I'm Dylan Shepard. Fourteen years building C-suite relationships inside healthcare provider organizations, and most weekends in season, a raft guide on the White Salmon River. Both jobs come down to the same thing: people decide fast whether they trust you.
The short version.
I've spent most of my career at one company — Eight Eleven Group / Medasource — growing from account executive to Senior Director of Enterprise Sales & Growth Strategy. That longevity is the point: accounts I opened a decade ago are still growing, because the relationships underneath them were built to last.
In 2025 I took that experience somewhere very different. Query Health was an early-stage company with three founders, a product, and nobody selling it but the founders themselves. One of them — and the entire development team — sat in Spain. I joined as fractional VP of Sales to build the commercial side from nothing, part-time, alongside my day job. ICP, segmentation and sales motion first, then the playbook, built with their Chief Product Officer.
That playbook landed the company's first design partner and two beta customers. A real part of the job was working across nine hours of time difference — getting a product team in Spain and US healthcare buyers pointed at the same thing, when neither side could wait on the other. What we learned from those accounts went back into targeting and messaging, so the pipeline got built on evidence instead of guesses. I left them a future-state sales org — headcount, ramp model, quota capacity — and the metrics to run it against.
Day to day the work is consultative and cross-functional — discovery, solution design with internal SMEs, contract negotiation, and Salesforce-based forecasting across IT, revenue cycle, research, and clinical service lines. I've launched new practice areas from scratch and led the largest EMR implementation in company history. MBA from the University of Washington, B.S. in Sales from Ball State.
The other half of the year I'm on the water. Guiding has made me better at the day job than any training I've taken — it's the same skill, compressed: read the situation, make the call, and get people to follow it before they've had time to decide whether they trust you.
Enterprise and strategic accounts across healthcare providers, pharma, and life sciences.
Led solution design, C-suite and VP stakeholder engagement, and contract negotiations through to signature — while delivering 128% of plan in 2024.
Coordinated C-level, VP, director, clinical leadership, and IT SMEs through vendor integration and on-time activation — while co-developing the first national sales strategy, an 18% revenue lift.
Launched the Western go-to-market footprint — Kaiser Permanente, CHI, UCHealth, SCL Health, Denver Health, Centura. Eight enterprise accounts, $5M+ net-new.
Epic alignment services ($5M+ net-new), clinical contracting and strike support, per-device SaaS deployment, and the first M&A infrastructure engagement — each a repeatable pattern.
Whitewater guide, White Salmon River — Husum, Washington.
Weekends in season I guide for PDX Raft on the White Salmon, about ninety minutes east of Portland. It's a spring-fed, Class III–IV run through a basalt gorge — continuous, cold, and pushy, with Husum Falls near the end: the largest commercially run drop in the country.
A guide's actual job isn't paddling. It's taking six strangers who have never met each other, giving them a job they've never done, and building enough trust in about five minutes that they'll dig in and pull when you ask — while the noise makes it hard to hear you and the consequences are real. You don't get a second briefing.
I started guiding because I wanted a weekend that had nothing to do with a laptop. I kept at it because it turns out to be the same job as the one I do Monday through Friday, with the timeline collapsed from eighteen months to eighteen seconds.
Full history, or grab the PDF résumé.
Open to Senior Director and VP roles in healthcare sales and enterprise accounts. Also happy to talk about the river.
