Ashlyn Donohue made a contract with herself that she was going to be an attorney who solved business problems, no matter how her path down the mountain looked. Today, she is the Director of Legal at Boston-based legal tech startup LinkSquares, front and center as “customer zero” helping the company solve legal, business, and product challenges on the daily. It takes drive, intentionality, and experience to help scale a growing startup’s legal team while also advising on its product strategy.
Ashlyn was raised locally near the base of Wachusett Mountain. She has two younger brothers, her mother was an occupational therapist, and her dad a small business owner. She thinks that’s part of how she ended up as an attorney. Ashlyn always wanted to own a business like her dad and thought that having a legal background would be a huge help to realizing her dream.
The thinking evolved over time, as it does, but the Donohue family always approached life through a business lens. Mr. Donohue owned a printing business and later entered business brokerage – helping SMBs buy and sell businesses – after he had sold his.
Ashlyn recalls that she learned a lot growing up around a business owner who spent his days in the weeds. It was the pre-internet era, for those who might remember, so she heard a lot about those challenges at the dinner table. His customer-focused mentality – and his willingness to understand the “why” behind things, and learn everyone’s role across his business – made an impression. He was always challenging people with questions like, “why are we doing it this way?”
Ashlyn’s mom is the most organized person she knows. Her approach enabled Ashlyn to constantly declutter how she approaches her personal and professional priorities. To this day, Ashlyn tries to keep a clean inbox.
Ashlyn went off to Union College in upstate New York to Major in Sociology and Minor in Economics and Political Science. While completing her undergraduate studies, she took a couple pre-law type classes where they were reading case textbooks. She just loved it and her interest was piqued.
As graduation crept closer, Ashlyn felt that if she didn’t dive right into law school she might never do it. She selected Northeastern because of their renowned co-op program. She didn’t know exactly what she wanted to do after law school but she did know that a large percentage of Fortune 500 CEOs had legal backgrounds. That’s a good enough reason right there!
Northeastern’s co-ops gave her a fantastic, well-rounded perspective. She held an internship at the AG office in Rhode Island and then found a great fit at a local company as an in-house legal team member. She had the opportunity to review, draft, and negotiate legal tech vendor contracts.
Lawyers out there know it’s pretty difficult to go in-house right out of law school. Kind of like going into private equity straight out of undergrad. Or Field Sales. Or even Broadway. Normally you have to start off Broadway, you know what I’m saying? Lawyers usually go to a firm and get some “experience” first. Ashlyn was determined to be an in-house attorney but she had to get creative. Even if it took her on a winding path to achieve her goal. It wasn’t a great time to find a job either back in 2012 as we slowly emerged from the recession.
She focused on networking and targeted roles that would give her tech contract experience. She would even network at dog parks! Because, well, that’s where she found her role. From a dog friend of a friend at Oracle. She entered Oracle as a Deal Manager which was technically a non-attorney role. Deal making, though, was a fantastic experience to gain a true understanding of the end-to-end contract lifecycle. At Oracle, Ashlyn grew to become the central deal hub liaison across sales, revenue, finance, revenue recognition, and other teams.
Ashlyn worked in deal management for a couple years before moving to an Operations role. She took a contract negotiations class with the goal of learning how to make better business decisions. She wanted to enhance her skill set through reviewing data and figuring out what was most actionable based on her review process.
She spent a lot of time driving strategic initiatives around the contract lifecycle process before moving over to run their global contract systems. She owned processes, coordinating with the readiness team, and user testing. “It was really helpful to sit in a business-facing role with tech exposure,” she recalls. She learned what an API meant, how to integrate systems, and what was technically feasible. Her previous technical experience allows her to make better decisions today through a more informed perspective.
But she missed being in the weeds of negotiating deals. Luckily, HubSpot happened to have an open role that fit her background perfectly. She was hired to serve in a hybrid role that covered transactional support on both the sales and vendor negotiation side of their business. Every in-house lawyer wears an operations hat to some extent and, at HubSpot over 4+ years, she grew a tremendous amount. Ashlyn became the Global Legal Lead as a Manager for their “vendor sub” practice area.
The HubSpot legal team was less than 15 people when she joined the company, and by the time she left the team had grown to more than 50 attorneys. This experience gave her the opportunity to witness (and be a part of) a period of rapid public company growth. Then another opportunity came calling.
A budding legal tech startup by the name of LinkSquares was looking for another hire on their legal team. Ashlyn had seen a demo of the LinkSquares product previously and was familiar with the company. She was also very impressed by how LinkSquares invests in its people. She had seen LinkedIn posts from leadership highlighting the company’s professional mindset coaching support – strengthening professional growth, team alignment, and personal mental wellness. So, when a recruiter reached out, she jumped at the chance to help build this team as an operator and customer. LinkSquares solves the problem every legal team has for contracts, helping businesses move forward faster.
Ashlyn says that her move to LinkSquares was the “culmination of her contract and legal experience” driving her passion for operational improvement through contract systems and how they can elevate legal operations. From a role perspective, she had wanted to step back into a smaller team where she could own a wider breadth of work. At LinkSquares she works on privacy work and on the commercial end (sales & vendor) and that’s what drew her to the company as “customer zero”.
In her early days at the company, Ashlyn rolled up her sleeves and went on a listening tour to figure out how her colleagues worked with legal. At a rapidly growing venture-backed company, it takes time to get into the weeds and gather the full perspective. And after just 3 weeks at the company she spoke at her first customer event, which she was invited to on her second day. Hey, in startups you’ve got to move fast and roll with the punches! Working at a legal technology startup gives her a unique perspective to take advantage of these types of opportunities.
Ashlyn reports to the VP of Legal but works collaboratively across all departments. She lets folks across the business shadow her and see what a day in the life of a legal professional is like. She owns their contracting process and how they manage and engage with business partners across both revenue and vendor sides of the business as a growing team of 3. Commercial contracting is the focus but she helps advise across LinkSquares’ legal and business needs. She also works really closely with their marketing team for events and other positioning they’re considering.
Managing work and a busy personal life ain’t easy – but Ashlyn has found a balance. Ashlyn commutes from her home in Central MA a couple times per week into the city where she used to live…before kids. 3 kids under 7, to be exact, with her husband of 10 years. Her husband is an elementary school principal with an offsetting schedule to help the family balance their growing responsibilities. She’s a big fan of bringing the family to the aquarium, checking out the ducks in the Boston Common, and finding Bon Me sandwiches on her days in the city. She’s also a fan of the Boston Ballet. She hasn’t brought the kids to a performance quite yet.. but in due time!
Here are the 3 things Ashlyn has learned across her career from legal operations, to in house attorney, to her work as “customer zero” at LinkSquares:
Embrace Change – “With changes comes opportunity. Things move quickly in tech. Every time there’s a shift in what you and your teams are doing, you have the opportunity to step in and become the subject matter expert. Be the person everyone comes to with questions. Those opportunities present themselves readily and you can use that to grow and become an expert.”
Be Intentional – “What learning and growth opportunities are you looking for with your time? Making connections with folks, building your community, and growing your skills and development is really important. To me, I’m intentionally electing to invest in specific areas to hold myself accountable”
Be Adaptable – “How you’re supporting your business partners, how you’re thinking about managing your team and being a leader. How are you understanding what the needs and goals are? Adjust your approach and guidance as needed. From a manager perspective, for example, people have different needs at different points in their career goals.”
Ashlyn wants to continue to broaden her breadth of experience as an in-house attorney adding to her expertise supporting commercial organizations. She’s a startup champion and supporter of growing startup (and legal) teams and organizations.
If you’d like to get in touch with Ashlyn you can find her on LinkedIn, around State Street looking for Bon Me, or raising three active children just to our west! Thanks for sharing Ashlyn. We’ll be watching the waves you make in the legal tech space as customer zero for LinkSquares in the years ahead!