Getting to your first wins feels like momentum. Scaling past $50M exposes everything that is not built to last.

On this episode of WinsDay, Jessie Lizak sits down with Kris Rudeegraap, Co-CEO and Co-Founder of Sendoso, and Mariam Slimane, CMO and Growth Marketing Advisor at CX Fractional Advisors, to break down what actually drives pipeline and revenue as companies grow.

Kris shares his journey from sales rep to building Sendoso into a category leader, offering a firsthand look at how sales strategy evolves as companies scale.

The conversation explores how AI-powered direct mail and gifting help sales teams cut through noise, create meaningful engagement, and move deals forward in competitive markets.

Mariam brings deep experience in scaling B2B SaaS companies from $50M to $100M+ ARR. She focuses on building AI-driven demand generation systems, aligning product-led growth with enterprise GTM strategy, and creating marketing engines that produce a predictable pipeline. She also addresses a common issue in growth teams, over-reliance on CRM data, which often leads to missed demand signals and weaker pipeline performance.

Together, the discussion explores:

1. AI-Powered Direct Mail for Sales Teams

2. Over-Reliance on CRM Data Hurts Pipeline Growth

3. From Sales Rep to $100M CEO

4. Why Growth Stalls After $50M

This episode focuses on what changes between early traction and scalable growth, from pipeline strategy and demand generation to marketing systems and execution discipline.

For founders, revenue leaders, and B2B operators, the conversation offers a clear look at what it takes to move beyond founder-led momentum and build systems that support long-term growth.