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Fireside Chat with Jeff Depa: CRO at Gainsight

Fireside Chat with Jeff Depa: CRO at Gainsight

Jeff has more than two decades of leadership experience across sales, marketing, consulting, and systems engineering. He has built, scaled, and led customer-focused, high-performing enterprise teams to drive hyper-growth across SaaS businesses.

As a full-stack GTM leader, Jeff has a proven history of crafting innovative GTM strategies and delivering results. Jeff is a passionate and creative architect of GTM teams with documented success.

During this fireside chat, Jeff will share his insights on building, scaling, and leading customer-focused enterprise teams, as well as driving profitable hyper-growth teams across an enterprise SaaS business.

Discussion topics

  • The mistakes he’s learned from his 2 decades of experience

  • Best practices for managing complex businesses with accuracy and efficiency

  • Overcoming challenges in leading teams through complex business environments

  • Building and leading customer-focused enterprise teams for success

  • Creating a culture of accountability and execution to produce remarkable results

  • Strategies for driving profitable hyper-growth team in software businesses

  • The importance of innovation and creativity in crafting GTM strategies

Key Takeaways

  • When you’re thinking of going international, don’t make the mistake of jumping straight in without conducting any analysis and saying, “ I need more TAM.” Be thoughtful. Make a 3-5 year plan, be patient and realistic. You can’t copy the current working playbook, but you can go back a few chapters - don’t need to reimagine, but you do have to reevaluate.

  • Leadership vs. Direct Management: It’s context vs control. As a leader, take a step back and focus a bit more on strategy. How is your message getting across. Do implement a management system where everyone knows what they’re accountable for.

  • When setting up your company’s vision the culture is super important. You want to make sure your people feel a part of that culture. It starts at the top with leadership. Think about what it means to lives the values at your company, it should be a part of everything you do.

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