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

02 May 2025

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Reggie Marable is the Head of Global Sales at Sierra, a conversational AI platform for businesses. Sierra enables companies like ADT, Sonos, SiriusXM, and WeightWatchers to build AI agents that transform customer experiences. The company has rapidly become a hypergrowth leader in Silicon Valley, recently securing a funding round that values it at $4.5 billion. Before joining Sierra, Reggie was the Head of Sales in North America at Slack and the Area Vice President of Enterprise Sales at Salesforce. In Today's Episode We Discuss: 02:50 "What I Learned from Failing Early as a CRO" 06:06 The Most Effective Sales Strategy and the BS Sales Methodology 06:55 How to Build Sales Processes from Scratch 12:28 When and How to do Verticalised Sales Teams 14:15 How to Become World Class as Sales Prospecting and Outbound 17:21 How to Use Proof of Concepts to Win Enterprise Deals 22:04 Enterprise vs. Self-Serve: Both or One and How 30:09 Building a Sales Team from Scratch 37:39 Structuring the Hiring Process 41:14 How Founders F*** Up Hiring in Sales 46:25 Handling Salary and Title Expectations 51:36 How to Run Effective Deal Cycles 57:06:07 How to do Onboarding for New Sales Hires 59:07:48 How to do Post Mortems in Sales Processes 01:04:24 Negotiating Enterprise Deals 01:08:04 Quick Fire Round: Sales Tactics and Strategies This episode is brought to you by Capchase, helping software and hardware companies close deals while accessing TCV upfront. Learn more at capchase.com/20vc.

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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

This episode hasn't been transcribed yet

Other episodes from The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?

20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg

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