It's the third time this week you've thought about it.
You need help. Things are slipping. The to-do list grew faster than your team did. And everyone — your investors, your advisors, the LinkedIn comments — is telling you to hire a Head of Operations.
You started writing the job description last night.
Stop.Breathe in. Breathe out. Whenever you're ready.
This is the story of one Pear-backed company that almost made the same hire — and what happened when they tried something else instead.
Every early-stage founder eventually writes this listing. Read it. Then tell it what it actually is.
We're a fast-moving health-tech startup coming off a Pear-led seed round. We need someone who can do everything operations until we're big enough to have a real team. You'll work directly with the founders on day one.
You'll own:This job doesn't exist.
These problems do. One oAT operator. Three months.
Every bullet in that listing maps to one of the functions below. Together they're the work of a small team, stacked onto a single hire.
That listing isn't one job. It's five. And you were about to spend eight weeks finding a unicorn who can do all of them at once.
What you actually need isn't one hire. It's this person — Sarah, the operator that one Pear-backed health-tech company embedded with for three months instead of starting a search.
Here's what one oAT operator covered over the first three months. Cross-functional execution typically spread across multiple specialized hires — completed by one person, live.
We launched eight months ago and we're already working with three of the top 10 pharmas, in no small part thanks to Sarah, our oAT generalist. Early on she effectively handled all of our stock to compliance, which was critical, and also set up our onboarding and HubSpot flow, which has given us a lot more confidence in the sales cycle. Everything feels very clear, and we had a lot of messiness before.
And once the operator is embedded, the founder's week starts to look different. Here's what that actually means in practice.
Drag the slider from left to right. Watch some items fly off to oAT. Watch others rewrite themselves into something strategic.
People ask: is this a freelancer? A consultant? Neither, exactly. The category doesn't quite exist yet. That's the point.
An oAT operator provides the continuity, internal context, and high-trust support of someone who genuinely works at your company. They're not calling in from the outside. They're in Slack, in the weeds, in the docs.
Engagement scope flexes with the company's stage. No 6-month contracts. No equity. No headcount line on your cap table. Short, dynamic engagements that adapt as the company learns what it actually needs.
Every oAT operator embeds AI into workflows from the start. Not as a gimmick — as an operating principle. Repetitive work gets automated. Human judgment gets focused where it matters. That's leverage that compounds before your first specialized hire.
A fast-growing Adtech startup faced rising demand, fixed headcount, and mounting burnout. Over three months, work shifted from people-bound execution to orchestrated, AI-enabled workflows.
The oAT operator didn't add headcount. They decomposed roles into discrete skills, designed AI-ready workflows, and became the orchestration layer — routing work, maintaining client context, ensuring quality.
Instead of designing an org chart the company couldn't hire into, the oAT operator created an operating model that assumed no new headcount — treating scaling as a workflow problem, not a staffing problem.
Recurring production work broken into discrete skills, steps, and decision points. That structure made tasks AI-executable and easier for the existing team to supervise — messy knowledge execution into a system that could run consistently.
With workflows in place, the operator became the control layer — routing work, maintaining context, ensuring quality. They handled the judgment calls AI shouldn't make, reviewed outputs, managed client relationships.
Our generalist operator is fantastic, and has become an essential member of our team in these early days. Usually when I describe him to other people, I usually say he's thinking for me at this point.
Two companies. Different domains, different problems, different founders. The same model worked. Here's why.
Three things that used to require three separate hires, an agency relationship, and a 6-month ramp. oAT brings all three in one operator, in one engagement, starting week one.
Senior operators who've run real functions in real companies. Not generalists who've read a lot. People who've owned outcomes. They embed like full-time hires — Slack, standups, strategic context.
AI embedded from day one. Every recurring workflow gets automated or augmented. The operator builds systems — not just completes tasks. What they build stays when the engagement ends.
This isn't advisory. Operators get things done. Deliverables ship. Playbooks get written. Audits get completed. Cost-efficient, cap-table-light execution across GTM, ops, hiring, and culture — simultaneously.
Pear connects you to oAT. One meeting. Three weeks to momentum. No headcount. No equity. No eight-week recruiting cycle burning your critical window.
Pear connects you to oAT. One meeting. Three weeks to momentum. No headcount. No equity. No eight-week recruiting cycle burning your critical window.
Connect via PearMedian time from intro to first founder meeting: 1 day. 65% of founders move forward after that first call.
Not sourced. Matched. Senior operators who've done this before, deployed with the context to move fast.
Week one isn't ramp time. It's a structured diagnostic. By end of month one, you know what's broken and what's being fixed.
The median engagement is 3 months. More than half of founders keep going. The systems built in month one are still running in year two.