Peter Reinhardt - Learning How to Sell – [Founder’s Field Guide, EP. 34]

05.20.2021 - By Invest Like the Best with Patrick O'Shaughnessy

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My guest today is Peter Reinhardt, co-founder and CEO of Segment, the market-leading data customer data platform that was acquired by Twilio last year. In our conversation, we cover the fascinating journey of Segment from an education feedback tool to the business it is today, Peter’s sales philosophy on meeting the customer where they are and not where you think they should be, and why revenue operations, or RevOps, is underrated for any business. This was an incredibly honest conversation on company building that any builder can learn a lot from. Please enjoy my conversation with Peter Reinhardt.   For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to by Dell Technologies. Dell Technologies and Windows can help you upgrade your business tech with its Small Business Month specials. Save up to 45% on PCs with Windows 10 Pro— plus business docks, monitors & more. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at ----- This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to or use code "Patrick." ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit   Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:02:47] - [First question] - What Segment currently does for its customers [00:03:37] - How this industry looked before Segment came along [00:04:30] - Overview of a simple data flow and the utility of capturing user data [00:05:55] - Insights that lead to developing the structure for a central data pipeline [00:07:52] - Why other companies don’t just build their own data collection API [00:10:04] - Early days of building the company and finding success outside their initial idea [00:12:29] - Pivoting from classroom software to providing software the world needed [00:16:17] - What Technology Wants  [00:17:06] - Sign that validated becoming a B to B software company [00:19:49] - Challenging moments trying to scale Segment after bootstrapping the startup [00:24:58] - Getting customers to articulate your value proposition helps grow your sales [00:26:42] - Deciding what would be sold and what would remain open source [00:28:05] - Structuring and developing an enterprise sales team and sales model [00:30:23] - Overview of a 2 million dollar  per sales person contract and how it’s allocated [00:31:38] - How it feels to be participant in the SaaS industry [00:34:02] - Lessons learned about revenue operations and how underappreciated it is [00:36:39] - Backwards efficiency and companies who use products to bootstrap scale economics [00:38:51] - Focusing on customer acquisition cost to maximize scale efficiency [00:40:52] - Potential disruptors to economies of scale [00:42:21] - Lessons learned from achieving massive scale and being acquired by Twilio [00:45:40] - Behind the curtain view of current data use trends [00:48:49] - His perspectives on the data privacy landscape and their implications writ large [00:51:48] - Legitimate businesses that will be hurt by changes in data privacy standards [00:53:11] - How data privacy standards may affect everyday merchants [00:54:03] - The worst advice he’s heard given to new entrepreneurs [00:56:20] - Impactful advice received along the way when growing Segment [00:56:47] - What has him most excited about the future [00:57:13] - Lessons learned about leadership from Jeff Lawson and his own experience [00:58:51] - The hardest changes he’s had to make as a leader [01:00:20] - The kindest thing anyone has ever done for him  

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