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We explore how intelligent gifting breaks through AI-filtered inboxes, using psychology, data, and timing to earn real conversations and long-term loyalty. Kris Rudeegraap of Sendoso shares playbooks for stage-based sends, retention strategies, and staying human in an agentic future. • reciprocity, curiosity and tangible novelty driving attention • AI-assisted personalization for interests, timing and delivery channel • stage-based guardrails that unlock premium sends mid-funnel • timely low-cost sends outperforming expensive but irrelevant gifts • CAC, velocity and opportunity cost framing for ROI • shifting marketing metrics toward revenue and NRR • proving value when users never log into your app • human-in-the-loop (HITL) creativity to avoid AI cringe • retention and expansion use cases for customer success A box at your door still beats the smartest subject line, sparks genuine conversations, and accelerates pipeline without feeling transactional. Kris blends a decade of logistics, a modern data engine, and a human-first ethos to explain why clever, timely sends often outperform expensive swag—and how to scale that tastefulness with AI. We dig into the psychology behind physical sending—reciprocity, curiosity, and the emotional lift of a tangible, personalized moment—and translate it into practical plays for sales, marketing, and customer success. You’ll hear how stage-based guardrails in your CRM can unlock premium sends mid-funnel, why delivery confidence (home versus office) matters post‑COVID, and how small, useful gestures—like a rideshare credit on conference day—drive replies that mass email can’t. Kris also shares how Sendoso is evolving from pure logistics to a data-rich recommendation layer that helps teams decide what to send, when to send, and where to deliver. We also explore the agentic future: AI agents summarizing inboxes, go‑to‑market engineers orchestrating workflows, and the reality that a human still signs the contract. Kris offers a candid view on pricing models, proving ROI when users never log into your app, and why NRR and expansion deserve a bigger share of marketing’s attention. If you’re ready to replace noise with nuance—earning meetings faster and strengthening renewals through meaningful touchpoints—this conversation gives you the framework and the guardrails to do it right. Prefer to watch/listen on Spotify?: https://open.spotify.com/show/0t4lQBu... Email us with any feedback for the show: sparkofages.podcast@position2.com Find more great content like this at: https://www.position2.com/ If you like what you here, please drop us a comment! SUBSCRIBE TO @Position2Inc FOR MORE EPISODES! Rajiv Parikh: / rajivparikh Kris Rudeegraap: / rudeegraap Kris Rudeegraap, the Co-Founder and Co-CEO of Sendoso, the leading Direct Mail and Gifting Platform which has seen over $250M+ spent on the platform globally. A self-described "Sales CEO" who is redefining how B2B companies cut through the digital noise to build authentic relationships, Before founding Sendoso, he was a top-performing Account Executive at Talkdesk and a founding team member at Piqora. Kris is a California native, an alumnus of California State University, Chico and currently resides in the San Francisco Bay Area. #gifting #entrepreneur #pipeline #innovation #growth #sales #technology #innovator #product #revenue #revenuegrowth #management #founder #entrepreneurship #growthhacking #salestechniques #salestips #enterprise #business #company #smartgrowth #efficiency #process #processimprovement #value #valuecreation #podcast