Q&A With Summer's Head of Finance, Kyle Jessey
As Head of Finance at Summer, Kyle Jessey plays a crucial role in establishing a culture rooted in quantitative decision-making. Inspired daily by working alongside some of the leading minds in the short-term rental space, Kyle has a unique front-row seat to Summer's market reception.
"Helping young companies establish their identity has always been exciting to me. It’s one thing to have an idea in a pitch deck-- it’s another to bring that idea to life and make it profitable."
Where were you before joining the Summer team, and what attracted you to Summer?
I’ve worked in finance throughout NYC over the course of my career. I started following the more traditional route of investment banking to private equity, before jumping to the operational side of things at my now second seed-stage business. Helping young companies establish their identity has always been exciting to me. It’s one thing to have an idea in a pitch deck– it’s another to bring that idea to life and make it profitable. I was attracted to Summer for two main reasons. One, the team is a bunch of rockstars. I get to problem-solve with some of the leading minds in the short-term rental space. Secondly, our product is financial in nature-- at the end of the day we’re helping people buy second homes--, so I have a front-row seat to how Summer is being received in the market.
"I play a role in telling a compelling, responsible story to investors looking to help us grow and put more people in their dream vacation homes."
What are some of the daily ins-and-outs of your role at Summer?
I would break my role up into three main buckets: Firstly, financial planning. I’m working hard to build an infrastructure that allows us to track performance against plans and budgets, so that for every goal missed, we are able to understand why. Secondly, strategic finance. It’s critical we leverage reliable data and financial logic to build a culture rooted in quantitative decision-making. Lastly, fundraising. The majority of companies our age need to raise lots of money to continue growing. I play a role in telling a compelling, responsible story to investors looking to help us grow and put more people in their dream vacation homes.
What would you say are the main elements of the Summer business model that separate it from its competitors?
To do right by all the financial thinkers out there, Summer is an extremely efficient way to gain equity in a second home. 50% of subscription payments convert into home equity value-- above the ~30% you’d gain with typical early mortgage payments. With other ownership structures, the effective cost-per-stay in a second home is outrageous. We subsidize downtime costs while you’re living in your primary residence, leaving you with less bills to pay, and a high-performing short-term rental home if you decide to purchase. On top of this, you have the flexibility to walk away if you decide the home isn’t for you (with the shirt still on your back).
"With other ownership structures, the effective cost-per-stay in a second home is outrageous. We subsidize downtime costs while you’re living in your primary residence, leaving you with less bills to pay, and a high-performing short-term rental home if you decide to purchase."
What excites you most about the future of Summer?
Investment-grade lending costs? Sure. Mature operating history? Definitely. The ability to vacation at any of our properties all over the world? Oh yea! We’re growing so fast that I can see our future just a couple blocks away. Before we know it, we’ll be serving prospective second-home owners all over the world. As an avid traveler and user of mainstream rental platforms, I couldn't be more excited to now be within the Summer ecosystem and enjoy the consistent, curated experience that our team has worked so hard to refine.
"We’re growing so fast that I can see our future just a couple blocks away."