David Osborne – Caseware’s new CEO talks growth and leadership

Photo courtesy of David Osborne.

David Osborne, a seasoned software and tech-enabled services leader, is passionate about helping organizations successfully integrate, operationalize, and scale. He currently applies that passion as CEO at Caseware, a SaaS (software as a service) company that designs technology  to help accountants, auditors, and financial analysts work more effectively, gain deeper insights, and see further down the road to implement change for a better future.

He believes the accounting and audit industry will look significantly different in the future as opposed to today. He is excited and honoured to lead Caseware towards supporting and driving the industry’s transformational change. Caseware provides innovative solutions to over 500,000 users in 130 countries and 16 languages.

The Edge, A Leader’s Magazine was pleased to interview Osborne to ask him about his leadership role in Caseware and how he plays an integral role in its development.

What was your vision for Caseware when you took over the company almost a year ago?

I had four main goals when I took over. The first was to hire an experienced executive team to help me define and execute bold, new ambitions for Caseware. The second was to start clearing existing roadblocks by implementing an effective software playbook. The third was to ensure that the company, which previously had various components that operated independently, was united under one Caseware, and to make sure that we are building a great company culture. The fourth was to expand our global footprint by executing our investment thesis, which includes a robust acquisition plan.

Where do you see Caseware in three to five years? And how are you planning on getting there?

My main goal over the next three to five years is to double Caseware’s size — organically and inorganically — by expanding our team and growing our number of partners and customers. The way we get there is by implementing a direct go-to-market plan and acquisition strategy globally, so that we can expand our market share and take the fate of new and existing customers into our own hands.

At your recent conference, CwX 2022, you spoke about the transformation of the accounting and audit industry. How is the industry transforming?

We recently conducted qualitative and quantitative research to understand our users — and the changes in the industry — better. The first observation is that firms need to do more with their current resources. Increasing their prices right now would be detrimental, so the only way they can make more money is to be more productive and more efficient by harnessing technology. They’re starting to realize that nurturing client relationships is more important than ever, so they’re in need of solutions that will allow them to do their best work, so they can build those relationships.

Secondly, the people in the industry are very different. They’re less old school. It’s not a bunch of boy’s club accountants. Thirty-five per cent of respondents to the survey for our research said they’re female. Sixty-three per cent see themselves as creative and curious problem solvers. They want to have more social impact through their jobs.

What role do you see Caseware playing in this transformation?

First and foremost, we understand the people in the industry and the change that it is going through, and we’re ready to drive the change. We are going to deliver high-end cloud products to lead the industry through this transformation. We’re the only ones thinking this way. If you think about other companies in this industry, they’re building point solutions and still talk about, “Our software is easy to use, reliable, and intuitive.” Our view is that these callouts are table stakes. Obviously, our software is all things, but we also want it to be transformational. We are going to bring insight-driven products to the global market that will help our clients do their best work.

At CwX 2022, you also talked about growing the Caseware team. What type of talent are you looking for?

Over the last 11 months, I’ve done a complete refresh of the entire executive team — either replaced or filled each role from Chief Commercial Officer, Chief Marketing Officer, Chief People Officer, Chief Technology Officer to Head of Mergers and Acquisitions. Also, we just hired our new Chief Financial Officer (CFO) recently. So, we now have a team that I think is really good at their craft and, culturally, is a good fit and can move our organization forward with clarity of purpose.

Historically, there has been lots of domain expertise layered into the teams, so, at the top level, I am focused on adding [people with expertise] to run a software company. A level down, we’re investing heavily in manager training and making sure that we’re building processes that attract and retain great talent. We’re looking to hire globally, not just in Toronto, and not because I’m looking for a cost advantage. I just want to hire great talent. This is the speed-to-market model we are focused on.

Was there anything else you wanted to add?

I’ve got the best job in the world. I’ve been at the company for a year, and I was fortunate enough to find an organization that foundationally has a really good product and a great reputation in the market. It’s almost a system of record-type stuff. So, our job now is to take the 30 years of history that we have and just build on it — we’re doing that as quickly and as efficiently as we can. 

Connect with David Osborne on LinkedIn.

Dave Gordon | Associate Editor



Edge Newsletter

Subscribe to our newsletter for updates from The Edge, A Leader’s Magazine.

Trending Articles

Available in all Indigo & Chapters stores. 

Pioneering Leadership

Featuring Fran Rider CEO of the Ontario Women’s Hockey Association. On shaping the landscape of the Game In Ontario and Beyond.