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: [email protected]

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 development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+

You can reach out to Jason through:

Email: [email protected]

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

ABOUT $100M EXITS

My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. 

For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. 

Be sure to subscribe and let me know who you want me to interview next.