Route 66 Ventures — Chief of Staff
AI is going to radically change healthcare.
Help drive it.
Route 66 Ventures is a digital health venture fund. We operate portfolio companies, incubate new ventures from scratch, and invest in the people and ideas reshaping how healthcare works. We're hiring a Chief of Staff to be at the center of all of it.
This is a two-year fellowship, not a career track — and definitely not a path to becoming a VC partner. It's a launchpad. You'll learn how funds, startups, and healthcare operations actually work from the inside. After two years, the goal is for you to leave and become a founder, an early operator, or a leader at a company doing something that matters.
Why are we hiring for this role right now? We're at a critical inflection point where AI is about to drive massive changes in how healthcare is delivered. We're looking for someone to help us be at the forefront of that evolution.
By continuing, you acknowledge this is an experimental AI tool that may have rough edges. We've done everything to the best of our abilities to protect your data. Your email, LinkedIn profile, and conversation are intended to be used only for this hiring process.
Why this role?
A lot of people talk about AI. Very few get the chance to actually push the boundaries of what it can do — with the space to experiment, the exposure to real problems across different companies and use cases, and a team that's genuinely committed to figuring out what works.
This role puts you at that intersection. You'll work alongside a team that uses AI every day — not as a buzzword, but as an operating model — across healthcare companies at every stage. You'll see how AI impacts clinical workflows, growth operations, venture strategy, and everything in between. And you'll develop deep healthcare fluency alongside deep technical intuition, which is a combination very few people get to build this early.
It's meant to be a launchpad. After two years, you'll have the kind of exposure, judgment, and hands-on experience that positions you to go build something that matters.
What you'll do
Help incubate a new venture from zero.
Primary research, market validation, financial modeling, workstream management. There's no org chart or playbook yet — just a thesis and a timeline. You'll help build the rest.
Support a live, scaling healthcare company.
Growth strategy, operational playbooks, partner development. Real patients, real revenue, real problems — not a pitch deck exercise.
Keep the fund running smoothly.
Board prep, deal flow follow-up, LP communications, portfolio operations — you'll help keep a dozen simultaneous workstreams from falling through the cracks.
Use AI as your operating model.
Research, analysis, content, automation — AI should be how you work, not something you're experimenting with. We use it every day and expect you to do the same.
Own the follow-through.
Strategy is easy. Execution is everything. You close loops, ship deliverables, and move things forward.
Who we're looking for
Genuinely curious.
You go down rabbit holes because you can't help it. You've taught yourself things nobody asked you to learn. You like understanding how things work.
Action-oriented.
You'd rather ship something at 80% and iterate than wait until it's perfect. You learn by doing.
Comfortable with ambiguity.
This role doesn't come with a detailed job description on day one. That should feel like an opportunity, not a red flag.
Quick to learn.
You pick things up fast and connect ideas across domains. You don't need to be an expert in everything — you need to get up to speed quickly.
Already using AI daily.
Not just trying it out — actually using it to get work done. You've built workflows, automated processes, or pushed tools further than the defaults. You have a feel for what AI is good at and where it falls short.
Why an AI conversation?
We believe AI is going to change how every industry works — healthcare especially. At Route 66, we don't just invest in AI-enabled companies. We use AI in how we operate, how we evaluate opportunities, and yes, how we hire.
This screener is a real example of that. It's an AI-powered conversation that explores how you think about healthcare, how you work, and what you've built. We think it surfaces things a resume never could — and it gives you a feel for how we actually work.
We also built it in the open. If you're curious about how it works under the hood, the source code is on GitHub.
How it works
Enter your email
We send you a magic link. No password, no resume, no form. Click it and you're in.
Have a conversation
15-20 minutes with an AI that knows enough to make it real. Talk about healthcare, how you work, and what you've built. It's not a test — it's a conversation.
We follow up
The AI generates a summary and scorecard from your conversation, which we review personally. You'll hear back within a week regardless of outcome.
Interested? Let's talk.
By continuing, you acknowledge this is an experimental AI tool that may have rough edges. We've done everything to the best of our abilities to protect your data. Your email, LinkedIn profile, and conversation are intended to be used only for this hiring process.
About Route 66 Ventures
Route 66 Ventures is a venture fund focused on digital health. Since 2014, we've invested in over 50 companies backing founders who are relentlessly pursuing better solutions to meaningful problems. We're investors, owners, and operators.
Learn more