Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241

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 at Zenefits where he helped the company scale to $70M in ARR. ---------------------------------------------- Timestamps: (00:00) Intro (03:08) Why Are Win Rates So Low in Sales? (05:40) Is It Easier to Sell Replacement Products or Net New Solutions? (06:44) Is Outbound Sales Dead? (08:40) How To Build an Effective Outbound Function (15:45) Close Rates Across SMB, Mid-Market & Enterprise Segments (22:05) Is Customer Success Overrated in Enterprise Sales? (24:30) How Matt Approaches Discounting in a Competitive Landscape? (27:42) Are Logos or Early Wins More Important for Startups? (30:50) Approaching Multi-Year Contracts (36:43) An Acceptable vs. Unacceptable Reason for a Deal to Slip (40:06) Lessons on Maintaining Morale During Volatile Times (43:07) What’s the Weakest Part of Matt’s Go-to-Market Team & Why? (47:28) The Revenue Split Across SMB, Mid-Market & Enterprise (54:46) Who Should Create the Playbook: Founders or Revenue Leaders (01:03:24) The Biggest Signs When Someone Isn’t Scaling (01:04:31) Quick-Fire ----------------------------------------------- In Today’s Show with Matt Plank We Discuss: - Challenges and Strategies in Outbound Sales - Building Effective Sales and Marketing Partnerships - Segmenting and Planning for Sales Growth - Pricing Strategies and Customer Success - Discounting and Urgency in Sales - Building Relationships for Successful Deals - Effective Deal Reviews: Asking the Right Questions - Pipeline Reviews: Frequency and Participants - Handling Deal Slippage: Acceptable vs. Non-Acceptable Reasons - Maintaining Morale in Volatile Times - Outbound Sales Strategy: Lessons Learned - Scaling Sales Teams: Hiring and Promoting - Challenges and Strategies in International Markets - Founders and Sales Playbooks: Who Should Create Them? - Signs of Scaling Issues in Sales Leadership ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Matt Plank on Twitter: https://twitter.com/mdplank Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #mattplank #rippling #sales #venturecapital #salesperson #discounting #outbound #playbook