Hiring salespeople who can work with AI

Hiring a salesperson who can work with AI means checking their sales judgement as well as how they use the tool. A short fictional buyer conversation followed by an AI-assisted follow-up gives the hiring manager something to discuss in each part.

Eric Siu describes a disagreement about hiring. He argues for finding someone who already has both sales and AI skills; the position he attributes to Neil is to hire for selling and teach the AI. His account describes their experience. It does not establish which hiring approach would work in another company. The manager still has to decide what the person must be able to do on arrival and what the team can help them learn.

What does the salesperson need to do?

Start with a piece of work the new hire will own. That makes the hiring question more useful than asking whether someone considers themselves AI-native.

Take a hypothetical company selling workshops to business teams. The salesperson needs to understand what a prospective customer wants to change, explain what the workshop covers and agree on a useful next conversation. The hiring manager can prepare a short fictional brief with the offer and a buyer situation. Use the same brief and available tools for the candidates being compared, and explain what the exercise is for.

Have the candidate talk with someone playing the buyer. The fictional buyer might want a workshop next month but be unsure which people need to attend. Listen to how the candidate finds out what the buyer needs before discussing a proposal. Afterward, ask what they learned and what they still need to ask. The discussion gives the manager an observed example to examine alongside the rest of the hiring evidence.

Can the candidate check an AI-assisted follow-up?

Ask the candidate to use an agreed AI tool to prepare a short follow-up from the fictional conversation. Keep the task small enough to discuss the result together. Use the fictional material, so the exercise does not require a candidate to share customer information from a previous employer.

Read the message with the candidate. Which details came from the conversation? What does it say the company will do? What would they change before sending it? If the draft says the workshop is booked while the buyer only asked about availability, ask the candidate to explain the difference and correct the message. That is a hypothetical error to look for, not a claim that the tool will produce it.

A polished message alone leaves the manager with limited evidence about how it was prepared. The candidate's explanation can show what they checked, which parts they kept and where they needed help. Someone who has used a different tool may need orientation. Keep that learning need separate from a decision to promise work the company has not agreed to deliver.

A brief exercise shows what happened in that exercise. It cannot establish how the person will perform across a sales role. Keep other relevant hiring evidence in view, and avoid turning one good draft into a general claim about selling ability.

Which learning gap can the manager support?

Name the gap before deciding that the company can teach it. If a candidate handles the buyer conversation well but needs help with the AI tool, identify who could provide that help and what the candidate would need to practise. Ask what that would require from the manager during the first weeks.

If the candidate operates the tool fluently but cannot explain what the buyer asked for, the manager has a different question to resolve. Discuss the part of the conversation that was missed. Decide what evidence or further discussion would help assess that gap before making the hiring decision.

Keep a short record of what the candidate demonstrated, what remains uncertain and what support the company is prepared to provide. A subscription price or an AI-native label does not supply those answers. The Sales Engineering manager's role raises a related leadership question: what standard will the manager hire to, and how much time will they have to develop the team?

A company planning to change its commercial work with AI can bring the actual role and the work it needs done to an AI advisory discussion. The useful starting point is the task the new employee will own and the learning the company can realistically support.