Tip of the Spear: Ashley Jacobson, Head of Operations & Partners at Cleo

June 1, 2026

By The Artemis Fund
The Artemis Fund believes technology can create prosperity for all. With offices in New York, Texas, Massachusetts, and Nevada, Artemis leads seed rounds for companies creating resilient families, individuals, and businesses across the US.
Tip of the Spear is an interview series highlighting The Artemis Fund’s expert network. Ashley Jacobson is Head of Operations and Partners at Cleo. For this interview, she is speaking in a personal capacity and not on behalf of her employer.

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Q: What did you learn from your first job and how does it shape how you work today?
A: I started my career in strategy and operations at a global professional services firm. In that role, I was leading preparation for quarterly business reviews. When analyzing the financial reports for accuracy, I noticed a disconnect between how leadership and the teams closest to the work measured success. To solve that problem, I developed a system that aligned incentives across levels and embedded financial accountability within each team.
What I took from that experience is how critical it is to align teams around shared goals. If people are working toward different definitions of success, you forfeit compounding effects. Part of my role today is ensuring everyone has clear visibility on our priorities and enough context to make business-aligned decisions. That's what allows an organization to move quickly and in the same direction.
Q: Moving from consulting into corporate strategy, what drew you to actually running the system rather than advising on it?
A: Consulting taught me how to step into ambiguity, quickly identify what matters, and bring structure to complex problems. Now, I develop strategies and have ownership over results. As an operator, I can close the gaps between strategy and execution that an external consultant might not have control over. By understanding organizational dynamics, what's been tried before, and the company’s appetite for risk, I develop plans that are both strategically sound and successful in execution.
Q: What are some of the biggest structural shifts you're seeing in how fintech companies are partnering with banks and financial institutions?
A: The bank-fintech relationship is moving from a distribution partnership to a deeper operating partnership. Banks bring expertise in risk management, regulatory frameworks, and balance sheet infrastructure, while fintechs excel at innovation and design. When those capabilities come together, these partnerships deliver superior value to customers.
This is showing up in two ways:
First, some fintechs are putting more emphasis on the bank relationship, and in certain cases, exploring bank charters or acquisitions themselves. That is a fundamental shift in the business model. For companies that take that path, direct access to deposits and payments infrastructure can strengthen long-term unit economics. For fintechs committed to a partnership approach, the relationship with the bank is becoming less transactional and more collaborative when it comes to product development.
Second, there’s an evolution in how banks view fintechs. Established financial institutions are increasingly recognizing the value fintechs bring, especially around customer experience and product innovation. Instead of viewing fintechs purely as distribution partners, many banks are integrating fintech UX directly into their own products through white-label models.
Both of these trends point toward a more collaborative and integrated bank-fintech relationship.
Q: What do you think about AI and the impact it might have on finserv operations over the next few years?
A: I'm at an AI-native company where AI is part of the DNA, both in the consumer-facing product and in our internal operations. That vantage point is unique because I see how advances in one area impact the other.
A great example is how our AI tooling is creating more self-serve moments for customers. When gathering information about a customer issue, we can now more quickly and accurately integrate the data into other systems for further investigation. In the industry, we're seeing AI meaningfully improve capabilities like fraud monitoring and dispute handling. These areas rely on processing large volumes of signals. AI is a powerful tool for summarizing information, identifying patterns, and helping teams resolve issues faster.
In the near term, AI is acting as a decision-support layer that allows operators to move quickly and focus their attention on the highest-risk or highest-impact cases. Over the next few years, we'll see AI move beyond individual tasks toward orchestrating the operating system itself. Automation will shift from flagging potential fraud or summarizing a case to routing work and coordinating across systems. That creates real leverage for operations teams because it will drive scalability without needing to grow headcount linearly.
The financial services industry operates in a highly regulated environment where auditability and trust are critical. The companies that succeed will be the ones that use AI to make operations faster and smarter while maintaining strong controls and human oversight.
Q: What's one trait you consistently see in resilient founders or teams?
A: Founders who stay focused on their strategy are the ones I've seen build the most enduring companies. Economist Michael Porter captured this when he said, “The essence of strategy is choosing what not to do.” As companies gain traction, they face numerous growth opportunities: another market to enter, a feature to build, or a partnership to pursue. However, every “yes” has an opportunity cost. It pulls capital, time, and attention away from something else. The founders who successfully scale understand that protecting focus is often what allows a company to execute and grow.
Q: Inside a fintech, what are some warning signs that operations or infrastructure aren't ready to scale as the organization grows?
A: One signal I watch closely is decision latency. How long it takes an organization to recognize a problem, make a decision, and act on it. As companies scale, that window can dramatically grow if systems and processes don't keep pace.
There are actually two distinct failure modes within decision latency. The first is recognition latency – the organization doesn't yet know something is wrong because data is siloed or signals aren't surfacing. The second is execution latency – the problem is understood, but execution lags because there are too many stakeholders, unclear ownership, or a culture of analysis paralysis.
From the outside, both look the same (solutions aren’t being enacted), but the root cause is important because the interventions are entirely different. Confusing the two is where scaling companies may lose time.
My approach is to diagnose scalability issues before they become problems. I do this by assessing current process and system performance in step-function growth scenarios. Strong operators don't just plan for current demand; they stress-test the system against future demand.
Q: What's something that actually has to happen behind the scenes to make a fintech product work that people might not understand?
A: As an operations leader, my goal is to make the ecosystem behind the product invisible to the customer. From the outside, fintech products look like software, but in reality they're coordinating an entire financial infrastructure stack. A single transaction might involve an issuing bank, an acquiring bank, a payment network, processors, fraud monitoring systems, and compliance rules – all working together in real time. One of the biggest challenges in fintech is orchestrating multiple partners and systems in a way that's reliable, compliant, and seamless to the customer.
Q: What's a trend, company, or founder you're excited about right now?
A: One fintech trend I'm paying close attention to is innovation at the infrastructure layer. The first wave of fintech improved the user experience. The next wave is rebuilding the systems supporting money movement. The financial system was built for banks, not for software companies building financial products. The focus is now on the operating system itself, including API-native banking rails and automated regulatory infrastructure.
The companies building these layers are serving more than just fintechs; they’re serving banks now, too. When incumbent institutions start pulling from the same infrastructure stack as challengers, you've crossed a threshold — it's no longer a fintech story, it's a financial services story.
Q: What's the best piece of career advice you've ever received?
A: A few years ago, I was helping my mother move her office. As we were packing up, we went through shelves of prestigious awards she had earned throughout her career. I was in shock when I saw many of them in the trash pile instead of bubble-wrapped in boxes. When I asked her about it, she said, “The award doesn’t define the quality of the work. The work doesn’t get any better after it’s done, and awards come way after that.” It's easy to focus on external validation, but the best work doesn't need a trophy to prove it.
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