Episode Details

From raising $100M from SoftBank to shifting from “growth at all costs” to building a durable business, Kris shares the real story behind scaling Sendoso to over $100M in revenue.

In this episode of $100M Exits, Kris walks through what it was actually like pitching Masayoshi Son over Zoom, deploying nine figures into aggressive hiring, then quickly pivoting when the zero-interest-rate era ended. He breaks down the hard decisions around efficiency, acquisitions, AI-driven sales automation, international expansion, and why building a 100-person advisory network became his secret weapon.

This isn’t just a fundraising story. It’s a lesson in adapting fast, evolving as a leader, and making bold moves when the market shifts.

If you're building toward nine figures in revenue — or trying to survive the jump from hypergrowth to operational discipline — this episode is packed with real-world insight.

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Here's what you're in for:

00:00 Welcome and Kris from Sendoso

00:36 How SoftBank found Sendoso

02:07 The call with Masayoshi Son

04:46 What Kris did after the $100M landed

09:20 Using AI to scale sales without more headcount

12:11 Switching from hypergrowth to efficiency

16:32 Why Sendoso bought competitors

25:58 Making the merger work day one

27:18 The integration plan that kept it on track

28:03 Who they kept and who they didn’t

28:46 The tech migration and what took longer

29:47 M&A advice for founders

31:00 Talking to competitors before you need to

33:15 Why Kris chose a co-CEO setup

38:49 How Sendoso expanded internationally

44:17 How Kris changed as a leader

49:24 The advisor network that became a cheat code

51:42 Wrap up and how to connect

ABOUT KRIS RUDEEGRAAP

Kris Rudeegraap is the Co-Founder and CEO of Sendoso, an AI-powered sending platform helping B2B companies create meaningful engagement through personalized gifts, swag, and eGifts. He founded the company after recognizing a gap in how sales and marketing teams build real connections, drawing from over a decade in software sales.

Under his leadership, Sendoso has scaled globally with strong venture backing, driven by his belief that authentic, personalized experiences win in a digital-first world.

You can reach out to Kris through:

LinkedIn: https://www.linkedin.com/in/rudeegraap/ 

Website: https://www.sendoso.com/ 

Email: kris@sendoso.com

ABOUT JASON KIRBY

Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. 

He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business