For Jack Gordon, the CFO role at Harri increasingly extends beyond finance—and into the mechanics of how an AI-powered business scales.
Harri, a workforce operating system focused on hospitality, has evolved from a point solution into a broader platform spanning talent acquisition, workforce management, and employee engagement. Gordon says the company’s opportunity rests partly on years of data accumulated across mission-critical workflows, an advantage that becomes increasingly important as AI reshapes workforce technology.
That evolution is also reshaping Gordon’s finance agenda. As Harri rolls out its AI platform, understanding the changing unit economics has become a priority. AI introduces new questions around usage costs, margins, pricing, and monetization. Inside finance, meanwhile, Gordon is pursuing “automations everywhere,” with the goal of eliminating much of the routine work performed by his team and creating more capacity for insight.
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His operating philosophy begins further upstream. Rather than waiting for financial results, Gordon watches customer satisfaction, usage patterns, support activity, and customer outcomes. “Financials are outcomes of a good product and happy customers,” he explains.
That emphasis on leading indicators is accompanied by an acute awareness of downside risk. After a planned Series B financing unexpectedly collapsed in 2023, Gordon restarted the process and ultimately helped secure new funding four months later. The experience reinforced a principle he carries forward today: understand the downside and build contingency plans.
Now Gordon is stretching the CFO remit again—working as a product owner alongside Harri’s product and engineering teams. For a finance leader who has deliberately accumulated new operating experiences throughout his career, building and launching a product represents another capability still to be added.
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CFOTL: For someone new to Harri, tell us something about the business. What does the business provide? Who uses it? What’s the opportunity you’re pursuing?
Gordon: Harri is an AI-powered workforce operating system, verticalized and very focused on hospitality. What that means is we unify the employee lifecycle onto a single platform that helps mainly restaurant operators hire faster, optimize labor, and maximize what we call four-wall EBITDA, which is the EBITDA that lives within a restaurant.
We exist because no company had ever built workforce software that understood what it feels like to run a busy restaurant on a Friday night. Our roots really are in operator history. Our CEO ran restaurants for a number of years before he started the company. So we didn’t stitch together a whole bunch of tools. We built an operating system, which is truly a platform that today McDonald’s, Shake Shack, Jack in the Box, and 14 of the 20 largest hospitality groups in the U.S. have chosen to run on.
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The really interesting thing is our opportunity to own the economic relationship with an entire industry. This is a $15 billion TAM. Restaurants are the largest employer of frontline employees in the U.S., and it gives us the opportunity to own the industry for a wildly overlooked workforce in our country.
Just a click deeper, we’re a system of record, which means we displace point solutions. I assume at some point we’ll talk about AI and moats and what gives us the right to win. Software that’s built on years of data foundations that span across multiple mission-critical workflows—that’s where we exist today. That’s where we believe companies have the right to win in an AI world.
CFOTL: Looking back, around the time of your arrival, Harri raised $43 million, I believe, shortly after you entered the CFO office. What did that capital allow the business to do?
Gordon: That’s right. That was October of 2023, so about a year after I joined the company. That capital allowed us to, practically speaking, complete our platform. What that means is we spent a long period of time, from 2020 until the middle of 2024, building enterprise-grade workforce management.
Fortunately for us, we built it alongside McDonald’s. We signed a contract with McDonald’s in 2020 to be their workforce management solution. Then, over the course of the next almost four years, we effectively co-developed what is now the industry-leading workforce management platform.
When I say workforce management, I mean scheduling, time and attendance, compliance, communications, and all the workflows that go into managing the people side of the day-to-day operations of a restaurant. You can imagine building enterprise-grade software is capital intensive. There was a big slug of CapEx that we spent, which this capital helped underpin to complete that part of our platform, and then to start building the next component of the platform, which is our engagement suite, which has just recently come live.
We operate across talent—what we call talent acquisition, which is sourcing and hiring—workforce management, which is scheduling, time and attendance, and compliance, and now employee engagement. So it truly has gone from a single point solution to a platform asset over the course of that period of time. That capital really underpinned mainly R&D build and go-to-market capabilities.
CFOTL: Before the financial results show up, what tells you Harri’s growth engine is working? What are you looking at?
Gordon: Ultimately, it starts with the customer. We measure everything: customer satisfaction, NPS score, what’s coming through our support tickets, how happy our customers are, and customer usage. These are my leading indicators. They’re the ones that we look at to better understand whether what we’ve built resonates with our customer, whether they’re using it, and whether they’re getting the outcomes that we’ve presented to them in the ROI case. It’s why they bought the software to begin with.
When we think about how leading indicators impact our business and how we make decisions, we spend a lot of time as a management team unpacking the nuance in customer satisfaction between a restaurant manager and an employee. Both are using Harri, but in very different ways. So understanding usage patterns, satisfaction, and ultimately outcomes across sub-segments of our user base is critical.
Financials are outcomes of a good product and happy customers. So we spend a lot more time on the leading indicators than the lagging indicators.
Harri | www.harri.com | New York, NY