Meet the Path Builders: Dermot O’Connor - Co-Founder

Who are you, and what do you do at Overpath?

I’m Dermot O’Connor, co-founder of Overpath and a three-time tech founder. I’ve spent twenty five years building and scaling B2B software businesses, including Boxever and Skillko, both of which were successfully acquired.

Outside of my career, I’m married to my better half Grace, and a devoted dad to our three wonderful kids. I also enjoy all sports, particularly endurance events.

At Overpath, I wear a few hats: product, technology, finance, strategy, and generally helping turn ambitious ideas into something customers actually love. I’m particularly passionate about building great products, assembling great teams, and figuring out how AI can fundamentally change the way we work.

What does a typical day look like for you at Overpath?

One of the things I love about early-stage startups is that there really isn’t a typical day.

I could be deep in a product discussion in the morning, working through a technical challenge with the team, talking to customers in the afternoon, and debating our go-to-market strategy by the evening.

We’re still at that exciting stage where everyone is close to the product, close to the customer, and has a real opportunity to shape the company. It’s chaotic at times, but that’s part of the fun.

What’s the biggest problem Overpath solves right now?

Salespeople spend far too much time doing work that isn’t actually selling.

Updating CRMs, preparing for meetings, documenting conversations, chasing information, and trying to figure out what to do next. There’s a huge amount of administrative and cognitive overhead in modern sales.

At Overpath, we’re building an AI-powered sales assistant that works alongside salespeople, understands their deals, and helps them execute better.

The goal isn’t just to save time. It’s to help every salesperson operate with the insight, discipline, and effectiveness of the very best performers.

What moment are you most proud of during your time at Overpath?

For me, it’s seeing the transition from an idea on a whiteboard to a real product that people can use.

There’s something incredibly rewarding about watching a small team take a complex problem, challenge conventional thinking, and build something that genuinely feels different.

We’re still early in the journey, but seeing the product come to life and the team develop around it has been a real highlight.

What’s a hot take of yours?

AI is going to do for white-collar work what industrial machinery did for physical labour: dramatically amplify what an individual can accomplish.

I think we’re too obsessed with the question of whether AI will replace people. The much more interesting question is what people will be capable of when AI removes the repetitive, administrative, and low-value work from their day.

My bet is on human augmentation, not wholesale replacement.

The biggest winners won’t necessarily be the companies that automate the most jobs. They’ll be the ones that figure out how to make their people dramatically more effective.

Fun fact about you?

I’m a two-time Ironman finisher. 😅

Apparently, once wasn’t enough to convince me that swimming 3.8km, cycling 180km, and then running a marathon was a ridiculous way to spend a Sunday.