Senior Account Executive- Healthcare Practice

Quandary Consulting Group • Greenwood Village, CO

2d • Remote

About The Position

Quandary Consulting Group is a boutique systems integrator seeking a Senior Account Executive to build its new Healthcare Practice from the ground up. This role involves owning net-new logo acquisition, expansion, and the sales motion within the healthcare vertical. The ideal candidate will work directly with the CEO to define the strategy for success in a market that requires operational coherence. Quandary specializes in iPaaS-led integration, AI-augmented operating models, and bridging the gap between core systems. The Healthcare Practice focuses on mid-market provider organizations, including health plans, multi-site clinics, and specialty practice groups. The practice offers productized service areas such as Provider Operations, Revenue Cycle Management orchestration, and Voice-Integrated Operations. AI is a core component of the sales process, used for prospecting, qualification, and proposal drafting.

Requirements

• 6+ years selling complex services or integration platforms (boutique SI, iPaaS partner, Big 4 advisory, or comparable).
• Demonstrated track record closing $75K+ services engagements through full sales cycles.
• Comfortable operating as the sole seller in a small, founder-led practice, reporting directly to the CEO.
• Strong AI fluency, with experience using AI tooling for outreach, research, or proposal drafting.
• Sound business judgment to flex pricing, scope, and timing within defined bounds.

Nice To Haves

• Healthcare experience (provider-side preferred).
• 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, with experience selling to CFOs, COOs, and VPs of Operations at $50M-$500M provider organizations.

Responsibilities

• Own the front of the funnel and the close.
• Generate net-new pipeline through targeted account-based outreach using AI tools, personal network, and conference presence.
• Run discovery, demos, and proposal cycles for healthcare provider organizations.
• Close Triage engagements ($15K-$25K) as an entry point, converting them to Build engagements ($75K-$140K) and Managed Evolution retainers.
• Manage accounts post-close, including expansion, retention signal, and reference cultivation.
• Operate the practice's sales system.
• Maintain accurate pipeline data in the CRM.
• Contribute to the sales playbook library with validated patterns, research templates, and objection handling.
• Log lost deals into a competitive tracker.
• Utilize SOW templates and pricing frameworks, seeking CEO approval for deviations.
• Partner with delivery and the CEO.
• Co-sell with the CEO on strategic accounts.
• Provide product/practice insights back to leadership regarding market needs and operational effectiveness.

Benefits

• Health, dental, vision, 401(k), PTO
• Compensation that reflects the role: $240,000-$270,000 OTE, flexible base/variable.
• Standard accelerators above 100% (1.5x at 100-150%, 2.0x above 150%); no commission cap.
• MBO bonus of 10% of variable target, paid quarterly.
• 90-day non-recoverable draw at 100% of monthly variable target.
• Profit share: % of practice contribution margin above a defined threshold, paid annually.

What This Job Offers

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