Episode summary
Stephen Tiller on Leadership, AI, and Picking Up the Phone
Dakota Rainmaker Podcast
· · 22 min · Hosts: Gui Costin · Guests: Stephen Tiller
Summary
Stephen Tiller traces his career from a northern Ontario mining town and varsity hockey at Western to decades in real estate finance, including CB Richard Ellis, RBC Capital Markets, Brascan under Bruce Flatt, and Bank of Montreal. He says the 1990s workout cycle, when he helped deal with bankrupt real estate and financial companies, shaped how he thinks about underwriting and building products today.
At Sterling Global Financial, Stephen says distribution is the firm’s number-one priority. He describes Sterling as a roughly $7–8 billion platform in six countries with trust companies, banks, private credit lending funds, and development and construction businesses, built on real estate DNA and a “microscopic-scale” version of Brookfield or Blackstone. In Canada, he says the firm leans heavily on FundServ and retail advisors, and success depends on understanding how to sell through that channel.
He also emphasizes high-touch communication, cross-selling, and a leadership style built on clarity, respect, and action. Stephen says Sterling is “all in on AI,” using it to connect multiple delivery systems and improve execution, but he argues the larger challenge is adapting to constant change. His advice to younger professionals is to ask better questions, keep learning, and remember that “everything is sales.”
Key takeaways
- Stephen Tiller says Sterling’s distribution engine is priority one, especially in Canada’s FundServ-based retail channel.
- He argues the 1990s real-estate workout environment taught lessons that still shape Sterling’s underwriting and product design.
- Stephen says the firm is “all in on AI” and is using it to connect multiple delivery systems and improve execution.
- His leadership style centers on constant communication, respect, and making sure teams pick up the phone instead of hiding behind email.
- He tells younger professionals to ask better questions, because “everything is sales” and the best operators think ahead like great athletes.
Notable quotes
“our DNA is real estate and we have many financial products around it”
“we're all in on AI”
“the biggest challenge is is the pace of change”
“grow or die”
How the episode opens
Welcome to the Rain Maker podcast with your host Geek Cen. The goal of this podcast is to give listeners a unique look into sales strategies from top industry executives. We introduce you to the heads of sales and heads of distribution who will help you understand the inner workings of the successful sales organizations from philosophy to execution.
This podcast is essential for sales professionals seeking wisdom from the best in the field. If you're not familiar with Dakota and their Dakota rain maker content, please check out dakota.com to learn more about their services.
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What is up everybody? It's Geek Cen, founder and CEO of Dakota. Welcome to the latest episode of the Rainmaker podcast. I'm so thrilled to be joined by Steven Tiller.
Steve has over 35 years of experience in the real estate finance, investment, and development industry. Steve holds a BA and MBA from the University of Western Ontario where he also played varsity hockey. Steve was formerly the president and managing director of Capital Markets Real Estate Group.
Prior to that, he was president of Brascan Brookfield Financial Real Estate and vice chairman of Royal Laage Real Estate. From 1999 to 2001, he served as president of Talaskar Corporation, a private investment and development company operating in the US, UK, and Canada.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- leadership communication
- ai in financial services
- real estate credit investing
- sales distribution channels
- regulatory and geopolitical change
Companies and tickers mentioned
- BN
- BX
- HUBS
- ASAN
- CBRE
- RY
- BMO
- Sterling Global Financial
- Brookfield
- Blackstone
- FundServ
- HubSpot
- Asana
- CB Richard Ellis
- RBC Capital Markets
- Brascan
- Bank of Montreal
Watch the episode
Watch “Stephen Tiller on Leadership, AI, and Picking Up the Phone” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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Dakota Rainmaker Podcast, this episode and its artwork belong to Dakota Team. Octagon is not affiliated with the show; this page is an independent summary.
