I recently went one-on-one with Sam Kidd, co-founder and CEO of LawVu.
Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Sam: I didn’t come from a legal background. Most of my career was spent working in an online project management software business in Ireland, back when SaaS was really becoming a thing. It was a long run with strong growth periods, and I learned a huge amount along the way.
The real inflection point for me was selling my shares in that company. That was the first time I worked deeply with lawyers, and it was eye-opening. When I started talking to in-house legal teams later, the same pattern kept coming up of different tools being used for different parts of the job, but nothing tied it all together. They were basically operating with Outlook as their tool. That’s really where LawVu started.
The biggest personal shift since then has been learning to operate without complete information. When you’re building in a category that isn’t well defined, you don’t have anything to copy, so you have to stay close to the users and test assumptions quickly. You also need to really listen to what they are doing, not what they always say they want. The gold is normally hidden somewhere in the middle there.
Adam: How did you come up with your business idea and know it was worth pursuing? What advice do you have for others on how to come up with and test business ideas?
Sam: I think when you’re deep in an industry, you can get used to how things work, even when they’re not working well. You stop noticing the friction because it’s just become the way things are done. When I started working closely with legal teams for the first time, it was so interesting, as I was coming in purely from a business perspective with no legal background. I could see clearly how fragmented everything was, with work moving through email chains and documents scattered across different places; no one had a full picture of what was happening. People inside the industry had just normalized it. I hadn’t, so it stuck out immediately where a lot of issues were.
That outside perspective is where LawVu started. When we began talking to in-house teams, we kept hearing the same thing. It wasn’t “we need a platform,” but very specific descriptions of pain points in specific workflows. So we spent a lot of time understanding how work moves inside these teams before we started building anything. My advice is to stay in the problem longer than you think you need to. Most people rush to solutions because it feels productive. And don’t rely too heavily on opinions because people are good at describing frustration, but less reliable when it comes to predicting what they’ll actually change.
Adam: What are the key steps you have taken to grow your business? What advice do you have for others on how to take their businesses to the next level?
Sam: This feels like counter-advice, as everything you read says to focus on a single issue. We took the other path and built broadly rather than narrowly. A lot of software companies in this space focus on owning one workflow, be it managing spend with law firms or how contracts are handled. The reason we took the broad path was because we saw legal work inside teams as all connected. If you solve just one piece in isolation, you’re just pushing the complexity somewhere else.
The second was staying obsessively close to customers. Not just listening to what they say, but watching how they actually work. There’s almost always a gap between the two, and that’s where the answers to a lot of product decisions live.
The third has been education. In this space, beyond just selling software, you’re often helping a team rethink how a core function of the business operates. That takes longer than typical growth playbooks account for, and you have to be patient with it.
If I had to boil it down to one piece of advice, it would be to never stop sharpening the problem you’re solving. The clearer that gets, the easier everything else becomes.
Adam: What are your best sales and marketing tips?
Sam: Be authentic. It sounds super cheesy, but I still believe people buy from people, even if it’s a massive enterprise you’re selling to. People are still involved at every step. Especially in the early days when you don’t have any reference clients, it’s all about who you meet and who is willing to take a chance on you. The other part is pretty straightforward, which is to deliver on what you say. The easiest marketing is happy customers saying great things about you.
Adam: What are the most important trends in technology that leaders should be aware of and understand? What should they understand about them?
Sam: AI is the obvious answer, but I think the bigger point is usually missed. Most of the conversation right now focuses on what AI can do in isolation. But if your workflows are fragmented and your data is inconsistent, AI will just reflect that back at you, and you end up with a faster version of a broken process.
The more important shift is toward connected systems where work, context, and data live together in one place. That’s what makes AI actually useful in an operational sense, as something that can act on a complete picture. A unified approach is something we’ve felt strongly about at LawVu since day one. We have some exciting updates coming on that front, making sure the platform is even more cohesive and AI-powered in ways that I think will change what teams are actually able to do day-to-day.
The other shift is around expectations. Every function is now expected to operate like a structured business unit with visibility, accountability, and measurable impact. Legal is no exception to that. The teams that invest in getting their house in order now are the ones that will actually be able to take advantage of what AI makes possible.
The third big point that people aren’t talking about is the cost of AI. Token usage and costs are going to hit hard soon. We’ve already seen quite a few of our suppliers say that they’re moving to consumption pricing models. The costs are going to increase a lot in a very short time period, so if you don’t have strong governance around how you’re using AI and how it’s being implemented, costs could get out of hand quickly.
Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?
Sam: Three things stand out to me: trust, restraint, and clarity. Trust means hiring people who are better than you in their domain and actually letting them do the job. That sounds obvious, but a lot of leaders, especially founders, struggle with it. When you’ve been close to every decision for years, stepping back feels uncomfortable even when it’s the right call.
Restraint is knowing when not to get involved. The impulse to weigh in is almost always well-intentioned, and it’s almost always costly. Over-management slows teams down nearly all the time. Clarity is making sure people understand the direction and the intent, not just the task in front of them. When people know the why, they make better decisions without you in the room, which is ultimately what you’re building toward.
On the development side, the biggest shift I’ve seen in leaders who actually get better is learning to listen in a way that changes how they think, not just confirming what they already believe.
Adam: What is your best advice on building, leading, and managing teams?
Sam: Get the right people, align them on the vision, and then get out of their way. The “right people” part is more about values than capability. Skills can be built, but misalignment on values is much harder to fix, and one person who’s out of sync can quietly create a lot of drag across an entire team. Culture is what people experience every day in how decisions get made and how problems get handled. You can’t design it top-down. You earn it through consistent behavior, especially when things are hard.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Sam:
- If you’re building something that requires people to change how they work, education will be a bigger battle than sales. Budget more time for that than feels necessary.
- Some of the best clarity comes from people who aren’t deep in your industry. They haven’t learned to live with the broken parts yet. So whether it’s a hire, an advisor, or just a fresh conversation, find someone who will tell you what looks obviously wrong from the outside.
- Be patient with outcomes, but impatient with learning. Results take time to compound. The thing you can control is how fast you update your thinking when something isn’t working.
Adam: What is the single best piece of advice you have ever received?
Sam: “The days are long, but the years are short.” I look back on the last 11 years building LawVu, and it feels like no time has passed and all the time has passed at once. That’s why I think it’s important to build something where you genuinely enjoy the journey, not just chase an outcome – because there are plenty of long days along the way. You have to be able to pause sometimes, take it all in, and feel good about what you’re building and the struggles you’ve pushed through. In the end, life is really the journey you look back on.
