It was a first meeting Naeem Ishaq tells us he’ll never forget: stepping into the Chief Product Officer’s office at Salesforce, he began pitching a bold new pricing model. Yet the officer cut him off, bluntly telling him to “figure out the (numbers) first, then we can talk strategy.” Ishaq admits the numbers he had inherited were somewhat messy. Despite the tough feedback, however, he refused to give up. He dove deeper—verifying metrics, updating budgets, and clarifying every detail—determined to show he could be both a financial expert and a strategic partner. By persevering rather than shrinking from the challenge, he eventually earned the trust needed to advance his pricing insights.
Read More
That wake-up call echoed lessons he’d learned as a child of immigrants. Ishaq tells us his father arrived in the United States with just twenty dollars, fueled by grit and hope. Growing up, Naeem watched firsthand how determination could unlock opportunity—even if the odds seemed stacked. This conviction led him to form his first business in 1999, forging a passion for technology-driven solutions that would guide him in future roles at Salesforce, Square, and eventually Checkr.
Today, as CFO and Chief Strategy Officer at Checkr, Ishaq’s mindset blends rigorous analysis with an entrepreneurial spark. He believes finance leaders create the most impact when they go beyond reporting numbers to envision what’s possible—and then rally others around that vision.
Made Possible By
Q: We want to talk to you about Checkr. We know a few things, but please tell us: what is Checkr about today? What are its offerings?
Ishaq: So, Checkr is transforming what has historically been a very sleepy, human-driven process: background checks. Before Checkr, people were literally cobbling together random pieces of information, comparing one document to another by hand, and then delivering the results via email, PDFs, or even fax machines. Our co-founder (Jonathan) came in with a simple idea: Can we take this human-driven workflow and automate it using AI? That’s exactly what we did, starting about 11 years ago.
Read MoreA core part of our IP is machine learning, which automates the entire background-check process—from the initial data point to delivering results to customers, typically via APIs. The outcome is faster, more accurate background checks, enhanced by modern technology, user-friendly interfaces, and an overall delightful customer experience. This approach has driven our significant growth. We’ve only disclosed that (as of 2023) we’ve crossed 700 million dollars in revenue, and the company continues to expand and remains quite profitable. Ultimately, we see ourselves as a data platform business built on a ‘people data graph’—and that’s opening new opportunities around trust and safety that we’re very excited about.
CFOTL: You’ve mentioned the AI opportunity, which Checkr has focused on for the past decade. What has happened in the last two years?
Ishaq: (It’s) one hundred percent (a priority). We had our ‘aha moment’—an ‘iPhone moment,’ if you will—when OpenAI launched ChatGPT about two and a half years ago. Generative AI suddenly became part of the public consciousness, and it’s advancing at a breathtaking pace. My first real experience with AI was back at Square, where we had a phenomenal team of PhD data scientists working on risk and fraud detection. It was incredibly resource-intensive then, but generative AI now makes this technology far more accessible to everyone.
At Checkr, one of my roles (as Chief Strategy Officer) is to lead AI efforts across the company, and we approach this in multiple ways. First, we’ve always used AI in our core product, and we’re now augmenting it with generative AI—both forms reinforce each other. Second, we’re applying AI to help customers interpret their background-check results without doing extra research. Beyond that, we’re driving a major initiative to empower employees across the board. Our top three priorities: leverage new AI tools (like Cursor and Debuild) to accelerate product development, use AI to boost our go-to-market and growth, and enhance customer support with generative-AI chatbots (a big leap from deterministic models).
We even hosted an ‘AI Day,’ where employees spent a full day in training and experimentation, integrating AI into their day-to-day work—and the outcomes have been incredible. We see a huge opportunity here: serving our mission more effectively, helping customers, driving growth, and enhancing efficiency all at once. We’re absolutely full steam ahead.
Checkr | www.checkr.com | San Francisco, CA