VP, Employer Sales

About Hike Medical

Hike Medical is reinventing musculoskeletal care, starting with feet. Our proprietary AI-vision platform turns a 30-second web-based (no sensors) foot scan into precision engineered, 3D-printed insoles that prevent pain before it starts. We're already protecting on-their-feet workforces at Fortune 50 leaders, major health systems, and middle America manufacturers.

Fresh off a stealthy round with top-tier VCs, we run a fast, no-BS, execution-first culture as we sprint toward $100M ARR and standing with 10M Americans as they step into their shoes daily.

• First and only PDAC-approved 3D-printed custom insole in the world

• 3 proprietary AI models that power the experience

• Two products: one for employers & health plans, one for clinics — creating a virtuous cycle of clinician-labeled data

• Expanded care access to 100,000+ Americans to date

What We're Looking For

These are not hard-and-fast requirements — we care more about crisp execution and ownership than checking every box.

• 10–15+ years of B2B sales experience, including senior individual contributor or leadership roles in employer benefits, healthcare, or adjacent enterprise markets

• Proven success selling directly to self-insured employers, large health systems, or Fortune 1000 buyers — with a track record of closing complex, multi-stakeholder deals

• Deep experience building and managing channel relationships through brokers, benefits consultants, and platforms (e.g., Gallagher, Lockton, Mercer, AON, WTW, NFP)

• Healthcare, employer benefits, MSK, occupational health, or med-device background

• Fluency in the HR/benefits buyer landscape — understanding how consultants influence, how platforms distribute, and how employers ultimately decide

• Ability to carry a personal quota while simultaneously developing partner channels — comfortable as both a player and a builder

• Proven ability to manage long sales cycles with multiple stakeholders across HR, Benefits, Finance, Legal, and Clinical

• Track record of consistently hitting or exceeding quota — as an IC and/or through the teams or channels you've built

• Exceptionally strong relationship-building and communication skills, from operators to C-suite

• Highly organized with a strong system for pipeline management, forecasting, and follow-through

• Experience partnering closely with Customer Success, Operations, and Product

• On-site in Boston

Nice-to-Haves

• Experience in venture-backed or high-growth early/growth-stage companies

• Existing relationships with national and regional broker/consultant networks

• Experience selling new or category-creating products into conservative or regulated markets

• Familiarity with benefits platforms and PEO channels as distribution levers

Primary Responsibilities

• Direct Enterprise Sales: Own a personal pipeline and carry quota for employer deals — from initial outreach through contract execution across multiple concurrent opportunities.

• Channel Development — Brokers & Consultants: Build and deepen relationships with national and regional brokers and benefits consultants who influence mid-market and enterprise employer purchasing decisions.

• Channel Development — Platforms & Networks: Identify and activate distribution through benefits platforms, PEOs, captives, and other intermediary channels to drive scalable top-of-funnel volume.

• Multi-Stakeholder Deal Leadership: Navigate complex buying committees across HR, Benefits, Finance, Legal, and Clinical stakeholders — both directly and in support of channel partners.

• Partner Enablement: Equip brokers, consultants, and platform partners with the tools, training, and materials they need to position and sell Hike effectively.

• Pipeline Generation & Management: Build and maintain a healthy pipeline through outbound efforts, inbound leads, partner referrals, and direct employer relationships.

• Value-Driven Selling: Clearly articulate Hike's differentiated value proposition, outcomes, and ROI to senior decision-makers — directly and through partners.

• Forecasting & Deal Discipline: Maintain accurate pipeline reporting and forecasts; proactively manage deal risks, partner commitments, and next steps.

• Cross-Functional Collaboration: Partner closely with Customer Success to ensure smooth handoffs post-sale and strong program launches.

• Market Feedback Loop: Share insights from prospects, partners, and closed-won/lost deals with Product, Operations, and Leadership to shape roadmap and GTM strategy.

What You'll Get

• Competitive cash compensation + equity

• Full medical, dental, and vision coverage

• $15K relocation bonus if needed

• Daily collaboration with the founding team and senior leadership

• Free custom insoles (of course…)