Sales Success Playbook: Ethical Gifting, Better Messaging, and Higher Win Rates with Sendoso's Kris Rudeegraap
Sendoso co-CEO Kris Rudeegraap joins Two Tall Guys Talking Sales to discuss how hyper-personalized gifting can break through digital noise and improve sales outcomes. He explains that the tactic works best when gifts are relevant and relationship-focused rather than transactional, and shares how AI is now powering smarter gifting decisions. Data from Sendoso shows gifting can increase win rates up to 9x and meeting booking likelihood up to 4x.
Summary
In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessy interview Kris Rudeegraap, co-CEO of Sendoso, a gifting and direct mail platform. The conversation centers on how strategic, personalized gifting can help salespeople cut through digital clutter and build meaningful relationships with decision-makers.
Rudeegraap opens by framing gifting as an additional outreach channel that complements traditional sequences of calls, emails, and LinkedIn messages. He emphasizes that the problem is rarely when to send a gift, but rather how it's done. Gifts paired with creative, personalized messaging aligned to the recipient's interests or the sender's value proposition tend to perform well, while generic gifts accompanied by aggressive asks can backfire and harm the relationship.
He shares two standout success stories: sending Kansas City baby back ribs to a VP who had broken their ribs skiing — a moment of levity that turned the prospect into a lifelong champion — and sending coloring books to a work-from-home prospect with kids, which demonstrated genuine awareness of the recipient's personal situation. On the failure side, he warned against sending gifts without research, such as sending alcohol to a non-drinker, and against coupling gifts with overly aggressive asks like demanding a meeting immediately in return.
The discussion also addresses cost concerns for salespeople who lack corporate gifting budgets. Rudeegraap argues that the ROI math often justifies personal spending, and that gifting doesn't have to be expensive. He cited an example of an empty pizza box sent with a note about being 'hungry for a new solution' costing only six dollars, which proved highly effective. He suggested that sellers who demonstrate success with manual gifting can then build an internal case for adopting a platform like Sendoso.
On the topic of AI, Rudeegraap explained that Sendoso began investing in what was then called data science and machine learning five to six years ago, and has accelerated AI feature development in recent years. The platform now uses AI to recommend what to send, who to send it to, what message to include, whether to use a home or office address, and when to send based on signals from CRMs, job changes, and company news — tasks that previously took sellers 20-30 minutes to complete manually.
The episode closes with Rudeegraap citing platform data showing that gifting in the sales cycle can increase win rates up to 9x and improve meeting booking likelihood up to 4x, with detailed case studies available on the Sendoso website.
Key Insights
- Rudeegraap argues that the problem with gifting is never the timing but always the execution — gifts fail when they lack personalization or are paired with aggressive transactional asks, not because gifting itself is inappropriate.
- Rudeegraap claims that Sendoso's data shows gifting can increase win rates up to 9x and make a prospect up to 4x more likely to book a meeting, positioning it as one of the highest-leverage tools in a sales cycle.
- Rudeegraap contends that gifting does not need to be expensive to be effective, citing a six-dollar empty pizza box with a pun-based note as an example that generated real pipeline, arguing that creativity outweighs cost.
- Rudeegraap states that Sendoso began investing in AI under the label of 'data science and machine learning' five to six years ago, and now uses it to automate decisions around what to send, when, to whom, and at which address — collapsing a 20-30 minute manual research task into seconds.
- Rudeegraap argues that gifting is most powerful when it demonstrates genuine knowledge of the recipient's personal life or circumstances — such as referencing a podcast mention of a sailing trip or knowing a prospect has young children — because it signals that the sender is paying attention beyond the transaction.
Topics
Full transcript available for MurmurCast members
Sign Up to Access