The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
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May 2, 2025 
Reggie Marable, Head of Global Sales at Sierra and former leader at Slack and Salesforce, shares insights on navigating the fast-paced world of sales. He reflects on his early failures and the importance of humility in leadership. The discussion delves into effective sales strategies, including proof of concepts for enterprise deals and the value of verticalized sales teams. Reggie also highlights how AI tools are transforming sales efficiency, negotiating techniques for large deals, and the delicate balance of rapid hiring during hyper-growth.
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Reggie's Leadership Reinvention
- Reggie was fired from a CRO role due to ego and poor leadership.
- He reinvented himself with humility and listening, finding success at Salesforce as a first-line sales leader.
Customize Sales Playbook
- Customize your sales playbook to fit your company; don't copy another organization's approach blindly.
- Build on existing strengths and tailor methodologies to create a unique, effective sales process.
Master Multi-Threading
- Map out executive alignment thoroughly to multi-thread the organization effectively.
- Engage leadership, technology, and business stakeholders as a team to build broad account relationships.