From 200-Mile Races to CMO: David Chase on Resilience and Goal Alignment

David Chase, an avid ultra-marathoner and the President at WorkBoard, joins Steven Pivnik to discuss the powerful intersection between endurance sports and business leadership. David shares how his professional rise to CMO coincided with his running journey, which has included multiple 100+ mile races and even a 200-mile event. He explains that for him, a startup isn't a sprint or a marathon—it's a 200-mile race, with extreme highs and lows that demand resilience and a relentless focus on moving forward. The daily habit of running, he finds, provides essential clarity for processing work challenges and making clearer decisions. Beyond the mindset, David dives into his work at Workboard, a platform that helps large enterprises align strategy with execution using AI. He details how Workboard's AI agents help managers and teams stay aligned, eliminating the lag and dilution of manual status reporting. He also provides tactical advice for scaling marketing teams, emphasizing the importance of in-person events and treating business goals with the same daily discipline as a marathon training plan. Finally, David shares a practical framework for effective, ongoing sales enablement, including an internal "checkout" process to let reps fail safely before engaging customers Takeaways: Treat Business Goals Like Race Training: Don't just set a quarterly goal and hope to get there. Break it down into specific, daily actions you must take to achieve it, just as you would with a daily training plan for a 5K or marathon. Embrace In-Person Connection: In an age of AI and Zoom fatigue, investing in in-person events (like small dinners, meetups, or user conferences) is a powerful differentiator. People crave real experiences and want to connect with real people and customers. Use AI to Test and Scale: AI gives marketing leaders the ability to test new channels and initiatives much faster. Use this to run more tests, get data quickly, and then decide whether to scale the initiative or discard it. View Sales Enablement as an Ongoing Process: Enablement is not a single meeting or a deck. It requires continuous investment, resources, and the active participation of senior, experienced sellers—not just junior team members. Create a "Checkout" Process for Sellers: When launching a new product or pitch, implement an internal certification. Have sales reps pitch to a panel of senior leaders who score them. This provides a safe environment to fail, get feedback, and improve before they are in front of a real customer. Reframe Resilience: A startup isn't just a marathon; it's a 200-mile race with much lower lows and higher highs. When things get tough at work, remember that it's rarely as hard as mile 177 of a 200-mile race. The key is to never quit and just keep heading in the right direction. Quote of the Show: "People correlate startups to running a marathon. It's a marathon. It's not a sprint. It's not a marathon, it's a 200-mile race, where the lows are so much lower than a marathon and the highs are so much higher than a marathon." Links: LinkedIn: https://www.linkedin.com/in/davidschase/ Website: https://www.workboard.com/