The impact of positive leaders early in one’s career can be the catalyst for pursuing leadership roles like CFO. For Naeem Ishaq, CFO of Checkr, his perspective on human capital, fundraising and automation comes from the influence of two monumental figures in technology and finance.
For a large portion of his career, Ishaq worked directly with OpenAI CFO Sarah Friar and Square (now Block) and Twitter (now X) founder Jack Dorsey. Ishaq not only credits both individuals for his ability to grow his career but also implements their philosophies in managing and scaling his company’s growing demands of the finance function.
Naeem Ishaq
Executive vice president and CFO, Checkr
First CFO position: 2016
Notable previous employers:
- Circle
- Boxed Wholesale
- Square
- Salesforce
This interview took place at the inaugural NYCFO event in New York City and has been edited for brevity and clarity.
ADAM ZAKI: You’ve worked for some technology giants in their early days and alongside some of the most prominent leaders in the industry. Who stood out the most and what type of impact did they have on you?
NAEEM ISHAQ: Looking back, I think there is so much value in working at established companies early on that are growing at a rapid pace. I worked in the startup environment, I started my own company, but I went to work for Intel shortly after, which I would call an academy company — strong culture, big picture. And I stayed there for six years and felt like I was in school the entire time because I was always learning.
A bit later in my career, I started working with Sarah Friar, who is now the CFO of OpenAI, and that was absolutely monumental for my career. She was my manager at Salesforce and Square, and she managed me longer than anyone else in my career. Her personality is magnetic and her ability to resonate and connect with people is admirable. I don’t know how she does it. She’s authentic, inspirational, vulnerable, and her energy inspires hard work and creativity in people in a way I have rarely seen in other leaders.
When I was making the decision to leave Salesforce for Square, I had the opportunity to take a very senior role at Salesforce when I was 31 — an amazing opportunity for me at the time. But I chose to go to Square because I wanted to continue working with Sarah and also get the opportunity to work with CEO Jack Dorsey.
I reported directly to Sarah at Square and she reported to Jack. They were both some of the most unique and impactful people I ever met. We all used to joke that Jack was Batman. He was so insightful, and his thoughts on business and life impacted me. Sarah’s stories were so entertaining, her perspectives were amazing and the environment she created as a leader taught me so much about being a CFO.
I’ve met multiple people who met Sarah for five minutes and told me she was the most impactful person they’ve ever met, and it’s why I am always so thankful for the time I got to work with her. Jack too. They both had an impact on me that directly shaped my career in a profoundly positive way.
Most recently, where have you seen the most ROI in your human capital expenses?
ISHAQ: I think from the very beginning, and this has played a considerable part in our growth, this company has taken what used to be an entirely human-driven process — one that still exists today around the globe when you look at our competitors — and used machine learning and automation for over a decade now to streamline processes. It’s so interesting because leveraging technology to drive efficiency has been the focus here since the origins of the company.
But we are still a people business. We take time to make sure we are hiring the right engineers, finance people and operators, and it’s important for us to continue developing ways to keep those people around. Employee enrichment and education have been a focus for us, and we have shifted toward helping our employees understand how they can enable AI specifically within their roles and beyond.
For technical employees, we’ve augmented agentive software development, and for nontechnical employees, we have implemented enterprise versions of LLM chatbots, which have been helpful for them.
We are doing a full-day training very soon, where everyone in the entire company will spend half the day learning and training around AI, and then the other half will be time for them to explore AI use and ask questions about specific tools or use cases on projects they are working on. It’s been a lift to put together, and there are costs associated, but it is super high ROI from my perspective.
How have you been able to successfully implement this automation strategy specifically within the finance function?
ISHAQ: We have been able to implement some mind-blowing tools on the finance front. A few months ago, we launched a generative AI-based revenue forecasting model, which most people would say is not even possible to do. But we did it, and it’s worked for us. It’s been so much more accurate than a group of analysts trying to pull all that information together. It’s refreshed on a regular basis, and it’s a great use of technology to drive efficiency via AI within our finance function.
One thing we are prototyping right now is taking a data repository of a lot of our core financial information. The good thing is that a lot of this data is very structured as is — already in tables most times — so this information is out there. But instead of communicating about the data over Slack or something, we’ve taken that data and dumped it into an LLM. So you can talk directly to an AI bot about that data specifically.
For one of my board memberships, for example, we have a Slack group called the Board War Room. To be able to use an LLM to call upon data we’ve referenced or have preuploaded to it and ask it questions as a group is also a valuable concept that I think is pretty successful and will become more popular.
With all of this automation, how do you think about risk management and data security?
ISHAQ: We have clear boundaries. We aren’t going to use an LLM to build a 10-K filing, for example. We have defined the difference between a one-way door versus a two-way door and what types of things we are comfortable using this technology for. We know hallucinations happen, but we recognize that human error occurs too. So it’s really about layers of control and review to prevent errors of all types.
We hold personally identifiable information as the most important and most protected dataset we have, but we have an appropriate amount allocated toward risk mitigation. That goes back to educating our employees, implementing monitoring devices and making sure our information is accurate and flowing at a rate where discrepancies are caught very early.
You’ve done a lot of fundraising in your career. What would you say is the CFO’s role in that, and is there a sales element to it?
ISHAQ: I don’t think of myself as a CFO when it comes to fundraising. I think of myself as a businessperson and an owner of a company trying to convey our exciting message and essence of the business. When I am trying to raise money, I prioritize honesty. I am not evasive, I recognize our challenges as a business, and I prioritize authenticity. That way, I get much more trust. Even if not everyone says yes, those who do have a really solid understanding of the business, and there are no surprises after they come on board.
I think humans are amazing, really smart and intuitive — especially those in business. There is no benefit to being untruthful, ever. I think it’s about resonating with the people you’re talking to, letting them know you are there to share how the product solves a particular problem or challenge. Sure, there’s a little bit of sales there, but if you look at the skill sets that make up professions of all types, the ability to sell can be an incredible upside and skill anywhere.
