A Woman’s Place is in Tech

VP of Engineering Kitt Caffall is on a mission to diversify Engineering teams, “The (tech) industry is more diverse than when I started, but not nearly as diverse as it should be.”

Kitt’s family moved to Silicon Valley when she was in junior high, right when PCs were coming into homes.* Kitt was fortunate she had access to a computer at home and was able to take a computer course in high school—one of the first ones they offered—and later went to UC Santa Cruz, which has a great software program. Kitt’s worked in Silicon Valley, moving from telecoms to startups to e-commerce back to startups, focusing the latter part of her career on engineering management.

Kitt joined Customer.io as the first Engineering Manager and a year later moved into the VP of Engineering role after demonstrating the necessary skills and drive. Starting with a team of 20, she’s doubled the size of the Engineering department and plans on doing it again this year.

VP of Engineering Kitt Caffall

“We have some of the smartest, brightest minds who are always willing to answer questions and help in a situation, whether that question is coming from another engineer or marketing or technical support. One of the things that I like best is that all of our folks respect skills the other teams have, recognizing that those are not the skills that we (engineers) have, but that those skills are super important for the success of the company, for all of us working as a single team.”

Kitt shares what it’s like to work on Customer.io’s Engineering team and her thoughts on getting more women into the tech industry.

What attracted you to the Engineering team at Customer.io? What work are you most proud of? 
Matthew Newhook (CTO) recognized some gaps in our Engineering team. Our tech leads were really good at architecture and technical aspects but didn’t have a lot of interest in people management. 

Matthew and I worked together to put in an engineering management layer. To grow the team, we need to be disciplined on onboarding, setting expectations, succeeding, and having opportunities to work on interesting problems as they come up.

I’m proud that we have hired great Engineering Managers who have come in and helped their squads work well together. We’ve seen an increase in the velocity of squads, the types and number of product features coming out, fixes, and improvements across the board. 

The job also includes keeping track of what folks are working on, whether they need help, are getting blocked, or pulled into a million different directions. It’s sometimes hard for individuals to recognize, whereas engineering managers have a better overview of the squad. Doubling the size of the team provides everyone with more bandwidth, so folks can concentrate on a single thing without constantly being interrupted.

What has been your biggest challenge at Customer.io?
Getting to know folks, identifying the root problem, and what process might help. You want to put in enough process to provide guardrails, but not so much there is red tape. Small teams are very nimble for a lot of reasons. It’s hard to integrate new folks into a team that’s been working together for a long time. 

Why do you choose to stay working at Customer.io?
I love working here. I have the utmost respect for our Engineering team. It is by far one of the most collaborative, open teams that I have ever worked with.

I’ve spent a lot of my time in Silicon Valley. I know what a company full of tech bros looks like and how detrimental that can be—folks who aren’t willing to help, not willing to share, and are not interested in talking to engineers, much less to other people within the company.

We have some of the smartest, brightest minds who are always willing to answer questions and help in a situation, whether that question is coming from another engineer or marketing or technical support. One of the things that I like best is that all of our folks respect skills the other teams have, recognizing that those are not the skills that we (engineers) have, but that those skills are super important for the success of the company, for all of us working as a single team. 

What advice would you give to other engineers looking to join the team?
Do it. We’re solving interesting, hard problems as a team. We like to experiment and work fast. We make mistakes and correct those mistakes as we go along. The stuff we’re working on is fun.

Anything else you’d like to add about what it’s like to work at Customer.io as an engineer?
The culture Customer.io has rooted throughout the entire company, but the People Operations team, in particular, does a great job and works hard to cultivate it. All the hard work with retreats, Sip n’ Sees, VR game time, etc., get my team working, playing, or watching something together and with folks from other departments. This builds a collaborative, strong, and diverse team across the board. 

Our engineering culture is a little different than cultures from other teams, but all departments have that base Customer.io culture led by Colin (CEO) and worked so hard on by the People Ops team.

Why do you think it’s important for more women to join the tech industry?
I think the tech industry is solving the wrong problems. When you solve problems for only one half of the population, you don’t view all of the things that can be solved. You’re leaving money on the table. Having more women in tech provides a different perspective. It’s not just what problems you’re solving, but how those problems get solved and how they’re thought about. How collaborative a team is. Whether a team works together as a team, or just a set of individual stars. It’s not just a gender thing. It’s important to have different views and ways of working and thinking about how a problem is solved. 

What advice would you give to women entering the tech field? Anything you wish you had known?
Don’t be afraid of making mistakes. Don’t believe the fables around imposter syndrome. Everyone feels like maybe they don’t measure up, but it’s true in some places. It is harder for women to move forward in their careers. And if you are in one of those places, leave. Come to a place like Customer.io, and don’t sell yourself short. Don’t get stuck somewhere. 

This article, Stop Telling Women They Have Imposter Syndrom, by the Harvard Business Review rang very true to me. 

Be your authentic self. Bring yourself to work. You have strong ideas; say them. Be at the table. Talk about what needs to be done. Again, if you are in a place where you are not given the opportunity or cannot make the opportunity for yourself, go somewhere else because there are places where that happens.

I spent the first part of my career being closeted, passing as straight, and even still had lots of opportunities that were not available to me. I enjoy what I do far more when I can bring my entire self to my work, to my team, where I can talk about my family. All of those things make a difference. 

What do you believe young women need to know/hear/see to consider a career in tech?
Young girls need role models and opportunities. You need to see your dream to envision being a step or two beyond that. We’re doing some of this as we go along, but we need more women in the higher ranks, on boards, as CEOs, and having mentors, asking questions, and having conversations about what someone wants in their life.

*NPR investigated what happened to women in computer science and found a correlation between PCs being introduced into homes and marketed as toys for boys.

Customer.io is people-first with a globally distributed team across 34 countries. Our Engineering team is always hiring. Check out our open positions!

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