Who Is Training the Next Generation of Great Technology Salespeople?
At our SaaS Leadership event last Friday, a question came up during the panel discussion that I haven’t been able to put down since.
Who is training the next generation of great technology salespeople?
It sounds like a simple question. The longer I thought about it, the less sure I was of the answer.
The companies that used to do it
When I started recruiting in technology almost 30 years ago, a handful of companies had a reputation for producing exceptional salespeople. IBM. Xerox. GE. ICL. Wang. Hoskyns.
They didn’t hand someone a territory and a target and wish them luck. They trained them. Properly.
Joining one of those organisations was close to a postgraduate education in technology sales. As a recruiter, you knew it. One of those names on a CV told you something before you’d read another line: this person had been taught the craft, and taught it well. They had an edge.
What did they learn?
- How to understand a customer’s business before talking about their own product
- How to ask good questions, and then listen to the answers
- How to talk to senior executives without being out of their depth
- How to navigate a complex organisation and find out who really makes the decision
- How to negotiate and close significant commercial deals
And they learnt it alongside people who had already mastered it. That part mattered as much as any classroom. You watched how an experienced account manager ran a meeting, handled an objection or walked away from a bad deal, and you absorbed it.
Many of the outstanding sales leaders I’ve met over the past three decades started in environments like these.
So what replaced it?
Certainly not university. Very few degrees teach anyone how to sell complex technology to a sceptical finance director.
Today’s salesperson has more technology, data, automation and AI than we could have imagined back then. CRM, intent data, sequencing tools, call recording, conversation intelligence, AI-drafted emails. The toolkit is extraordinary.
But a better toolkit and better selling are two different things. Giving someone better technology isn’t the same as teaching them how to sell.
My suspicion is that investment in sales productivity has outpaced investment in sales people. When every quarter is under scrutiny and the brief is to do more with less, the tool with a clean ROI slide gets signed off. The six-month development programme doesn’t.
To be fair
I’m not saying sales training has disappeared. Plenty of SaaS businesses run onboarding programmes, sales methodologies and enablement teams, and some do it very well.
The landscape has also changed dramatically. Buyers do much of their research before they ever speak to a salesperson. Sales roles, cycles and routes to market look nothing like they did in the 1990s, and nobody is suggesting we rebuild the old corporate training centre.
But the sense I hear from experienced leaders is remarkably consistent. There is less of it. It is more piecemeal. And it is rarely taught with the intensity it once was.
Why this matters for SaaS leaders
This isn’t nostalgia. It shows up in hiring.
When I’m searching for a VP Sales or CRO today, one of the questions I keep coming back to is where the candidate learnt their trade. Some had a brilliant early manager. Some worked in a business with a real coaching culture. Others learnt entirely on the job. That can produce resilient, resourceful people, but it can also leave gaps that only show when the deals get bigger and the stakeholders more senior.
For growth-stage and PE-backed SaaS businesses, that has consequences:
- Thinner benches. If nobody is developing the next layer of sales talent, everyone ends up competing for the same small pool of proven leaders.
- Slower ramp times. You hire for experience you assume someone has, then find out they never had the chance to build it.
- Leaders who can sell but can’t teach. Great salespeople who were never properly coached often struggle to coach others.
It also feeds straight into succession planning. You can’t promote from within if nobody within has been developed.
If the old academies have gone, the responsibility has moved. Every SaaS business that wants great salespeople in five years’ time has to help produce them now.
What good looks like today
The best businesses I work with tend to share a few habits:
- Onboarding that goes beyond the product. New hires learn the customer’s business, the buying process and the commercial model, not just the demo.
- Time with people who have done it. Shadowing, paired calls and proper deal reviews, where experienced sellers explain their thinking.
- Coaching as part of the manager’s job. Front-line managers are measured on how their people develop, not only on the number.
- Technology that creates time for coaching. AI and automation take the admin away so managers and reps can spend more time on the craft.
Over to you
Which company, or which leader, gave you your real sales education?
And who is doing it brilliantly today?
I’d like to hear the answers. If your business is building a genuine sales academy, or you learnt your craft somewhere that deserves the credit, get in touch. And if you’re looking for a sales leader who can build and develop a team, not just hit a number, talk to us about SaaS executive search.
Frequently asked questions
Which companies were known for training great technology salespeople?
Over the past 30 years, IBM, Xerox, GE, ICL, Wang and Hoskyns were widely regarded as producing exceptional technology salespeople. Their programmes combined intensive formal training with learning alongside experienced sellers.
Is sales training still happening in SaaS?
Yes, but experienced sales leaders report there is less of it, it is more piecemeal and it is rarely as intensive as the programmes run by the large technology companies of the past.
Why does sales training matter when hiring a VP Sales or CRO?
Where a sales leader learnt their trade shapes how well they can coach, build a team and handle complex, senior-level deals. Leaders who were never properly developed can find it harder to develop others.