How to build a team around a product
Plus: Uptick in A.I adoption and insights on how to the best SaaS companies acquire and convert customers.
Happy Tuesday!
Kia ora Caffeinators,
It’s another great day in startup land. We’re kicking off with the latest guest article from LiveRem co-founder Kathleen Webber and rounding out with a great event and some meaty data to unpack.
Here’s what’s brewing in your Daily Shot:
How to build a team around a product by Kathleen Webber
Event: Collisions with BlackBird
Datacom’s annual State of A.I report shows surge in adoption
SaaS Go-To-Market Report insights
As always, thank you to everyone who has upgraded to a paid subscription or simply recommended Caffeine to friends and whānau. We couldn’t do any of this without you.
Finn and the CAFFEINE team
How to build a team around a product
By Kathleen Webber, LiveRem co-founder
There’s a well-worn playbook in the startup world: come up with a great idea, pitch it, raise capital, and build your team with someone else’s money. That sequence is so ingrained, it almost feels like the only way.
We didn’t do that. In fact, we never planned to.
From the outset, we wanted to build LiveRem without venture funding. That wasn’t a philosophical stance as much as a practical one. We didn’t want to answer to investors before we’d even proven the product, the business model, or the scale of the opportunity. We also acknowledge our privilege in being able to do that. We have another business that could sustain the early bootstrapping period, giving us the breathing room many founders don’t get.
That breathing room wasn’t unlimited though. We still had to be incredibly deliberate with every dollar. And that shaped the way we thought about building our team.
Designing the team before building the product
After completing our first product sprint, a somewhat loose interpretation of the Google Design Sprint process, we had clarity on what LiveRem should be. The product made sense. The customer needs were clear. But the leap between a validated concept and a functioning product is always the hard bit.
We didn’t have a team. We didn’t have a war chest. And we knew that building a permanent, salaried team the traditional way was off the table if we wanted to stay lean.
So we flipped the question. Instead of asking, who can we afford to hire full-time?, we asked, what is the minimum expertise we need to deliver this product well? And from there, how do we access that expertise without the cost burden of permanent headcount?
That thinking led us to build a 100 percent fractional, remote team. A collection of highly capable people, working with us part-time, brought in specifically for their expertise. Some of our team are seasoned professionals at the top of their field. Others have retrained into their roles, bringing a depth of experience from previous careers.
What they all have in common is that they’re adults. Experts. People who don’t need hand-holding, who don’t need a manager checking in on them every day, and who are driven by the work itself, not by KPIs or clock-watching.
Finding the right people
We didn’t post job ads. Instead, we started with our networks, people we’d worked with, respected, or been recommended. When that wasn’t enough, we tapped into founder circles, trusted introductions, and niche industry communities.
The thing about hiring fractionally is that the bar is higher. You’re not just looking for skill, you’re looking for people you can trust to be autonomous. Someone who knows their craft so well that even if they only work five hours a month with you, those five hours count.
We also ran a bit of a test on ourselves. When we brought people on, we’d often start them on a small contract — ten hours to prove themselves. That was enough time for us to see if they were as good as they said they were, and whether they could deliver without needing constant direction. It was also enough time for them to see if they wanted to work with us. It’s a mutual test, and it keeps the stakes low in the early days.
How we operate day to day
When people hear that our team is entirely fractional, the immediate assumption is that we must run some highly structured, asynchronous communication model. But the reality is far simpler. We work on email, and that’s about it.
Each team member knows the outcomes they’re accountable for. If they need help to achieve that outcome, they’re empowered to reach out directly to whoever they need, whether it’s the CTO, the product and UX lead, or a developer. We don’t require cross-functional meetings to get things moving.
We have a fortnightly check-in where the whole team comes together. But it’s not a status update parade. It’s a space to re-anchor around the bigger picture, raise any blockers, and ask the questions that don’t fit neatly into an email thread.
Beyond that, we operate on a philosophy of forgiveness, not permission. Every team member knows how much we, as founders, earn. That’s deliberate, it gives them context to weigh up decisions. They’re trusted to ask themselves: will it cost the business more to ask for permission, or to just make the call?
Of course, there are boundaries. Any decisions involving customer data need explicit sign-off from the CTO or myself. But if it’s a UI tweak, a product iteration, or a marketing shift, they have the mandate to collaborate with the relevant team member and make it happen.
The reality, of course, is that sometimes things aren’t done exactly how you’d want them done if you were doing it yourself. That’s part of the deal. But you have to trust that your way isn’t necessarily the right way. Just because it’s different doesn’t make it wrong. In fact, more often than not, different means better.
When you’re funding a company out of your own pocket though, watching people make decisions in ways you wouldn’t have can be an... interesting experience. But that’s the price of high trust. And so far, it’s been worth it.
And when you’re bootstrapping, that kind of scrutiny applies to everything. You have to weigh up the cost versus the outcome of every single thing you do, including your people. That doesn’t mean paying them less. In fact, we often pay above market rates for the expertise we need. But it does mean every cost has to be justified by the outcome it delivers. If the value isn’t there, it doesn’t stick around.
Building a different kind of culture
This isn’t a traditional team, so it doesn’t have a traditional culture. There are no weekly quizzes, no virtual drinks, no company playlists. Our culture is built on mutual respect and a shared standard:
● Be great at what you do
● Communicate clearly
● Treat others with respect
We call it the lowest acceptable standard of behaviour. It’s not glamorous, but it works. When you have a team of highly capable people working across time zones, roles, and varying capacities, you don’t need a curated vibe. You need clarity and trust.
But let’s be honest, this model isn’t for everyone. Some founders thrive on building culture through rituals, connection, and energy. If you need that, this can feel sterile, even lonely. It works for us because of the stage we’re at and the way we operate, but it’s not a universal playbook.
The trade-offs
There are downsides. Sometimes progress is slower than it would be with a full-time team. There’s less immediacy when you’re not the only thing on someone’s plate. And yes, it can be lonely as a founder, there’s no daily camaraderie, no team energy to feed off.
But the upside is that we’ve built a business that can flex with demand. We don’t carry unnecessary costs. We’ve maintained profitability without external funding. And when we need to, we can scale, not just by throwing people at the problem, but by engaging the right people for the work that matters.
Would we do it again?
Absolutely. This model has given us freedom to build the business we want, on our terms. At some point, we may bring some of these roles in-house. But that’ll be a choice made from strength, not desperation.
Because the reality is, you don’t need a big, expensive team to build something meaningful. You need the right people, the right incentives, and the trust to let them do their best work.
In the next article in this series, I’ll share how we’ve bootstrapped and grown LiveRem without taking venture capital, what we’ve learned about sustainable growth, how we’ve funded key stages, and the moments where, despite everything, we did consider raising a round.
Event: Collisions with BlackBird: Our friends over at BlackBird are hosting a great event in a few weeks time. Collisions is an ‘unconference’-style gathering of 150 of Aotearoa’s sharpest founders and operators.
Collisions is designed around the conversations that usually happen in the hallways between keynotes - raw lessons, war stories, honest questions, and surprising answers. Which is, lets be honest, where all the best connections actually happen. It’s mainlining the thing most of us actually go to events for for.
The format is simple: hosted sessions where everyone teaches and everyone learns. You’ll leave with five new connections who’ll help you go faster, and three ideas you’ll put into practice tomorrow.
Programming Sneak Peek
No panels. No slides. No velvet ropes.
Collisions plays out across three spaces inside two neighbouring creative venues - built for live gigs, lounges, and recording sessions. Now reimagined for unscripted huddles, open debate, and hallway magic.
Expect a choose-your-own-adventure of:
Peer-hosted sessions
Off-the-record conversations
Espresso-fuelled chats that spiral into something bigger
The kind of energy where ideas outlast the event, and conversations turn into collaborators.
Who’s in the Room
Founders of early-stage and scaling companies
Product leaders, engineers, marketers, and other operators solving real, hairy problems
Kiwis building overseas with deep ties to home
Ambitious new voices with bold ideas and fresh momentum
Why Come?
Leave with 5 new connections who can help you build what’s next
Take home 3 real ideas you’ll put into practice the next day
Share something, and learn something
An energising reset for your founder/operator brain
Get your tickets here
Wed, 3 Sep, 12:30pm - 8pm NZST/ Glasshouse + BIG FAN || Morningside, Auckland
Datacom’s annual State of A.I report shows surge in adoption: Datacom’s annual State of A.I report is a great data point for illuminating what the actual uptake of the emerging technology looks like on the ground in Kiwi businesses. It surveys 200 senior managers across the country and in diverse sectors and now its third year.
Chris Keall over at the Herald has an early report on the newest entry and is shows a strong positive trend in adoption. From only 39% in 2023, this year adoption has risen to 88% and to 92% at firms with more than 200 staff. Of course there’s a a lot of nuance within those numbers and plenty more to parse to I highly recommend checking out his full article here.
We love finishing on a chart here at Caffeine at the team at ChartMogul have a stack of them in their SaaS Go-To-Market Report, where they analyze how 2,500 SaaS companies acquire and convert customers.
A few key insights below.
Top-performing B2B companies reach 1,000 subscribers in just 11 months, while the median B2B company takes 2 years.
Embracing full PLG at lower price points can grow new business faster. At low price points, adding sales creates friction. Companies that stay self-serve grow faster.
Starting at a $100 ASP, most B2B PLG companies begin layering sales on top of PLG. Adding sales helps buyers make decisions as products and purchase processes become more complex.
Trial-to-paid conversions spike around day 7 for both PLG and SLG companies. No matter the GTM strategy, success comes from getting users to reach the 'Aha' moment fast.
Discounted subscriptions often follow similar timelines to full-price ones. At lower ASPs, they can even take a bit longer.
Check out the full report for yourselves here.
That’s it for today, thanks for reading. Want to get in touch with a news tip, bit of feedback or just to chat? Email hello@caffeinedaily.co