Founding Account Executive

Healthcare's largest cost center runs on software that doesn't decide anything

Labor accounts for roughly 56% of what American hospitals spend. Tools to manage it exist, but they are systems of record: they store the schedule, they do not build it. So coordinators still rebuild rotations by hand every week or month. Clinicians still lose personal time to changes nobody saw coming. Executives still approve staffing and contract labor with limited visibility into what either actually costs.

YouShift is building the AI-native workforce operating system for healthcare. Our agents do the work that used to consume an entire operations team: they build and rebalance schedules, hold the line on compliance and clinician preferences, plan capacity against demand, and surface where labor spend is leaking. Scheduling is where we start with most customers. It is not where we stop.

We are 17 people, backed by Y Combinator. The product works, some of the largest physician groups in the United States are paying for it, and our founders have closed those deals themselves. What we do not have yet is someone who is not a founder closing deals repeatably. That is the job.

Why this role matters

You will not be joining a mature sales organization with years of playbooks behind it. You will work directly with our leadership and founders to build the outbound engine that fuels our next stage of growth, as one of the first people on our commercial team.

That cuts both ways, and we would rather be honest about it. There is no script waiting for you, no library of proven sequences, and some of what you try will not work. In exchange, the decisions you make in your first six months will still be visible in how this company sells three years from now.

Two levels, one opening

We are hiring one Account Executive and we are genuinely open at two levels. Rather than post a number we do not mean, here is exactly how we think about it.

Mid-level

You own the Growth segment: physician groups of roughly 30 to 400 clinicians, with ACVs ranging from $7.5k to $100k, full cycle, weeks-long deals, dozens of similar conversations a year. You execute the playbook and sharpen it as you go. This is the seat if you have closed B2B SaaS successfully and want the step up into founding-team ownership.

OTE: $220,000 to $260,000, always uncapped.

Senior

You own the Growth segment and also take the larger, more strategic groups: more stakeholders, longer sales cycles, and materially larger contract values. Today, our $200k+ ACV enterprise deals are mostly founder-led by necessity. We are still early, and these are months-long processes involving executive buyers, procurement, security review, and complex commercial negotiations.

Over time, you'll partner with the founders on these accounts and earn the opportunity to pursue organizations of any size, rather than being limited by territory or account segment. You are expected to arrive with judgment we do not have yet, and to set the standard for every rep who follows.

OTE: Up to $350,000, always uncapped.

What moves you between the two is not years. It is whether you have carried complex, multi-stakeholder deals at this size before, and whether you can build a segment rather than work one.

Apply once. We will tell you early in the process which level we are considering you for, and why. If you are between the two, say so in your application and let us make the call with you.

What you'll do

• Own full-cycle sales into physician groups and health systems: discovery, demo, proof of value, negotiation, and close.
• Sell to Operations leaders, Medical Directors, schedulers, and clinical executives, and build the internal case they will have to defend to a board or a partnership.
• Run proof-of-value engagements with our Customer Success team, and protect their capacity by qualifying properly rather than starting POVs you cannot close.
• Drive deals to a first published schedule, not to a signature. Activation is the metric that matters here.
• Write win/loss honestly into Attio, including the deals we nearly lost and why, so the qualification bar stops being instinct and becomes a list.
• Partner with your BDR on targeting and messaging, and work inbound, events, and referrals alongside outbound.
• Turn what you hear on calls into product and positioning feedback, with direct access to the founders and no layers in between.
• Help write the playbook, discovery template, and objection handling the next reps will inherit.

What we're looking for

Required, at either level

• Two or more years closing B2B SaaS, with a quota you owned and a number you can talk about specifically.
• Native or near-native English. You will be on the phone with American physicians and executives every day.
• Authorization to work in the United States.
• Based in New York City, or able to relocate before your start date.
• Genuine comfort with senior operational and clinical buyers, and the instinct to ask a better question rather than deliver a pitch.
• Real discipline on process: every deal has a dated next step, the CRM reflects reality, and forecasts mean something.
• Comfort selling without complete air cover. Some collateral you want will not exist yet, and you will help build it rather than wait for it.
• Curiosity about how healthcare organizations actually operate, which is messier and more interesting than it looks from outside.

We pay a 50/50 split between base and target variable, uncapped, at both levels:

Additionally, for the senior level

• Five or more years closing, including deals with several decision makers, procurement, and security review.
• Consistent quota attainment you can evidence, not a single strong year.
• Experience as an early or founding AE, ideally before a playbook existed.
• Contract values well above $50,000, and comfort with a cycle measured in months rather than weeks.
• The judgment to tell us when our targeting, pricing, or qualification bar is wrong, with the evidence to back it.

Nice to have, at either level

• Exposure to healthcare, whether commercial, clinical, or operational.
• A track record displacing an incumbent system rather than creating a new budget line.
• Fluency with modern sales and AI tooling. We use Attio, Apollo, LinkedIn, and AI assistants such as Claude to do the work of a larger team.

What we offer

• Full ownership of a segment, not a slice of a territory.
• Direct work with our CRO and founders, with no layers in between.
• A BDR hired alongside you, dedicated to your pipeline.
• A product with paying enterprise customers behind it, so you are selling something that already works.
• Health insurance.
• 20 days of paid vacation plus company holidays.
• A team of 17 that likes building together and is candid when something is not working.

Compensation

• Mid-level: base $110,000 to $130,000 USD, with equal target variable. OTE $220,000 to $260,000.
• Senior: base $150,000 to $175,000 USD, with equal target variable. OTE $300,000 to $350,000.

These ranges reflect what we expect to pay for this role in New York City. Level is decided during the process on the criteria above, and where an offer lands within a level depends on demonstrated ability. Equity is included at both levels, weighted toward the senior one.

A note on how we pay: variable compensation is tied to closed business and activated departments, not to proofs of value started. We would rather you walk away from a deal that will not close than fill a pipeline we cannot deliver on.

Hiring process

Hiring should be thoughtful, transparent, and respectful of your time. Ours runs in four steps:

1. Meeting with our Chief Revenue Officer.
2. Discovery and demo exercise, run live and reviewed together.
3. Final conversation with the leadership team.
4. Offer.