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Account Executive (Enterprise Sales)

Hikemedical, Boston, Massachusetts, us, 02298

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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…)

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