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.  

Taavet Hinrikus is a Partner at Plural, the early-stage fund that backs the most ambitious founders on a mission to change the world through technology. He co-founded Wise in 2010, where he was CEO and later Chairman, which went public in the first-ever direct listing in Europe in 2021. Prior to that, Taavet was Skype’s Director of Strategy until 2008, having joined as its first employee. He’s been an active investor for more than a decade,with personal investments in the likes of Bolt and Synthesia. In Today’s Show We Discuss: 04:08 VCs are Spreadsheet Monkeys 05:41 Why Banker European VCs Suck More Than The Others 11:20 Why Serial Entrepreneurs Are Better 14:48 Why the 2:20 Fee and Carry Model in VC is Broken 18:01 What are the Biggest Ways VC Investment Decision-Making is Broken 28:26 Why is it BS when VC Firms Need Every Partner to Meet the Founder 31:24 When and Why Will Founders Realise Multi-Stage Firms are Bad Early Investors 34:35 Why Does Europe Need to Build it’s Own Tech Now More Than Ever 37:24 Will Putin Invade More European Countries 39:29 What are the Dangers of Having US Made Tech in Europe 47:12 How Does the Change in Relationship Between the US and Europe Impact How We Build Our Tech Ecosystem? 52:36 Quick Fire Questions and Reflections