1214: The CFO Checklist Keeps Growing | Jack Gordon, CFO, Harri
Jack Gordon, CFO of Harri, discusses his deliberate career path from IBM to his first CFO role, the company's AI-powered workforce operating system for hospitality, and how he's navigating AI integration in both product and finance operations while managing a failed Series B fundraise and building data foundations for decision-making.
Summary
Jack Gordon shares his 20+ year journey to becoming a CFO, having deliberately built a "checklist" of competencies needed for the role. Starting at IBM learning foundational FP&A skills, he moved through RBS (gaining financial services and M&A exposure during the 2008 crisis), OneMain (executing a $4+ billion transaction), and Wiley (developing leadership and divisional CFO experience) before taking his first full CFO role at Harri in November 2022. At Harri, an AI-powered workforce operating system verticalized for hospitality, Gordon inherited significant operational challenges—four global entities on QuickBooks, no integrated systems, and no controller. The company serves major restaurant chains including McDonald's, Shake Shack, and 14 of the 20 largest hospitality groups in the U.S., targeting a $15 billion TAM.
Gordon emphasizes that his leadership philosophy centers on being an operational CFO who gets deeply involved in business strategy, not just accounting. He led the company through a dramatic Series B experience: just one week before closing a deal in June 2023, a European LP pulled funding and the deal died. He then restarted the fundraise, met with 70+ funds during one of the toughest SaaS environments in a decade, and closed $43 million with a new sponsor in October 2023. This experience taught him the critical importance of hedging against risks and building contingency plans.
On Harri's AI capabilities, Gordon details two major implementations: Sally, an agentic layer providing managers with knowledge base access and proactive suggestions, and the Autonomous Scheduler, an AI-driven demand forecasting and scheduling tool that improves accuracy by 98%, reduces schedule creation time by 93%, cuts weekly labor costs by multiple hundreds of basis points, and ensures 100% wage-hour compliance. These solutions are changing the business model from pure SaaS to hybrid seat-plus-usage pricing. However, Gordon stresses that none of this was possible without first building proper data infrastructure—a data lake architecture and organized, accurate data foundations that took most of his first two years to establish.
Internally, Gordon is tackling automation across finance to avoid headcount growth while scaling revenue, implementing MCP server connections and agentic analytics, and building a data-driven decision-making capability by early 2025. He's also serving as pseudo product owner for a new product launch in the coming six months. Gordon reflects on his unconventional belief about finance shifting from investment banking to corporate finance as a service function supporting the broader organization, and highlights the importance of understanding leading indicators (customer satisfaction, NPS, usage patterns) over lagging financial metrics.
About this episode
<p>For Jack Gordon, the CFO role at Harri increasingly extends beyond finance—and into the mechanics of how an AI-powered business scales.</p><p>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.</p><p>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.</p><p>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.</p><p>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.</p><p>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.</p>
Key Insights
- Gordon built his career using an explicit 'checklist' of competencies—intentionally selecting roles to check boxes rather than following conventional progression, which he credits for being well-prepared for the CFO role.
- At Harri, Gordon inherited four globally-separated QuickBooks entities with no integration, no controller, and was immediately thrust into a Series B fundraise—illustrating the operational chaos typical of scaling startups.
- The Series B deal died one week before closing due to an LP capital call affecting the sponsor's fund closure, forcing Gordon to restart fundraising from scratch in a severely depressed SaaS market (June-October 2023), meeting 70+ funds.
- Harri's Autonomous Scheduler uses AI demand forecasting incorporating external data like weather to run 57 million permutations, improving schedule accuracy 98%, reducing creation time 93%, and cutting labor costs by hundreds of basis points while ensuring wage-hour compliance.
- Gordon states that despite having invested heavily in AI features, Harri's financial decision-making AI is still nascent—the company only recently crossed 'the chasm' into organized data infrastructure last year, demonstrating that accurate structured data is a prerequisite for AI decision-making.
- The business model is fundamentally shifting from pure SaaS to hybrid seat-plus-usage pricing with caps because AI-driven features have non-zero marginal costs through token consumption, eroding the traditional software margin structure.
- Gordon prioritizes leading indicators (customer satisfaction, NPS, usage patterns, employee-vs-manager segmentation) over financial lagging indicators to assess product-market fit and platform adoption, particularly given the varied adoption curves across early-adopter vs. conservative restaurant operators.
- Gordon is committing to zero net headcount adds until the company hits new revenue targets, forcing finance team automation at scale to free capacity for higher-order analytics and insights rather than tactical transaction processing.
Topics
Transcript
Support for CFO Thought Leader comes from Salesforce. Unify selling and billing for a seamless customer experience. And OneStream. Trusted data. Faster decisions. Hello, this is Ross Granger, CFO of Nasuni, and you are listening to the CFO Thought Leader podcast. This is episode 1214. podcast. This is episode 1240. In arguably one of the toughest SaaS funding environments that existed in the last decade, coming off of the highs of 2021, middle of 2023, the market was just repricing assets and repricing them on a daily basis. We met with at least 70 funds as part of the process. Fortunately for us, it only took about another four months. We found the right sponsor. We got the round closed…
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