Brandon speaks with Avrum Laurie, VP of Product at Wealthsimple and his former boss at Freshbooks over a decade ago. Avrum is an exceptional product mind, and is equally cogent in engineering and design. Brandon and Avrum discuss his journey from big company PM at Microsoft to his foray into startups Freshbooks and Wealthsimple, which he helped build into two unicorns over the last decade. Given their shared history at Freshbooks, Avrum and Brandon go deep on some key projects they worked on, and reflect on the challenges and lessons they held. Avrum shares his philosophy on product leadership, and finally explains why Wealthsimple has so many damn apps.

Avrum Laurie on the path from the Microsoft to startups, his product leadership philosophy, and product stories from Wealthsimple and Freshbooks | The Black Box of Product Management

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Brandon speaks with David Hariri, co-founder of Ada, an AI powered customer support platform that raised at a 1.2B valuation in May 2021, entering the very rare echelon of Canadian tech startups reaching unicorn status. Ada enables large customers like Zoom to deliver great customer support experience at scale. David recounts his upbringing, and the myriad of experiences that led him to be a developer and designer at Teehan and Lax, which was acquired by Facebook. He also covers the epic story of founding his first startup, Volley, almost shutting it down, and then betting their last 9 months of runway into pivoting into what became Ada. It's a great example of persistence and the ups and downs of startups.

David Hariri on co-founding Ada, the pivot that created a unicorn, and what product-market fit feels like | The Black Box of Product Management

In our first episode ever, Brandon speaks with Craig Miller, the former CPO & CMO of Shopify and a company legend. He joined the company when it was worth less than $100M and 70 employees, and by the time he left it had grown to over $130 BILLION and 10k employees. He was the company's first marketer, and then built up the growth team as it's CMO. Mid-tenure, Craig took over the product team which he grew from 5 to 250.  The winding conversation covers Craig's early career in engineering and marketing, mental models for leadership and product, and tons of stories from his 9+ years at Shopify, from the earliest days to the present. 0:00​ - Intro  1:06​ - What's the vague experience listed on your LinkedIn called, "Owner"?  3:52​ - What happened after "Owner", aka Kijiji  6:52​ - How Craig came to run Marketing at Kijiji despite being an electrical engineer 8:54​ - The start of the Shopify story 11:49​ - The PS that changed Craig's Life (https://medium.com/inside-shopify/the...​) 14:33​ - Craig's Big Hairy Audacious Goal for Shopify 16:00​ - Canadian tech imposter syndrome 18:44​ - "If you have ambition, you're an entrepreneur" 25:35​ - Why Craig hired me, and his thoughts on interviewing/hiring 30:13​ - Being a product exec role at a hyper-growth company 34:32​ - Leading through others 45:52​ - Projects or features that launched at Shopify that are great examples of PM thinking at the company 53:38​ - The importance of the details 1:02:10​ - Scaling the product management team from 5 to 250 1:08:30​ - What Craig is most proud of during his time at Shopify 1:10:00​ - What Craig is doing now 1:15:00​ - Final question - what's the single most important mental model or principle you have for life, work or both?

Craig Miller on being Shopify's CPO, Marketing by an Engineer, Leadership, and Scale | The Black Box of Product Management

The Black Box of Product Management

Avrum Laurie on the path from the Microsoft to startups, his product leadership philosophy, and product stories from Wealthsimple and Freshbooks | The Black Box of Product Management

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