April 8, 2020

162 | Growth & Evolution: Lessons Learned from Mergers & Acquisitions – with Dominic O’Connor

This show focuses on how you can steer a team or organization through growth and change, and one common form of growth — explosive growth, in some cases — is when two companies merge or one company acquires another. In these instances, you have to combine not just different platforms or technologies but different groups of people who have different processes, philosophies, and perspectives.

So, in this episode, we’re joined by someone who has already gone through a big merger: Dominic O’Connor, the current CTO of EmployStream and formerly of InterFolio, where he led the engineering team from startup to M&A and growth. We learn what the transformation looked like, what he learned as a leader, what went well and, more importantly, what Dominic would do differently if he had to start again today.


Now that Dominic is on this side of a big transformation — the merging of two teams and two technology platforms — what advice would he give someone who is about to do the same thing?

  • “As good of a job that I think we did in planning, we planned the wrong thing.”
  • You can plan what a piece of technology is going to look like or what a new team might look like, but a lot of that goes out the window when the rubber meets the road.
  • You can’t keep doing the same thing you did but with a bigger team or just do it better. You’re playing on a different playing field now.
  • “So, what you should be planning,” Dominic says, “is what the process is going to look like and how you’re going to react to the things that you don’t see coming, whether that’s what your leadership team looks like, what your decision tree looks like, or what the communication processes looks like.”
  • What does your leadership team need to be to make those decisions? And what does the process look like to bring other people in to make the decisions? What are employees thinking? What are they feeling when you make big strategic decisions about how you’re going to deploy the thing that they built for a number of years? How are you going to communicate any changes that you’ve decided?

We can’t emphasize enough that communication is key in any transformation…

  • …and communication from leadership goes down even smoother when it’s blended with humility.
  • You need to create a culture of sharing information in both directions — from senior leadership to middle management to teams and vice versa — so the people on the frontlines know what the business is trying to do, what you’re trying to do with your organization, and why.
  • Then, when someone runs into a problem that might conflict with the plan, they know to raise that flag to their manager, or all the way up the chain if it’s that important, so that leadership can amend the plan or provide the team necessary resources.
  • “Early on, as a leader, I really thought that the head of an organization or a senior manager was supposed to be the one that had the answers,” Dominic says, “and they would give those answers to the people that reported to them, and those people would do the work based on that information.” But Dominic quickly realized that this is almost never the case, and it’s actually ridiculous to expect any one person to have all of the answers.
  • “So, rather than banging your head against the problem that has probably been solved 10 times, it really goes back to getting information from the people around you that you’re working with, and also leaning heavily on your mentors.”



About The Innovation Engine

Since 2014, 3Pillar has published The Innovation Engine, a podcast that sees a wide range of innovation experts come on to discuss topics that include technology, leadership, and company culture. You can download and subscribe to The Innovation Engine on Apple Podcasts. You can also tune in via the podcast’s home on Spotify to listen online, via Android or iOS, or on any device supporting a mobile browser.