Women in Tech: Digibee’s Cait Porte On the 5 Steps Needed To Create Great Tech Products

Currently, only about 1 in 4 employees in the tech industry identifies as a woman. So what does it take to create a successful career as a woman in tech? In this interview series called Women in Tech, we spoke to successful leaders in the tech industry to share stories and insights about what they did to lead flourishing careers. We also discuss the steps needed to create a great tech product. As part of this series, I had the pleasure of interviewing Cait Porte.

Cait Porte

With more than 15 years of experience in high-growth SaaS businesses, Cait has helped companies grow from $1 million to over $100 million. She is currently the chief marketing officer for Digibee and is the former chief product officer at Zmags. Cait has her MBA from Babson College, was a co-founder of the Boston Women in Product, and was on the board of directors for the Boston Product Management Association. She teaches product management at General Assembly and speaks at various technology leadership conferences throughout the years.

Thank you so much for joining us in this interview series! Before diving in, our readers would love to learn more about you. Can you tell us a story about what brought you to this specific career path?

Although the tide is changing when it comes to how people get into product or technology, mine was "right place, right time." I was considering a move from NYC to Boston and ended up getting a job as a product manager. I had no idea what it was, but the interview team thought I would be a good candidate for the role. Fast forward 15 years later and it was the best thing that could have happened to me.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I am sure I am not alone when I say I have had my fair share of mistakes, embarrassing moments, and things I’ve learned from. One that comes to mind is very early in my career during a team meeting. I was working with a team in the U.K. and they were six hours ahead. We were all on a conference call and I was heading into work. I neglected to turn myself off mute and was caught yelling at traffic during the morning rush. We all had a good laugh about it, but I was mortified. Now I triple-check that I am on mute during calls—just in case.

What do you feel has been your ‘career-defining’ moment? We’d love to hear the lead-up, what happened, and the impact it had on your life.

After shifting from large, global companies to startups, I had a career-defining moment while getting my MBA and working at a startup. I was getting certified to be an executive coach, and one of the instructors encouraged me to read a book titled “I Didn’t See It Coming.” The book talked about how to separate business from personal and spot the signs of incoming change within an organization—whether an org change, acquisition, or layoff. The book proved to be a turning point in my career as I was passed over for a promotion and the company was acquired within two weeks of each other. To say I was devastated is an understatement. Only part of the company and technology was purchased, leaving two separate groups. The experience turned out to be career-defining because I could have sulked and pouted about the changes, or I could have leaned in and used it to my advantage. I decided to put on my big girl pants and lean in. This proved to be challenging but extremely rewarding, putting me on a path to leadership that I could never have imagined or predicted. Charles Swindoll is well known for saying “Life is 10% what happens to you and 90% how you react to it.” In that moment, I could have chosen to be bitter, and because I didn’t it changed my career, (I think) for the better. 

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Early in my career, I got hired by a company that was going through a dramatic transformation. Not only was the company shifting from waterfall to agile, but it was shifting from printed materials to digital materials and software products. The environment was fairly toxic for someone like me who was bright-eyed, bushy-tailed, and ready to learn. There were so many times I wanted to throw in the towel — thinking that I wasn’t smart enough, couldn’t learn fast enough, and couldn’t get people on board to help innovate. I doubted my technology and product skills regularly but I was lucky to have managers and a small team who supported me in the journey. I ended up spending two years working extremely hard to shift the culture. We launched a 1.0 product for the industry that completely changed the way companies in that sector did business. I’d like to think I had a profound impact on the company as a whole because the work they did (and continued to do) was really transformative.

We’d love to learn a bit about your company. What is the pain point that your company is helping to address? How does your company help people? 

I am currently working for Digibee, an integration platform for developers. My product background has helped immensely — not only because I can understand the technology we are developing but because I’ve had years of practice translating technology features into business value. We are on a mission to redesign enterprise integration by revolutionizing the way IT delivers business value. Our tools and our team empower developers to accelerate innovation—and based on my own personal experience, I think that’s really powerful. IT departments can sometimes get a bad reputation, but our technology helps them deliver more product, faster, and with more security. Seeing this challenge firsthand makes me appreciate the technology we’re building.

If someone wants to lead a great company and create great products, what is the most important quality that person should have, and what habits or behaviors would you suggest for honing that particular quality?

Great leadership comes in all forms, and everyone has their own idea about what the most important quality is. Communication is the first thing that comes to mind when thinking about what it takes to be a great leader. I’ve been really lucky to have some of the most impactful people mentor me along in my career—and all of them have been exceptional communicators. Whether painting a vision or delivering bad news, the best leaders are the ones who can do this tactfully, gracefully, and with compassion. I’d add one more—grit comes to mind as the difference between success and failure. Persevering through whatever challenge is thrown at you becomes increasingly important as you navigate any part of your life—whether it be personal or professional. To hone both of these, I suggest writing things down and setting goals for yourself. Then, deliver on them and figure out how to communicate the success (or failure, or challenge) that you’ve had. 

Next, let’s talk about teams. What’s a team management strategy or framework that you’ve found to be exceptionally useful for the product development process?

I have always encouraged my teams to self-organize and select a practice that works best for them. The two that come to mind which are particularly popular right now are Agile Scrum and Agile Kanban. There are some key differences. Kanban is generally used as a tool to visualize work, whereas Scrum is a full framework you can use to run your teams. Scrum is much less flexible than Kanban but a great way for agile teams to collaborate and get high-impact work done. Given that both are project management frameworks and I like organization, I tend to lean toward Scrum—but I always encourage teams to select a method that they understand, can implement, and more importantly, can deliver value by using.

When you think of the strongest team you’ve ever worked with, why do you think the team worked so well together, and can you recall an anecdote that illustrates the dynamic?

We can’t forget that there’s a human element to team building. If you look at the most successful teams, whether in sports, sales, or development, the common element is that they all trust each other. And this trust starts at the top. When I look back at the teams I’ve built or worked on, the most successful ones were the ones who trusted each other and had clear guidelines on what we were being asked to do. An example of this always comes out when people are out of the office or on vacation. The most successful teams rallied around each other and got the job done—regardless of what it took. They trusted each other and knew that when one person wasn’t able to pick up the slack or was out, the other team members were going to step up and help.

If you had only one software tool in your arsenal, what would it be, why, and what other tools (software or tangible items) do you consider to be mission-critical?

I’m a little old school here—but I think Post-Its, spreadsheets, and Word documents are underrated. If that’s all I had on my desk (including a pen and a computer) I could definitely get all of my work done. This is not to say that some software tools don’t help, but (oddly enough) I take a minimalist approach when it comes to technology. When I do select software products, I make sure that right away they’re usable and provide impact. If they don’t do it right away when I am engaged and excited about the value they offer, I’m unlikely to use them in the future. We take the same approach when building our products.

Let’s talk about downtime. What’s your go-to practice or ritual for preventing burnout?

This is one of my favorite questions. Taking a walk and getting some fresh air, even if it’s just to go to the mailbox and back, really helps me reset. Whether it’s the afternoon lag or recovering from a tough meeting, the fresh air always reinvigorates me and keeps me going.

Based on your experience, what are your “5 Steps Needed to Create Great Tech Products”?

1. Talk to your customers.

I can’t stress this enough. One of my goals is to speak to at least one customer a week. I used to talk to customers daily but my role is a little different. If you don’t talk to the people you’re building products for, what’s the point?

2. Deeply understand their problems.

Empathy is a key driver of success. Too often we jump to a solution. Focus on the problem—and every aspect of it. Understand how the customer comes across this problem, how they solve it today, and what is the expected outcome when they solve the problem. Albert Einstein once said, “If I had an hour to solve a problem I'd spend 55 minutes thinking about the problem and five minutes thinking about solutions..”

3. For the top problem, come up with a solution.

When you’ve identified the top one or two problems, start thinking about solutions. This is where the magic happens. Everyone wants to be the “idea person”—but make sure you’ve got the most qualified people in the room to help build the solution. Remember, the best idea wins—not the highest-paid person’s.

4. Check-in with your customers.

Before jumping into development, check in with your customers. Share a prototype, get feedback, and watch how they might use it. You may be surprised that you and the team were wrong about something (and right about other things). This also gets your customers bought in before you even build anything—saving tons of time and money.

5. Build and launch the product.

While this one takes A LOT of time and effort, it’s ultimately the most well-defined and common part of the process. What I mean is, we’re quick to jump to solutions because we see the output. Building a product or feature can take time—and still needs customer feedback, but if you’ve followed the first four steps, you’re likely on the right track and can build what is necessary.

Are you currently satisfied with the status quo regarding women in tech? What specific changes do you think are needed to change the status quo?

I don’t think I’ll be satisfied until there’s equal representation at every level in every department across every business. As a C-level executive and mom of two kids under four, I know how difficult it can be to balance work and life. I think it’s hugely important to see someone who “looks like you” in roles that you want to have, so I put an enormous amount of pressure on myself to be visible to others who might want this support. Women in technology represent such a small percentage of the population—we need to support each other and our prospective teams to pave the way for the future. I think it’s critical that companies and organizations go out of their way to make sure they have diverse teams with varying perspectives. Women have to put themselves out there to help drive change.

Is there a person in the world with whom you would love to have a private breakfast or lunch, and why?

I’ve been really fortunate to meet many influential product and career people over the years. I recently read the book “The Trillion Dollar Coach” about Bill Campbell. Bill was a football coach turned executive. He was an influential CEO and executive coach for folks at Google, Facebook, and many other businesses. While the book was inspired by Bill, he sadly passed away a few years ago. I’d love to meet him mainly because of the consistent stories people told about how brutally honest he was and how he asked the hard questions. Great leadership skills are so crucial in career advancement. I’d love his advice as I try to navigate the next phase of my career.

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