Account Executive (Enterprise 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 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…)