In this episode we ask the unpack the question of: Do COO's have a two year shelf life? We discussed this topic with Casey Woo, CEO @Operators Guild.  We discuss the following with Casey:  What is the role of the COO? Why does the COO have a two year shelf life? If that is the reality, how should one think about their career? What does this mean for 4 year option grants? What are the key terms every COO should negotiate?  References www.operators-guild.comhttps://summit.operators-guild.com/2024 Biography:  Casey Woo is a seasoned multi-stage operator and 7x CFO with over two decades of experience in business operations and finance from investment banking on Wall Street to Silicon Valley tech start-ups.  Casey now leads 800+ CFOs, COOs, and Biz Ops company builders as the co-founder of Operators Guild, a community for professionals in strategic finance and operations roles. He believes strongly that community is what makes the difference for start-ups and professionals.  When he’s not working, Casey is spending time in California’s Bay Area with his wife and three children.  Summary: CEO shelf life and software frustrations. 0:06Brandon and Bethany discuss their least favorite piece of software, with Brandon naming Microsoft Teams as his least favorite and Bethany agreeing due to its poor performance on Macs.Both agree that the entire Microsoft suite, including Word, has always been problematic and frustrating to use.Bethany and Brandon discuss the pros and cons of Google Docs and Microsoft 365 for collaboration, with Bethany preferring Google Docs for its ease of use and collaboration features.Brandon shares his experience of transitioning from Microsoft to Google Docs, finding it difficult to adjust to the new platform but ultimately appreciating its collaboration capabilities.Bethany: Transition from growth to optimization occurs around 50 million in revenue and 250 employees.Brandon: First two phases of growth and commercialization are enjoyable, but third phase of optimization is less enjoyable and happens around 50 million in revenue and 250 employees.Communicating option value to employees and talent acquisition teams. 7:57Bethany suggests using a product like Lecce to help employees understand the value of their options and how they vest over time.Brandon agrees that communicating the value of options as part of compensation is important, and notes that their company could have done a better job of this in the past.Brandon and Bethany discuss the importance of educating employees on option grants and their value, including providing a clear framework for career progression and regular updates on the terms and benefits of option grants.Casey Woo, founder of the Operator's Guild, shares his experience of implementing option grants for employees, including tying them to job role and seniority, and providing awards for top performers to increase their options.CEO role and responsibilities. 12:50Casey Woo shares insights from 35,000 hours of listening and talking to CEOs, highlighting the diverse reasons why people want to be CEOs, including wide impact and not being a CFO or...