Stephen Tiller on Leadership, AI, and Picking Up the Phone

In this episode of The Rainmaker Podcast, Gui Costin sits down with Stephen Tiller, who joined Sterling Global Financial roughly 13 years ago after a 35-year career across some of the most respected names in real estate finance and investment banking. Sterling, founded by David Kosoy more than 50 years ago, manages roughly $7–8 billion in assets across six countries and runs a platform that includes private credit lending funds, development and construction businesses, trust companies, and banks. Stephen describes it as a microscopic-scale version of the Brookfield or Blackstone model, with real estate as its DNA.The conversation opens with Stephen's origin story growing up in a northern Ontario mining town, playing varsity hockey at Western, and starting his career at CB Richard Ellis as it was first entering Canada. He spent the 1990s working out distressed real estate and financial companies at RBC Capital Markets, an experience he credits as foundational to how Sterling underwrites and builds products today. He later ran the merchant bank at Brascan under Bruce Flatt, and led global investment real estate banking at Bank of Montreal before joining Sterling.On sales, Stephen explains that distribution is Sterling's number-one priority. The firm's Canadian retail engine runs through FundServ the platform owned by the major Canadian banks and dealers which connects the firm to thousands of retail investors. Once approved, the platform allows an IA in Vancouver to invest a client on Friday after a Thursday request. But the efficiency of the back end only works if the front end is covered: Sterling's sales team is built around managing the IA and RIA channels, understanding each advisor's book and decision-making.Communication inside the firm is high-touch and high-frequency, with twice-weekly calls at critical junctures. Stephen leans heavily on time-tested sales discipline tell them what you're going to do, do it, then tell them what you did combined with a modern tech stack including HubSpot, Asana, and a growing AI layer. He's candid that Sterling is "on the 5-yard line" with AI but treats it as a top-down priority, with senior executives leading the rollout themselves.On leadership, Stephen credits founder David Kosoy, who at 60+ years in the business is still first in the office. He emphasizes buy-in by example, boots-on-the-ground decision-making, and picking up the phone which he argues has become a real leadership differentiator as email turns into a CYA tool. His marina infrastructure example captures it: only by being physically on site did the team realize they didn't have a development site with a marina, they had a marina with a development site.His advice for young professionals: ask better questions and anticipate where the puck is going, not where it is. He closes on the biggest challenge facing the industry today the pace of regulatory and geopolitical change and his answer to it: grow or die. Constant improvement, reinvesting in people, and adapting the business, because the people are the business.Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.