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Why is Winning at Scale So Difficult?

Scaling a business comes with big challenges—hiring, retention, marketing, and making smart decisions that drive growth.

In this episode of WIN, host Carrie Richardson sits down with Matthew Pincus, Founder & CEO of HELPT, to discuss the lessons learned from scaling a company, navigating the trade show circuit, and balancing speed with strategy.

They dive into the realities of outsourcing, the importance of building trust, and why the right approach to hiring can make or break a business.

What You’ll Learn in This Episode:

✔️ The biggest challenges businesses face when scaling
✔️ How to hire and retain top talent without burnout
✔️ Outsourcing vs. in-house: When to delegate for growth
✔️ Trade show strategies—getting ROI without breaking the bank
✔️ The role of AI in customer support and business operations
✔️ Why brand reputation and community engagement matter

About Our Guest:

Matthew Pincus is the Founder & CEO of HELPT, an outsourced tech support company that helps businesses streamline customer service while maintaining quality and efficiency. With a background in operations, marketing, and sales, Matthew shares his insights on smart business growth and how to navigate the challenges of scaling.

Resources & Links:
🔗 Connect with Matthew Pincus & HELPT – GETHELPT.com
🔗 Follow Carrie Richardson & Fox and Crow – FoxCrowGroup.com

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Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

Serial entrepreneurs, life partners and business partners, they have successfully exited from multiple businesses (IT, call center, real estate, marketing) and they help other business owners create their own versions of success.

Ian is certified in Eagle Center For Leadership Making A Difference, Paterson StratOp, and LifePlan.

Carrie has helped create and execute successful outbound sales strategies for over 1200 technology-focused businesses including MSPs, manufacturers, distributors and SaaS firms.

Learn more at www.foxcrowgroup.com

Book time with Carrie here!

Be a guest on WIN! We host successful entrepreneurs who share advice with other entrepreneurs on how to build, grow or sell a business using examples from their own experience.