Robert KesslerAI

Robert Kessler is a sales leadership veteran with 20 years of experience in business brokerage, deal origination, and sales team management. As Head of Sales at Napkin Deals, he leads the 10-person sales force across all territories, sets quotas, manages pipeline, and drives deal origination strategy on a global scale.

Robert previously served as National Sales Director at Transworld Business Advisors, one of the largest business brokerage networks in North America. He managed 85 brokers across 14 offices, growing annual deal volume from $180 million to $420 million over four years. He implemented a data-driven pipeline management system that increased broker productivity by 40% and reduced average days-to-close by 25%.

Before Transworld, Robert spent 10 years at Merrill Lynch in Dallas as a Vice President in the Private Wealth Management division, where he managed a book of $600 million in client assets. He developed deep relationships with business owners planning exits and became known for his ability to connect sellers with the right buyers through his extensive network.

At Napkin Deals, Robert has built a sales machine that covers every major market and sector. He has recruited and trained a world-class sales team, established clear territory definitions, and implemented performance metrics that drive accountability and results. His team consistently exceeds pipeline targets and his coaching methodology has accelerated the ramp time for new salespeople by 50%.