Sheila Connolly had a dream. Her love of politics was going to propel her through undergrad, onto law school, and across the Atlantic Ocean into a career as an international human rights lawyer at the Hague. She did make it across the Atlantic Ocean, but not quite as far as the Netherlands. We’ll get there.
Sheila grew up on a farm in York, Maine where her dad lived his dream working long days as an organic farmer and her mom commuted down to MA as a computer parts executive. She was exposed to the joys of pursuing what you love and working hard from a young age.
Bill Connolly gave an interview to the Portsmouth Herald in 2008 where he shared this advice for aspiring gardeners: “it’s not complicated to start a garden but it’s imperative that, once you’ve decided what you want to plant, you read a book or go on the Internet to investigate when that plant grows and how it grows,” Connolly said. “You need to understand the basics.”
Sheila probably heard something like that around the house and took it to heart. After completing her undergraduate studies at Emmanuel she went off to Galway, Ireland to study law after a memorable study abroad experience. She got her Masters of Laws in 2 years (!) and went to work understanding how things worked at the Hague as part of her graduation thesis evaluating the effectiveness of modern tribunals. If she was going to make a career of it, best to understand the basics of how this system actually functioned.
What she came to learn is that from the Holocaust, to war crimes in Sri Lanka, genocide in Cambodia, and beyond the wheels of justice move slow. The courts are limited in the justice they can administer too. It was a little discouraging. Even if you can live in The Hague.
Instead of continuing East to the Netherlands she returned to the U.S. Northeast and made plans to move down to Boston with her then boyfriend, now husband, Marty to search out a new career with the same intellectual stimulation but a faster pace.
Arriving in the city, she loved that Boston felt manageable. There’s great restaurants and a lot to do but it wasn’t overwhelming. She loves to play golf, especially at some of the prized local muni courses like Franklin Park & George Wright (when she can get on!). She loves Boston sports and going to local establishments to have a Guinness and watch a game. You might find her frequenting one of her favorite restaurants – Coppa – in the South End. On other nights she’s comfortably watching a documentary on white collar crime, her favorite genre. Or if there’s nothing new and interesting she’ll go back to the West Wing. A timeless classic.
Working with a recruiter for roles in the legal or legally adjacent space, she was placed at the FinTech startup Forward Financing located right in Downtown Crossing across from Sam Lagrassa’s. She assumed a Finance company was going to be pretty buttoned up but was pleasantly surprised to see colleagues in jeans, music playing, and a basketball hoop in the back. The team was hardworking but had a lot of fun with their work too. This was a different type of Finance company. Sheila’s transition to startup life was on!
She onboarded as a Closing Analyst helping the company better underwrite their customers. Over time that work led her into a Business Operations role helping to administer internal process through their Salesforce instance. As the company grew she helped streamline the underwriting & operations process and better integrate it into the core product offering by advising on the process infrastructure. While she enjoyed the operational aspects of her role, she loved the top of the funnel decisions – process flow, identifying pain points & visualizing solutions. The ideating & brainstorming gave her energy. No surprise her work caught the eye of a couple colleagues & mentors who encouraged her to transition into the Product org as a Product Manager.
I asked her what her onboarding into the Product role was like: “trial by fire, drinking from the firehose, all those things” she shared. She initially worked on individual workstreams for a specific business unit honing her product skills. From there, she graduated to a Principal Product Manager where the problems got “squishier”. Sheila brought structure to broad business goals. She ran workshops, mind mapping exercises, and now helps kick off larger initiatives while simultaneously gathering buy in from executive leaders. There is a lot more strategy involved!
Sheila shared a number of invaluable insights from her tenure at Forward:
Getting Inspiration: Sheila has trained herself to seek inspiration from many different places. Whether she’s booking a flight and noticing how the software filters departure & return dates or seeing any other good user experience during everyday life, she’s learned to pattern match. Admittedly she describes herself as a “chronically online person”. In her own words, when she notices a vendor or product experience she likes “I’ll always take a closer look from a product lens and try to see what’s behind it. What’s the data model? Process flow & systems? The more critically you look at things you use every day the easier it is to think of things from scratch when you’re in the ideation phase of a problem you’re trying to solve”. Brilliant, Sheila!
Emergency Triage: She’s had to learn that “not everything is a 5 alarm fire”. When someone comes to you with a problem, their huge emergency might not be the company’s emergency. She relayed that she’s had to balance having empathy against being a strong steward of the product roadmap integrity. Or, in her own words: “if you take in a request from a stakeholder and they’re struggling with an inefficiency, you have to run it through the metrics pipeline. How often is this issue happening? Is there an established workaround? How long does that workaround take? If we do this, are you OK bumping down this other initiative? When your stakeholder(s) better understands the finite resources and tradeoffs you can collaboratively make the best decision together”
Goal Setting: Sheila relayed that bottoms up goal setting for her team has been an important accountability process. She’s found it really helpful to have the team go through a goal setting exercise whether the goals are on a sprint (bi-weekly), monthly, or quarterly cadence. She has found that proper goal setting helps drive effective prioritization.
Relationship Building: Working in Product is a little different than being a leader on some other teams. Your main stakeholders are definitely not in your reporting line and aren’t necessarily even in the same org. Sheila described to me “being a product manager is difficult because the people that help you achieve your goals don’t necessarily report to you. You can’t just have relationships with your engineering team. You need to reach across the aisle to have business relationships too to help everyone understand why your process is a certain way and why it will help the organization overall to follow that process”. Sounds like that aspiring political career has manifested in a new way! Today, especially with remote work, relationship building has taken on a whole other meaning entirely. Sheila believes she’s needed to put herself out there even more – whether it’s informal video calls with colleagues, quick Slack huddles, or additional “one off” catch up meetings. Bridging the gap between different team members who have different ways of working is a future we all share.
Sheila wants to continue to grow as a Product leader. She loves project management – the details, scheduling, and all the small things. She also really enjoys the bigger strategy & “squishy” problems. Squishy – one of Sheila’s favorite words from our chat – and one I think I’m going to steal! She enjoys tackling big, broad open ended problems the most and wants to continue searching for new white space to color in. Her growth as a strategist will help her drive big impactful change in any direction her career goes. No doubt that it will be forward. From the ground floor to a ten thousand foot view, keep an eye on Sheila because she has the talent, moxie & drive to cover it all.
If you want to learn more about Sheila’s career path in product, reach out to her on LinkedIn or reply to this note and I’m happy to make the connection. Thanks for sharing all your insights Sheila!