Most founders who’ve been experimenting with AI for the past year or two have the same collection of things.
A ChatGPT or Claude subscription someone uses for drafting. Copilot in the codebase. Maybe a chatbot on the website that was set up and then quietly forgotten. A few team members who’ve found prompts they like and use them for specific tasks. A Slack thread somewhere with “useful AI prompts” that nobody’s looked at in three months.
That’s not an operating system. That’s a drawer full of tools.
And the difference between a drawer full of tools and an operating system is roughly the difference between a 1x business and a 5x business.
Tim Barker, former CMO at Salesforce and CEO of a 600-person healthcare company, now running a five-person AI-native startup, spent seven months building the latter from scratch. He came to Business of Software Europe 2026 to explain what it actually involves.
The answer is not more tools. It’s not better prompts. It’s a system. And most businesses don’t have one yet.
Let’s be honest about what’s underneath AI resistance.
It’s not technophobia. Most founders who’ve built software businesses are not afraid of new technology. It’s something more specific, and actually quite reasonable.
You’ve seen the hype cycles before. You’ve watched tools get adopted across your industry with breathless enthusiasm, only to discover that the ROI was questionable, the implementation was painful, and the main beneficiaries were the vendors. You’ve built a business on judgment, not trends. You’ve learned to be sceptical of things that promise to change everything.
And now you’re watching every conference, every newsletter, every LinkedIn feed fill up with AI content, most of it superficial, much of it plainly wrong, and something in you is saying: wait.
That instinct is not wrong. But it may be leading you to the wrong conclusion.
I watched Tim Barker walk through his business OS, went home and built one for BoS.
Giselle had just joined the team. Jann was on maternity leave. I needed to onboard Giselle fast, hand off Jann’s context, and figure out how we’d work together short-term. All in the run up to a conference. Our onboarding docs were out of date, probably had been for years. We needed something that reflected how we actually work, not how we worked three years ago.
Tim’s insight cut through everything I’d been reading about AI:
Ignore AI. Start with the System.
Every company runs on the same basic structure. Strategy. Roles. Active projects. Outputs. Most founders have all of this. It’s mostly undocumented, siloed, or living inside someone’s head.
If you overlay AI on a system you haven’t mapped, you don’t get clarity. You get speed in every direction.
Speed is not Velocity.
Map the system first. Then overlay agents.
What surprised me: the benefit isn’t just AI governance. When you have to articulate how your company actually works, everything else gets sharper too. Onboarding becomes real. Decisions get logged. Context doesn’t evaporate when someone leaves or joins.
We’re still early. But it’s already changed how BoS operates.
One founder I spoke to this week mentioned he had 1,200 lines of ideas for blog posts, to-dos, market observations, product thoughts, things he’d meant to follow up on…
There’s at least one document somewhere in your system – it’s called ‘ideas’ or ‘backlog’ or ‘misc’. It’s been there for a while. You lost it once. Started a new one, You add to one or the other. You rarely take things out. You know you should deal with it and you don’t.
The document is a partial record of stuff you’ve decided to care about without deciding what to do about it. Every item = a small claim on your attention. Together, it’s a lot of background noise.
What The Document Costs You
Most people treat their backlog doc as a minor irritant. Minor irritation => minor irritations => major irritation => a nasty rash => bubonic plague… Where to draw the line?
Every unresolved item is a deferred decision. Deferral becomes the default. You stop dealing with it. You manage around the list rather than resolve. The stuff, your ideas, your intentions, your plans for the business you meant to build. You feel a faint sense of failure every time you think about it and move on.
The problem is not time. If time were the constraint, you’d have dealt with it in a quieter week years ago. The constraint is the absence of anyone else who can process it. In any business where you’re the main strategic brain, the backlog is yours alone. You can add to it, but you can never quite clear it, because clearing it requires the same thinking capacity that everything else in the business is already competing for.
Why This Matters Now
Today, you can use tools to execute the boring stuff so you can focus on the stuff that you decide matters. Not the decisions, but the processing. Taking raw input and turning it into something you can look at and act on: that work no longer has to wait for you to have a free afternoon.
Back to the Founder…
He said he had put aside time next week to work through this then decide what to do with it. I asked directly, it turns out that setting time aside next week for this has been going on a long time.
We tried an alternate option, we pasted the whole doc into the OS.
As we watched, in the space of 3 minutes, the document got digested and organised into structured content plans, a separate list of prioritised to-dos, and 60 blog and video topics. He watched it happen.
His response: “It’s done what I was going to do next week AND organised it. I can see how I can use this now.”
A lightning bolt of realisation,
“AI just gave me a day I was dreading back”.
He wasn’t surprised by the capability. He was delighted by the outcome. He didn’t leave the session with a framework to think about his backlog, he left with a plan.
We’ve all got at least one similar document.
The document isn’t waiting for you to have more time. It’s waiting for you to stop being the only one who can process it.
AI should work for you. When it does, it can delight.
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After Business of Software Conference, we got a lot of messages.
Not about the after-party. About one talk – Tim Barker’s session on building an AI operating system for your business. Founders wanted to know where to go next. How to start. Whether there was somewhere to actually work through this with people taking it as seriously as they were.
There’s a version of this you’ve probably told yourself.
“We’re heads down on the product right now.” Or: “Our engineering team is already using Copilot, so we’re covered.” Or the most common one: “We’ll get to it properly once we’ve got past this quarter.”
You’re not alone. Most founders are saying some version of this. And that’s exactly the problem.
Tim Barker spent 20 years building SaaS businesses. He scaled a company from 100 to 600 people and $80 million in revenue. He knows how founders think, because he was one for a long time.
And in April 2026, standing at Business of Software Europe, he said something that should make every founder who’s been putting this off sit up:
“I honestly thought that in two or three years, my currency in SaaS would run to zero. I’ve got to reinvent myself for this next chapter.”
That’s not a warning from an AI evangelist with something to sell. That’s a practitioner who’s spent seven months inside an AI-native business, watching the gap open up between companies that moved and companies that waited.
This week, founders, CEOs, and product builders from across the globe made their way to Cambridge, UK for BoS Europe 2026. Two days of honest talks, unhurried conversations, and the kind of community that makes you realise you’re not figuring this out alone.
The problems you’re facing right now aren’t new. But the solutions that actually work are rarely found in blog posts or LinkedIn thought leadership.
They’re found in honest conversations with people who’ve been exactly where you are, and figured out what works. That’s what Business of Software Europe 2026 is about.
Cambridge. April 13-14. Two days with founders and leaders who’ve built real companies and are willing to tell you the truth about what worked, what didn’t, and what they wish they’d known sooner.
In the world of B2B software, there’s a dangerous temptation to treat positioning like a checkbox: a workshop you run once, a tagline you set, and a “mushy” value proposition you leave on the homepage for three years.
But in a recent Business of Software AMA ahead of her talk at BoS Europe in Cambridge, positioning expert April Dunford made clear that even for the people who wrote the book on it, positioning is a living strategy that demands constant refinement.
As she prepares for her upcoming talk at Business of Software Europe in Cambridge, April shared why she decided to release an updated and expanded edition of her seminal book, Obviously Awesome.
In a recent AMA hosted by Business of Software with Kristie Jones, a familiar tension surfaced:
Founders know they can’t scale forever on founder-led selling.
They know they need help. They know revenue has to become more predictable. And yet, when it comes time to hire their first salesperson, many are about to make the same mistake: they think what they need is talent.
At Business of Software, we’ve always believed that great thinking shouldn’t be long-winded. Sometimes the best lessons come in short bursts: direct, usable, and memorable. That’s where Lightning Talks shine.
These brief, practical sessions pack high-value ideas into a few minutes, and they’ve become one of the most talked-about parts of our events.
As we gear up for BoS Europe 2026, we wanted to spotlight some of the standout Lightning Talks from BoS USA 2025, talks that cut through noise and deliver real insight you can use now.
The fundamental challenge in building a resilient business often boils down to talent. However, most companies approach hiring backwards.
In his powerful talk at BoS Europe 2025, Jobs to be Done (JTBD) expert Bob Moesta challenged founders to adopt a demand-side perspective: “employees hire companies more than companies hire employees”.
Bob’s research, based on over a thousand job transition interviews, asserts that “every job switch is caused, luck has very little to do with it”.
By understanding the progress employees are trying to make, leaders can drastically improve their teams and retention.
Robin Landy , a leading expert in software pricing strategy, delivered an insightful talk at BoS Europe 2025 focused on moving beyond simple price points to create sophisticated pricing structures based on customer value and segmentation.
He highlighted that many successful software companies still rely on outdated pricing structures (sometimes the same ones set by founders on day one), which are often suboptimal and fail to capture the increasing value delivered by continuous product development.
Ever feel like the relationship between a Founder/CEO and a Head of Product is… One awkward meeting away from a Netflix drama?
At Business of Software Europe 2025, Melissa Appel delivered a crucial guide for founders and CEOs titled “The Founders’ Guide to What Product Teams Need”, focusing on transforming potentially adversarial relationships into highly successful collaborations.
She opened with the story of two goats meeting on a narrow bridge, neither backing down, both falling into the ravine.
Sound familiar? Founders pushing last-minute ideas… Product leaders refusing to build unvalidated features… Both sides frustrated… Nobody wins.
Melissa’s talk is the antidote. She breaks down FOCUS, a framework every founder and product leader should honestly tattoo somewhere visible.
An insightful look into Elizabeth Lawley‘s talk at BoS Europe 2025 on the rapidly growing and complex world of AI companionship.
At BoS Europe 2025, Elizabeth Lawley took attendees on a deep dive into the controversial and fascinating world of AI companionship, exploring why humans are seeking digital relationships and what this trend means for our future.
Lizzie drew her experience creating experimental AI companions, including the widely unexpected success of AIs launched on LinkedIn. She presented data and profound user feedback suggesting that AI companions are serving a fundamental human need currently unmet by real-world interaction.
Here are the key takeaways from Elizabeth Lawley’s presentation:
At BoS Europe 2025, Ryan Singer, author of Shape Up, opened the conference by tackling one of the most persistent challenges in product development: how we use our time.
His talk, “Framing and Hard Conversations” wasn’t about productivity hacks or squeezing more hours out of already exhausted teams. It was about something much more fundamental: how to use our time and getting clear on what we’re actually trying to solve.
Ryan has this way of making you realize that half the stress we feel in product development comes from chasing problems we haven’t properly defined. We jump into solutions, scope expands, engineers stay blocked, and suddenly everyone is busy… but nothing is really moving.
What he reminded us is that the most valuable thing we can do is slow down long enough to frame the problem properly.
Benedict Evans produces his take on macro and strategic trends in the tech once a year and it is a must read. It’s been titled, ‘AI Eats the World’ for the past three iterations…
In 2025, in light of the rate of change, he’s decided to publish twice yearly.
Well worth looking through if you’re interested in an informed and non-hyperbolic view on where tech is heading.
Even without commentary, the slides speak for themselves.
Great analysis of where we are and where we might be going.
At BoS Europe 2025, Greg Baugues, took the stage with a talk that challenged a lot of assumptions about how we think AI works.
Using the quote“any sufficiently advanced technology is indistinguishable from magic”, Greg made a clever connection between what feels magical about AI and what’s actually going on under the hood in his talk “AI You’ve Been Doing It All Wrong”, available now in the BoS talks library.
He showed how understanding that difference helps us use AI in a smarter, more effective way. Get to know more about it:
You’re not losing customers because your features aren’t good enough. You’re losing them because your story doesn’t hit where decisions are made: In the gut, not the brain.
At Business of Software Europe 2025, Sara Kathleen Gordon, a reformed brand strategist and General Manager, unpacked one of the most provocative questions in marketing:
What if the secret to great positioning isn’t logic… but desire?
In her talk, “The Seven Deadly Sins & Positioning” Sara explored how our deepest human motivations (the same ones that have driven behaviour for centuries) still shape how we buy, believe and belong today.
The Business of Software (BoS) Conference USA 2025 has wrapped up three incredible days in Raleigh, North Carolina, marking our third year in the city and our first at The StateView Hotel.
This year’s event brought together founders, CEOs, product leaders and builders from around the world to connect, learn, and share real experiences about building enduring, profitable, and people-first software businesses.
The venue was new, but the BoS spirit was the same: honest conversations, practical insights, and an extraordinary sense of community (plus a few hot peppers, of course).
Oh. And this year, hot peppers were officially added to the BoS tradition.
Missed BoS USA?
We’ll send you the talks as soon as they’re available.
