Chief Commercial Officer

Direct Recruiters Inc.; Columbus (OH); On-site; USD 150,000 - 200,000; Full time

Benefits offered by this job

Health Insurance

Unlimited PTO

401k Plan

Employee Stock Options

Health Savings Account

Flexible Spending Account

Job summary

Direct Recruiters Inc. is looking for a dynamic Head of Sales to lead its efforts in the healthcare technology sector. You will be instrumental in closing high-value deals and will oversee the establishment of a commercial function from the ground up.

The ideal candidate will have experience building sales teams in B2B SaaS environments and a strong background in managing enterprise sales cycles with healthcare providers. You will collaborate closely with executive teams to drive strategy and market education.

Qualifications

• Experience building a commercial function at a B2B SaaS or healthtech company.
• Proven track record of carrying and hitting quotas on enterprise deals.
• Experience in navigating enterprise sales cycles involving legal and procurement.

Responsibilities

• Close seven-figure deals with major health system executives.
• Build and manage the team's sales processes and practices.
• Educate the market on healthcare technology and trends.

Skills

B2B SaaS Sales

Healthcare Technology

Enterprise Sales

Sales Cycle Management

Job description

Client Summary

• Healthcare technology company focused on automating and streamlining administrative workflows between providers and payers
• Provides an EHR-integrated platform that eliminates manual effort and friction across a critical revenue cycle process
• Helps health systems reduce administrative burden, improve approval rates, and decrease claim denials
• Serves a large and growing base of major health systems with a proven, high-retention platform
• Backed by institutional investors with strong growth trajectory and multiple industry recognition awards
• Positioned in the growing healthcare automation and revenue cycle management market with demonstrated product-market fit at scale

Position Responsibilities

• Close seven-figure enterprise deals personally for the first 12–18 months. You will not be running this from a corner office. You will be in the room with VP Revenue Cycle, VP Managed Care, CFO, and CIO buyers, and you will be on the phone with their legal teams when contracting stalls.
• Build the repeatable motion: ICP, outbound, RFP response (Rhyme faces real RFP volume today and the team is AI-enabling it; you will lead that forward), security/legal playbook, pricing, and stage definitions that hold up under board scrutiny.
• Hire 2 AEs and design the org we’ll need at $40M. You will inherit a proven senior seller and a long-tenured junior; the first hires sit around them, not over them.
• Stand up the BD function. Scope the role, hire the first BD leader, and close the first two channel agreements that actually produce pipeline — not logos on a slide. R1 and Ensemble are already in late-stage discussions.
• Educate the market. Providers and payers largely still think connectivity is the answer; they know it isn’t. You will own how that story lands at Becker’s, HLTH, HFMA, and on stage with customers.
• Run the operating cadence. Weekly pipeline, monthly forecast, quarterly board. Salesforce discipline that you and your team will live in, not work around.

Experience & Skills

Required Experience and Qualifications

Must-Have Experience

• Has built a commercial function at a B2B SaaS or healthtech company from sub-$15M ARR. Not inherited one, not scaled one that was already running. Built it.
• Has personally carried and hit a direct quota on enterprise deals with large health systems in the last five years.
• Has run a 9–18 month enterprise sales cycle with procurement, legal, and security review as routine — and has made cycles shorter without losing rigor.
• Has managed through at least one layer and has personally hired, coached, and transitioned out sellers who weren’t working.
• Has sat in a venture- or growth-equity-backed board meeting and defended their own number.

Must-Have Skills and Traits

• Player-coach by instinct. You would rather win a deal than watch one.
• Builder temperament. You are energized, not frustrated, by a sub-$15M commercial function with a new CRM, an 18-month-old brand, and a CMO you’ll need to partner with.
• Grit. You’ve lived through a 60-day legal red-tape drag on a closed-won deal and kept the team’s head up.
• Founder partnership. You can operate independently and keep a first-time CEO in the loop without making him the bottleneck.
• Data-driven. You don’t forecast on vibes. You instrument the team from day one.

Preferred Experience and Qualifications

Compensation

• Health Insurance with some options fully-funded by the company
• Unlimited PTO
• Fidelity 401k plan with Roth and Traditional options, BrokerageLink is available, expanding investment choices
• Employee stock option plan
• Health Savings Account (up to $100 monthly company contribution), Flexible Spending Account, Dental, Vision, Life & AD&D Insurance, Disability Insurance, Critical Illness