20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank

Listen to this episode from The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch on Spotify. Matt Plank is Rippling's Chief Revenue Officer where he oversees all Sales and Account Management functions in the US and Internationally. Matt joined Rippling in the very early days when Parker Conrad (founder) was building V1 in a basement with $0 in revenue. Today the company is a market leader with 100s of $Ms in ARR. Prior to Rippling, Matt was a Sales Director @ Zenefits where he helped the company scale to $70M in ARR.  In Today’s Show with Matt Plank We Discuss:  08:25 Challenges and Strategies in Outbound Sales 10:29 Building Effective Sales and Marketing Partnerships 13:37 Founders and Sales Playbooks: Who Should Create Them? 20:45 Pricing Strategies and Customer Success 24:43 Discounting and Urgency in Sales 33:57 Building Relationships for Successful Deals 34:22 Effective Deal Reviews: Asking the Right Questions 35:30 Pipeline Reviews: Frequency and Participants 35:59 Handling Deal Slippage: Acceptable vs. Non-Acceptable Reasons 39:17 Maintaining Morale in Volatile Times 42:14 Outbound Sales Strategy: Lessons Learned 46:03 Scaling Sales Teams: Hiring and Promoting 47:15 Challenges and Strategies in International Markets 01:00:45 Signs of Scaling Issues in Sales Leadership