Staff & Training

The People & Finance Journey at UpKeep with Jim Lightsey

Ryan Chan

We talked with Jim Lightsey, Chief Financial Officer, to get a glimpse into his journey building our People and Finance Department at UpKeep. We are excited to share his story, and how he and his department are enabling the whole UpKeep team to do our best life’s work.

Where We Started

I joined UpKeep in 2019, first as a consultant, then as the company’s Chief Financial Officer. Before my tenure, People & Finance responsibilities were spread throughout the organization. There wasn’t an established team on either front, but the startup mentality was strong – team members managed these aspects of our business because it was what we needed. Since People & Finance was already in the fabric of UpKeep, I was able to pick up the baton quickly – hiring people to take each function to the next level, just in time for a global pandemic.

But, I’ve gotten ahead of myself.

My first introduction to UpKeep was at a coffee shop in the Mission District of San Francisco. UpKeep’s CEO, Ryan, and I met to discuss the state of the business and their goals for the coming years. During this initial meeting, I was struck by Ryan’s enthusiasm and passion for helping UpKeep’s customers. I was excited to take on a short term engagement to help the company prepare for their next phase of hypergrowth. As I got into the weeds and planned for the future of UpKeep, I felt a real resonance with both the entire staff and the wider company vision. 

After my first in-office visit, I was struck by the entire team’s focus on making customers successful. Every time I visited, I noticed people talking to customers, not just among themselves.

”To me, that’s a sign of a successful business – are you out there talking to customers day-in and day-out? Are you acting on the feedback you’re receiving quickly? At UpKeep, I saw this commitment to customers happening at all levels.”

I was also drawn to the company’s incremental approach to resource investments. We invest small amounts in experiments quickly, when other companies bet big, spend large amounts, and hope things work out. Iterating quickly means we’re making more investments with more certainty. We minimize risk in this way, and I knew this philosophy was something I wanted to build upon.

Therefore, when Ryan approached me about coming onto UpKeep’s team full-time (after a lot of hinting!), that next step just felt natural and I accepted happily.

Where Are We Now

A lot of people look at People & Finance as polar opposite departments. But, they both are centered around unlocking resources and potential for the company. This may be a less common perspective, but I’m a human-first CFO. For that reason, we brought both functions officially under one department with a mission to  “enable individual and company success.”

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  1. Alignment with the rest of the organization:
    P&F’s impact spans the entire company. Alignment is important to get the right resources into the right places.
  2. Documenting everything:
    I’m a huge advocate for process and progress, and documentation is a huge support system for both. As we scale as a company, we must continue to develop our processes to scale; the only way to do that, however, is if we write down what we’re doing. From there, progress and iteration will be natural, as we track and revise our processes.
  3. Hire people who are masters at what they do:
    Within P&F, it’s essential to have individuals hyperfocused on their responsibilities. In my experience, not everyone does this, but it’s crucial. We didn’t try and stretch a few people too thin, but instead focused on creating more specific roles and documenting how they would all work together for the good of our team and customers.


These strengths were tested very early on in the People & Finance team’s life cycle. Less than two weeks after hiring our Director of People, COVID-19 forced our entire company to go remote overnight. Not only that, but all three of our initial Finance hires had to onboard one week after this transition – we still haven’t all met in-person! Through this very turbulent time, our fundamentals – alignment, the right people, and commitment to documentation allowed our team to prove we could weather any storm. Looking ahead, I’m excited for the People & Finance department to continue delivering on our promise to our fellow UpKeep teams.

Where We Are Going

For many Series B companies, working with Finance is a slow, hindering process. Finance at UpKeep will continue to have a hyper-aligned working relationship with all departments to mitigate risk and make investments when they make sense. We know we’re being successful as a department when we’re able to unlock success for others.

We also remain committed to keeping ‘one version of truth’ for our key financial and operating metrics.”

Having dozens of contradictory numbers and reports can take energy away from our goals and customers. Therefore, our department ensures that we all have correct metrics and analytics, allowing the company to adapt to changing times. The current COVID-19 situation has shown us that companies must adapt to thrive. Pivoting quickly now and in the future requires accurate, dependable data from our department.

On the People side, we are focused on enabling the entire company by developing each individual who works here.”

While working at UpKeep, do our teammates feel fulfilled? Do they make the world better? Are their career trajectories better because of all they learned at UpKeep? We hope through investing in the growth of our teammates, UpKeep can be known as a place where stellar performers are given the runway and resources they need to be true thought leaders and innovators.

Our People team ultimately wants to ensure we are enabling people to do their best life’s work here at UpKeep.

”The entire company’s success is based on each individual’s successes.”

Each person’s success NEEDS to be aligned with our success. There are, of course, some additional functions like a dedicated IT specialist and in-house legal we still need to build out, and we’ll get there when it’s the right time.

Though People & Finance is the newest department at UpKeep, our functions have been running since day one. I am so appreciative of the people who laid the groundwork for our department before us. Thank you to the entire UpKeep team for welcoming me with open arms – I’m excited to continue dominating our internal Rock, Paper, Scissors tournaments and drink La Croix with you all hopefully sometime soon! Most importantly, I’m so excited to enable each of you to do your best life’s work here.

The only place we are going is up!

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