Lily Macomber is from the smallest town in the smallest county in the smallest state in the country but there’s nothing remotely small about the impact she is making today supporting founders. Lily has been supporting founders all her life.
Her dad owned a dairy distribution business for the majority of her childhood and she saw the highs and lows of his experience as a small business owner. She witnessed that her father didn’t have a lot of time for trivial things. Lily has two younger sisters and sometimes business came before the girls’ school events. As the oldest, Lily got to see her dad’s experience growing his business up close over the course of her childhood. More balance came later but she got to experience the founding journey riding shotgun. Or maybe in the back in a car seat but you get the picture.
Lily’s mom, who didn’t have a college degree, was a successful sales executive who rose the ranks as a VP of Sales for a healthcare company before later leaving the workforce after the removal of a brain tumor during Lily’s freshman year of high school. She was lucky enough to stay home after the health scare as Lily’s dads business had grown to be able to support the family. It was labor intensive work but he was lucky enough to retire before a normal 401k or pensioner’s distribution age, something that Lily watched and would eventually want for others and their families.
The real lesson from her childhood that became much relevant later on is the impact entrepreneurship could have on a family, a workforce, and a community. Growing up in Warren, RI Lily attended La Salle Academy and was a competitive dancer as a kid. Anyone that knew her back then would have told you that Lily was the quietest person in class. She was in Honors & AP classes but mostly kept to herself. She was a little anxious and wasn’t quite ready to come out of her shell. When it was time to look at colleges, the one across the street was not near the top of the list. But after she toured the campus Providence College grew on her enough to apply (Go Friars!). She really liked it and decided to enroll as a History & Education double major with a Political Science minor with the intention of entering the teaching profession.
She also made herself a promise – she wasn’t going to be that timid kid she was in high school. She wanted college and the rest of her life to be different. She didn’t want to be so scared of speaking her mind or confidently talking to people. At Providence she made the decision to be the person her closest friends knew her to be. She thinks her high school peers would be pretty surprised at the growth she’s undergone to put herself out there as the professional networker she is today.
After doing some student teaching, Lily realized that she was more interested in learning about what her students were going through structurally and how the system might be better optimized for students than delivering a curriculum handed to her. She began to think perhaps teaching wasn’t the best fit for her aspirations and dropped the Education major. Her sister is a 3rd grade teacher and Lily really admires the work she does daily on behalf of her students, but Lily decided to shift her own career journey.
She thought she might enter law school. But again, she received some sage advice that you should really only go to law school if you’re sure you’re ready to practice law. She wasn’t. Instead, upon graduation, she ended up getting a job as a grant writer at YOU, Inc. for children with mental health issues. This was a continuation of the work she did during undergrad working part time in the fundraising office, talking to parents about making donations to the school.
Working at YOU Inc., she learned a lot about fundraising & writing grants through an analytical approach. She did a lot of development, marketing, and learned about the higher education academic sector. Non-profit work appealed to her as a young idealist trying to help people. Her boss there, Fred Kaelin, was awesome too. He has a definite skill for developing young people into professionals.
At this point she moved to the Boston area with her boyfriend (now fiance & also a Providence grad) and sought to find a role that incorporated non-profit work and entrepreneurship. She landed at MIT as a Partnerships Coordinator. Lily helped fundraise, through research and prospecting, for an “impact marketplace” that helped founders who are social entrepreneurs.
Recalling that fateful move up to Boston, Lily said she loves working in Boston tech because a lot of people “look to help you in your career” and it’s a vibrant scene of new companies being built across numerous sectors. She loves that the city is on the water. There are great oyster bars. Sometimes she loves to grab a couple slices of pizza at Upper Crust on Charles St with her fiance before bringing their dog Eddy, named after the first street they lived on together, out for a walk around the Commons or Public Garden. Or sometimes they’ll stop at Greystone in the South End, which has great turkey sandwiches I hear!
Working at MIT brought her back to working with founders again, a mission she really enjoys – implementing systems and interacting with talented people changing the world. The world of technology entrepreneurship was fascinating and Lily was hooked. Through this role she learned what drives her to work harder & better – helping other people achieve their dreams. Building a company isn’t easy! Lily has seen up close that founders need cheerleaders and support systems to become successful.
Lily sought to work even more closely with founders. She learned how to become an expert interviewer – showcasing herself, fielding questions, and self-selecting for roles that supported her mission. She learned to build a story around her career, incorporating the systems and fundraising skills she had built at Providence & MIT. This brought her to Netcapital as a Business Development representative. She secured her position, even though she didn’t have any sales experience, by handing each interviewer a handwritten thank you note personalized for the opportunity & their time. She made it a point to send an extra follow up e-mail too that covered the talking points of their discussion. That extra touch is something Lily looks for today when hiring.
Netcapital is an online funding portal that allows anyone to invest in startups, an asset class traditionally reserved for accredited investors only. The crowdfunding platform, similar to competitors like Republic or Wefunder, allows anyone to invest as little as $100 in startups. Their aim is to democratize access to equity fundraising through crowdfunding campaigns. Netcapital was a big turning point for Lily’s career. There were multiple identifiable moments that solidified a lot of her beliefs about the world, business, what she likes doing & what her talents are. As the only woman seller at the time in a FinTech business, there was a lot to navigate and her colleagues were extremely helpful in getting her up to speed. They taught her a lot of what she now knows about sales, business, tech, and more. Sales are good “life skills”, Lily tells me, and she excelled. It brought out natural skills she wasn’t aware she already possessed.
Sitting in Business Development, Lily noticed that Netcapital had gaps in how clients were being onboarded after the initial sale. They were winning deals but then no one was taking care of the operations of running customer fundraising campaigns. She went to her boss and great mentor Rob Burnett, now the company’s CEO, and let him know there was a gap and she had a plan to fix it. She was going to start the “Community team” to take care of the platform’s customers’ marketing materials and investor communications after they signed up.
She laid out what this role would entail and Rob replied “so you’re giving yourself a promotion?” “Exactly!” Lily replied. But he saw the value. The Community team was live! She was also helping to grow their newsletter subscriber base, a big acquisition channel and driver of revenue for the fundraising campaigns brought onto the platform. She scaled the weekly newsletter into a comprehensive communications framework, driving over $3M in investment commitments to companies raising on the Netcapital platform over the course of her 2.5 years at the company.
Lily invested a lot of time optimizing and learning the key drivers of newsletter growth. To successfully scale digital content, Lily tells me “you need to know your audience and segment appropriately. Which content will resonate with your various audience demographics?” She learned from various words, phrases and the subsequent performance data to help drive a closed performance feedback loop. When she started the community team she brought the newsletter responsibility with her. It was her baby! And she learned a lot about the need to delegate as she began to juggle multiple responsibilities, including being a hiring manager for the first time.
Then, an opportunity arose that was too exciting to pass up. A Community Lead role at Scroobious. Scroobious is increasing diversity in the startup ecosystem by teaching diverse founders how to create investable pitch material through a scalable online platform and making it easy for investors to discover them through data-driven curation. This role would have Lily working directly alongside founders as the company’s first employee. The job description was “right up my alley” and she immediately clicked with Scroobious’ Founder & CEO, Allison Byers, a leader she knew she could trust.
Oh and by the way she was finishing up her MBA at Babson part time while all this was going on with a focus, naturally, on Entrepreneurship & Marketing. A little much, don’t you think Lily?? She chose Babson because she knew it had a tremendous program to help level up her skills for the next stage of her career. Lily’s dad, the Macomber Entrepreneur in residence, gave the advice that sealed her move to Scroobious: “Lily, do what you like right now. If you end up needing a higher salary later on then go do that. But who knows what this could lead to?” He was right!
There’s a ton of opportunity at Scroobious and they’re just scratching the surface of building out their platform. When she applied, Rob agreed to be one of her references to get some additional due diligence on Allison. Lily trusted Rob to get the goods. After their call he agreed she would be a great boss and leader, and knew Lily would excel there. That’s mentorship and sponsorship right there!
Lily’s been at Scroobious for a year and a half now. She’s doing a ton of work building Scroobious’ presence in the Boston tech ecosystem, confidently networking and doing what she loves most – delivering founders amazing value beyond the platform. The team has expanded over the last year and a half and has big plans to help underestimated founders create investable pitch materials in the years ahead.
Here are the insights Lily shared with me that have informed her work and career:
Trusting Your Gut – “In all of my roles there have been times where I was younger and you will let certain mistakes or experiences slide. When something feels off, trust your intuition and your gut.” You need to create a great career experience for yourself and you owe it to yourself to be in situations where you can thrive
Being Helpful – “Knowing how to help people and be intentional about helping people. When I go to networking events, I network to help other people. That has done way more for my career & my company than putting my own motivations first”. It’s not necessarily reality to be completely selfless when networking but by networking without expecting anything in return Lily has found to deliver more dividends than leading with selfish intentions
Creating A Track Record – Lily has learned a lot through documentation & details. “Being detail oriented and building a track record that incorporates and involves your deficits to show you actively work on your deficits is important.” Some lead with documentation & others sell “ahead of things” but working on your “areas to improve” in order to show you’re actively growing in areas that need some additional work is critical
Lily sees herself and Scroobious doing great things in the world in the years ahead. She wants that for all of her previous employers too! Personally, she wants to continue helping founders. She finds a lot of fulfillment in this space. Maybe that involves breaking into venture capital later or starting her own company, but today her mission is closely aligned with her role and with the success of Scroobious! It’s also increasingly important to her how wealth-creation through entrepreneurship can help people and solve the problems. Helping people realize their dreams and company vision’s can help change the lives of the founders, their children, and their communities.
For more about Lily, check her out on LinkedIn or perhaps walking Eddy around the Public Gardens with a delicious slice of pizza this spring. Thanks you for sharing. We’re all excited to see the impact you & your team have at Scroobious on helping more investable companies in the years ahead!
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