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

Most companies treat events as a logo parade or a chance to walk the floor, relying on hope, dreams, and prayers to scan badges and make money later. Mason Cosby argues that if your event is not ROI positive before your plane takes off, you are doing events wrong. Events should be viewed as a relationship accelerator for existing connections rather than a place to blindly hope for new ones.

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Mason breaks down a tactical plan to ensure every event generates a return. He outlines four core sections: pre-event preparation, event execution, follow-up, and speaking sessions. He explains how to identify exactly who is attending, how to book meetings before you arrive, and why you must leave the event with next steps already scheduled.

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What We Cover

1. The four core sections of an event strategy: A breakdown of pre-event, during the event, follow-up, and speaking sessions.
2. Identifying attendees early: Using past event lists, event apps, social media hashtags, and location filters on LinkedIn to find people before the conference starts.
3. Strategic meeting scheduling: How to book meetings around relevant agenda sessions and find people actively seeking solutions to specific problems.
4. The BAMFAM rule: Why you must "Book A Meeting From A Meeting" to ensure sales cycles continue moving after the event ends.
5. Leveraging speaking sessions: Creating a specific content offer for the room and using the session to segment the audience into hand-raisers and future prospects.
6. The "Free Consultant" approach: How Mason uses speaking opportunities to offer help without selling, while directing immediate buyers to the sales team.
7. Hosting private side events: Using dinners or cocktail hours to target top accounts and ensure the trip is ROI positive through a few key opportunities.

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Resources Mentioned

1. Scrappy ABM Newsletter: Get actionable tactical playbooks delivered to your inbox.
2. Scrappy ABM: Visit for more ABM tips and strategies.
3. Connect with Mason on LinkedIn: Start a conversation about ABM.

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If you enjoyed today's episode and found valuable insights for your business, be sure to subscribe to the Scrappy ABM podcast for more expert discussions. Don't forget to leave a review and share this episode with your team or fellow marketers!

Mason Cosby sits down with Gillian Hinkle to discuss the complexities of marketing within a portfolio company. When an organization moves from a single product to a suite of services, marketers often struggle to build intentional sequencing. Gillian shares her approach to identifying customer behaviors and mapping the overlap between different buying committees.

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She explains why you cannot go it alone: you must work with other teams to find commonalities in lead information and problem sets. A critical part of her strategy is to market to the internal sales team first. If sellers do not understand the deal cycle or how a new product addresses a specific pain point, they will not present it to their customers.

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Gillian also details how to protect the customer relationship by validating data with product managers before launching a campaign. She emphasizes the importance of "small measures"—tracking observable behaviors and engagement rates in internal channels like Slack—to understand program success before revenue numbers come in.

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Guest Bio

Gillian Hinkle is a seasoned marketing leader currently serving as the Senior Director of Product Marketing at Salesforce, with a focus on Heroku, a cloud platform as a service (PaaS). Her career trajectory transitions from an initial background in arts administration and education to technical B2B marketing leadership in the SaaS and cloud infrastructure sectors. Before joining Salesforce, Hinkle served as Director of Growth Marketing at Earnix.

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What We Cover

1. Using behavioral data to identify which customers are ready for expansion products.
2. How to map the overlap between different buying groups—like marketing buyers versus data buyers—in a portfolio company.
3. Why you must understand sales compensation before asking account managers to sell a new product.
4. The strategy of "marketing to sellers" first: using enablement sessions to test if an offer is right for the current market.
5. Protecting customer relationships by excluding unqualified accounts and validating pain points with product teams.
6. Using Slack channels and lists to manage program execution and track internal engagement.
7. The importance of reporting "small measures" and observable behaviors when revenue data is not yet available.

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Resources

1. Heroku: A cloud platform as a service (PaaS) supporting several programming languages.
2. Slack: The primary communication tool Gillian uses for program management.