Becoming a CTO

What did it take?

• Growth through others
• Hard work and long hours
• Aggressive Learning
• Thinking through many scenarios
• Strategy and policies
• Make Decisions
• Constantly evolving the way I communicate
• Leadership development
• Evolving System Thinking
• Learning other parts of the business
• Being curious and not judgmental
• Forgiveness
• Build systems to reduce your workload
• Hiring for uniqueness not fit
• Leaving and moving on

Growth through others

Getting to be an actual Chief Technology Officer for me has been about standing on the shoulders of so many engineers who have coached me, mentored me, educated me, listened to me, challenged me, critiqued me, appreciated me, and let me lead them.

As well as all the engineering leaders who have being there for me and great recruiters who have being true partners

Thank you

The humans who helped me get here:

David Witts, David  Picknett

Sam Livingston-Gray, Avdi Grimm, David Dosset

Willian Kral, Patrick Audley, Rafe Hatfield, Polly Allen

Marcin Popielarz, Zach Moshansky, Denise Kwok, Yourdon Jou, Lan Zheng

Eric Dagenais, Michael Brown, Christo Coetzee, Brooklyn Zelenka, Jennifer Cooper, Xavier Perez, Rachel Teo, Abinyah Walker

Jeff Miller, Gopi Guntupalli, William Best, Rachel Caileff, Nick Matelli, Yevhen Strohanov, Roman Halaida, Dustin Hansen, Jef Jonjevic, Danila Ulyanov, Blake Thomas, Todd Pierzina, Zachary Gallup, John Schloman, Matt Danforth, Jonathan Yeo, Adrian Thomas-Peterson, Eli Albert, Greg Hubband, Robert Chen, Zamir Syed, Diwant Vaidya, Kenneth Gass, Jeff Lunt, Sam Elston, Allen Dean, Jame Wilton, Michael Blatter, Alan Zoppa, Tyler Jefford, Dave Pollak, Matt Moore, Dan Olsen, Pranav Moktali, Parul Schroff, Dan Kotowski, Saahithi Gunda, Emmanuel Sambo, Aditya Mattos, Arpan Patel, Vishak Seshadri, Christine Schwerdtfeger, Sara Lupp, Chris Stavisky, Vaughn Bullock, Srivathsava Rangarajan, Matt Larraz, Joe Mastey, Kelmer Perez, Lawrence Walters, Jon Locker, Kevin Harriss, Jerry Seeger

Daniel Schepers, Trent Kan, Gabe Kuhlman, Bogdan Pozderca, Jack Deters, Alex Negrete, Steve Raden, Dennis Huh, Oswaldo Rangel, Tamara Duhamell, Corinne Maloof, Edward Bryant, Aziz Benjamin Harrington, Alex Dinh, Andrew Kellams, Madeline Levinson, Kevin Jacob, Rob Timpone, Ryan Casler, Danielle Scherr, Amanda Hinchman-Dominguez, Marian Dadzie, Terrall Jorden, Jordan Schweigel

Larry Kiss, Rob Mills, Alan Deitch, Lynette Midy, Ieshe Washington, Ashwin Sawh, Ryan Perkins Mata, David Van Noten, Zachary Arrigoni, Jarod Cohen, Tim McCoy, Attila Domokos, Benjamin Goldberg, Michael Wilson, Greg McLain, Nicholas Kincaid, Mark Theisen, Noah Lawrence, Brian Chorus, Megan Rose Bui, Andrew Kirkham, Nicholas DeCraene, Brian Drupieski, Jake Sikora, Andrew Holbrook, Erika P. King, Robert Alan Dinneen, Tony McNevin, Chris Ramacciotti, Cezar Jenkins, Duncan Gillis, Sunghwan Cho, Demonze Spruiel-Rose, Peter Zouck, Chris Eden, Boiar Qin, Matt Ritsman, Nathan Caraker, Matt Przybylski, Tom Schroeder, Harry Nicholls, Seth Thomas, Tyler Williams, Eddie Padin, Mark Levy, Zack Gill, Kyle Haptonstall, Reed Hogan, Luke Quigley, Joe VanDeventer, Carl Hill-Popper, David Ryan, Limin Peng, Benjamin Piatt, Mateusz Perlak, Mike Beirne, Matthew Kemper, Will Atlas, Sam Rees, Jim Werwath, Jonathon Carlyon, Tom Wessels, Grant Nicholas, Samuel Corzine, Zachary Lawson, Shuyuan (Lance) Deng, Geoffrey Hunter, Michael Yan, Anthony Smaniotto, Ryan Carlson, Philipp Birklbauer, Schuyler Sanderson, Cody Connelly, Justin Gomez, Julia Lee, Todd Schreiber, Brian Suarez, JAKE JOHNSON DE JESUS, Lizzie Clark, Riley Hutchinson, Tyler Knell, Saheel Bhatt

As well as meeting with many peers in Engineering leadership and engineers, to hear their stories and learn from their experiences.

Hard work and long hours

I have not experienced an Executive role where you can really have a good balance of work and the rest of your life. Every Executive role I have taken has taken between 40 to 60 hours a week. With most vacations being interrupted ( good lessons on delegation in here when possible)

Aggressive Learning

Every year I think about what I want to learn and how I can learn it. Whether it be a new technology, a new evolution in humankind, a new leadership perspective, a new way to think about business, or a new way to turn data into insights

Learn and listen to your people, peers, and network. Be approachable.

Sometimes you will get it wrong. Regardless of how you get the feedback, understand it. Take time to learn and deeply reflect on what you should do differently and then do it.

You need extensive technical knowledge, which is often different for each organization you work for, you need to pay attention to tech trends – carving out time to do both is critical to this career. Great research skills will keep you up to date.

Be mindful just because you know something, to not become a dictator in all choices technical, if you do, you will reduce opportunities for your managers and engineers to grow and own something.

Thinking through many scenarios

A strategic mindset is needed at the C-Suite level. When planning ahead I consider the good, the bad, and the ugly of what could happen next. After six Executive roles, looking ahead or around corners becomes important. and the more you can do this with your peers the better.

Not only should be able to do this for the Business but also for what’s next in technology. A strong network of CTOs will be important as a new tech in one industry sector may cross to another.

I also tend to view problems as an opportunity, this opens up the approaches you can explore for different scenarios. The more complex it is the more I love it.

Make Decisions

As you grow through the leadership ranks, you will discover that at each level you will have less information to make concrete decisions. Make the best decisions with the information you have, if they are BIG ones with an impact you cannot change, yes take a moment, seek advice. But for the others that can easily be changed make them fast and ensure a tight feedback loop so you change if needed.

In Startups and small organizations, you will often be faced with many tough choices, and it’s important to understand the context and be pragmatic rather than try to build perfect fully scalable solutions.

And don’t forget to explain the Why!

Strategy and policies

People want to know where they are going and why. Sometimes they will want to know How (great opportunity for you to let them have space to figure that part out). In Startups you will often also need the disciple to stick with a plan as many things challenge this in Startups.

Reviews, post-mortems, and milestones will also help you figure out in hindsight what worked and what did not.

Policies often reflect the way you want to do things and preferred behaviors. Consider the cost or weight of each, review them at appropriate intervals, and question whether they need to exist at all.

Constantly evolving the way I communicate

How you translate very complex things to help people who do not have the same technical skills is incredibly important. Trying out different analogies to help different groups of people understand what the team is working on. How do you drive more transparency so others can understand what is going on and allow others to help.

Having lived and worked in multiple nations, you will often make mistakes in how you communicate and how you are perceived. Learn about each nation you work with, and the dos and do nots. Still, remember every person is unique.

For really important things you will need to communicate multiple times, in multiple channels.

Collaboration with peers

Working with the rest of the Executive is critical to your success.

A big part of this is to be able to translate from highly technical language to language and analogies that others understand.

Thinking about how you can support your peers, their knowledge, their people, and their systems to be able to achieve organizational goals.

Also building some time to just know each other is important, as a lot of the time you will be having to resolve tough operational situations or complex strategic problems to navigate.

Leadership Development

Looking for opportunities for my leaders and managers to take something off my plate so I can look out further and sometimes deeper. Whilst mentoring behind the scenes so they can keep ownership. Sometimes it’s waiting until the leader notices and then supporting them (if needed) through the growth.

Evolving System Thinking

Thinking about what is getting in the way, bringing others into the conversation in how to improve things, whether it be automation, a different flow, new skills, new people, etc

Learning other parts of the business

The more that you understand the complete chain of events, the more you will help the business and not just your department. We succeed or fail together. As Technologist understanding the flow of data through all the tools, who needs, and why allows you to support Finance, Operations, Customer Services, Sales, and Marketing – much better

Being curious and not judgmental

Really allows you to navigate, many tough conversations and build better alignment where possible.

Technology is constantly evolving, if your perspective on how to do things does not evolve you will likely be left behind by the pace of technology both evolutions and revolutions. You will have to adapt many times, being curious really helps.

Forgiveness

Is one of the most powerful tools you have in your toolkit. People will sometimes get it wrong, and they sometimes they will go toxic. It may be nothing to do with you and sometimes it is. Either way, hear and understand what they have got to say, but don’t hold it against them. Find a way to show that to not just the individual but the team.

This is not to say you don’t fight lies and gossip that have manipulated the truth for their own ends. Be thoughtful about how you do this and the cost to you and your team.

Build systems to reduce your workload

Strong organizational skills will be critical to your and your team’s success.

If most places I have worked as the scale of the team or systems increase I find ways to analyze what is going on and make it easier for others to see the big picture, whether it be a Google sheet with all the people and what they are working on, or who owns what.

Hiring for uniqueness not fit

When I think about a team, I believe that a good team has many different “types” of people. This helps us see and explore many different ways of solving the same problem. Infinite diversity leads to infinite possibility.

This does not come for free, there will be misunderstandings and differences in communication styles. This will create conflict. So help your team to be good at conflict. Encourage tight feedback loops, encourage people to talk directly with the person they have an issue with rather than you or the people team, and assume positive intent.

Leaving and moving on

You own your career growth. Not your boss. If you are lucky they will help, but often they will not.

Have a plan about what the exit looks like. My perspective regardless of the style of exit, is to do right by your team, even if costs you a little. As an Executive leader, your exit should not create an outcry, yes there will be a grieving process for those close to you, and some maybe be friends. But if you were tasked with building a team and paid for it, that is what you should leave.

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