Meet Leah Chapman: A fireside chat with Ontra’s Director of Billing & Collections

July 25, 2024
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Can you share a bit about your professional journey and what led you to join Ontra almost four years ago? How has your role evolved since you first joined the company?

My interest and skills in legal billing really evolved during my tenure at Covington & Burling, where I worked for over three years. It was late 2020, and I was in the midst of fiscal year-end. A message about a job opportunity at Ontra (then InCloudCounsel) popped up in my LinkedIn inbox. Initially, I hesitated because it was such a busy time, but I decided to explore the opportunity. During the interview process, I crossed paths with several ex-BigLaw alumni, and their enthusiasm for Ontra was infectious. Their stories of the company’s dynamic environment and growth potential resonated with me. I realized it was an opportunity to be part of something innovative and impactful. I am incredibly grateful I took that leap.

Since joining Ontra, my role has evolved significantly. I’ve grown the Billing & Collections department from a team of two to soon-to-be five full-time employees. I led an RFP and the subsequent implementation of a new third-party invoicing system. Additionally, I’ve supported the financial demands of launching multiple SaaS products and the acquisition of another company, both of which required new processes and technology for billing and collections. Experiencing these milestones has been a substantial growth opportunity and has allowed me to contribute to the company’s success in ways that I couldn’t have imagined.

Could you describe your main responsibilities as the Director of Billing & Collections?

The team I manage is an absolutely critical part of the order to cash cycle. You might think it’s as simple as sending an invoice and getting payment. In reality, it is extremely complex. In large companies, billing, invoicing, and collections are often split into separate departments or even siloed away in the dreaded General & Administrative bucket.

My team at Ontra is unique in that it runs the full receivables cycle. Every month we generate thousands of invoices, many of which conform to specific customer requirements. We also play an integral role in month-end close and delivering Ontra’s financial reports on time. The team partners cross-functionally on a variety of tasks such as account set-up, support, and maintenance. In short, this is not your typical Billing & Collections team.

How does your team work to build long-term relationships with customers?

Building relationships is one of the team’s greatest strengths. Just like the rest of Ontra, we deliver excellent service to our customers. The team monitors a general e-mail inbox for customer inquiries related to billing and collections. Customers know they can count on us to respond. If our team doesn’t have the answer, we bring in someone else who can help. The team also has incredible knowledge about our customers: their typical payment cadence, if they need to allocate services across multiple invoices, if their invoices require a custom format, etc. This gives the team a personal touch when interacting with customers.

How do you ensure that the billing and collections team stays aligned with the company’s overall business objectives, especially given their primarily internal focus?

The team understands the company’s overall business objectives because its role is remarkably cross-functional. The team also benefits from the clear vision that senior leadership brings to everyone at Ontra. On the Finance team, we know that our jobs contribute directly to the bottom line — after all, if we weren’t collecting any payments, there wouldn’t be any revenue.

How does your leadership philosophy shape your approach to billing and collections at Ontra?

I like to lead by example. Leadership is about mutual trust, honesty, and most importantly, showing up. If the team needs me in the trenches, that’s where I’ll be. I make it a priority to support my team and get it the resources it needs.

We understand your team has a fun way of celebrating successes through light-hearted competition. How did this tradition evolve and how has this helped shape the culture of the Finance team?

Our competitions began in 2021 with something we called Bounty Hunters. Things can become a bit of a blur when you work in accounting. Some tasks are repetitive, and I wanted to bring a little variety to my team’s day. One evening I was kicking around ideas with my husband, and the concept of Bounty Hunters was born — a quarterly event where the team, as Bounty Hunters, would compete to collect the largest Bounty from our outstanding Accounts Receivable balance. The winner would get a prize and be featured in a video shared with the entire Company.

Over time the team became more invested in the competition, and the videos got more and more complex. My husband and I would plot video content months in advance, but it was worth it! It was a light-hearted way to bond with team members, and the videos celebrated and showcased the team’s hard work and success. We continue the tradition with Bounty Hunter Power Hours and plan to release a new video soon. Stay tuned and catch the repeat reel here.

 

If the Finance team had a yearbook, what would your “most likely to” be?

Most Likely to Remember the Password.

My superpower is my pattern recognition and recall ability, especially for numbers. I can recite over 200 digits of pi, always remember where my husband left his keys, and spot a penny missing from a single invoice. It’s a strength I bring to the Finance team and Ontra every day.

Can you share a couple of fun facts with us?

I was born on an island! My family lived on Nantucket until I was five. I can remember catching crabs off the dock and shucking scallops straight from the Bay. Both eating seafood and being near the ocean hold a special place in my heart.

My husband and I live in San Francisco with our daughter, Cora (5). Most weekends, you can find us riding our bikes or checking out a new park.

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