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Senior Account Executive - Healthcare Practice 

Denver/Colorado preferred  ·  Remote OK  ·  Reports to CEO 

Build the healthcare vertical of a boutique systems integrator from the ground up. This is not a territory to inherit — it’s a practice to shape. You’ll be the first dedicated seller in healthcare, owning net-new logo acquisition, expansion, and the sales motion itself. You’ll work directly with the CEO to define how we win in a market that doesn’t need more SaaS — it needs operational coherence at the organizational level. 

At a glance 

About Quandary

Quandary Consulting Group is a boutique systems integrator. For the last several years we've been known as one of the top Quickbase development partners in the country. We've built complex operational systems for clients across financial services, professional services, and healthcare — work that turns spreadsheet-and-email operations into governed, integrated platforms. 

We're now repositioning around what we actually do best: making operations coherent. That means iPaaS-led integration (we're a Workato partner), AI-augmented operating models, and a productized approach to the messy middle between core systems. We're small enough to actually own outcomes, big enough to deliver them. 

The Healthcare Practice is our newest vertical. We're building it deliberately — anchor client live, productized service areas defined, AI-native delivery model in place. The Senior AE we hire will be the first dedicated seller in this vertical and a defining hire for the practice. 

Our healthcare clients are mid-market provider organizations — health plans, multi-site clinics, specialty practice groups, and provider services firms running real operational complexity across healthcare systems. 

Our anchor client is a healthcare services organization where we run an active engagement orchestrating healthcare systems. They're a strong reference we use thoughtfully and with permission. 

Our productized service areas in healthcare include Provider Operations (credentialing, onboarding, scheduling integration), Revenue Cycle Management orchestration (denial management, claim status visibility, AR aging), and Voice-Integrated Operations (telephony tied to clinical and billing workflows). Each comes with a defined Triage → Build → Managed Evolution motion that creates clear sales paths and clear delivery scope. 

AI is core to how we operate, not a buzzword. Our AE uses an AI-augmented operating model for prospecting, qualification, and proposal drafting. The principle: AI drafts, you decide, you send. We're hiring someone who treats AI as native tooling, not a novelty.What you'll do 

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. 

• 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. 

Partner with delivery and the CEO. 

• 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. 

What you'll need 

Required. 

• 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. 

Strongly preferred. 

• 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. 

What you'll get 

Compensation that reflects the role. 

• $240,000-$270,000 OTE, flexible base/variable, candidate-specific within band. 

• 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 against three system behaviors that compound the practice over time. 

• 90-day non-recoverable draw at 100% of monthly variable target — we expect a real cold-cycle ramp and we fund it. 

• Profit share — % of practice contribution margin above a defined threshold, paid annually after books close. You're not just selling a quota; you're building economic upside in the practice. 

How we work. 

• Direct reporting line to the CEO. No layers of sales management. 

• Genuinely flexible work setup. Denver/CO preferred for in-person collaboration; remote considered for the right candidate. 

• Real autonomy. The practice has clear goals, clear non-negotiables, and trust between. 

• Health, dental, vision, 401(k), PTO.  

How to apply 

In your cover letter/ resume include 

• One thing you've done with AI that wasn't trivial. 

• Why a boutique SI building a healthcare practice from the ground up sounds like the right next move. 

• What you’ve sold and to whom — include 1–2 specific deals (deal size, buyer role, and problem solved), not just titles. No need to share company names. 

Quandary Consulting Group is an equal opportunity employer. We evaluate candidates on the work and the judgment they bring, not on protected characteristics. Healthcare experience is a plus, not a requirement — we hire for sales instinct and operational thinking first. 

This role's compensation band is disclosed in compliance with Colorado pay transparency law and reflects our actual offer range for the position. 

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