20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
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.
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman.
If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.
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