SaaS onboarding averages 5.7 months, not the three companies plan for. Hire for coachability, start with the customer, and measure competency, not time.
Key takeaways
Two interview questions predict performance months out: “What research did you do to prepare for this meeting?” and “What did you learn that you didn’t know?” Regan’s two best hires gave the standout answers.
Order matters. Mission and values, then the customer and their problems, then sales process, then product, then role play, then independence. Start with product and you build feature-floggers.
Separate compliance training from the development plan. Tick-the-box modules cause fatigue that bleeds into the real learning.
Fight the forgetting curve with a living company handbook. New hires forget 90 percent of week one. Give them somewhere to go back to that isn’t a buddy’s calendar.
Build in teach-backs, a practice from Stripe’s sales academy discussed on air, and role play in a safe environment. Practise on avatars, not customers.
Map 30, 60, 90, and 180-day milestones and grade competency against key skills. Week-one red flags, like ignoring feedback or waiting to be handed work, predict the rest.
They think onboarding lasts about three months, but with SaaS it’s actually pushed out to about 5.7 months. There’s a 40 percent increase in that time for more complex sales.
Regan Barker, co-founder, Ricavi
If you don’t give them the time, that individual will start to build certain habits, potentially bad habits, and then you’re trying to re-manage them. This is where things go south.
Luigi Prestinenzi, co-founder, Ricavi
Why does onboarding take twice as long as anyone plans for?
Because “meet the team, have lunch, here’s your laptop” isn’t onboarding. Regan Barker’s numbers put software ramp at nearly six months, and professional services, manufacturing, and financial services longer still. David Fastuca does the cost: recruitment, legal, the buddy’s lost time, and the salary paid before a single dollar closes. Hire the wrong person and you start again. The founders’ argument is that most of that risk is decided in the first month, not the first year.
What should you hire for?
Agency. Luigi Prestinenzi tells the story of a rep who came to him with no sales experience and became the best performer in the business. The energy and the thirst to learn were obvious in the interview. Regan hires on two questions about preparation and learning, and the people who answered well are the people winning now. David’s red flag is the reverse: an A-player in onboarding doesn’t wait to be handed a customer. They go looking, then bring questions.
The founders differ on speed. David thinks a strong hire should be on the tools inside a week. Regan cites six months for anyone, including high performers. Luigi’s reconciliation is that a founder-led company and a mid-market enterprise are different animals, and the plan should say what “good” looks like at day five, day 10, day 20, and beyond.
What does the plan actually contain?
Customer first. Luigi’s view is that most programs jump to product and miss the people you serve. Regan traces the best sellers she’s seen to time spent with customers before they ever sold. So the first 90 days go: who we serve and what hurts them, then how we sell, then what we sell, then role play, then the deep end. Bake in a competency matrix with five to eight key skills and grade against it. Add teach-backs, where the new hire explains a module to others. Add a handbook, which David and the team use as the company’s DNA for a remote team. And treat the whole thing as a project with an owner, because you’re spending one of the most expensive resources you have.
Questions this episode answers
How long does sales onboarding really take?
About 5.7 months in software on average, according to figures discussed on the episode, and materially longer for complex B2B sales. Most leaders plan for three.
What should sales onboarding start with?
The customer. Who they are, what problems you solve, and how they buy. Product training comes after that context exists, otherwise new reps learn to list features instead of diagnose problems.
How do you tell in the first week whether a new sales hire will work out?
Watch for agency. Strong hires research, self-start, and act on feedback within days. Waiting to be assigned work and repeating the same mistake after feedback are early warnings.
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David Fastuca
CEO & Co-Founder
