WIN at Scaling Your MSP with Matthew Pincus and Helpt

Send us Fan MailWhy 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 matterAbout 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🎧 Enjoying the show? Subscribe, rate, and leave a review! Your support helps us keep bringing you expert insights. Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses.Learn more at:Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel VendorsFox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses Book time with Carrie here!Be a guest on WIN!  We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.