Director of Onboarding Operations

We are a U.S.-based software company. Our platform handles registration and payments for everything schools run outside the classroom: after-school enrichment, summer camps, athletics, and facility rentals. We are a team of about fifteen people, and we lean on AI heavily in our day to day work. Several functions here are supported by AI agents we built ourselves, and that shapes how we approach most problems.

This is an operations role more than a support role. The work is designing the system: who does what along the way, how long each stage should take, and which parts we can automate so nobody has to do them again.

In one sentence: you own how a school gets from a signed contract to running our platform confidently on its own, and you turn that into a repeatable system rather than a series of one-off efforts.

Today our onboarding works because talented people work very hard. A school signs, one of our team members meets them, builds out their programs, walks them through registration, and stays close through the first season. It usually goes well, and schools genuinely enjoy working with us.

What we are missing is the structure underneath that. Because there is no defined process, every school is handled a little differently. Because there is no shared definition of "done," no school ever feels like they finished onboarding. And since nobody finishes, schools that went live months ago keep coming back with setup questions that land on whoever happens to be closest.

As a result, schools that launched a year ago are still requiring too much of our time. We need someone to own designing an onboarding process that can scale systematically.

The process itself. The onboarding stages, what happens in each, who does it, how long it should take, and what the school is responsible for versus what we do for them. Today this lives in two people's heads, and we would like it to live in a system anyone on the team can follow.

Graduation. Define what it means for a school to be successfully onboarded, build the checklist that demonstrates it, then hold schools to it and hand them off. We think this is the most important thing you will do, and also the hardest, because it means telling a school we enjoy working with that they are ready to move on.

Post-go-live enablement. Live schools still sometimes need help setting up the next season, changing pricing, pulling reports their finance office asks for, or training a staff member who joined mid-year. Your role is less about answering those questions than building a system that answers them: the self-serve library, templates, defaults, and routing that mean most schools never need to ask, and the ones who do get pointed to a resource rather than handed to someone who does it for them.

Automation and AI. We expect you to look at your team's work and steadily reduce it. Some of that is templates and defaults in the product, some is a request to engineering, and a meaningful portion is you building AI agents and workflows yourself.

The numbers. Time from signed contract to go-live, schools onboarded per person, the share of schools graduating within their first season, and whether post-go-live requests are coming down per school. You would establish the baseline in month one, since we do not have one today, and then own moving it.

First 60 days. A written definition of graduation agreed with your team. Baseline metrics in place so we know our real time-to-go-live and per-person capacity. One meaningful step of onboarding automated end to end.

First year. Every new school runs through one defined process with clear stages, owners, and timelines. Schools graduate on a predictable timeline and the handoff is real rather than theoretical. Post-go-live questions have a clear home and a self-serve first line of defense. Each person carries measurably more schools without a drop in quality, and onboarding capacity is no longer the constraint on how fast we can sell.

• 8 or more years in customer onboarding, implementation, or customer operations at a B2B software company, including 3 or more years leading a team.
• You have owned an onboarding or implementation function rather than only worked inside one. Ideally you stood one up, or rebuilt one that was not working well.
• Your customers were not technical. You are comfortable with people who are excellent at their jobs and uneasy with software.
• Written and spoken English at a near-native level. You would author the material our customers learn from, and you will be on calls with heads of school and business officers.
• You work US business hours.
• We do not require experience in education or edtech. The transferable skill is getting non-technical customers successfully onto software, and we can teach you how schools work.

This is not a support or ticket-queue role. If the work you are proudest of is measured in tickets closed, queue coverage, or CSAT, this may not be the right fit, and we would rather say so now than discover it later. The success we are hoping for looks like questions that gradually stop being asked.

You would report directly to the CEO with a lot of access and a lot of autonomy. There is no playbook waiting for you. Writing it is a large part of the job.