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Jess Kennedy of Beeline: “How many times things would change”

Be yourself and stop questioning everything you do and whether it is “enough”. Go back to my motto from before — just do your best. You won’t be able to please everyone but you will know you gave it your all. As a part of our series about strong women leaders, I had the pleasure of interviewing Jess […]

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Be yourself and stop questioning everything you do and whether it is “enough”. Go back to my motto from before — just do your best. You won’t be able to please everyone but you will know you gave it your all.


As a part of our series about strong women leaders, I had the pleasure of interviewing Jess Kennedy, co-founder and General Counsel/CCO of Beeline.

A real estate law expert and powerful advocate for female executives, Jess is the co-founder and General Counsel/CCO Beeline. Prior to co-founding the innovative proptech platform set out to revolutionize home lending, Beeline, Jess acted as a real estate atoner for several years. She’s passionate about providing a solutions-based approach to legal and compliance issues within the mortgage and refinance industries.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Prior to Beeline, I helped build a new division of a prominent real estate services company with Nick (another co-founder). Nick founded that company in 2005 and eventually sold it in 2016 to a Canadian company that eventually went public. Peter was our investment banker and long time friend of Nick’s who helped usher through the sale. While working with Nick, I knew there was no one else I’d rather build a company with. The way he thinks about technology, customer experience and team building were totally aligned with my thinking and his positive energy is infectious. So when we started the conversation about Beeline in 2018, I was totally in. Prior to meeting Nick in late 2014, I was a real estate finance lawyer at a large Boston law firm. My time practicing law gave me a great foundation for the regulatory landscape. But I never saw myself as a law firm lifer. I like to push the envelope and challenge the status quo and I had ideas that weren’t going to go far in a law firm environment. So I knew I was better suited to be in the business world. Starting with Nick in early 2015 gave me a taste for what that meant and I felt like I had a lot I could contribute so I just started doing and had the runway to be really successful on the business side. I haven’t stopped since and the rest is history.

Can you share the most interesting story that happened to you since you began leading your company?

There isn’t one story or event in particular. It’s really about the journey we’ve been on since 2018 to get the company conceptualized and launched. There have been so many brainstorming sessions and late nights and ideas that pop in my head while washing my hair…it’s when I think of all those events together that I think — “wow — this is really special”. In the last two years, I’ve helped shape the face of the company and overall strategic goals. It’s incredibly fun and rewarding and making mistakes along the way has been a learning experience that I would not have had but for co-founding Beeline. A big piece of starting a company is the people you choose to join you in the fun, wild adventure. Working with my other co-founders has been incredible. We are all really different and come from opposite ends of the earth (three are from Australia) and I have immense respect for each of them. It’s an amazing team that I’m so honored to be part of.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’ve been fortunate enough to be surrounded by a number of people who helped me get where I am today. My mother and grandmother were amazing examples of working women who were way ahead of their generations. They taught me the value of hard work and grit. In my professional life, I attribute who I am to the firm partner who I worked with most, Charlie Ognibene as well as other firm partners (Rebecca Lee and Cindy Mitchell) who pushed, challenged and nurtured me beyond what I thought I was capable of at the time. Some of these people Tiger Mom-ed me, but I wouldn’t be who I am today without them. I also have to give a big shout out to my co-founder, Nick — he took a chance on me 6 years ago as I waddled into his office for an interview very pregnant. He’s always been a cheerleader for me and has seen things in me that I didn’t see in myself.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

I have always lived by the motto of “Just do your best”. I can’t do any better than that so trying to control everything or focusing on the stress is counterproductive. If I know and believe I’ve brought everything I can, then I’m happy with that — no matter the outcome. It’s actually a really freeing mantra. Leaders also have to be perfectly fine being wrong. We don’t admit we are wrong enough — everyone wants to win or be right or get the gold star. Sometimes, I am just wrong and I’m cool with that (and usually prefer it since it means we came up with a solution or decision that is better).

As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

Yes, this is super obvious, but in any organization, the best ideas come from robust discussion and that can only happen when those in the room have different life experiences to bring to any dialogue. Sure, it may seem easier or involve less conflict when everyone in the room agrees or comes from similar backgrounds, but in the end the people, the organization and whoever the organization aims to help is harmed. Some of the best conversations I’ve had are with those who are markedly different from me. People with diverse backgrounds give an important perspective that you can’t get from reading books or listening to podcasts. It’s an organization’s responsibility to ensure there is diversity from top to bottom.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

We have to acknowledge our own fears and bias first. We all have inherent bias — there are a lot of studies published about this. So we have to be willing to say to ourselves that we don’t want to let those biases control us.

Then we must make a conscious effort to get to know people who are different than us or who have different life experiences. This may mean volunteering, traveling, and/or enjoying activities of other cultures. There are so many ways for people to expand their view of the world if they are interested in doing so. A lot of this happens at the individual level but it is also the responsibility of community, business and government leaders to set the right example as well.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

Executives are given the hard task of seeing into the future. We have to have the vision before it is ever reality and we have to understand what it will take to execute on the vision and then empower and excite others to help make that happen.

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

Myths: we are scary or unapproachable. Employees at Beeline know they have access to any founder. They chat us, call us, etc. on the fly, which tells me they feel super comfortable and trust us to empower and help them.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

Women executives face the same challenges as their male counterparts and a few additional challenges. I’ve found that women execs are not always given the same deference as men or will get cut off or interrupted by others in a meeting. While this has not happened to me at Beeline, I’ve experienced it and seen it in other organizations. I won’t speak for all women on this one, but I am always questioning whether I am being too feminine or too masculine. Being a woman executive does not mean I need to act like a man — in fact, I shouldn’t — I should just act like me. That can be a hard line to walk sometimes. I know many other women have talked or written about this as well, but it’s real and difficult to navigate.

What advice would you give to other women leaders to help their team to thrive?

Be yourself and stop questioning everything you do and whether it is “enough”. Go back to my motto from before — just do your best. You won’t be able to please everyone but you will know you gave it your all.

How have you used your success to make the world a better place?

I hope I’ve given the people that I work with a sense of belonging, purpose and empowerment for them to reach for things they may not have believed to be possible. I also hope that I’ve spread positivity, even when things are challenging. Beyond the workplace, I give a lot of my time and lend my experiences to my board membership with Child & Family, a non-profit serving families, youth and the elderly my community.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

I wish someone would have told me:

How hard this would be — the US mortgage industry is freaking complicated — all highly regulated businesses are and the last 2 years have been filled with constant learning

How many times things would change — when building technology alongside an operation, things change…quickly and often. Those changes mean new processes and new enhancements for our team to adopt.

How much room for innovation there is — this industry is sleepy and the opportunity to create a really unique experience for people is limitless

How hard it would be to build a team in a pandemic — video calls and document collaboration go only so far. I have not met most of the team in person. Those interpersonal interactions are really key to building trust and connection. We have done remarkably well with the limitations but I can’t wait to form deeper bonds when I am able to see people in person.

How hard it would be to launch in a pandemic generally — we are constantly building technology and changing processes. Getting that information disseminated and adopted is challenging in an in-person environment — like pushing a boulder uphill. In this remote working environment, it’s like pushing gravel uphill. You try to lose as few pieces as possible from rolling back down but inevitable you will and you have to be ready for that.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

It really is the one I said before (and I swear I didn’t know this question would be asked when I said it) — just do your best. You have to be willing to hold yourself accountable to that and know what your best really means. It’s neither a cop out nor is it an impossible hurdle. Just bring yourself fully to whatever you are doing. I’ve lived by this since I was a child thanks to my mom repeating it so many times I thought I’d scream.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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