WIN
I'm Carrie Richardson, and this is WIN: a podcast for MSP owners and IT channel sales leaders who are done guessing at sales and marketing and ready to get good at it on purpose.
My co-host Ian Richardson and I have both sat on both sides of the table. Ian built and exited an MSP and I've spent 15 years building pipeline for MSPs and channel vendors.
Between us, we've made the calls, missed the quotas, and closed the deals that actually moved revenue.
Every episode we sit down with an MSP owner, a sales leader, or a vendor exec and ask:
How are you winning?
No theory.
No recycled advice you've already read on LinkedIn.
Just the actual plays IT channel leaders are running right now to land new logos, protect MRR, and build something worth selling one day.
New episodes weekly. Learn more about Fox & Crow Group at https://foxcrowgroup.com/
WIN
WIN at Scaling Your MSP with Matthew Pincus and Helpt
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
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
🎧 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 Vendors
Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses
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.
