Scaling Rocketships, Scar Tissue and Building a Culture of Ownership with Blakely Cragun

SummaryIn this episode of the Vertical SaaS Podcast, Host Gavin Savage interviews Blakely, the Chief Strategy Officer of Redo, who shares his extensive journey through the tech and startup landscape. Blakely discusses his transition from a corporate environment at Dell to the fast-paced world of startups, highlighting his experiences at Instructure and Divvy, where he played pivotal roles in scaling these companies.He also introduces Redo, a new venture focused on simplifying e-commerce returns, and shares insights on the current market dynamics affecting startups, particularly in relation to interest rates and innovation. In this conversation, Blakely discusses his multifaceted role at Redo, emphasizing the importance of product management, finance, and operations in a startup environment. He shares insights on identifying companies poised for rapid scaling, the nuances of vertical versus horizontal SaaS, and the challenges of product expansion.Additionally, he offers valuable advice for career advancement in startups, highlighting the significance of impact, leadership, and understanding business value drivers.TakeawaysBlakely transitioned from a corporate job to startups for a faster pace.His career began at Dell, but he found fulfillment in startups.At Instructure, he proposed a go-to-market strategy that was implemented immediately.Scaling a startup feels chaotic, like a rocket ship losing parts mid-flight.Having 'scar tissue' from past experiences helps in navigating challenges.The importance of connections in job searching cannot be overstated.The startup environment is currently challenging but fosters innovation.Redo aims to simplify e-commerce returns without charging SaaS fees.Market dynamics have shifted, making it harder for startups to thrive.Bundling services is becoming more common as money becomes scarce. My role has become something like if product, operations, and finance had a baby.We think of ourselves almost like a VC investing in these different startups.I care a ton about the people that are involved.You can't just be better, you have to be different.It's a true meritocracy. Best people, more money, more equities, please stay.You need to crush it.If you want to grow a lot in your career, you got to hitch your wagon to the really good leader.We're building a platform that's going to be multiple products.You need to understand what matters to the business.I have seven mini CEOs at the company. Hosted on Acast. See acast.com/privacy for more information.