When a startup moves beyond the seed stage to raise significant venture capital to scale operations and accelerate growth, devoting resources toward the finance function often take a backseat to sales and marketing.
Jon Anderson, CFO of Payouts Network, a B2C payment and disbursements provider based in Bozeman, Montana, shares how he’s been able to elevate the finance function as his Series A company rapidly scales, and what other startup CFOs can learn from his experience.
What key lessons can other early-stage CFOs take away from your experience?
Series A is a unique time in a company’s lifecycle. The company likely has a product and has found some modest interest in the market. Often led by a founder and visionary, they’ve understandably invested most of their scarce resources in product development and made initial efforts toward sales and marketing. Foundational functions like finance, operations, risk and people often lag behind.
Good quality financial and reliable operational data are hard to come by, and the CFO role is often filled by a tenured accountant relying on unsophisticated infrastructure. With that in mind, there’s a lot to do to start building a solid foundation and to navigate the growth and challenges that come with this stage.
First, don’t wait to build your financial infrastructure. Align your financial and operational data with your business, products and plans. Get clarity on your cash position and burn, sales pipeline and attribution, margins, unit and customer economics, and the KPIs that drive the business.
This level of insight helps the leadership team make informed decisions and manage capital effectively. Each of these components directly affects your company’s ability to succeed. It takes rolling up your sleeves and getting into the details, but it doesn’t have to require significant spend.
Second, build relationships, processes and collaboration. Many CFOs tend to stay in their lanes, but at this stage, it’s essential to work cross-functionally. The company is still maturing, and data is just data until it becomes actionable information.
CFOs can bring insights that inform strategy, highlight risks and help course-correct in real time. This can only happen by building trust and collaboration across the leadership team. Transparency and process go a long way in driving alignment and clarity.
Lastly, focus is essential. In a startup, it’s easy to get distracted by shiny objects. But with lean teams, limited capital and a working product, staying focused on the North Star is critical. Everything mentioned above, from infrastructure to alignment and transparency, helps you stay on course.
Beyond traditional reporting, how do you strategically engage with Payouts Network’s board to not only ensure financial oversight but also actively drive and support the company’s growth objectives?
The composition and dynamics of a board of directors at a Series A company are fundamentally different from those of a later-stage organization. At this stage, the board often includes founders alongside principal investors who have taken a meaningful stake. At Payouts Network, we’re fortunate to have a board made up of both strategic investors and experienced operators, individuals who understand the challenges of building and scaling a business.
One of the advantages of this stage is natural alignment around growth. Series A investors have made a deliberate choice to back the company’s current strategy. They may bring their own views on how to scale, but unless there’s a major disconnect, gaining support for initiatives is typically smoother. This alignment helps foster faster and more confident decisions.
Still, transparency is the foundation for sustained alignment. Clear, consistent communication about business performance, capital needs, opportunities and risks builds trust and credibility. Regardless of whether a board member comes from an operating or investing background, they understand that challenges are part of the journey. Honest dialogue builds credibility and ultimately leads to stronger support.
I’ve seen firsthand when I was with another company how transparency and open dialogue helped the board and management team align on a difficult truth: We were better positioned to succeed as part of a larger organization. That clarity led to a successful acquisition where the product could thrive.
Beyond traditional financial metrics, what non-financial indicators or strategic insights do you prioritize to inform critical business decisions, and how do you ensure these insights are effectively communicated and acted upon across the organization?
We track a set of leading and lagging indicators for each function of the business. In addition to comparing performance to goals, we monitor trends to anticipate risks or opportunities. We’ve built disciplined weekly management meetings and pipeline reviews to ensure execution and accountability. In my experience, meetings too often default to updates with no clear outcomes. We’ve been intentional about changing that culture.
In sales, we track qualified lead volume, opportunity pipeline, win/loss ratios and conversion funnels. These tell us how revenue will trend and where we need to improve performance.
In customer support, we monitor the ratio of support tickets to payment volume, ticket categories and resolution times. These metrics help us identify root causes and direct product improvements that enhance the customer experience and reduce cost.
In engineering, we review sprint velocity, incidents and outages, and the business impact of roadmap initiatives. These indicators help us evaluate system performance and make informed staffing and prioritization decisions.
With the acceleration of digital transformation, what emerging technology or data analytics trend do you believe will have the most significant impact on the finance function in the coming years, and how are you preparing your finance team to leverage it effectively?
AI automation is steadily changing how finance and accounting teams operate, particularly in areas where process efficiency and data analysis intersect. Three areas I’m especially watching: autonomous reconciliations and close, which has the potential to shorten close cycles and enhance accuracy over time; predictive forecasting, supporting more flexible and data-informed scenario planning; and enhanced analytics, enabling more meaningful insights from both structured and unstructured financial and operational data.
Preparing to use these tools effectively starts with getting your data house in order. At Payouts Network, we’ve focused on making our data usable, which has allowed us to lean into automation without putting pressure on engineering. Using AI tools to help with scripting and configuration, our finance team is now more directly involved in processes like billing, accruals and reporting. As a result, our preliminary close timeline is now just a few workdays.
In a payments company, reconciling data from financial institutions, merchants and networks is complex. We’re currently automating those reconciliation workflows, which means our team can shift from manual spreadsheet work to higher-value exception handling. We’ll continue to refine these efforts as the technology develops, and they are already contributing meaningfully to our scalability.
