Robert M. Fierro is a logistics technology entrepreneur, AI strategist, and seasoned revenue leader with over two decades of experience scaling startups, building strategic partnerships, and driving companies to successful acquisitions. Based in the San Francisco Bay Area, Robert is the CEO and Co-founder of HappyFleet AI, a platform that automates driver phone screenings, ranks top candidates instantly, and eliminates the scheduling delays that cost carriers time and money every day.
His logistics career runs deep. Robert spent seven years at Onfleet — one of the most widely used last mile delivery platforms in the industry — growing from customer development to Director of Partnerships, managing over $10M in annual revenue and cultivating the partner ecosystem that fueled Onfleet's growth. Today, he advises Openforce on AI strategy and previously guided Gridwise in optimizing analytics for gig economy operators.
Robert's writing sits at the crossroads of AI and logistics — exploring how agentic systems, automation, and data-driven operations are reshaping last mile delivery, DSP management, and the gig workforce. He holds an MBA from Northeastern University's D'Amore-McKim School of Business and has been recognized as an Honored Listee for his contributions to the industry.
When he's not building or advising, Robert is thinking about the next wave of technology that will make moving things smarter, faster, and more human.
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