The Go-Live Gap, episode 2

What is the hardest part of customer onboarding?

The hardest part of onboarding a B2B customer is rarely the software. Skyler Johnston has spent twenty years in support, sales, implementation, and onboarding for inventory and warehouse software, including years of on-site training, and he describes the work as solving for a customer's pain and their future pain, with people at the center of both. He explains why two companies in the same industry can have opposite problems, why he puts executives and warehouse staff in the same room on purpose, how he handles an economic buyer who wants to stay hands-off, what AI should fix first in implementation, and why a leader measured on time to value still asks his team for patience.

Key takeaways

From Skyler Johnston, SVP, Premier Tech Partners; twenty years across support, sales, implementation, and onboarding for inventory and warehouse software.

1. Solving for pain means the current pain and the pain the customer will hit next. Two flooring companies with similar bills of materials had opposite problems, one with materials and vendors, the other with staffing. Discovery rarely templates cleanly by industry.
2. Jumping to the solution is the mistake he learned the hard way. When you assume the answer, the customer stops feeling heard and the whole project gets harder. Patience and repeated why questions, asked with sincerity, are the fix.
3. The person on the warehouse floor often has insight the C-suite does not. Putting stakeholders and operators in one room and asking them to walk through pick, pack, and ship tends to surface the real problem, even when they turn on each other.
4. A hands-off economic buyer sometimes wants deniability. Separate one-on-one conversations, regular health checks, and restated expectations keep them attached to the outcome.
5. Scope changes constantly, and sign-off from every stakeholder on each change is what prevents isolation and frustration later. A migration that grew from one year of data to four is his example.
6. Implementation does not pause the customer's day jobs. Weekly or monthly realignment calls, plus forgiveness when life derails a week, keep projects moving.
7. AI's first job in implementation is carrying the first discovery call intact to a go-live that might be ten months away, so the customer does not repeat themselves at every handoff. He does not expect AI to skip the process itself.
8. Notes that capture only words miss the energy. Document how a customer reacted to a module, since that reaction builds the relationship and predicts success.

Questions this episode answers

How do you find the real problem when a customer describes a symptom?

Ask why several times, with patience and sincerity. Skyler's experience is that the person describing the problem often knows how to solve it and needs someone to work through it with them, since they know their industry better than any consultant.

What does a good sales-to-implementation handoff look like?

The implementer is brought in before the close where possible, so the relationship starts early. Sales notes capture the main pain points and how the customer reacted to what they saw. At the support handoff, an account manager or project manager stays with the customer so they are not thrown into a pool.

How do you measure time to value when the customer wants to skip to the end?

Break it into phases, call out the small successes, and call out red flags early, including a problem that was not fully scoped. Keep the focus on the challenge rather than on whose fault it was, because blame wastes time.

Should implementation professionals worry about AI taking their jobs?

Skyler expects jobs to evolve and some tasks to need fewer people, with new opportunities opening up. His advice is to stay hungry, stay curious, and use the tools to learn faster, since people remain central to implementation.

Where Stipulate fits

Skyler's wish list for AI in implementation is that the first discovery call survives to a go-live ten months later without the customer repeating themselves, and that handoff notes capture what mattered and how the customer reacted. Stipulate reads the shared Slack channel across sales, implementation, and support, so the pain points, decisions, and open commitments stay attached to the customer through every handoff.

About Skyler Johnston

SVP, Premier Tech Partners; twenty years across support, sales, implementation, and onboarding for inventory and warehouse software

• linkedin.com/in/skyler-johnston

Related reading

• How to Track Decisions and Action Items in Customer Slack
• Sales to Onboarding Handoff: Checklist & Playbook (2026)
• Time-to-Value & Go-Live