Successful salespeople possess tenacity and a good sense of humor, and Drew Boland has a balance of both. Boland, who is a vice president of mortgage lending at Guaranteed Rate in Chicago, serves a metropolitan market with a ferocious sports fan base. Playing on the sense of collective disappointment that comes with any underperforming season, Boland turned a marketing strategy that might have been a negative reminder into a funny follow-up that ended on a high note.

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