SaaStr 270: How To Scale Leader While Retaining Humanity and Personality, Why Starting At SMB Actually Makes Culture Easier & How To Make A Part-Remote Team Your New Superpower

Jeppe Rindom is the Founder & CEO @ Pleo, the simple spending solution for your company automating expense reports and simplifying company expenses. To date, Jeppe has raised over $78m in funding for Pleo from some European favourites of mine in the form of Creandum and Vaestfonden and then also their most recent round led by Stripes Group in NYC. As for Jeppe, prior to founding Pleo he was the CEO @ Nodes, a design and development house that worked with brands including Loreal, BMW and Lego. Before that, Jeppe was the CFO @ Tradeshift where he first hand saw their scaling to 190 countries with offices in 6 different locations. 

In Today’s Episode We Discuss:

• How did Jeppe make his way into the world of startups and SaaS with his becoming CFO @ Tradeshift? What were his biggest learnings from Tradeshift and how did that impact his operating mentality? What was that a-ha moment for him with Pleo?
• Why did Jeppe decide to focus on SMBs from Day 1? How does the product build in the early days differ when building for SMB vs enterprise? Why does Jeppe believe that building for SMB makes it easier to build a great culture internally? How does Jeppe think about when is the right time to move into enterprise? What changes?
• How does Jeppe respond to 3 common concerns VCs have with SMBs:

1. The price points are so low that it takes huge volume to scale to meaningful revenue?
2. The mortality rate of SMBs is so high that you are going to always have high churn due to the customer segment?
3. Serving SMBs in the way that Pleo does is an intensely competitive space, is this a winner-take-all market? How does Jeppe think about competition? 

• How does Jeppe think about NPS today? How does Jeppe approach the problem of agency when the buyer is not the user? How does Jeppe think about being customer informed but not customer-driven?
• Pleo has a part-remote work structure, why does Jeppe advocate for this structure in the face of many saying it either has to be remote or not? What has Pleo done to make it work? What tool stack do they have to ensure seamless communication between remote and non-remote? Where are the challenges? What must one always do?
• How does leadership change for Jesse in the face of scale? How does Jesse think about scaling humanity and the personal touch with the scaling of his leadership? What are the challenges? When do they start to arise? How has raising in the US compared to raising in Europe? What are the core differences? 

Jeppe’s 60 Second SaaStr:

1. What does Jeppe know now that he wishes he had known at the beginning?
2. How did raising from the US differ from raising with European investors?
3. What would Jeppe most like to change about the world of SaaS today?

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Jason Lemkin

Harry Stebbings

SaaStr

Jeppe Rindom