Career Summary
Kayla Dowd has been in and around insurance all her life. As Hi Marley’s first Customer Success Manager, she is on the front lines of representing “simple, lovable communication” for this rapidly growing insurtech startup. Which actually undersells it. Her family has been in the insurance business for 125 years. If her family business did one of those “cumulative team experience” slides it might have a fourth digit on it. Are careers predestined? Do we find our way to an inevitable destination based on our talents, backgrounds, or family dinner table conversation? You have to wonder!
Kayla grew up in Western Mass around the family insurance brokerage business where her dad works, preceded by her grandfather, preceded by her great grandfather, preceded by her great great grandfather who started the business after immigrating to America from Ireland with his 13 siblings. Yeah, that’s not a typo. The road rose to meet the Dowds. And in the years since they’ve built the longest continuously family owned insurance business in MA that spans Property & Casualty, Benefits, and Wealth Management.
From an early age she got to see that her Dad was really passionate about what he did. He taught her that insurance helps people protect the things they love the most. He is passionate about helping other people and demonstrating that insurance is “so much more” than people think. Her two brothers work there too! But Kayla didn’t want to do what everyone else in her family did. She wanted to carve her own path.
Majoring in Business Administration and playing collegiate tennis at St. Michael’s College, she learned a lot about what it means to be on a team and carry the responsibility of winning an individual match. After St. Mike’s, she started her career at Wayfair as an entry level merchandising analyst. Eventually insurance came calling. She made her way over to Marsh McLennan Agency as an Operations Coordinator which led to a Regional Sales Coordinator role where she worked alongside a team of 60 in different functions like P&C and employee benefits.
Kayla knew Mike Greene, Hi Marley’s Co-Founder & CEO, and his family socially from vacationing in the same area in New Hampshire. It was Mike’s wife that suggested Kayla might be a great fit for his budding startup, Hi Marley. She wasn’t ready though. She loved MMA. A year later? The full court recruitment press was on. Hi Marley was at 20 employees and needed some help! Bryan Ginsberg, Director of Growth, was also instrumental in helping to recruit her.
Kayla thought of startups as chaotic places without structure or process. And she wasn’t..exactly wrong. She onboarded as the first Customer Success Manager and dove in. The change excited her, she likes being challenged, and she learned she thrives under pressure. Kayla was on the road with the sales team almost every week to meet with insurance carriers and present to rooms of 50 adjusters at a time. Chaos in the best way.
She feels like she’s truly making an impact building out processes and scaling the company even though she came in without knowing anything about startups or Customer Success. She admits she herself probably wouldn’t have been hired by today’s standards/requirements! She’s just grateful they gave her a chance. There’s something to be said for “the best resume isn’t always the best fit. If you see potential it’s worth giving someone a chance”.
Hi Marley has grown to almost 100 employees and Kayla helps manage some of their largest & most complex accounts as a Senior Customer Success Manager. She is most proud of creating a process to collect feature requests from customers and channel them internally to the appropriate teams for roadmap scheduling.
Kayla is really passionate about what she does. Since you insure the things you love the most, if you’re in the claims process, you’re likely in an upset state. Kayla & the Hi Marley team constantly think about how customers can feel more loved & comforted through those really stressful times. They’re trying to change an industry. At Hi Marley you’re encouraged to share new ideas and all opinions are valued. Kayla co-leads their Wellness Committee internally and participates in a bunch more internal cultural initiatives too.
Customer Success is Empathy
What is one way it means to be great at Customer Success? For Kayla, it’s about putting herself in the shoes of others using empathy. Internally and externally. How can you alleviate customer concerns? How can you understand the challenges of internal product & engineering teams when a bug occurs? You’ve got to walk a mile in their shoes.
Externally
Kayla explains “when I prepare for calls, I try to figure out ‘why is this important to them?’ ahead of speaking with a customer.” She goes on to share..
- I try to understand the industry first and the personas I’m speaking to. What does Hi Marley do for them? Why are they making this big purchase and what problem are they hoping it solves for them?
- When I think about hearing customer challenges and retaining them, I think about how to better understand how a platform challenge or bug impacts the people that work there.
Internally
She’s made an effort to spend time with different stakeholders across the business in order to build relationships across every functional area whether it’s Product, Engineering, or Growth (Sales). Challenges are going to happen. It’s easy to point fingers. And it’s satisfying, how can you not? But it’s better to understand all the different perspectives and resist playing the blame game. When she worked at MMA, every team helped her understand what they were working on and she’s tried to replicate that same cross functional understanding at Hi Marley.
- Forming relationships with teammates across different functions is critical. I’m always trying to connect with others on different teams to better understand what they do
- Understanding various functions and their pain points in order to see things better from their perspective is a priority. If I can understand their workflow, I can see why a feature gets delayed for an extended period. It’s much better to talk it through and understand the “why”.
- In a remote world, I have to go out of my way to see more people & build relationships and, when necessary, make things uncomfortable in the nicest way to get stuff done!
Career Insights
Don’t Be Afraid to Take Chances – “Go out of your comfort zone. That is what I did to come to Hi Marley and I’ve never been happier professionally.”
Be Confident & Just Do It – “Related to taking chances, raise your hand to do things that you know you’d be uncomfortable doing. If someone asks to present a slide at an all team meeting, and you know you hate presenting, do it. No one is judging you more than yourself. Take every opportunity you can to go outside your comfort zone.”
Build Your Network – “I still see people that I worked with at MMA. Our paths cross in the craziest of ways and I made so many strong relationships there. I love coming into the office so I can spend time with people that aren’t on my team to get to know them better. Making connections like that are so important because you never know where you could be in the future. Having connections and relationships are huge. I love being customer facing and working with people to build those relationships too”
Kayla doesn’t know what the future holds. She didn’t even foresee herself inside of a rapidly growing venture backed startup in the first place. So wherever life takes her! But first and foremost she wants to stay at Hi Marley and see the mission though. She believes in the company, its vision, and its leaders. One day, when the timing is right, she’d like to manage a team or help own a strategic initiative.
If you want to learn more about Kayla, you can check her out on LinkedIn or potentially at a local tennis court. Thanks for sharing. Excited to see the policyholders you & the Hi Marley team help in the coming years!
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