Triangulating Closed-Lost Opportunities

Sendoso has solidified its position as a leader in the direct mail space by acquiring competitors like Alyce and Postal. But acquiring a company is only the first step. The real challenge is retaining those customers and expanding the relationship. Host Mason Cosby sits down with Kris Rudeegraap, Co-CEO of Sendoso, to discuss the specific playbook they used to merge three platforms into one without alienating their user base.

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Kris Rudeegraap details a strategy built on patience and data. Instead of forcing an immediate migration, Sendoso unified its data sources and focused on education. Kris explains why they waited up to two years to sunset the Alyce platform and how offering "warm welcomes" mattered more than immediate upsells. They also discuss a specific certification program that led to a significant jump in customer spend. This conversation breaks down how to manage consolidation while keeping both customers and employees happy.

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Guest Bio

Kris Rudeegraap is the Co-Founder and Co-CEO of Sendoso, a leading Sending Platform designed to help revenue teams engage customers through direct mail and gifting. An alumnus of California State University, Chico, Kris spent over a decade in sales roles at companies like Talkdesk and Yapstone before founding Sendoso in 2016. His philosophy centers on the "pattern interrupt"—using physical items to break through digital noise. Under his leadership, Sendoso has raised significant capital and executed major strategic acquisitions, including Alyce and Postal.io, to consolidate the corporate gifting market.

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What We Cover

1. The First Step in Acquisition: Why unifying data sources and establishing a single CRM source of truth must happen before any sales outreach.
2. Relationship First, Sales Second: How Sendoso used office hours, LinkedIn messages, and VIP warehouse tours to welcome new customers before discussing contracts.
3. The Power of Certification: Kris Rudeegraap shares data showing that certified customers increased their spend on the platform by over 70%.
4. Patient Migration Timelines: The strategic decision to keep the Alyce platform running for two years to allow customers to self-select when to switch.
5. Leveraging Job Changes: How the team tracks users across Sendoso, Alyce, and Postal who move to new companies to drive new business.
6. Win-Back Opportunities: Using combined data from closed-lost deals across multiple companies to triangulate why a deal was lost and how to win it back.
7. Measuring Success: Why metrics like EBITDA, margin improvement, and employee Net Promoter Score (eNPS) are just as critical as revenue retention.

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Resources

1. Sendoso - The leading Sending Platform for revenue teams.
2. Email Kris Rudeegraap - Connect directly with Kris.
3. Scrappy ABM: Visit for more ABM tips and strategies.
4. Connect with Mason on LinkedIn for a conversation about ABM.

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