“Great products are like great stories and product leaders need to be among the chief storytellers in their company,” said Matt Kaplan, who has had a successful career building and leading products for early stage and high growth tech companies.
“Most stories have a hero or protagonist, a key tension or problem they’re faced with, and hopefully a happy ending or resolution. Products have the same structure with a target user, a key pain and a product vision that solves it,” said Kaplan. “If you treat your product like a good story, it’s much easier to imagine how you can bring it to life and get others to listen and lean in.”
“Whether it was my time doing theater, writing and performing music, giving company presentations or launching software products, I’ve always been passionate about creating stories that paint a vision of the future and bringing them to life. I look back at many of the companies I’ve worked for and think how those experiences helped shape my beliefs and values as a product leader.”
Kaplan, who is currently the GM of Emerging Products at LogMeIn, was raised in a suburb of New York City, but has called the Boston area his home for many years. He currently lives there with his wife and three children. He got his love for performing from his mother and his work ethic from his father, a CPA who ran his own small business accounting firm based in Manhattan.
After spending time working for his father over multiple summers, Kaplan knew he didn’t want to follow the same path of credits and debits. He was accepted into MIT crediting his diverse skill set (he also did theater, gymnastics, and played music) as the main reason he got in. “I didn’t have perfect SAT scores but I was very strong in math, and I did a lot of theater, so I think my angle was that I was a well-rounded math geek,” he said.
Over his summers in college, Kaplan worked at Cambridge Technology Group (CTG), a company that educated executives on the “coming era” of client-server technology and began his career there after graduating MIT with a degree in Mathematics with Computer Science in 1987. CTG eventually launched a systems integration business and spun off Cambridge Technology Partners (CTP) where Kaplan was one of the first project managers leading integration projects for the American Red Cross and Salomon Brothers.
Despite this being a valuable experience for Kaplan, it’s also when he had a wistful encounter with a member of his project team, Stuart Moore.
“Stuart and his friend Jerry asked me if I wanted to start another consulting company with them. Thinking it was too big a career risk, I said no.” Stuart and Jerry then founded Sapient which went on to become a publicly traded company and was part of the S&P 500 for a stretch of time before being acquired by Publicis Group. It’s the road not taken, so it’s not the best part of my story,” Kaplan said with a laugh. “I did learn, though, that I needed to take some more risks.”
This isn’t to say, however, that Kaplan would never enter the world of startups. It was the exact opposite. In 1991, Kaplan was a co-founder at a venture-backed start-up called The AdValue Network, where he ran product and engineering. “We set out to make it easy for buyers and sellers of radio and television advertising to conduct business online. This was the early days of Internet connectivity, so we had to run leased lines to our customers offices to create a private TCP/IP network. Seems crazy now that I think about it.”
The company was sold to Reuters at the tail end of 1996, and Kaplan stayed on for a few more years. “It was my first taste of a startup, and it’s where I realized my love for building products. I was thrown into it without any experience, and was in charge of building a product from scratch. I really cut my teeth as a product leader at AdValue.”
In 1998, Kaplan was reunited with several CTP alumni to join Quadris Consulting as VP of Technology. Soon after, Quadris merged with Interactive Solutions to become the Boston office of AGENCY.COM, which was the largest interactive marketing agency in the world at that time. He stayed for 4 years through the successful IPO in 1999 and helped launch their worldwide Intranet and knowledge management portal. For Kaplan, his time at AGENCY.COM became a lesson in UX.
“I gained a deep appreciation for user experience and design. Coming from a technology background, I didn’t realize there was a whole discipline surrounding user experience and UI design. Working with designers is very different than working with engineers, so I learned how to give constructive design feedback and the importance of navigation, labeling and good visual design.”
In 2003 Kaplan had an itch to start something on his own, so he launched a side business called Backyard Jams that combined his entrepreneurial spirit with a passion for music. Backyard Jams provided a studio and stage for aspiring musicians to play, perform, and record music, similar to the now famous School of Rock franchise. After some early struggles, the company pivoted to focus on rock and roll birthday parties and events.
“It ended up being such a great product, but the burden of running a side business while working full-time was too much especially with 3 young kids at home. I learned that you have to be 100% focused on something to make it work,” said Kaplan. “It’s really hard to split your time, energy, and passion.”
Kaplan then reunited with the previous founder of AdValue to join his newly formed company, PermissionTV, a venture backed enterprise video platform company with a twist. It provided marketers and publishers tools for creating interactive videos, enabling consumers to navigate on their own journey through a video. For example, a consumer could watch a video from the Boston Symphony Orchestra and choose which piece of music they wanted to watch next, creating a more personal experience.
“This was the pre-YouTube era. We went into it with the belief that online video was going to be the next big thing, and we set out to make it happen. But rather than focus on streaming video like the other online video platform companies, we wanted to take advantage of the interactivity of the medium,” said Kaplan. Although they did make some progress working with clients like MGM, BBC, Bob Vila, and Activision, PermissionTV ultimately ran into content-related issues.
“The challenge was, most people just wanted to take their existing linear content and put it online. Our vision was to build an interactive platform that enabled richer user experiences, but we were quite ahead of our time.” Kaplan’s experience at PermissionTV was incredibly beneficial, as it taught him a very valuable lesson. “It’s great to have a vision for the future, but it’s important to focus on the problems that exist in the world today.”
Kaplan’s career would then take him down the path of working at a few startups before joining LogMeIn as a Vice President of Products for their Access & Management product line in 2012. “I wanted to work for a larger company that had a track record of success but was also still very entrepreneurial. LogMeIn gave me an opportunity to bring Agile and Lean principles to a larger company and do it at scale.” It proved to be an eye-opening experience for Kaplan, as he had to figure out how to manage global product and engineering teams in Boston and Budapest.
His team was responsible for several of LogMeIn’s products, including LogMeIn Pro, Central, Cubby, Hamachi, and join.me. Two years later, he was promoted to SVP of Products where he took over all of engineering, design, and product management for the entire suite of LogMeIn’s products. At that point, he was leading a team of 350 engineers, designers, and product managers, which grew to 425 people by 2016. “Managing such a diverse portfolio with products at various stages of their lifecycle is incredibly challenging”, said Kaplan. “I learned that you can’t just apply the same organizational model and tactics across all product lines, you need to consistently re-evaluate your approach.”
Earlier this year, LogMeIn merged with Citrix’s GoTo business unit to create one of the world’s largest publicly traded SaaS companies. Kaplan was then appointed to General Manager of Emerging Products, where he is now responsible for two of LogMeIn’s fastest-growing product lines, LastPass, the leading password manager and Grasshopper, a cloud-based phone system for small businesses.
There are very few product executives in the Boston area who have the same level of experience as Kaplan, in terms of running a whole product portfolio at such a massive scale. So, when asked about what advice would he pass along to entrepreneurs or product managers, he mentioned three points.
First, in terms of thinking about building and growing a product line, one needs to be able to answer three fundamental questions that shape your product’s story:
- Who is your product built for?
- What problem are you trying to solve for them?
- Why is your solution so unique?
“If you can’t answer those three questions early on, you have very little chance of having a successful product.”
Second, he mentioned that you need to be able to share and evangelize your ideas with others early and often. He advises against keeping ideas to yourself, because if it’s a good idea, they’ll likely add to it. If it’s a bad idea, they’ll surely let you know.
And third, he said that you must infect the organization with your passion. “The key to being a successful product champion is not just about being passionate yourself, but being able to convince others of your passion. That’s why it’s so important to master your storytelling skills.”
Images courtesy of Matt Kaplan and LogMeIn.
Alexander Culafi is a contributor at VentureFizz. You can follow him on Twitter @culafia.