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THE INTERVIEW
THURSDAY
STATE
OF SALES
The State of Sales right now….
It's very muddled. So much noise, so much uncertainty over how quickly the tech has evolved. Roles are getting completely tweaked, they're becoming much more technical, and it's moving away from general sales toward process and efficiency.
THE SETUP
Jonathon Ilett is CEO and co-founder of TrustedIQ, the AI-native platform turning signed contracts into trusted commercial data. Before that he was VP of Global Sales at Cognism. So he has scaled the old outbound playbook, and now he's betting against parts of it.
THE 60-SECOND VERSION
Hire technically minded reps. One systems-builder managed five times the opportunities of everyone else.
28% quota attainment is leadership maths. Aim for 60% hitting and 90% at the 80% mark.
Land tiny pilots and expand. AI buyers are allergic to 12-month upfront contracts.
Watch your token economics. SMB outbound has roughly two years left.
3 THINGS YOU'LL STEAL FROM THIS
The rep profile that managed five times the opportunities of everyone else
Why only 28% of reps hitting quota is a leadership choice, with the maths
The unit economics warning every CRO selling AI needs to hear
01 · Hire the rep who builds systems
The core attributes haven't moved: hunger, intelligence, drive. What's changed is the layer on top. Jonathon now hires for technical mindedness and asks for proof: show me where you've optimised something and increased output.
At Cognism we had one great rep in the enterprise team who could manage probably five times the opportunities of everyone else, because he built all these systems and processes and created the context for the LLMs. The next wave will be very similar to that.
The winning teams he sees follow the same pattern at the org level: very senior people, sometimes ex-directors returning to IC roles, given room to produce rather than a bloated team beneath them. "You hire very good people, you max them out, and then you add people. Rather than throwing headcount at a problem with very junior people."
DO THIS THIS WEEK
In your next interview, ask the candidate to walk you through one process they've automated end to end. No example is an answer too.
02 · 28% of reps hit quota. That's a decision someone made
We asked whether quota attainment collapsing to 28% is a rep problem, a leadership problem or a data problem.
Mainly a leadership issue. In VC-backed businesses, leadership comes in with an expectation that 80% of the team will miss, and if 80% miss, we still get our overall number. That transcends down to the reps.
His alternative maths is a framework any leader can adopt tomorrow:
60% of reps hitting quota. The health marker.
90% at 80% of quota or better. The floor.
The bottom layer either gets performance-managed or leaves naturally.
STEAL THIS
Run your team against those three numbers today. If you're miles off, the fix starts in planning season, never on the sales floor.
03 · Land tiny, prove it, expand
On channels, Jonathon doesn't hedge. Cold calling still breaks through. Face-to-face is back, with small ICP dinners paying off. Email just doesn't work anymore. But his sharpest point is about how AI-era buyers want to commit.
There's a lot more risk aversion with AI tech. Getting 12-month contracts upfront is not really the way. The old way of selling has to change: how do you create an environment with limited friction, get them live and operational, and then naturally upsell that account?
His own motion at TrustedIQ: find the team inside the company with the highest interest in AI rollout, run a small pilot, get the proof point, expand. The enterprise fundamentals still wrap around it: multi-threading, business cases aligned to corporate OKRs, and executive presence in the room.
TRY THIS THIS QUARTER
Take your smallest sellable unit and price a 60-day pilot around it. Measure expansion revenue, never initial contract size.
04 · The token bill is coming for your unit economics
Jonathon's most urgent warning came from inside his own portfolio work: an AI company selling at around £80k a contract while spending roughly three times the contract value on LLM compute per customer. Every deal burned cash, and the next fundraise stalled on it.
Everything's moving from seats to token consumption. We had an instance in our own business where we didn't have the right parameters in place, and in a month it completely threw our financials out. You need a really good understanding of the unit economics across your different segments.
That logic drives his boldest prediction: SMB outbound has roughly two years left. With SMB GDR churn running at 60 to 70% in the portfolios he's seen, and SDR salaries pushing cost per lead ever higher, the economics simply stop working. "True sales will sit in enterprise and upmarket, and it'll be very strategic selling."
THE MOVE
Calculate the fully loaded cost per lead for each segment you sell into, including AI spend. Kill or automate any segment where churn eats the margin.
THE ONE THING
Know your numbers. You can backtrack your entire target from your conversion rates.
WHERE TO FIND JONATHON
Jonathon Ilett is CEO and co-founder of TrustedIQ, the AI-native contract-to-cash intelligence platform giving RevOps, finance and legal teams a single source of truth across contract data. Find him on LinkedIn or visit trustediq.com.