Senior Account Executive- Healthcare Practice

Quandary Consulting Group • Greenwood Village, CO

22h • Hybrid

About The Position

This is a unique opportunity to build the healthcare vertical of a boutique systems integrator from the ground up. As the first dedicated seller in this practice, you will own net-new logo acquisition, expansion, and the sales motion itself. You will work directly with the CEO to define the strategy for winning in a market that needs operational coherence. The role involves generating pipeline through targeted account-based outreach, running discovery, demos, and proposal cycles, closing Triage engagements, and converting them to Build engagements and Managed Evolution retainers. You will also manage accounts post-close, owning expansion, retention, and reference cultivation. Additionally, you will operate the practice's sales system, maintain CRM data, contribute to the sales playbook, and log lost deals. Partnering with delivery and the CEO, you will co-sell on strategic accounts and provide market insights back to leadership. The ideal candidate will have strong AI fluency and sound business judgment, with healthcare experience being a strong preference.

Requirements

• 6+ years selling complex services or integration platforms — boutique SI, iPaaS partner (Workato, MuleSoft, Boomi), Big 4 advisory, or comparable.
• Demonstrated track record closing $75K+ services engagements through full sales cycles.
• Comfortable as the only seller in a small, founder-led practice — you can operate without a sales manager between you and the CEO.
• Strong AI fluency. You've used AI tooling for outreach, research, or proposal drafting and have a perspective on what makes it work.
• Sound business judgment. The role flexes pricing, scope, and timing within defined bounds; we hire people we can trust to make those calls.

Nice To Haves

• Healthcare experience (provider-side preferred). If you don't have it, you can demonstrate fast learning of new vertical vocabulary — we'll get you fluent in 90 days.
• Existing relationships with Workato, healthcare integration ecosystems, or provider-side IT/operations leaders.
• Experience selling productized services (defined scope and pricing) rather than fully bespoke engagements.
• Mid-market sales DNA. Our buyers are CFOs, COOs, and VPs of Operations at $50M-$500M provider organizations — not enterprise-track sellers comfortable with 18-month cycles.

Responsibilities

• Own the front of the funnel and the close.
• Generate net-new pipeline through targeted account-based outreach using our AI-BDR operating system, plus your own network and conference presence.
• Run discovery, demos, and proposal cycles for healthcare provider organizations evaluating integration and operational coherence work.
• Close Triage engagements ($15K-$25K) as a wedge, then convert to Build engagements ($75K-$140K) and Managed Evolution retainers.
• Manage your accounts post-close — owning expansion, retention signal, and reference cultivation.
• Operate the practice's sales system.
• Maintain accurate pipeline data in our CRM — we run on real numbers.
• Contribute to the sales playbook library: validated hook patterns, account-specific research templates, objection-handling refinements.
• Log lost deals into our competitive tracker so the practice learns from every loss.
• Use our SOW templates and pricing framework; deviations require CEO approval.
• Co-sell with the CEO on strategic accounts where executive presence matters.
• Feed product/practice insights back to leadership: what's working, what's not, what the market wants that we don't yet productize.

Benefits

• Health, dental, vision, 401(k), PTO.
• Profit share — % of practice contribution margin above a defined threshold, paid annually after books close.
• MBO bonus of 10% of variable target, paid quarterly against three system behaviors that compound the practice over time.
• 90-day non-recoverable draw at 100% of monthly variable target.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed