Insights from Craig Jones, CRO at Star Compliance
Craig Jones has spent 25 years in go-to-market roles — from Accenture to Oracle, SAP and Workday, and most recently leading revenue at high-growth private equity-backed businesses. As CRO at Star Compliance, he’s grown revenue by 30–40% with a smaller sales team than when he started. We sat down with him on Rev-n-u Unplugged to get into the how.
What follows are the lessons, frameworks, and hard-won insights that any sales leader or rep can put to work.
The Biggest Positioning Mistake You’re Probably Making
Most companies position themselves as better than the competition. The problem? That forces your sales team into comparison conversations, price pressure, and endless feature debates. Real positioning, Craig argues, does something completely different.
“Great positioning answers three things clearly: who is it for, what problem is urgent now, and why the status quo is no longer acceptable. If a rep can’t explain why a buyer should act this quarter rather than next year, your positioning isn’t finished.”
The shift is from selling what the product does to selling why a buyer should change. It sounds straightforward, but it’s a discipline most organisations haven’t truly built. The result of getting it wrong is the most frustrating outcome in sales — the no decision. Not a lost deal, just indefinite stalling.
When companies fix this, win rates go up and the pipeline starts moving again.
How to Know If Your Messaging Is Actually Working
Craig doesn’t look at brand surveys or NPS scores to gauge messaging effectiveness. He looks at call recordings and deal reviews.
The questions he asks are simple: Are reps leading with the same problem framing? Are they handling objections consistently? If your top performers are rewriting the pitch, that’s not a sales problem — it’s a messaging failure.
The clearest signal that messaging is working? New reps ramp faster. They become fierce product learners because the story is clear and repeatable. The heavy lifting shifts from figuring out what to say to actually saying it well.
If win rates aren’t improving and you’re blaming the reps, it’s worth asking whether the message they’ve been given is actually fit for purpose.
ICP: The Honest Conversation Most Teams Avoid
Most sales teams have an ICP. Most of them also quietly ignore it when things get slow and start chasing the edge cases — the deals that sort of fit, that might convert, that are better than nothing.
Craig is direct on this: chasing the wrong customers kills win rates, wastes sales cycles, and produces customers who don’t stick around long enough to generate real ROI. The fix isn’t more qualification training — it’s tightening the ICP itself and being willing to walk away earlier.
He recommends revisiting your ICP every 12 to 18 months at minimum. At Star Compliance, they run a formal targeting and segmentation process every year, actually removing companies from their ICP when they no longer represent the best right to win. They call it “new dirt” — a fresh set of accounts for reps to go after with genuine conviction.
The other critical concept Craig introduces is the economic buyer. Knowing who uses the product is table stakes. Knowing who feels the financial pain if the problem isn’t solved is what closes deals. When you can map that out and build a business impact analysis around the cost of indecision, you put the urgency in the buyer’s hands rather than relying on artificial pressure from your side.
What the First 90 Days Should Actually Look Like
There’s a temptation for new sales leaders to go in hard on new logo wins early — to show results, prove themselves, and move revenue quickly. Craig takes a different view.
In his first 90 days at Star Compliance, he deliberately avoided touching headcount, comp plans, or tooling. Instead, he focused on diagnosing three things: ICP clarity, win/loss patterns at deal level, and what the top reps were doing differently from everyone else.
“Most go-to-market problems are upstream,” he says. “They’re positioning, qualification, sales motion. Scaling chaos just makes things worse faster. Fix the story and the target first, then worry about scale.”
The other thing he did immediately was segment new logo and expansion business into separate motions. The skills, DNA, and mindset required to win a new customer are genuinely different from those needed to expand an existing one. Keeping them blended means neither gets done particularly well.
For anyone asking how to get board buy-in for this slower, diagnostic approach: Craig’s answer is quick wins. Identify low-hanging fruit that delivers immediate impact, build trust, then layer in the structural changes. By the end of year one, you’ve got a track record and the credibility to ask for the budget you actually need.
SPICED: A Methodology Worth Knowing
Craig has worked with Challenger, MEDIC, MEDPIC, and SPICED across his career. At Star Compliance, he chose SPICED — and the results speak for themselves: funnel conversion from 7% to 47% through advanced stages, a 30% reduction in pipeline age, and sales cycle reductions across both new logo and expansion.
SPICED stands for:
Situation — Do you understand enough about the prospect to know why they’d act? (Why do anything? Why now? Why us?)
Pain — What do you know about their business that your solution meaningfully addresses?
Impact — What’s the ROI? What does solving this problem actually mean for their business?
Critical Event — What’s the urgency driver? A contract expiration, a regulatory audit, a breach with another vendor, a cost-containment initiative?
Decision — Who decides, and how?
The reason SPICED worked in Craig’s context was that it mapped naturally onto the buyer journey across multiple subsectors in financial services. The pain points vary; the framework doesn’t. That consistency is what makes it repeatable at scale.
One of the most impactful operational changes Craig made was cutting the pipeline from nine stages to five. Not because nine was inherently wrong, but because some stages in the middle couldn’t justify their own existence. Consolidating them forced cleaner entry and exit criteria — and as a result, reps spent less time managing pipeline admin and more time actually selling.
Sales Enablement: The Function Most Businesses Underestimate
Craig’s first hire at Star Compliance was a sales enablement leader. Not a senior AE, not a RevOps analyst — someone whose entire job was to make the rest of the team more effective.
The reason was straightforward. When he arrived, there were 45 different decks going to 10 different types of customers. Every rep was telling a slightly different story. That inconsistency doesn’t just create confusion — it makes it nearly impossible to diagnose what’s actually working.
“Most sales enablement fails because it focuses on content instead of behaviour,” Craig says. “More decks don’t change performance. Repetition and coaching do.”
At Star Compliance, this means a weekly enablement series covering objection handling, product updates, and competitive positioning. Every team member goes through certification. And critically, enablement isn’t just a sales function anymore — it’s been extended across customer success, professional services, and finance, so the entire organisation understands what the company does and how it creates value.
The test Craig applies to any enablement initiative is simple: can you clearly explain what reps will do differently in their next call? If not, it’s noise.
Doing More Revenue with Fewer People
For 2026, most sales leaders are being asked exactly this: hit a bigger number without adding headcount. Craig’s done it. Here’s what he says actually drives it.
The single biggest lever is targeting and segmentation. Not TAM, SAM, and SOM — those are abstractions. What matters is your total relevant market: the companies where you have the best and fastest right to win right now. Focusing there, obsessively, is what drives efficiency.
Combined with tighter positioning, better ICP qualification, and a genuine partnership with marketing — aligned on the product roadmap, campaign infrastructure, and sales motions — the engine runs harder with less waste.
Craig’s team today is roughly 15% smaller than when he started. Revenue is significantly higher. The difference is that every rep is working the right accounts with the right message using a consistent, repeatable process.
The CRO vs. the Super Sales Manager
There’s a distinction worth making clearly, because a lot of companies hire for one while wanting the other.
A Chief Sales Officer can be highly effective in a remit focused on new logo only, or on expansion, or on a specific segment. They’re close to the ground, driving execution.
A Chief Revenue Officer is a revenue architect. They’re pulling marketing, product, sales, and customer success into a single operating flywheel. They look at data to understand where the leakage is, where the drift is, and where to apply pressure.
Craig spent 10 years at Accenture learning to make decisions from data at C-suite level. That background shapes how he operates: “Senior leaders don’t make decisions on ideas. They make them on data.” Building a business case from facts, not instinct, is what allows a CRO to move a company in a particular direction — and get the board to follow.
The Takeaway
The common thread across everything Craig shared is this: precision beats volume. Precision in who you sell to, what problem you lead with, how you qualify, and how consistently your team executes the methodology.
The companies that do more with less in 2026 won’t be the ones with the biggest teams or the most tools. They’ll be the ones that have genuinely answered the question: why should this customer change, and why now?
If you can’t answer that clearly, everything downstream — the calls, the demos, the proposals — is harder than it needs to be.
Craig Jones is CRO at Star Compliance. This article is an AI-assisted adaptation of content originally published on the Rev-n-u Unplugged podcast. Watch the full episode here – https://www.youtube.com/watch?v=YZ8RtG7gXlw&t=
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