20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI

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

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