Don’t hire a seller. Hire someone who runs the customer conversation themselves, thinks from the customer’s problem, works with your team and agrees results in measurable terms.
The problem with “we understand sales well enough”
I’ve had dozens of intake conversations with IT and cybersecurity companies looking for interim sales. Almost every one starts with the same question: can you sell?
The question worth asking is a different one. Do you understand what we sell, and are you going to do it yourself?
At CounterCraft, where I built the Benelux market, we sold deception technology. Digital bait and traps that detect an attacker early in the network, before he reaches the crown jewels. Try explaining that to a CISO without understanding yourself how an attacker thinks and what he watches for.
Doing the work is the test
Plenty of parties offering interim sales deliver advice. A strategy, a plan, a recommendation. After that your team has to execute it, with knowledge that often isn’t there yet.
That’s rarely what an IT organisation needs at the moment it gets stuck. They need someone who does the work alongside them: who runs the conversation with the customer, brings the deal in, and teaches the team how it works afterwards.
That’s how our commercial sales support is set up.
Ask the question literally in the intake conversation. Does this person run the customer conversations himself, or does he deliver advice that we then have to carry out? The answer separates an adviser from someone who actually works with you.
From selling products to the customer’s problem
The move from traditional IT services into cloud and cybersecurity is a commercial shift. Where you used to sell a product, you now sell an answer to a risk the customer doesn’t yet fully see.
A generic sales professional can hold a perfectly good conversation about budget, timing and decision-making. But the moment the technical architect joins and the question becomes “what do we risk if we do nothing”, it goes quiet. And in cybersecurity that question is at the table more often than you’d like, if you selected on sales skill alone.
Ask for concrete evidence that someone speaks that language, rather than taking it as read. I hold all 5 commercial Splunk accreditations. I did them because I wanted to understand what I was talking about the moment I sat down with a SOC manager. That kind of evidence is checkable. “I have 20 years of experience in IT” isn’t.
One business owner reached that conclusion the same way, in a conversation that started somewhere else entirely. His story is in Business development starts a step earlier.
Working with your team
Sales is not a solo activity. Ask how an interim professional works with your team, whether that means training your salespeople, setting up joint campaigns or approaching new markets. A joined-up approach delivers more than someone who works from an island and disappears the moment the engagement ends.
I should be honest about a real trade-off here. An agency has something a self-employed interim professional doesn’t: scale, and cover during illness or holidays. With a freelancer you get that one person, and nobody else.
What you get in return: no account handoff, no briefing lost between intake and execution, and someone who stays responsible for the result with your team and with the partners around it. For a complex, technical proposition with a long sales cycle, plenty of companies weigh that more heavily than the cover an agency offers.
Measurable results
When I started at CounterCraft there was no market for deception technology in the Benelux. No category buyers were searching for, no established competitive comparison, no reserved budget. That’s different work from taking over a running pipeline with existing leads.
So don’t ask a candidate for past revenue figures as a standalone fact. Ask how he makes results measurable: which KPIs he agrees upfront, how often he reviews them, and what happens if a target isn’t met. A good interim professional is willing to have that conversation before the contract is signed, rather than after.
What to ask before you sign
A few questions you can put literally in the intake conversation:
- Does he run the customer conversation himself, or does it stay at advice your team then has to execute?
- Can he hold the conversation from the customer’s problem, at the table with a technical architect or CISO, without you having to step in
- What demonstrable evidence of knowledge in this field is there, beyond “years of experience”?
- How does he work with your team and with the partners you need, rather than operating solo
- Which KPIs does he agree upfront, and how does he review them along the way?
Push on each of these. The answers tell you more about the fit than any sales pitch.
Frequently asked questions
What’s the difference between hiring interim sales and engaging a sales agency?
At a sales agency you often have the intake conversation with the most experienced person on the team, while a junior business development rep does the actual work. With a self-employed interim professional you get that one person for the whole engagement: no account handoff, and also no cover during illness or holidays. The choice depends on whether you need volume work or a complex, technical proposition with a long sales cycle.
How much domain knowledge does an interim sales professional need in cybersecurity?
Enough to hold the conversation the moment the technical architect or CISO joins, without you having to step in. Concrete evidence such as accreditations is checkable. “Years of experience” isn’t.
How do you tell whether an interim professional runs the sales conversation himself, or only advises?
Ask it literally in the intake conversation: who is sitting at my customer’s table in 3 months’ time? An adviser delivers a plan your team has to carry out. Someone who does the work runs the conversation himself and teaches your team how it works afterwards.
What are realistic KPIs to agree upfront with an interim sales professional?
That varies by engagement, and it’s about the process rather than one fixed number: which KPIs the professional agrees upfront, how often he reviews them, and what happens if a target isn’t met. A good interim professional has that conversation before the contract is signed, rather than after.
