Naeem Ishaq, Chief Financial Officer (CFO) of Checkr, attributes his leadership philosophy to the lessons learned from two prominent figures in technology and finance—OpenAI CFO Sarah Friar and tech visionary Jack Dorsey. Their influence has guided his approach to human capital, automation, and innovative financial strategies.
Ishaq’s career spans global tech giants like Intel and Salesforce, as well as his entrepreneurial ventures. However, his time working under Friar and Dorsey during the early days of Square (now Block) proved to be the most formative.
“Working with Sarah Friar at Salesforce and then following her to Square was a pivotal decision,” Ishaq recalled. “Her ability to connect with people while remaining authentic is something I try to emulate daily.”
At just 31, Ishaq turned down a senior leadership role at Salesforce to join Square, where he gained direct exposure to CEO Jack Dorsey. Reflecting on that period, Ishaq said, “Jack’s insights on business and life were profound. Sarah’s energy and leadership style were magnetic. Together, they shaped how I approach scaling a modern finance function.”
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Driving Innovation Through Automation and AI
At Checkr, a technology-driven background check company, Ishaq applies these lessons by championing automation while maintaining a human-centered culture. Under his leadership, the company has embraced artificial intelligence to streamline operations while investing in employee development.
“We’ve prioritized using machine learning to drive efficiency while remaining a people-first organization,” Ishaq explained. “Our AI training program ensures every employee understands and can effectively use artificial intelligence in their roles.”
One of Ishaq’s recent initiatives is a generative AI-based revenue forecasting model. This groundbreaking tool, once considered unattainable, now delivers more accurate projections than a team of analysts. His team is also developing a large language model (LLM) that enables employees to query financial data via an AI-powered chatbot.
“For one of my board memberships, we use a ‘Board War Room’ on Slack,” Ishaq said. “With our LLM integration, we can access real-time financial insights, enhancing collaboration and decision-making.”
