Greg Montemurro is a fast talking, hard charging product & community leader who opened doors..so he could knock them down. His own dad was even named after him! Greg just wants to build things and make a dent in the universe with the help of 900+ of his closest Boston area friends. Today he serves as the Chief of Staff to the CPO at fast growing fintech AI startup Posh and is the Founder of GenZ community platform Capital Z.
Born in Cologne, Germany the Montemurro family had moved to Europe for Greg’s job. No, not that Greg. Come on now, he was an infant. The elder Greg Montemurro happens to be a six sigma master black belt who led manufacturing strategies & facilities for Ford. The family then relocated closer to Ford’s HQ in Michigan and eventually made their way back to Massachusetts. Old(er) Greg leads manufacturing quality at Toast these days. And Greg’s mom is a legendary schoolteacher, also built Ford Tough.
From an early age, Greg learned about structuring and solving problems with an “end to end” mindset. He remembers learning about six sigma techniques as an eight year old. But when it came to the classroom, processes didn’t click into place as soundly. He was a varsity runner (currently training for his first marathon) and, in his words, “an awful student”.
Greg thrived in the extracurricular realm. There was an early iOS game, Dark Summoner, where he found a backdoor bug which allowed him to manufacture tokens for new characters. When he posted it to the Internet, a side business was born. His parents desperately wanted to know where the $300 in this new PayPal account came from. 100% legal, mom & dad! Greg mined Bitcoin, he modified video games, and he was just more interested in life outside the classroom.
His first internship was before college as a teenager at FLIR Systems, where he was able to automate his entire job in just a few weeks. Their lack of meaningful work (for an 18 year old) after this led him to want to work with startups. Although it was a lot better than working at Whole Foods!
UMass Lowell was kind enough to grant him admission under the stewardship of new business school dean Sandra Richtermeyer. Sandra was determined to find real world opportunities for her students and Greg took full advantage. When he was a freshman he started a company in the blockchain & biometric space before FaceID to help prevent bank fraud. He quickly realized he was in over his head, not quite ready to be a founder, but he won some prize money in a campus pitch competition to fund his ambitions. It turns out though that removing passwords altogether is a scary proposition for traditional consumers. Jim Regan and David Arajuo were both judges at the pitch competition and encouraged Greg to check out the DCU FinTech Innovation Center in Boston
Greg was ambitious, eager, and determined. So he e-mailed over to the center to get involved. Once, twice, seven times..nothing! But they did add him to their newsletter distribution so he could see their upcoming events.
Then one fine day Managing Director Vasilios Roussos gave him a shot. He e-mailed Greg back that they were hosting an event that afternoon and he could hold doors at the entrance if he could make it in time. Greg shot out of Lowell, skipped a calculus class (sorry again mom & dad!), and borrowed a friend’s car to hightail it to Boston.
He opened doors as only a namesake Greg Montemurro could. Jennifer Jordan, the TechStars FinTech Managing Director at the time, saw the Greg-arious teenager in action and ushered him into the pitch sessions to see what it was really like for startups to pitch investors.
When Vasilios landed funding to secure an intern in 2018, he brought Greg onboard full time to join the center. Greg was a freshman! He juggled a full work week, school work, and campus leadership positions like being the President of the Real Estate Association, then forming a new student consulting group the Manning Consulting Group, and finally serving as Student President of the Business School his senior year. Oh and he was commuting back and forth to Boston too.
Vasilios Roussos, the Centers Managing Director, kept putting Greg in positions to succeed. He has been the most influential person in Greg’s career, empowering him by asking pointed questions and giving him the space to go find the right answers. When he joined, the Center was onboarding their first accelerator class which included an MIT student founded startup named Posh.
Greg dreamed of being a future management consultant, so Vasilios empowered him to lead DCU’s partnership with McKinsey on Go to Market to help the corporate world interact with DCU’s startup accelerator cohorts. By working closely with the McKinsey team, he learned about the work they did and came to his own conclusion that perhaps McKinsey was not his trail to trod. And Greg continued to receive new opportunities at the Center.
He led marketing, due diligence, sourcing, automating & building new tools all the way through college and COVID. Upon graduation he became their Operations Coordinator. The FinTech startups that went through the DCU accelerator program have raised $600M in capital and created hundreds of jobs. Vasilios was the strategic mind and Greg was their workhorse.
Greg got to work with a lot of experienced leaders who were excellent sounding boards. It was awesome. But he also wanted to meet more peers his age. So he organized a happy hour in Charlestown at Anchor with some local GenZ VCs he had worked with. Ten people showed up, all introducing themselves in a circle, and four of them remain Greg’s closest friends today. Capital Z was born.
Underscore VC opened up space for their next happy hour and they had 30 Zoomers join in the fall of 2021. Happening more or less monthly, the group has continued to grow every month. Smart people keep showing up. They brought on partners like Citizens Bank, First Republic, SVB, TriNet and more to sponsor their events. They hosted their first holiday party at the Center and over 70 people joined. The best GenZ founders, investors, & operators in Boston have used CapZ to get more connected and the group is now more than 900 strong in 2024.
Professionally, Greg had been at the Center for 5+ years on a rocket ship and was starting to think about what was next. He had an offer to join a venture capital firm through a prior co-worker, but Posh was looking for Operations help and he really liked building stuff. In particular, automating systems and removing his job by solving hard problems.
Posh had scaled to dozens of employees & clients and Greg jumped at the chance to work with SVP of Client Solutions Michelle Earle. He led project management responsibilities, built an internal tool that helped team members write code for their chatbots in plain text, and made their processes & products work better. Bringing customer & event data into Salesforce and Coda, Greg helped their customer facing teams gain better visibility from a product perspective with their accounts & activities.
After a year in Client Operations, Greg joined Posh’s co-founder & CTO Matt McEachern as his Chief of Staff. He’s rediscovering his technical roots on their “second biggest” product problems, working on hard product problems to help make their AI voice product perform better, faster, and reduce customer implementation time too. In his new role he has additional responsibilities to help pull in the resources across the entire team so they can all move fast and drive progress forward.
Getting Comfortable Through Repetition
With his career starting when he was just a teenager, Greg has gotten really comfortable being uncomfortable. In fact, his anxiety response just doesn’t kick in very often. Even while working alongside very gifted engineers, he doesn’t feel out of place.
After working on so many problems at the DCU FinTech Innovation Center, seeing so many founders and teams, he’s proven he can break things down into component parts. Repeatedly asking questions to smart people, and learning the right questions to ask, is a skill he has honed over the past 5+ years.
He writes things down, breaks those problems down into a system, runs through them, and is totally fine putting together simple prototypes without over obsessing about perfection. He listens a lot too. They built the DCU program around the lean startup methodology and Greg got to witness some of the smartest and most ambitious people in FinTech on their best & hardest days over years.
72 companies, hundreds of founders, and almost a thousand more ran through diligence, Greg has learned to always ask more questions by figuring out “what are you doing this for? Who is it for?” Greg has learned how to ask questions he knows people will have struggled with, so they can search together for better answers…and then design the solutions to follow.
3 Career Insights / Learnings
Be Excited – Excitement is palpable and contagious. People can tell when you’re excited. And they love helping excited people”
Just Try – “We could talk for a long time about all the things I”ve tried that haven’t worked very well. But I learned so much every time I tried. It’s very rewarding when I see all the experimentation I put in at the Center being put into practice at Posh. You’ll never be completely ready!”
Figure Out Who You Are – “I’ve been lucky in my career to be around so many authentic people. I’ve seen that people who don’t change who they are, regardless of the audience, have a big advantage. People can sense authenticity. Learning who you are and embracing it has really helped me get more comfortable and perform better”
One day, Greg wants to start a company. He’s really thankful to have been in highly unstructured roles where he can go find problems and implement end to end solutions. He’s happiest building hacky solutions, solving hard problems with smart people and seeing where it goes. Being paid to learn a lot from smart people is something he absolutely loves. All he knows is that if he ever has to work at a company with a badge on his waist, he won’t be very comfortable.
For more about Greg you can find him building FinTech AI at Posh, running his merry band of 900+ community members at CapZ monthly(ish) events, or on LinkedIn. Thanks for sharing. We’re excited to see the teams, technologies & community you continue to build in the years ahead!