The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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
Fri, 20 Dec 2024
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
Full Episode
Founders definitely should not create the playbook, but I think founders wait too long to hire a go-to-market. And I think they do that because they feel like they can't hire a good salesperson potentially without a bunch of traction. The big mistake that people make as they transition to the next phase is people don't increase price into a point where they find friction.
This is 20 Sales with me, Harry Stebbings. Now, 20 Sales is the monthly show where we sit down with the best sales leaders in the world to discuss how they built a sales machine. And today, we're joined by one of the best, Rippling's CRO, Matt Plank. Matt joined Parker Conrad, Rippling's founder, when Rippling was just a V1 idea in a basement and had zero dollars in revenue.
Today, the company has hundreds of millions of dollars in ARR and is a market leader. Prior to Rippling, Matt was a sales director at Zenefits, where he helped scale the company to $70 million in ARR. But before we dive into the show today, one of the easiest investment decisions I have made over the last three years is investing in 11X.
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I've heard so many good things, both from Ashley and from Parker. So thank you so much for joining me today, man.
Yeah, absolutely. Thanks for having me. Likewise, I've heard a lot of great things and watched a lot of great episodes on the podcast. So excited to join you.
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