Enterprise Account Executive (Employer)

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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 out of Boston’s Seaport 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.

• 6–10 years of B2B sales experience, with a strong track record closing enterprise or upper-mid-market deals
• Experience selling into employers, HR, benefits, healthcare, or adjacent enterprise buyers
• Healthcare, employer benefits, MSK, occupational health, or med-device experience
• Experience working with large enterprises and complex programs (e.g., Fortune 1000 employers, major health systems, large manufacturers)
• Deep understanding of the HR/benefits buyer and buying process
• Proven ability to manage a full sales cycle with multiple stakeholders and long timelines
• Track record of consistently hitting or exceeding quota
• Exceptionally strong relationship-building and communication skills, from operators to C-suite
• Extremely comfortable leading sales meetings, presentations, and executive discussions
• 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
• Familiarity working with benefits consultants or brokers (e.g., AON, Mercer, WTW, Gallagher, Lockton)
• Experience selling new or category-creating products into conservative or regulated markets
• Experience with HubSpot or similar CRM tools

Primary Responsibilities

• Enterprise Sales Ownership: Own the full sales cycle for employer prospects, from initial outreach through contract execution, across multiple concurrent opportunities.
• Pipeline Generation & Management: Build and maintain a healthy pipeline through outbound efforts, inbound leads, partner channels, and broker relationships.
• Multi-Stakeholder Deal Leadership: Navigate complex buying committees across HR, Benefits, Finance, Legal, and Clinical stakeholders.
• Value-Driven Selling: Clearly articulate Hike’s differentiated value proposition, outcomes, and ROI to senior decision-makers.
• Forecasting & Deal Discipline: Maintain accurate pipeline reporting and forecasts; proactively manage deal risks and next steps.
• Cross-Functional Collaboration: Partner closely with Customer Success to ensure smooth handoffs post-sale and strong launches.
• Market Feedback Loop: Share insights from prospects and closed-won/lost deals with Product, Operations, and Leadership to help 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…)