Episode 338: Rethinking Customer Engagement Through Gifting with Kris Rudeegraap

GUEST: Kris Rudeegraap, Co-founder and Co-CEO of Sendoso

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In this episode of The B2B Revenue Executive Experience, Kris Rudeegraap, Co-founder and Co-CEO of Sendoso, joins host Cory Cotten-Potter to discuss the transformative power of gifting and direct mail in sales, the evolving role of AI in customer engagement, and innovative strategies for optimizing go-to-market efforts.

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Strategic Shifts in Gifting

Strategic gifting has evolved from being a simple prospecting tool to becoming an integral part of the entire go-to-market cycle, touching every stage from marketing and sales to renewals and customer success. Initially aimed at sales leaders, it quickly became clear that marketing wanted to own it, driving broader adoption and diverse use cases, like boosting demo show rates, enhancing customer experiences, and improving event attendance.

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“We also have a smart send feature where you can plug in someone's email address or persona, and we'll suggest very hyper-personalized gifts.”

Kris Rudeegraap, Co-founder and Co-CEO of Sendoso

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Rethinking SaaS Pricing in the Age of AI

AI is reshaping SaaS pricing by driving efficiency and enabling fewer users to achieve greater productivity. Traditional per-seat pricing is being replaced with usage or transaction-based models like Salesforce charging per conversation or Intercom billing per ticker resolution. As AI continues to power automation and transform workflows, SaaS companies are rethinking pricing strategies to align with the value delivered, making it more dynamic and performance-focused.

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“AI is creating a lot more efficiencies and automations so that fewer people can drive way more productivity and way more output.”

Kris Rudeegraap, Co-founder and Co-CEO of Sendoso

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Mastering SaaS Pricing

Navigating SaaS pricing transitions, like moving from per-seat to transaction-based models, requires proactive planning and collaboration. Leaders should regularly engage in pricing and packaging discussions during executive offsites, gather frontline feedback, and consult customer advisory boards. It's essential to embrace short-term discomfort for long-term growth and stay ahead of competitors with creative pricing strategies.

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“I think it's critical to have ongoing quarterly pricing and packaging conversations.”

Kris Rudeegraap, Co-founder and Co-CEO of Sendoso

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How Strategic Planning Fuels Long-Term Success

Leaders often get caught up in short-term goals, but setting aside time for strategic planning can unlock creativity and long-term success. Identifying potential risks and building a "strategic reserve" of responses allows executives to balance immediate priorities with big-picture thinking. This helps sales and marketing teams stay aligned but also highlights the importance of roles like product marketing managers early on.

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“We just need marketing to be good. We need it to be aligned. We gotta talk.”

Kris Rudeegraap, Co-founder and Co-CEO of Sendoso

‍Now that you know how personalized gifting might skyrocket your sales numbers, discover the full list of episodes at The B2B Revenue Executive Experience. If you enjoy the show, instructions to rate and review it are found here.