In the SaaS business, growing revenue tenfold, expanding product offerings, increasing headcount internationally while maintaining efficiency, launching an IPO and implementing AI — all in under a decade — makes for a significant challenge. However, PagerDuty, led by CFO Howard Wilson, has done just that.
Wilson recently completed his eighth year with the cloud-based incident management and digital operations platform. He originally joined PagerDuty as chief commercial officer in early 2017 and transitioned to CFO in September 2018. Just seven months later, in April 2019, he helped take the company public. The IPO process dominated much of Wilson’s early tenure as CFO, but he also was aware of the importance of improving the foundation around the finance function and acted accordingly.
Despite an increasingly crowded SaaS market, particularly in areas where PagerDuty operates, the company remains highly competitive. In its most recent earnings report, PagerDuty demonstrated revenue growth and achieved non-GAAP profitability despite reporting a GAAP net loss.
For Wilson, his front-row seat to the company’s evolution provides valuable lessons for CFOs navigating high-growth, high-competition environments — especially those facing the challenges of scaling efficiently while managing financial performance.
Howard Wilson
CFO, PagerDuty
First CFO position: 2018
Notable previous employers:
- Dynatrace
- Keynote Systems
- Oracle Corporation
This interview has been edited for brevity and clarity.
ADAM ZAKI: As the organization has grown under your leadership, particularly post-IPO, how have you ensured the finance team has been able to keep up with the increased workload?
HOWARD WILSON: When I joined the company, we weren’t even at $50 million in annual recurring revenue and now we are approaching $500 million. As a team, we’ve seen considerable revenue growth over the years. We’ve had to grow headcount significantly, not just in finance but across the organization. When I joined as chief commercial officer in 2017, before becoming CFO, we had about 170 employees. Now, we have around 1,200.
Finance started with around five people, but now if you take into account corporate strategy, investor relations and business operations we are approaching 100 people in the finance function. So we’ve grown finance’s headcount, but with efficiency in mind. When I first became CFO, it took us almost a month to close the books. Once the month ended, we’d spend the next 20-something days trying to close the books again, only for the month to be over. This is typical for a lot of startups early on but is a level of maturity that would not work in the public markets.
We focused on building an organizational maturity pathway, especially in finance, before we focused on our IPO preparations. We had to mature our finance function by implementing foundational systems, such as a proper ERP and the right infrastructure to manage the boring stuff, as many would say. However, we needed to have systems in place to withstand the scrutiny of a public audit while also reducing our time to close the books and meet the deadlines that come with being a public company.
We set small goals and achieved them. We got our close time to under 10 days, then under eight, then less than five. We also needed to geographically diversify our workforce to provide global services and time zone coverage for our customers, so we expanded key positions in regions like Australia and the U.K. Early on, I knew we needed to think about the infrastructure to be a global business, with a sound business model to expand the reach of our product and be successful.
We’ve now started looking at technology and how it can allow our people to take on more responsibilities and provide growth opportunities. I encourage my team members to not “stay in their lane” but be open to new ways of doing things. I think technology can not only supplement tasks but also expand our people’s capabilities in ways that weren’t previously accessible.
Are there areas within the finance function where new initiatives have had an upside? What are you looking forward to possibly implementing in the future?
WILSON: What excites me about ROI from new technology is not only predictive and analytical AI, but the power of generative and agentic AI. We’ve already made effective use of an AI portal and several tools powered by the likes of ChatGPT and Gemini to provide personal productivity benefits while doing so safely.
We’ve been evaluating AI tools from a finance-specific perspective for a while now. One area we’re looking into is revenue accounting. Memo development in revenue accounting can be tedious, and using AI here can be a major time saver for our team. There are also new products that will help us interrogate our data more effectively and make better decisions around FP&A.
Agentic AI also excites me. Finance often deals with a large number of internal requests that can be distracting, creating noise, and this is an area where agentic AI could help. For example, we’re considering how to use these tools to help employees get questions answered about the stock purchase plan, or status of a customer order, or how to process a purchase requisition in a way that keeps employees informed. There are also customer and partner-facing benefits that we envision such as managing inbound finance-related requests.
How do you balance being passionate about the company’s technology implementation without having the finance team overstep IT?
WILSON: I’m grateful to have a great relationship with our CIO [Eric Johnson]. We talk regularly about what we’re trying to solve and how we can bring as much insight as possible into the company’s technology plans.
We’ve created a group with representatives from across the company, and I have someone on my finance team focused specifically on finance transformation who participates in these meetings. The tools finance wants will benefit finance, but it’s our job to explain how technology within finance can benefit the entire organization.
A CFO with your experience and tenure has likely had plenty of opportunities for a new role. What is keeping you around?
WILSON: You’re right — there are always opportunities, particularly for public company CFOs. But I’ve stayed because I love our mission and being part of it. We’re focused on revolutionizing operations and helping our customers deal with the unexpected so they can deliver to their customers, and that has always resonated with me.
While we have had financial success, I am delighted to know that our platform positively impacts our users and delivers significant business value. I’ve had customers tell me how our products have improved their lives, reducing distraction, improving their effectiveness and allowing them to manage their time to limit the impact on their lives of managing critical business systems. One person even told me it saved his marriage!
I also value working with great leaders, like our CEO, Jennifer [Tejada]. We’ve worked together at three companies for over 16 years. We have a strong understanding of how to create a workplace where people want to do their best work and how to develop the next generation of technology leaders. That leadership opportunity has had a huge impact on me.
How has that relationship developed over time, and what are some of the perks of it now?
WILSON: It has developed into an open and honest relationship. I believe you can measure an executive relationship by whether they’re comfortable delivering bad news. Many executives hold off on sharing bad news because they don’t want to disappoint.
For me, when there’s bad news or an issue that needs to be addressed, she’s my first call. We don’t always agree, but we’ve always respected each other’s opinions and considered them when collaborating. She’s a passionate, enthusiastic leader, with an inspiring level of energy. In that way, we complement each other well, and that ability to play off each other’s strengths is invaluable in a CFO-CEO relationship.
How do you apply lessons from your tenure at both PagerDuty and Oracle, as well as your relationship with your CEO, in your strategies around talent retention?
WILSON: It’s important for my employees to know I’m invested in their success beyond their ability to do their job. I spend a lot of time driving engagement, and our leadership development training — held four times a year — gives us structured opportunities to focus on building capability and career growth.
Within my finance team, I give leaders opportunities to help employees grow and develop their own teams. It is also important to listen for the signal, so I take our employee engagement surveys seriously, and one thing I’ve been particularly interested in as CFO is how much employees want to develop their business acumen and understanding of AI — things that aren’t directly related to finance or our products.
We’ve started putting together a program that curates experiences to help employees upskill and stay informed about topics that interest them. We do this so they can develop capabilities that will allow them to build and manage their careers. I am excited by the opportunities that we can create, and that investment and opportunity focus create reasons for people to build on their success here.
