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October 14, 2021

Meet the team: Kieran Gutteridge, CTO

1. What attracted you to working at Cutover? How did you get involved?

Marcus (Wildsmith, CPO) approached the agency I had previously founded. He needed a solution for the seemingly simple problem of making Microsoft project plans more readily visible to senior management on iPads during a large merger of two UK telecommunication companies. After this project, I worked with Ky (Nichol, CEO) and Marcus on the early prototypes for the initial tool to fill this gap in project delivery. The problem resonated with me, having been regularly frustrated with the last mile of software delivery into customer hands which usually involved partners, third parties, and other obstacles. For example, mobile app stores, which were not as easily defined in software and needed humans to bridge the gap. This felt like a problem a lot of my peers were having.

2. What are the main responsibilities as CTO?

I'm lucky enough to work with people that are smarter than me and I have been able to hand off considerable parts of the role since we started. One thing’s for certain, the “job” changes every six months. Now I am focused on how we scale our technical team and the platform itself to address other parts of the development, release, and human-and-machine-communication ecosystems.

3. What are you most excited about at Cutover in the coming months?

We have been fortunate right from our early days to have our customers, advisors, and mentors from the likes of Techstars find use cases that we had not considered in their use of  Cutover. 

We are opening up the product into something that is more in my comfort zone and exposing our developer API to our customers, giving them the ability to self-serve connecting with other systems. So I cannot wait to see what our customers will be able to come up with when pairing Cutover with their machines and systems.

4. What has been, or will be, your biggest challenge?

The largest challenge has been “giving away the Lego” as we have evolved. It has definitely been hard to let go of certain pieces of the day job to others. In hindsight, I always wish I had managed to do it earlier. 

Looking ahead, moving into wider industrial verticals will mean adapting and keeping the product nimble for what those organizations in those new verticals will consider “table stakes”, which are likely different from those we have encountered thus far.  

5. What’s one thing that surprised you about working at Cutover during the pandemic?

Onboarding people, particularly new engineers, remotely has both been a challenge and an opportunity and I’ve been really pleased with how we’ve met it. It’s definitely one of those areas where our culture has enabled us to scale as we were definitely caught “off guard” like everyone else by the pandemic. Not everything was smooth which required us to adapt quickly.

6. Resilience is important from both an operational and personal perspective. What does resilience mean to you?

From a personal perspective, completing the Deloitte Ride Across Britain - riding 970 miles in nine days on a bicycle - was definitely a challenge both mentally and physically. Threshold’s motto is “more is in you” and you have to dig fairly deep when things are not going your way i.e getting three punctures in one day is definitely “testing” but you can, with the help of others on the ride, find a way to achieve it. 

From an operational perspective for me, it is very much just how you deal with the unexpected. I am a big believer in process being the thing that you rely on in an emergency and not the first thing that goes out the window, that way it’s a lot easier to lower the stress in a situation and for humans and machines to excel at what they are good at to get you through to the other side of an unexpected situation.

7. The past year or so has created a lot of challenges, but is there anything new from the last year that you would like to keep?

Software development for me has always been as much of a communications problem as it is a syntactical one. The situation of forced remote working has been beneficial in helping us to work out which of our processes we’re able to scale in a lower bandwidth but with more asynchronous communications. Having our teams already split between New York and London probably helped but it has definitely meant we have got better at being asynchronous as a team.


The Cutover technology team is growing, find your role at Cutover. 

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