Onboarding is where retention starts. A customer who launches on time and sees results in the first weeks is far easier to renew and expand than one who spent three months stuck in setup. This is the checklist I use with enterprise customers, from the moment the contract is signed to the first value check.
Before kickoff
- Read the contract and the sales notes: what was promised, by when, and why they bought.
- Get a warm handoff from sales: the people involved, their goals, any concerns raised in the deal.
- Identify the customer's project owner and executive sponsor.
- Prepare a draft project plan with your proposed go-live date.
- Check any technical requirements: integrations, single sign-on, data imports, security reviews.
Kickoff call
- Confirm the customer's goals and how you'll both measure success.
- Agree on owners on both sides for every workstream.
- Agree on the go-live date and the key milestones before it.
- Agree on how you'll communicate: a shared channel, a weekly check-in, a status update format.
- Surface risks early: other priorities, holidays, approvals, technical blockers.
Setup and configuration
- Provision admins and users, with the right permissions.
- Complete integrations and test them with real data.
- Configure the product for the customer's first use case, not every possible one.
- Import or create the content and data they need on day one.
- Log every technical issue with a clear owner and a reproducible description.
Training
- Train admins to run the product without you. They're your long-term champions.
- Give end users only what they need to start, in short sessions or short guides.
- Record sessions and share them for people who couldn't attend.
Go-live
- Run a final check the day before: access, integrations, content, communications.
- Agree on who's on call on launch day, on both sides.
- Be available and watching on the day. Fix issues fast and communicate clearly.
- Send a short summary at the end of the day: what went live, any open issues and next steps.
Launch days don't always go to plan. On one launch I spent more than seven hours with the team fixing issues as they appeared. Customers remember who stayed with them.
After launch: the value check
- Two to four weeks after go-live, review adoption against the kickoff goals.
- Share the early results with the sponsor, in their terms.
- Agree on the next goal and the next phase.
- Hand over to ongoing customer success with a written success plan.
When the deadline is hard
Some launches can't move: a semester start, a product release, a contractual date. For those:
- Plan backwards from the date and build in buffer for the riskiest steps.
- Agree on what's essential for day one and what can follow later.
- Prepare a plan B for the riskiest dependency, and tell the customer you have one.
- Report status more often as the date gets closer.
This is how I've helped customers launch on deadlines, including Harvard's paid content and a partner who went live well before a hard September date.
Want onboarding run for you?
If your team doesn't have time to run onboarding like this, see how I run customer onboarding, or read how to reduce churn for what comes after launch.