Head of Commercial

About the Role

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.
What You'll Do

• 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

You Might Be a Great Fit If You...

• Have proven commercial leadership - with 12-18+ years of experience in sales roles with progressively increased scope. You've led sales or commercial teams in digital health, value-based care, or benefits innovation, built and scaled revenue functions from early traction through growth, and know what it takes to move from founder-led sales to a high-performing, repeatable engine.
• Are a strategic operator - you've managed complex, multi-stakeholder sales cycles with employers, payers, and channel partners from initial engagement through contracting and launch, and are adept at navigating RFPs, procurement, and financial modeling. You're equally fluent in GTM design, revenue forecasting, and pipeline strategy as you are in storytelling and relationship building, connecting the dots across marketing, sales, partnerships, and retention to build alignment across stakeholders.

Here are some of the attributes that make a strong candidate for this opportunity:

• Experience building a category, not just selling in one. You've worked in environments where the solution didn't fit neatly into an existing box and you know how to educate the market, not just compete in it. You're 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. 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.
• Team builder and coach. 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.
• Roll-up-your-sleeves mentality. 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.
• Strong verbal and written communicator. 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.
• Consultative approach. 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.
• Data-driven & realist at heart. 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.

This role might not be a good fit for you if:

• You only want to focus on high-level strategy. We have aggressive sales goals and are looking for someone who's ready to hustle day in and day out. While you will be responsible for setting our sales strategy, you will be spending a good chunk of your time on the ground-generating pipeline, crafting emails to prospects, scheduling meetings, attending conferences, using sales tools, etc. We're looking for a player-coach, not just a coach.
• You expect to step into a mature, fully built sales engine. We're still in build-and-learn model-refining our product, pitch, and positioning based on real-time feedback from employers. There isn't yet a large sales ops team, polished enablement library, or steady inbound funnel. You'll be creating the playbook as much as executing it, helping us shape what "great" looks like as we grow.
• You're uncomfortable with ambiguity or taking initiative without a roadmap. We're building quickly, learning constantly, and evolving just as fast, which means there won't always be clear direction or precedent to follow. You'll need to be proactive, resourceful, and willing to make judgment calls rather than waiting for permission.
• You're not excited about working for a company that values documentation and process. As a fully remote team, written communication is how we stay aligned through memos, pre-reads, and detailed meeting notes. We don't rely on memory or hallway conversations. You'll be expected to keep your CRM up to date, document deal progress clearly, and share written context so others can plug in without needing a meeting. If that level of organization feels tedious rather than empowering, this probably isn't the right fit.
• You want to be the only sales leader. Our CEO will be partnering closely with you on our commercial efforts and heavily involved in the sales process so if you're wanting to go at it solo then this is probably not the right opportunity for you.

Bonus Points

Outside of the specific role, here are qualities that make someone successful at WellTheory:

• Empathy for the autoimmune experience. 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.
• Beginner's mindset. You have a love of learning and like to solve problems from the ground up. You're a curious person and embrace the opportunity to explore the unfamiliar aspects of your role, ask questions, and seek understanding without fear of judgment. You openly admit when you make mistakes and are open-minded when it comes to new approaches of problem-solving.
• Unreasonably relentless. You've been called a "force of nature" and have 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). Persistence is your middle name and you don't give up easily.

There are very few moments in life where you can change the world at scale and out of those few moments, there are even fewer moments where it is the right combination of passion, impact, and personal growth. We'd be thrilled to have you join us.

What We Offer

• A team that genuinely cares about each other and the members we serve
• A fully remote company that gathers every year for an annual retreat
• On Target Earnings: $500,000 with final amount depending on directly relevant skills and experiences you bring to the role.
• Additionally, you'll receive meaningful equity and benefits.

For your safety: Please remember that WellTheory will only contact you from a [redacted].com email address. Be cautious of emails from other domains. Our recruiting team will never ask for money, fees, or banking information as part of our hiring process. If you're ever unsure, don't click any links and apply directly to a posted role on our career site.