Lessons from 30 years in enterprise tech sales, with Bob More, CRO at KetteQ
Most revenue leaders know they should be doing these things: tightening their ideal customer profile, understanding where product-led growth fits their business, and thinking creatively about talent. But knowing and doing are very different things — especially when the board is breathing down your neck and the pipeline isn’t where it needs to be.
Bob More has spent three decades navigating exactly these pressures, from IBM and SAP through to a string of high-growth startups. In a recent conversation on Rev-n-u Unplugged, he got into the detail of what actually works — and what sounds good in a pitch deck but falls apart in practice.
Stop Confusing the Investor Deck with Your Go-To-Market Strategy
The tension between TAM and focus is one of the most common sources of early-stage failure. Investors want to hear about a big addressable market. That’s fine — for the fundraising conversation. The danger is when that same broad ambition bleeds into your actual go-to-market motion.
“Don’t confuse the pitch deck to the investors with the go-to-market deck,” Bob puts it bluntly. “A big TAM is better for the investor slides, but it’s kind of a death knell if you try to go too broad too quick.”
The mistake most companies make isn’t ignoring ICP altogether — it’s defining it too shallowly. Industry verticals and revenue bands are a start, but they don’t get you to ideal. If you’re selling a supply chain solution, there could be two manufacturers of identical size in the same sector — one is a perfect fit, the other would be a nightmare. The difference lies several layers deeper than the demographics.
Bob’s approach is to look backwards from your existing customers. If you’ve got a handful of accounts that are renewing, expanding, and genuinely getting value — that’s your map. Find the consistent attributes across those wins: the use cases, the geography, the company archetype, the pain profile. Then find lookalikes and go again.
The mistake he sees repeatedly is confusing paying customers with product-market fit. “You might have 30 customers doing 28 different use cases across eight different industries. What you actually have is a bunch of companies paying you for a custom solution.” That’s not a scalable motion — it’s a professional services business in disguise, and the churn will eventually prove it.
The broader lesson: you can always widen later, but it’s very hard to narrow once you’ve scaled wide. Going narrow first lets you find repeatability. And repeatability is the only thing that lets you move from founder-led sales to a team that can actually replicate the motion.
Reviewing and Updating Your ICP
ICP isn’t set-and-forget. As Bob explains, the review cadence depends on your sales cycle — if you’re running 30-day transactional deals, you’ll accumulate data quickly. Enterprise sales are slower, so patience is required before drawing conclusions.
What you’re looking for are adjacent expansions rather than wholesale pivots. Bob describes how one company started in pharma data management, then followed the data into healthcare payers, and from there into property and casualty insurance — each step a logical extension rather than a leap. The ICP broadened naturally as success created the evidence to support moving.
The sales team piece matters too. Without proper enablement and clear direction, reps will follow their own instincts — which leads to what Bob calls “sales-led selling.” That’s when individual reps are effectively setting go-to-market strategy themselves, and almost nobody wins in that scenario.
PLG Is Not a Sales Motion — It’s a Company Motion
Product-led growth was the defining buzzword of a certain era in B2B software. The thesis was compelling: let the product sell itself, reduce friction, grow through usage. And for many companies, it genuinely is the right model. But the pressure to adopt PLG has caused a lot of enterprise-focused businesses to waste significant time and money chasing a model that was never going to work for their product.
“You can wish it all you want,” Bob says, “but trying to take an enterprise product and make it PLG — it really doesn’t happen.”
The fundamental issue is that PLG isn’t something you bolt onto a sales motion. It has to be designed in from the product outward. In the PLG world, time-to-value is measured in hours, not months. If your product requires an 18-month implementation and a seven-figure SI engagement to go live, no amount of sales cleverness makes that a self-serve experience.
That said, Bob is careful to distinguish between being PLG and learning from PLG. There are genuine lessons worth taking:
- Usage and adoption data — tracking how customers actually engage with your product gives you early signals on expansion and churn risk. Enterprise software was often blind to this; it needn’t be.
- Reducing time to value — even if you can’t get to hours or days, shortening from 12 months to 6 is a meaningful competitive advantage.
- Ease of adoption — consumer app experiences have raised user expectations across the board. Enterprise software that’s genuinely pleasant to use retains better.
On the churn question specifically, Bob makes an interesting observation about seat-based licensing models. As companies adopt AI tooling to do more with fewer people, user count contracts — and with it, the revenue tied to it. That’s a structural pressure on a pricing model that many SaaS businesses haven’t fully reckoned with yet.
The practical advice for enterprise businesses: if you want to test lower price points and higher velocity, it generally requires a different product, not just a different sales motion. Running two parallel product development tracks is expensive and often beyond the means of earlier-stage companies. Better to nail the enterprise motion first, get to profitability in that lane, and then consider what a genuine mid-market product might look like.
The Case for Hiring Athletes and Veterans — and How to Actually Do It
The war on talent in enterprise sales is real, and everyone is fishing in the same pond: looking for the proven rep with a track record in the right vertical, who can ramp in 30 days and carry quota from day one. Bob’s view is that this approach is both expensive and increasingly difficult — and that there’s a better one.
His preference is to hire for what he calls “raw sales athleticism” — the underlying traits that make someone coachable, resilient, and capable of operating in complex, high-stakes environments — and then build the product knowledge and methodology around them. The places he looks? Former Division 1 college athletes and military veterans.
What Athletes Bring
Enterprise sales is fundamentally about managing complexity. A deal with 10 to 12 stakeholders, each with different priorities and agendas, requires the kind of mental organisation and resilience that most people haven’t been tested on. Athletes have.
The traits Bob looks for aren’t the headline ones. It’s not the competitive fire (though that helps). It’s the willingness to run the same drill a thousand times. It’s the ability to review what went wrong without falling apart. It’s being genuinely open to coaching — even when you think you already know. “The highest paid athletes on the planet all have coaches,” he points out. “They’re open to that.”
Crucially, failing four out of five times and getting back up is the job description in enterprise sales. Athletes know what it is to lose and come back. Many candidates who’ve never faced real adversity struggle more than they’d expect when that reality lands.
What Veterans Bring
The military brings a related but distinct profile. Mission orientation, discipline under uncertainty, and the ability to operate within a structure while still making decisions — these transfer well. Bob has done mentoring work with the Honor Foundation, which supports special forces individuals transitioning to civilian careers, and notes that many of the best candidates find sales genuinely hard, in a way that’s unfamiliar to them.
“I’ve had several Navy SEALs say this was the hardest job they’ve ever had.” That’s not a negative — it’s evidence of self-awareness and a willingness to engage with difficulty. The ones who stay are often the most driven, precisely because they’ve chosen to take on something new.
One real barrier is that some hiring managers simply don’t know how to read a military background — or hold preconceptions that work against candidates before an interview even starts. Bob’s advice to veterans is to network relentlessly, ask for introductions at every stage, and use those conversations to figure out whether sales is genuinely the right path.
How to Screen and Onboard
The interview process matters. Bob looks for communication quality in both spoken and written form — a thoughtful follow-up note tells you more than many interview answers. He looks for self-awareness: how someone describes a time they faced adversity, and what they learned from it. Anyone who can’t point to a real setback is, in his view, probably not ready for the reality of the job.
What he doesn’t do is assume cultural background automatically equals readiness. His best performer at one company was neither an athlete nor a veteran — but she had all the same underlying traits, expressed differently.
The onboarding approach hinges on what Bob calls a “selling system” — a structured framework that removes the reliance on intuitive know-how and instead gives reps a repeatable process. He references the Force Management methodology, built around four essential questions every rep must be able to answer consistently: What business problems do we solve? How specifically do we solve them? How do we solve them differently? Where have we done it before?
“The number one answer to those questions is usually ‘it depends,'” he says. “That’s the challenge. Getting crisp around those answers is what makes everything else in the go-to-market easier.”
The Meta-Lesson: Network More, Know Less
The thread running through all three topics is a disposition that’s easy to undervalue: intellectual humility. Bob’s parting advice to any CRO stepping into an enterprise motion for the first time is simply to call people who’ve done it and ask them what they learned.
“A lot of sales leaders want to have all the answers themselves and aren’t good at asking for advice.” His playbooks from even a few years ago are already outdated — the market moves too fast for any individual to stay current in isolation. The leaders who compound their learning fastest are the ones who stay curious and stay connected.
It’s a simple point. It’s also probably the most actionable one in the conversation.
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=vLxx9B9TlOs
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