Head of Strategic Sales

OhMD•Burlington, VT

17h

About The Position

OhMD is hiring a Head of Strategic Sales to lead strategic selling of its AI patient communication platform to multi-site groups, management services organizations (MSOs), and large specialty practices. The platform includes two-way patient texting, digital forms, automated workflows, EHR integrations, and an AI voice agent that handles routine inbound calls and transfers conversations to a human when needed. The role owns strategic new-logo sales, expansion opportunities, and the development of OhMD’s sales motion. The Head of Strategic Sales will personally source and close deals of $100K+ ACV, typically over three-to-six-month sales cycles, while coaching a small team of account executives and establishing sales practices the team can adopt. The position also carries customer and market insights to product and marketing. The first 90 days include learning the product and customer experience, building a target account list and pipeline, joining customer and sales calls, establishing deal reviews, improving discovery and demo practices, and closing or advancing a strategic deal. The role reports to the CEO and can be based remotely in the US or hybrid in Burlington, Vermont.

Requirements

At least 5 years of experience selling B2B software.
At least 3 years of experience closing deals of $100K+ ACV with executive buyers.
Experience selling healthcare software into physician practices, multi-site groups, MSOs, or the ambulatory side of health systems.
Demonstrated, consistent sales performance, including quota attainment for the last three years and an account of the largest deal closed.
Ability to build pipeline independently rather than relying on marketing.
Demonstrated value-selling skills, including discovery that identifies business costs and examples of changing a buyer’s understanding of what they were buying.
Expected familiarity with MEDDIC, Challenger, or a similar sales methodology, with demonstrated application.
Strong follow-up, negotiation, and closing skills, including experience navigating procurement and security reviews.
Ability to build credibility with COO, CIO, and CEO-level buyers and communicate professionally under pressure.
Experience improving other sellers’ performance through management, player-coaching, or informal mentoring.
Ability to run product demonstrations and discuss EHR integrations, workflows, and OhMD AI call behavior in depth.
Active use of AI tools in work such as research, account planning, drafting, and preparation.

Nice To Haves

Experience selling AI, voice, contact center, or patient engagement technology into healthcare.
Existing relationships with multi-site groups, MSOs, or PE-backed physician platforms.
Founder or early-employee experience at a startup that had to find its first fifty customers.
Working knowledge of the EHR landscape.
Prior player-coach experience at a Series A–C company.

Responsibilities

Source, develop, evaluate, negotiate, and close strategic new-logo deals with multi-site groups, MSOs, and large specialty practices.
Manage deals of $100K+ ACV, typically with three-to-six-month sales cycles and executive buyers such as COOs, CIOs, or CEOs.
Identify expansion opportunities among existing customers, including additional locations, service lines, and adoption of OhMD AI.
Lead value-based discovery that quantifies the business impact of customer problems and develop proposals that express the value in financial terms.
Run product demonstrations tailored to each buyer’s workflows.
Coach account executives through weekly deal reviews, call reviews, joint calls, and consistent sales cadence and follow-up.
Develop and document account plans, sales sequences, mutual action plans, and forecasting practices.
Share buyer feedback, objections, competitive information, and market language with product and marketing teams.
Represent OhMD at industry conferences and partner events, including events involving EHR partners.
Help shape future sales hiring and participate in interviews as the sales motion grows.
Learn the product, attend go-lives, listen to OhMD AI calls, shadow active deals, speak with customers, and build a target account list during onboarding.