Remote Senior Account Executive- Healthcare Practice

Senior Account Executive - Healthcare Practice Denver/Coloradopreferred · RemoteOK · Reports to CEO Build the healthcare vertical of a boutique systems integrator from thegroundup. This is not a territory to inherit —it’sa practice to shape.You’llbe the first dedicated seller in healthcare, owning net-new logo acquisition, expansion, and the sales motion itself.You’llwork directly with the CEO to define how we win in a market thatdoesn’tneed more SaaS — it needs operational coherence at the organizational level. At a glance Role Senior Account Executive, Healthcare Practice Reports to CEO (with practice operating support) Location Denver/Colorado preferred; remote (US) considered for the right candidate Travel Up to50% — client visits, conferences (HIMSS, HFMA), QBRs OTE $240,000 – $270,000OTE (flexiblebase/variable, candidate-specific) Year 1 quota $1.5M - 1.7M total bookings (new logo + expansion) Ramp 90-day non-recoverable draw at 100% of monthly variable target Profit share % of practice contribution margin above defined threshold Start date ASAP About Quandary Quandary Consulting Group is a boutique systems integrator. For the last several yearswe'vebeen known as one of the topQuickbasedevelopment partners in the country.We'vebuilt complex operational systems for clients across financial services, professional services, andhealthcare — work that turns spreadsheet-and-email operations into governed, integrated platforms. We'renow repositioning around what weactually dobest: making operations coherent.That means iPaaS-led integration (we'reaWorkatopartner), AI-augmented operating models, and a productized approach to the messy middle between core systems.We'resmall enough toactually ownoutcomes, big enough to deliver them. The HealthcarePractice is our newest vertical.We'rebuilding 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. About the Healthcare 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 healthcaresystems. Our anchor client isa healthcare services organization where we run an active engagement orchestrating healthcaresystems .They'rea 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 weoperate, 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'rehiring someone who treats AI asnativetooling, not a novelty. Whatyou'lldo Own the front of the funnel and the close. Generatenet-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 thepractice'ssales system. Maintainaccuratepipeline data inour CRM— we run on real numbers. Contribute to thesales playbooklibrary: validated hook patterns, account-specific research templates, objection-handling refinements. Log lost deals into our competitivetrackerso 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'snot, what the market wants that wedon'tyet productize. Whatyou'llneed Required. 6+ years selling complex services or integration platforms — boutique SI, iPaaS partner (Workato, MuleSoft, Boomi), Big 4advisory, or comparable. Demonstratedtrack recordclosing $75K+ services engagements through full sales cycles. Comfortable as the only seller in a small, founder-led practice — you canoperatewithout a sales manager between you and the CEO. Strong AI fluency.You'veused 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 youdon'thave it, you candemonstratefast learning of new vertical vocabulary —we'llget you fluent in90 days. Existing relationships withWorkato, healthcare integration ecosystems, or provider-side IT/operations leaders. Experience selling productized services (defined scope and pricing) rather than fully bespoke engagements. Mid-marketsalesDNA. Our buyers are CFOs, COOs, and VPs of Operations at $50M-$500M provider organizations — not enterprise-track sellers comfortable with 18-month cycles. Whatyou'llget 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-cyclerampand we fund it. Profit share — % of practice contribution margin above a defined threshold, paid annually after books close.You'renot just selling a quota;you'rebuilding economic upside in the practice. Howwework. Direct reporting line to the CEO. No layers of sales management. Genuinely flexible work setup. Denver/CO preferred for in-person collaboration;remoteconsidered 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 thingyou'vedone withAI thatwasn'ttrivial. Why a boutique SI building a healthcare practice from the ground up sounds like the right next move. Whatyou’vesold and to whom — include 1–2 specific deals (deal size, buyer role, and problem solved), not just titles.Noneed 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. Thisrole'scompensation band isdisclosedin compliance with Colorado pay transparency law and reflects our actual offer range for the position.