Remote Enterprise Sales Manager

We’re Heidi.

We’re building the future of healthcare by giving every clinician the earth’s finest AI Care Partner. In just 18 months, our clinical AI products have absorbed the administrative chaos of 73 million patient visits. Today, we support over 2.5 million patient sessions a week across 190+ countries.

Healthcare systems are failing us; clinicians spend more time on documentation than on patients, and the human connection that makes medicine worth practicing is eroding.

Our mission is simple: double the world’s healthcare capacity and strengthen the human connection at its heart.

We found product-market fit with a freemium medical scribe that clinicians love. Now, we’re expanding. Every task a clinician hands to Heidi is a patient who feels more attended to, a health system unclogged, and a clinician who gets to be a clinician again.

If you don’t choose easy and you want to build something way bigger than yourself then, choose the challenge, choose Heidi.

The role

Our Enterprise motion is young, and that’s the point. We have Enterprise Account Executives closing real deals with health systems and hospital networks, but the playbook they’re running is still being written in real time, deal by deal. We need someone who’s built an enterprise motion before and knows the difference between a repeatable process and a pile of Notion docs nobody follows.

You’ll manage our Enterprise AEs day to day, which means you’re in their deals, not just their pipeline reviews. You’ll be on calls with health system procurement teams, helping navigate security reviews and multi-stakeholder buying committees, and coaching your team through the moments that actually decide whether a deal closes. At the same time, you’re building the muscle behind the team: qualification criteria, deal stages, forecasting discipline, and the enablement that turns one rep’s win into everyone’s win. Success looks like a team that closes more, forecasts accurately, and has a motion sharp enough that the next AE we hire ramps in weeks, not quarters.

What you’ll do

• Manage and coach a team of Enterprise Account Executives, with regular deal reviews that dig into strategy, not just stage and close date

• Get directly involved in complex, high-value deals, sitting in on calls with health system stakeholders when your experience changes the outcome

• Build the qualification framework and deal stages that give us an honest, predictable view of the Enterprise pipeline

• Own forecasting accuracy for the Enterprise segment and report on it with numbers you’d defend to the board

• Design the onboarding and enablement path that gets new Enterprise AEs productive fast, grounded in what’s actually worked in real deals

• Partner with Product and Clinical teams to bring the right people into procurement conversations and security reviews at the right moment

• Identify where our current sales process breaks down against large, multi-stakeholder health systems, and fix it

• Recruit and hire the next wave of Enterprise AEs as the team scales

What You’ll Need

• 5+ years of enterprise sales leadership experience, though we care more about what you’ve shipped/built than years on the clock.

• A romantic streak about software. You believe great products can transform someone’s day.

• You’ve built a sales process from scratch and know the difference between “we have a playbook” and “we have a Notion page nobody opens.” You coach reps in the deal, not just in the debrief.

• Passion for AI, shown through hands-on building, prototyping, or side projects.

• You default to building over requesting.

• You’re confident in your thinking and open to being wrong. Great ideas win regardless of who surfaces them.

Filter Questions

• Are you able to execute without a legion of data analysts, product marketers, and research coordinators at your beck and call?

• Does the prospect of making health systems a lot nicer make you feel fuzzy inside?

• Have you ever talked a deal back from the dead?

How We Show Up

• Build for the next decade, not next quarter. Our targets are outrageous on purpose. The world’s health doesn’t have the luxury of incrementalism.

• Lead, don’t wait. We treat tomorrow’s problems today. Sometimes we build what’s needed before it’s wanted, and we’re fine with that.

• Follow the evidence. Trust the patient. We pursue truth relentlessly. But when the subjective and objective disagree, we treat the patient, not the numbers. Ego is a comorbidity we can’t afford.

• Own the outcome. Everyone here carries the company. Raise problems with solutions, solve them end-to-end, and never be a bystander.

• Ship, measure, go again. A button today, a workflow tomorrow. More iterations beat better planning. We’re precise at pace, not reckless.

• Live in clinicians’ reality. Not the ideal workflow, the twenty-patients-before-lunch actual one. We build for exhausted humans, and we’d better be decent ones while we do it.

Why Heidi?

You’ll join a team focused on real-world impact over imaginary valuations and glossy PR. We live and breathe the challenges of modern health systems, and are laser-focused on exacting the change we’d like to see. We’re medicos, engineers, builders, and designers who’ve felt the moral and practical toll of what non-care feels like. True A-players progress extremely fast here.

The nature of the scale-up game is demanding, but we value sustainable performance and mental health. You’re trusted to perform, and you set your schedule. We operate on outcomes > inputs, not process theatre. We all take the bins out, metaphorically and literally.

Building what we’re building isn’t always easy. But we didn’t choose easy, we chose to build something that actually matters. We hold ourselves to a higher standard because healthcare demands it.

If you join Heidi, you recognise that the deeper question isn’t whether AI can solve the global healthcare crisis, but whose hands will shape it. The work is hard, but you will trust and admire the people you work beside, and rest easy knowing you’re doing the defining work of your career.

We Take Care of You

We offer a $1,000 annual learning and development budget, a $150/month health and wellness allowance, a $500 home office budget, 26 weeks paid primary parental leave and 18 weeks paid secondary parental leave, fertility support up to $10,000, four weeks of work from anywhere per year, and serious equity.

We chose to open-source our benefits hub, if you care to take a peek.