with autoimmune conditions take control of their health through personalized care, nutrition guidance, and ongoing coaching. We're a team of 60+ passionate people who care deeply about helping our members reduce symptoms, feel better, and live fuller lives — while helping employers and payors reduce their spend. We're looking for a Head of Commercial to lead and scale the commercial engine powering WellTheory’s next stage of growth. In this role, you’ll report to the CEO and own the full go-to-market strategy, building a unified sales organization that drives predictable revenue and deep, long-term relationships with our employer and health plan partners. You'll also thoughtfully build and lead an exceptional team as it scales to 20+ members over the next 12–18 months. This is both a strategic and hands-on leadership role: one that requires the ability to think at the portfolio level while still diving into deals, coaching a pitch, or refining messaging yourself. You'll be tasked with leading and developing a world-class sales team, joining sales calls as needed to help with day-to-day deal coaching. You’ll become an expert at pitching WellTheory and empowering a team that understands the art and science of the sale. You'll set the tone for how WellTheory builds trust, forges lasting partnerships, and delivers measurable impact across the healthcare ecosystem.

Requirements

Proven commercial leadership — with 12-18+ years of experience in sales roles with progressively increased scope.
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.
Experience moving from founder-led sales to a high-performing, repeatable engine.
Managed complex, multi-stakeholder sales cycles with employers, payers, and channel partners from initial engagement through contracting and launch.
Adept at navigating RFPs, procurement, and financial modeling.
Fluent in GTM design, revenue forecasting, and pipeline strategy.
Skilled in storytelling and relationship building.
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.
Experience educating the market.
Comfortable introducing new models of care, creating urgency where there isn’t yet awareness, and getting decision-makers to see problems — and possibilities — in a new light.
Energized by pioneering a category that doesn’t yet exist.
Led high-performing teams with empathy and accountability.
Experience hiring exceptional talent, fostering collaboration, and creating a culture of ownership and momentum.
Ability to elevate those around you by setting a high bar and bringing out their best.
Leads by example, inspiring excellence without ego.
Roll-up-your-sleeves mentality; excited to get into the weeds to figure things out.
Energized by building — not inheriting — the commercial infrastructure.
Comfortable iterating fast, refining based on feedback, and adjusting the playbook as the company scales.
Comfortable in boardroom setting strategy as well as in the trenches helping close a deal.
Strong verbal and written communicator; expert in storytelling.
Strong presentation skills.
Ability to craft effective written communication (i.e. emails, proposals, etc.).
Acts as an editor for the team, helping to weigh in on what sentence to cut from an email or slide title to revise in a deck.
Approaches sales as a partnership, not a transaction.
Asks thoughtful questions, uncovers unspoken needs, and guides clients toward new perspectives.
Challenges assumptions when it helps clients make smarter decisions.
Ability to effectively read a prospect on a call and adjust pitch as needed.
Specializes in meeting partners where they’re at and figuring out when to push and when not to.
Builds systems for clarity, uses data to inform decisions, and forecasts with accuracy.
Values precision and process as much as creativity and adaptability.
Spots risks early, asks for help when needed, and keeps forecasts rooted in reality.
Believes hope is not a strategy.
Sets the tone for accountability, ensuring that the path forward is always clear, measurable, and grounded in results.
Skilled at juggling multiple tasks with a strong intuition about keeping the main thing the main thing.
Empathy for the autoimmune experience.
Beginner’s mindset; love of learning and solving problems from the ground up.
Curious person who embraces the opportunity to explore the unfamiliar aspects of their role, ask questions, and seek understanding without fear of judgment.
Openly admits when mistakes are made and is open-minded when it comes to new approaches of problem-solving.
Unreasonably relentless; has been called a “force of nature” and has done something most people wouldn’t.
Persistence is key and does not give up easily.

Nice To Haves

You don’t need to have an autoimmune condition for this role but you need to have deep empathy for the lived experience of autoimmune patients and be able to effectively convey that to potential customers.
You’ve worked in environments where the solution didn’t fit neatly into an existing box.
You thrive on pioneering a category that doesn’t yet exist, and you’re as energized by shaping the narrative as you are by closing the deal.
You’ve led high-performing teams with empathy and accountability.
You know how to hire exceptional talent, foster collaboration, and create a culture of ownership and momentum.
You elevate those around you by setting a high bar and know how to bring out their best.
You lead by example, inspiring excellence without ego.
There’s no job that’s too small and you’re excited to get into the weeds to figure it out — even the most unsexy or complex.
You’re energized by building — not inheriting — the commercial infrastructure.
You’re comfortable iterating fast, refining based on feedback, and adjusting the playbook as the company scales.
You’re as comfortable in a boardroom setting strategy as you are in the trenches helping close a deal.
You consider yourself to be more of an expert in storytelling rather than “sales.”
You have strong presentation skills and love to be in front of an audience.
On top of that, you also know how to craft an effective written communication (i.e. emails, proposals, etc.).
You see your role as an “editor” for your team helping to weigh in on what sentence to cut from an email or slide title to revise in a deck.
You approach sales as a partnership, not a transaction — asking thoughtful questions, uncovering unspoken needs, and guiding clients toward new perspectives.
You aren’t afraid to challenge assumptions when it helps clients make smarter decisions.
You know how to effectively read a prospect on a call and adjust your pitch as needed.
You specialize in meeting partners where they’re at and figuring out when to push and when not to.
You build systems for clarity, use data to inform decisions, and forecast with accuracy.
You value precision and process as much as creativity and adaptability.
You spot risks early, ask for help when needed, and keep forecasts rooted in reality — not wishful thinking.
You believe hope is not a strategy, and that teams win when everyone operates with clarity, honesty, and alignment.
You set the tone for accountability, ensuring that the path forward is always clear, measurable, and grounded in results.
While you're skilled at juggling multiple tasks, you have a strong intuition about keeping the main thing the main thing.
You’ve done 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).

Responsibilities

Shape how WellTheory shows up in the market and guide how we tell our story — from brand to buyer journey to outcomes
Work directly with the CEO to build sales strategy and plans, and meet or exceed revenue targets for the company
Develop the sales team, hire exceptional talent, and build a high-performing, repeatable commercial engine
Build and refine the playbook as the team scales over the next 12–18 months
Close your first WellTheory deal as part of your onboarding process, including generating pipeline, crafting outreach, running calls, and closing contracts