C-suite career advice: Frank Laura, EngageSmart

How important are specific certifications? “To me, it’s more about internal motivation and the ability to produce results, not how many certificates you’ve earned.”

Headshot of Frank Laura, CTO at EngageSmart

Name: Frank Laura

Company: EngageSmart

Job Title: Chief Technology Officer

Location: Detroit, MI

Frank Laura has nearly 30 years of technology experience in industries ranging from banking and loans to marketing and promotions. Frank joined the EngageSmart team in 2019 as the Chief Technology Officer and has helped the company cement its position as a leader in customer engagement software while going public in September 2021. Before EngageSmart, Frank served as Chief Information Officer at Progressive Leasing, Entertainment Publications, and Quicken Loans. Frank’s specialties include systems architecture, technology planning, data center development, software engineering, technical operations, and IT governance.

What was the most valuable piece of career advice that you received? Make something you love your career. I love to help people. A career in technology has given me the opportunity to help a lot of people, whether they be customers or coworkers. If your career is something you genuinely enjoy doing at its core, your day-to-day will be interesting and fulfilling.

What was the worst piece of business advice that you received? There’s a bad assumption out there that if you’re stuck between two opportunities, to take the job that pays the best. Financial stability is important, but I’m a firm believer that money can’t buy happiness. Doing what you love and what you’re good at will bring you joy, and financial success will follow.

What advice would you give to someone starting their career in IT/tech? There can be a lot of pressure to become an expert in your domain as quickly as possible. I’d advise those starting out in IT/tech to take their time and explore the entire field—it’s changing every day, and new opportunities are always popping up. Once you’ve explored, you’ll have a clearer idea of what it is that you really want to focus on going forward.

Did you always want to work in IT/tech? Honestly, no. My father was a high school teacher and was the first to expose me to working in technology. When I was younger, I studied to become an architect. My professional start in technology came through CAD in my first job.

What was your first job in IT/tech? My first job was as a CAD drafter at Computerized Facility Integration, which led to programming and eventually networking. After that, I continued looking for opportunities in IT/tech.

What are some common misconceptions about working in IT/tech? Technology can be intimidating to a lot of people because they think it’s beyond their understanding. There’s no reason to fear IT/tech! The field is so broad, and there are so many opportunities catering to a range of interests, that I’d encourage everyone to at least consider a career in IT/tech. If you’re willing to learn, it’s a great field.

What tips would you give to someone aiming for a c-level position? I’d suggest reflecting on why you’re interested in a c-level position. Typically, the higher you go in IT/tech, the less hands-on you are with technology in your daily activities. If you love the hands-on problem-solving that comes with day-to-day technology roles, you need to carefully consider how you’re going to drive value from your work if your day-to-day is different—and the C-Suite is very different. 

What are your career ambitions and have you reached them yet? I love a challenge, especially when it comes to growing businesses and teams. I’m rarely satisfied and always wanting to help more people, which is why I love working at a company like EngageSmart. Being part of a company that has solutions uniquely suited for different industries means that each day’s challenges are different and that I need to think creatively. It’s certainly never boring!

Do you have a good work life balance in your current role? Work is part of life, and I’m lucky that my work is something that I love to do. Though it can be hard to keep a steady balance, I have found a schedule that works for me, with the help of my company’s flexible working hours. I also make sure that I’m respectful of my team’s boundaries, as I know work life balance looks different for everyone.

What, if anything, would you change about the route your career path has taken? Sometimes, I wish I had waited a bit to start my career, but I truly believe that everything happens for a reason. I’m thankful for all the experiences I’ve had and all the people I’ve had the opportunity to work with, and for where I’ve ultimately ended up.

Which would you recommend: A coding bootcamp or a computer science degree? It totally depends on your desired outcome and learning style. Both bootcamps and degrees have their pros and cons, so it’s more about which will be a better learning environment for you, and which is more necessary for the jobs you want. Trying out different roles and ways of working in technology is most valuable of all, so choose the path that allows you to explore as many aspects of the technology field as possible. You’ll understand how it all fits together much more clearly than you might by a coding or computer science path alone.  

How important are specific certifications? To me, it’s more about internal motivation and the ability to produce results, not how many certificates you’ve earned. I’d prefer a highly capable and motivated person without any certifications on my team over a competent candidate with a resume that looks like a NASCAR car with certification logos. There’s plenty of highly educated and certified people that cannot produce valuable results, so being hard-working and dedicated is most important.

What are the three skills or abilities you look for in prospective candidates? I always look for a desire to learn, ability to learn, and how well a candidate fits in with the company culture. At EngageSmart, collaboration is essential to our success and culture, so if a potential employee is willing to jump in and learn something new alongside our team, I’m confident that they’ll do well.

What would put you off a candidate? As I mentioned, EngageSmart really values collaboration (as do I), so if any candidate seems focused on “what’s in it for me,” then that would really put me off. Everything should be about the team and achieving team goals.

What are the most common mistakes made by candidates in an interview? How can those mistakes be avoided? It’s easy to tell when a candidate is not being sincere or transparent. And when candidates aren’t genuine—whether it be about their interest in the company or about the kinds of work they’re passionate about—it’s hard to build trust. An easy way to combat this is to do your homework. Before an interview, research the company and the role, and spend some time reflecting on why you personally connect with the team, the role, and the company. 

Do you think it is better to have technical or business skills – or a mix of both? Technical skills are business skills—it’s an outdated perspective to look at IT as separate from “the business.” Technology is a critical domain that must be treated as an asset to any business.