Sales onboarding is broken in a way that most companies don’t seem particularly interested in fixing.
Companies hire a salesperson, give them access to a mountain of training material, product decks, competitive battlecards, process documents, CRM training, objection-handling scripts and a library of videos, and then expect them to start selling.
Some companies at least give new reps a compass. Others essentially throw them into the ocean and tell them to figure it out.
Then, when the salesperson struggles to create pipeline or close deals, everyone starts looking at the salesperson.
I’ve been through several sales onboarding programs myself, and there is one thing that has always bothered me: very few of them properly teach the buyer.
I was taught the product. I was taught the features, pricing, competitors, objections, CRM and sales process. All of those things are important, but they answer a relatively simple question: What are we selling and how do we sell it?
The more important question is often left unanswered: Who are we actually selling to?
Sales Onboarding Should Start With the Buyer
Before a salesperson learns every feature of a product, they should understand the person sitting on the other side of the table.
What is that person measured on? What targets are they expected to achieve? What problems keep coming back? What are they under pressure to deliver? What keeps getting escalated to them? What happens if they don’t solve the problem? Who else is involved in the decision? And, most importantly, what problem are we actually solving for them?
These aren’t nice-to-have questions that a salesperson can figure out after joining the company. They should be at the centre of the onboarding process.
A salesperson can know every feature in a product and still have a terrible sales conversation. They can explain the technology perfectly, walk through every capability and answer every product question, yet completely miss what the buyer actually cares about.
Knowing what you sell doesn’t automatically mean you understand why someone should buy it.
That distinction is particularly important in B2B sales, where buyers aren’t simply purchasing features. They are trying to solve business problems, reduce risk, hit targets, save time, increase revenue, reduce costs or make their own jobs easier.
A good salesperson needs to understand that context before they can have a meaningful conversation.
Your Best Sales Training Material May Already Be Inside the Company
The interesting thing is that companies often already have most of this knowledge. They just don’t package it as sales onboarding.
Start with the founder.
In many companies, the founder started the business because they experienced a problem themselves or saw it closely enough to believe it needed solving. That story contains something a product presentation rarely can: the original reason the company exists.
A salesperson who understands that story can explain the problem differently. Instead of saying, “Our platform has these 15 capabilities,” they can explain why the company was created, what problem it set out to solve and what they have learned from customers along the way.
Then talk to the product team.
Product managers and product leaders have spoken to customers, prospects and internal teams. They know which problems repeatedly come up in conversations and which customer requests eventually became product features. They also know which features customers actually use and which ones sound impressive in a demo but rarely influence a buying decision.
That is valuable sales knowledge.
Then talk to the implementation or customer success team.
They have seen what happens after the contract is signed. They know how customers were solving the problem before the product was implemented, where the old process broke down and what changed after implementation. They have stories about customer outcomes that are often far more persuasive than a generic product pitch.
That is sales gold.
These are the stories that salespeople can take into customer conversations because buyers can relate to problems, situations and outcomes far more easily than they can relate to a list of features.
The First 30 Days Shape How Reps See the Market
At one point, I seriously considered starting an agency called First30Days to help companies rethink their sales onboarding.
As part of the research, I spoke with around 30–40 AEs and SDRs, along with several Sales and Sales Enablement leaders. What I found was surprisingly consistent.
The technology and format varied, but the underlying philosophy didn’t change much. Some companies had sophisticated LMS platforms with structured learning paths. Others relied on documents, Excel sheets, presentations and videos. But most followed roughly the same sequence: teach the product, teach the process, teach the tools and then send the rep out to sell.
Very few started with the buyer.
That matters because the first few weeks aren’t simply about transferring information. They are shaping how a salesperson understands the market.
If the first thing a new rep learns is a product deck, they naturally begin to see the world through the company’s product. Every customer problem starts looking like an opportunity to demonstrate a feature.
If the first thing they learn is the buyer, they start from a different place. They learn to recognise problems before jumping to solutions. They understand the pressures their prospects operate under and can connect the company’s offering to those problems more naturally.
That shift can fundamentally change how a salesperson approaches discovery, qualification and even prospecting.
Product Knowledge Is Necessary. Buyer Knowledge Is What Makes It Useful.
This isn’t an argument against product training. Salespeople absolutely need to understand what they’re selling.
But product knowledge should be the foundation, not the destination.
A new salesperson should be able to answer three questions before they are expected to confidently sell:
Who is our buyer? What problem are we solving for them? Why does our company exist to solve that problem?
Once those questions are clear, the product, features, competitive positioning, sales process and CRM training start making much more sense.
The salesperson isn’t memorising information anymore. They are building a mental model of the market and learning where their product fits into it.
And perhaps that’s what good sales onboarding should really be about.
Not teaching a salesperson everything the company knows, but teaching them enough of what matters to have a meaningful conversation with the people they are expected to sell to.
When a salesperson struggles after onboarding, the first question shouldn’t always be, “What’s wrong with the rep?”
Sometimes we should ask a different question:
“What did we actually teach them about the buyer?”
Because if we spend the first 30 days teaching salespeople everything except the customer, we shouldn’t be surprised when they spend the next 300 days struggling to sell to one.