093: Boston Speaks Up with Stephanie Roulic, Startup Boston founder and CEO
Stephanie Roulic is the founder and CEO of Startup Boston where she’s become a driving force behind Boston’s startup ecosystem. Through Startup Boston, Roulic is on a mission to bring networking opportunities that bridge connections between people from different industries and companies from all stages. She leads a team of dedicated volunteers who are all aligned in fulfilling Startup Boston’s vision to establish a more connected Boston business ecosystem.
Since co-founding the martech company nDash in 2016, she recognized the need for meaningful connections in the local startup community. This led her to also launch Startup Boston Week in 2017, an annual event that brings together thousands of attendees and hundreds of speakers, including industry luminaries such as Brian Halligan and Jules Pieri.
Throughout her journey, Roulic’s leadership and passion have shone brightly. From being the first non-engineering hire and employee number 11 at Goldcast, she built out and managed customer success and support teams. She’s played an instrumental role at MassChallenge and nDash as well, demonstrating her expertise in community-building and client support. Her accomplishments extend to education where she advises Suffolk University’s Management & Entrepreneurship Career Community Advisory Group.
In 2022, her efforts with Startup Boston were recognized by the Boston Business Journal as she was named one of BBJ’s 2022 40 Under 40 Honorees; and prior to that was named to BBJ’s Power 50 for 2020. Her strategic prowess is evident in securing sponsorships, developing onboarding strategies, and creating year-round initiatives and events. With a commitment to diversity, her leadership has resulted in Startup Boston Week drawing a majority representation of women and people of color among speakers.
Roulic’s journey began with a Bachelor’s degree in Communication and Media Studies from the University of Massachusetts Amherst. Her dedication to her craft and community led her to embrace roles at Geek Girl, where she served as Program Coordinator as a dedicated volunteer. From nDash’s inception to the birth of Startup Boston, Stephanie Roulic’s profound impact on Boston’s startup ecosystem is truly commendable.
You can listen to our podcast discussion embedded below or on any podcast platform you prefer (YouTube, SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play):
Written Q&A:
Where did you grow up and how would you describe your childhood?
I grew up in Billerica, Massachusetts, which is North of Boston. I was a pretty big loner and spent most of my time writing stories and reading books. I also really loved planning imaginary summer camps and future school curriculum — something about planning a schedule and layout of what could potentially turn into a real thing was exciting. Looking back, it definitely makes sense that Startup Boston Week would have been something I took on planning!
Who have been your biggest mentors in life and what have they taught you?
I look up to my Mom the most. She instilled a lot of confidence in me growing up and showed me first-hand how valuable hard work and having a great work ethic is.
Could you share the story of your transition from co-founding nDash to becoming the Founder & CEO of Startup Boston? What motivated this journey?
They both occurred fairly simultaneously! Startup Boston was created because of my time at nDash. It was my first time building a startup and, as most startup-ers know, there truly is no playbook for how to build a company or start and scale a department. Everyone’s journey is going to be different, but what helps us the most along the way is having a community of others with the same drive and motivation as you, who are also going through similar challenges. It’s really lonely as a founder — or even an early startup employee — I built the community I wish existed when nDash was first born.
Startup Boston Week has evolved significantly since its inception in 2017. Can you explain how you transformed this event into an organization showcasing the New England startup ecosystem?
When I created the first Startup Boston Week in 2017, I truly had no plans to build an organization on top of it. Heck, back in 2017, I was just hoping a few hundred folks showed up (we ended up receiving 2,200 registrations that first year).
It truly wasn’t until 2020 that I started thinking this could be more than a conference — we could connect and support one another year-round. And, of course, due to the pandemic, a strong community was needed more than ever.
It was in 2020 that we really put an active effort into creating events and opportunities for folks to connect year-round, not just during the one week in September.
Congratulations on being selected as one of Boston Business Journal’s 40 Under 40 honorees! How does this recognition impact your vision for your work moving forward?
I truly felt so incredibly honored to receive this award. It came as a huge surprise to me — I didn’t even know that I was being nominated (a huge thank you to Phil Kasiecki for nominating me!).
I was already really jazzed about building and supporting the startup community, but receiving that award provided me with an opportunity to take a step back and really look at what myself and the Startup Boston Team had accomplished over the years.
I think, too often, myself and others are constantly thinking about what needs to happen next, what milestone has to be hit, what our never-ending to-do list is. We don’t often take a moment to take a step back and look at how far up the mountain we’ve climbed — I’m nowhere close to where I was the organization to be, but I felt incredibly privileged to have that moment to self-reflect (but not for too long — still so much more to do!).
Your leadership at Goldcast has been impactful. Can you outline how you cultivate teams and initiatives that drive innovation and growth?
I look for a strong work ethic and the motivation to continuously learn. When I first started in the startup scene, I had zero experience. My background was in lifeguarding, retail and waitressing. I am a huge believer that you do not have to have previous experience in order to succeed.
When I hire anyone for one of my teams — whether it was at Goldcast or Startup Boston — I look for that drive within the person. Drive is an intangible trait that you cannot teach — every other skill you’ll need for your job is teachable.
Diversity and inclusion have been key in Startup Boston events. How do you ensure a balanced representation of women and people of color in your events?
You will never have the full picture on the best way to do something without diversity of thought. If you surround yourself with folks that have the same background as you and think the same way as you, you’ll never grow.
For us, when we kick off planning in January for the season, we make it a point to share how important it is to find diverse speakers. You have to make it a part of your everyday conversations, diversity cannot be a checkbox on your list.
Tell us about your role in Suffolk University’s Management & Entrepreneurship Career Community Advisory Group and how it aligns with your mission at Startup Boston.
Suffolk University has been such an incredible partner of Startup Boston throughout the years (they’re hosting ALL of Startup Boston Week 2023 too!). I was honored when they asked me to join their Advisory Group.
Startup Boston’s mission is to connect the entire startup ecosystem — founders, startup employees, investors, mentors, startup curious folks AND STUDENTS.
It has been incredible working so closely with Suffolk University, it’s providing me with the opportunity to learn more about the challenges entrepreneurship programs at universities face and what students are looking to learn.
Drawing from your experience, could you offer insights on fostering connections and engagement within the startup ecosystem?
The startup community is incredibly welcoming! The biggest thing I’d suggest, when you do reach out to someone for an intro chat, is to have a plan in mind: what is the one thing you want to take away from the conversation? That will help you know how to lead the conversation and you’ll walk away from the chat feeling fulfilled.
Having managed customer success and community initiatives, what’s crucial for ensuring a positive user experience and a vibrant community?
Your entire company needs to be on the same page. While this sounds simple, it’s incredibly difficult to accomplish. You need your sales and customer success team to have a close relationship and you need a product supporting what your user base wants.
It is a group effort to ensure customer delight.
How do you balance day-to-day operations and long-term strategic goals as Startup Boston has grown from an event to a comprehensive platform?
I am definitely still working on this! I’ve found myself working IN the business and not ON the business a lot lately. I think the first step is learning to be self-aware and knowing when you’re working IN it versus ON it. Then take a look at the list for what IN the business looks like, take a step back and figure out what you can delegate out.
Your commitment to education and mentorship is evident through Geek Girl and other initiatives. How has this shaped your leadership philosophy?
Leading by example is crucial. You can’t ask folks on your team to work harder than you. There are also multiple sides to the same story, so if someone on your team isn’t doing what you were hoping they would, it’s important to take a step back and think, “Did I give them the proper guidance to do their job to the best of their ability?” And to then approach any conversation with that mindset.
What strengths and challenges do you see in Boston’s startup ecosystem, and how does Startup Boston contribute to its growth?
The startup ecosystem in Boston has become less fragmented — but we still have a long way to go. Through initiatives that Startup Boston organizes — Startup Boston Week, Cofounder Matching, Dealflow Mixer, etc. — our goal is to bring that ecosystem together. I think SBW is a great way to do this because the whole conference is free, there is no VIP access, everyone — whether you’re a founder, student or investor — arrives with the same level of access.
What are your aspirations for the future of Startup Boston? How do you envision the organization evolving to sustain its impact?
I want Startup Boston to be the organization to help bring it all together — showcasing where to go, who to meet and what resources are available to you. We don’t need to be everything for everyone, we just want to play a role in being the glue that helps bring this community together.
Could you please recount an intriguing startup anecdote, such as a memorable all-nighter or a particularly intense pitch day experience, that offers insight into the challenges and dynamism of the entrepreneurial journey?
I will never forget the night before the first Startup Boston Week in 2017. I don’t think I slept at all — I was the perfect mix of stress and anxious. And I was incredibly worried no one was going to show-up.
I think that night also embodies what a lot of founders go through before a big launch or the night prior to a potentially life-changing conversation. It just comes with the territory!
FINAL QUESTION: We like the idea of ending our episodes with a challenge for the listeners/readers. Whether it be reaching out to an old friend, reading 5 pages a day from a book, creating a new healthy habit… What is one challenge you have for the listeners?
We all have that list of folks that we think, “It would be so great if I had the opportunity to meet them.” Take the leap and reach out. Startup Boston Week never would have gotten off the ground if I didn’t reach out to a few hundred folks, with more experience than me, that I didn’t know.
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Boston Speaks Up is a podcast owned and operated by Value Creation Labs. Visit the Value Creation Labs blog for more inspiring stories; subscribe to VCL’s ‘The Curve’ newsletter; and recommend Boston Speaks Up guests by contacting team@valuecreationlabs.co.
