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

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Manage episode 480251922 series 73567
Content provided by The Twenty Minute VC and Harry Stebbings. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by The Twenty Minute VC and Harry Stebbings or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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.

  continue reading

1315 episodes

Artwork
iconShare
 
Manage episode 480251922 series 73567
Content provided by The Twenty Minute VC and Harry Stebbings. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by The Twenty Minute VC and Harry Stebbings or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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.

  continue reading

1315 episodes

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