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

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

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