What happens when your biggest sales advantage suddenly disappears overnight?

In this episode I sit down with Kris Rudeegraap, Co-CEO and Co-Founder of Sendoso. In this first of two parts, we rewind to the scrappy early days of his business when Kris was manually packing boxes at night just to stand out in sales. Kris shares how a personal frustration inside his own sales role sparked the idea for the platform that would later raise over $150 million in funding. We talk about pre-selling before the product is ready, building momentum through outbound, and why he refuses to wait for perfection before talking to customers.

Kris breaks down the critical decisions that transformed early traction into scalable growth. He explains why hiring external salespeople early is essential to proving true product-market fit, how strategic tech partnerships accelerate momentum, and what it actually feels like to jump from $1M to nearly $5M in a year. We explore the realities of raising multiple funding rounds, building repeatable systems, and surrounding yourself with advisors who have seen the movie before. This all sets up part 2, where we'll take a close look at the advantages of using physical gifting to grow B2B relationships.

Topics covered during this episode include:

• How a growth-hacker mindset shaped Kris' earliest sales experiments.
• The homemade mail merge system that gave him a competitive edge.
• What happened when new email automation tools eliminated that early advantage.
• How testing handwritten notes and surprise gifts opened unexpected sales conversations.
• Why pre-selling the unfinished product accelerated Kris' early market validation efforts.
• How disciplined outbound prospecting built the company's first meaningful pipeline.
• The surprisingly high response rates from personalized cold outreach campaigns.
• Why hiring SDRs and AEs early proved true scalable product-market fit.
• The danger of mistaking founder-driven passion for repeatable revenue traction.
• How strategic tech integrations can unlock exponential co-marketing and partnership growth.
• The deliberate investment Sendoso made in content and data to strengthen category authority.
• The importance of building a customer community filled with influential power users.
• How successive funding rounds accelerated hiring and infrastructure expansion.
• What consistent traction and repeatable systems signal to serious institutional investors.
• The mindset shift required to scale beyond pure founder-led hustle.

Listen in to uncover the early decisions that shaped a nine-figure growth journey.

Kris Rudeegraap on LinkedIn: https://www.linkedin.com/in/rudeegraap