Karen O’Leonard – Willis Towers Watson

Spøtlight : 6 min read

We first met Karen O’Leonard, Head of Innovation at Willis Towers Watson, a couple of years ago and were immediately impressed with the impact she has made on the business. We recently caught up with her to explore how the innovation function is set up on a global basis, the importance of getting the culture right and what advice she has for any insurance company currently considering setting up an innovation team.

This is a must read. If you work within corporate innovation it’s a definitely must read.


What was your background before joining Willis Towers Watson? And can you tell us more about the timing of what was going on in the business when you joined.

Early in my career I worked in new product development roles at Apple and the Java Software group of Sun Microsystems. Then I joined a startup and helped it get off the ground before we were acquired by Deloitte.  So, the journey from big tech to startup to consulting /insurance brokerage has been fascinating, with so many different cultures.

I was hired at Towers Watson about 5 years ago, and on my first day we announced we were merging with Willis to form Willis Towers Watson.  The merger was very beneficial to me because there were so many changes happening.  Big changes like a merger, a corporate transformation, or a crisis like COVID can be opportunities to try some new ideas and ways of working.  


I’m fascinated by the culture of innovation you’ve managed to achieve over there. Tell us more about how innovation is set up on a global basis and your team’s role in that. 

We have a small team at the corporate level, and I see our role as evangelising, facilitating and accelerating innovation. We focus on large adjacent and breakthrough projects (rather than incremental innovation), and especially projects that cross our lines of business and have the ability to scale globally. Our investments are geared to creating a pipeline of projects that can generate long-term growth for the company.

One of the ways we support early-stage ideas is through our Growth Board, which meets monthly to hear proposals for new ideas that can be real game-changers for our company. For the ideas selected, the Growth Board provides funding and resources for teams to incubate these ideas: to really get clear on the problem they are trying to solve, and then validate the proposed solution by getting feedback from prospective buyers. The teams then come back with their findings, recommendations, and financial projections for developing and commercialising the solutions, and then we decide whether to provide the next round of funding.


Why is a culture of innovation important to you as a business and what are the key factors that have enabled it to be successful?  

I think the question of why innovation is important is self-evident: companies that don’t innovate don’t survive. So fostering a culture of innovation Is one of our key priorities, and in a company as large and as distributed as ours, this takes a lot of time and effort. And not everyone in our industry has grown up in an environment of risk-taking. So it’s critical that leadership continually send a message about the need to take risks and experiment, and if it doesn’t work out to learn from it.  Colleagues need that psychological safety to be able to stick their necks out and try something new that might fail.

We started a program called Innovation Masters to provide training and experience in design thinking, rapid prototyping and testing methods. We are building a network of these masters who can engage in innovation projects both internally and with clients. We now have hundreds of Innovation Masters and these colleagues are helping to support innovation projects and be our ambassadors within their businesses and regions.

Innovation in any company or industry takes perseverance. You will always run into people who resist change or are not on board with new ideas or ways of working. So influencing skills, stakeholder management and overall change management practices are critical elements of innovation.


Let’s get into the weeds a little. How do ideas make their way up through the business, get evaluated and ultimately get brought to market?

Ideas come from a lot of different sources… from colleagues and leaders at all levels of the company. One of our programs is called Horizons, which is an annual innovation challenge open to all colleagues worldwide. We encourage colleagues to collaborate in teams or join jam sessions that are held in local offices (or now, of course, virtually). We also encourage them to work with idea coaches to help them flesh out and articulate their proposals. And we receive hundreds of idea proposal through this challenge.

Once the proposal is submitted through our idea management platform, BrightIdea, we have a team of reviewers from our different businesses and geographies evaluate the ideas. We conduct several sessions with these reviewers to discuss the ideas from multiple perspectives. Diversity is really important, both in forming the ideas and evaluating them. The review team chooses their top picks, which are then put out to all colleagues to vote on the ones they think our company should pursue. This process results in 8-10 finalist teams, who then pitch their ideas to a team of executives. This year we held the pitches virtually for the first time. We had men and women from seven countries pitching their ideas, and it worked out remarkably well.

The judges then choose the ideas to fund for the next phase, which involves prototyping and testing the concepts with prospective buyers. Through an iterative build-measure-learn process, the teams validate the viability and desirability of their proposed solution. This process lasts four months, at the end of which the teams present to the executive team their findings and business cases, looking for the next round of funding to take their solutions to market. We are just going through this phase now with this year’s Horizons teams. We have been very successful in the past in commercialising the projects that make it to the testing round in Horizons. I am hoping this year is no exception.


One of the struggles we often hear from companies is how best to track their innovation activity, in particular who has met which startup and where those conversations are now at. With such a huge global team, how do you go about this? 

We have a network of liaisons from our businesses who meet monthly to discuss activity with startups – which companies have we met, what are we doing with them, what have we learned. We certainly don’t monitor everything, but this catches a lot of the activity going on.

For our corporate investments in innovation projects, we meet regularly to review progress and learnings – this could be every 1-2 months for early-stage projects and quarterly for later-stage projects. We have a relatively well-baked process for each stage to determine a go/no go for the next round of funding. 

Every year we produce a scorecard on our innovation efforts that tracks our KPIs, including pipeline stats, revenues, investments, participation in innovation activities, our employees’ perceptions of our innovation efforts based on our employee survey. We are fortunate to have a Board of Directors who are very engaged and supportive of innovation, and we provide a quarterly report to the Board on some of our key metrics.


Last question: Traditional insurance companies are not known for their innovation albeit I appreciate that’s slowly changing. What are your top 3 pieces of advice for any company looking to set up a sustainable and impactful innovation team?

My three pieces of advice would be as follows:

  • Get leaders on board with the concept of experimentation, taking risks, and the fact that many projects won’t come to fruition (i.e.  will fail) but will provide learnings. Have leaders promote these concepts internally and make sure they recognise/reward colleagues for innovating.
  • Aim for a balanced portfolio of innovation projects:  some short-term, low-risk projects with low/moderate impact; some long-term, risky projects that could be real game-changers; and some in between. In other words, the portfolio should be comprised of projects with different impacts, risks, and timeframe profiles.  It’s nice to get some quick wins to build credibility, but the real game-changers to longer to play out.
  • Set up a process that enables rapid progress with clear decision points to go forward or fail fast.
  • Make sure you have people who understand the innovation process – how to test and validate the problem and the solution, how to develop a solution using agile, and how to commercialise and scale a new solution in the market.

Oh, sorry, I guess that’s four!



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