business
Hosted by Carrie Richardson · business · EN-US
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/
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Contact path
Public web form
Booking probability
32%
Guest openness
Selective
Sign up to generate a grounded pitch for WIN.
Signup to Generate a PitchI'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.
WIN is hosted by Carrie Richardson. The show has published 97 episodes to date.
Recent episodes include "WIN x West McDonald: Closing the AI Readiness Gap in the MSP Channel" (28 September 2026, 22 minutes), "Matt Tomlinson: MSPs will WIN with AI" (17 September 2026, 24 minutes), and "Doug Miller at Brightworks Shares on How Sales Coaching Builds WINNING MSP sales teams." (11 September 2026, 34 minutes).
WIN publishes roughly weekly, with episodes averaging 20 minutes across 97 episodes.
Booking probability for WIN is 32%, and the host is rated Selective on guests. WIN requires a Pod Score of 80 or higher. WIN's contact route on record: public web form.
The strongest fits for WIN are IT Services & Software Development. WIN has a business audience.
Carrie Richardson hosts WIN, a business podcast with 97 episodes published.
Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.
WIN
Send us Fan Mail Fewer than 250 companies out of 110,000 technology service providers in the Fox & Crow Instinct database show up talking about AI workflows, AI policies, or monetizing AI. On this episode of WIN, host...
WIN
Send us Fan Mail Read the accompanying article on the Fox & Crow group blog here. Matt Tomlinson has spent years on both sides of the MSP world, first inside it, now helping MSPs deploy AI at Fixify , and he's watched...
WIN
Send us Fan Mail Doug Miller of Brightworks spent 15 years trying to fix his MSP's sales problem. Cold email blasts, LinkedIn programs, hired reps who couldn't prospect - everything, really. Then he found a process that...
WIN
Send us Fan Mail How David Reid Sold His MSP for 8X (and Got a Decade of His Life Back) David Reid sold his business before he turned 50. That wasn't luck. It was the plan. He built Epic Information Solutions in...
WIN
Send us Fan Mail Matt Koenig Shares Winning MSP Event Strategies for New IT Channel Vendors Trade shows eat a huge chunk of a new vendor's marketing budget, and most of them get it wrong in the same handful of ways...
WIN
Send us Fan Mail 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...
WIN
Send us Fan Mail In this episode of the WIN Podcast, host Carrie Richardson sits down with Jennifer Roy to unpack how vendors can successfully connect with enterprise-grade managed service providers. Roy shares insights...
WIN
Send us Fan Mail If you're heading to Pax8 Beyond —or any major MSP channel event—this episode is your tactical prep guide. Channel legend Len DiCostanzo joins host Carrie Richardson to share strategic insights from his...
WIN
Send us Fan Mail Rex Frank on the Process-Powered MSP: Why Heroics Aren’t a Strategy In this episode, Carrie Richardson sits down with Rex Frank, VP of PAX8 Academy, to unpack the real reasons most MSPs stall out. From...
WIN
Send us Fan Mail Join channel veteran Nick Wolf as he shares MSP event engagement strategies with Carrie Richardson from Fox & Crow Group. Learn how Nick's career progressed from sales intern at Datto (Nick was employee...
WIN
Send us Fan Mail Winning Through Strategic Partnerships with Eric Roach of Dropsuite In this episode of the WIN Podcast, host Carrie Richardson sits down with Eric Roach, SVP of Global Sales and Marketing at Dropsuite...
WIN
Send us Fan Mail 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...
WIN
Send us Fan Mail Winning MSP Event Planning with Alec Stanners In this episode, we dive deep into what it really takes to plan MSP events that create community, drive real ROI, and elevate vendor relationships beyond...
WIN
Send us Fan Mail From Booths to Buy-In: Aaron Peterik’s Playbook for Winning Pax8 Beyond Episode Description: What separates a vendor with a busy booth from one that builds a sales pipeline? Aaron Peterik, Director of...
WIN
Send us Fan Mail 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...
WIN
Send us Fan Mail In this episode of The WIN Podcast , host Carrie Richardson interviews Craig Fulton , M&A Advisor at Evergreen Services Group, about how to maximize your experience at industry events like PAX8 Beyond...
WIN
Send us Fan Mail In this episode of WIN , host Carrie Richardson chats with Allan Jocson, CEO of Agilitec and member of the PAX8 Partner Advisory Council. Allan shares his playbook for getting the most out of major MSP...
WIN
Send us Fan Mail Trade shows are back in a big way, and Pax 8 Beyond 2025 is one of the most important events on the MSP calendar. In this episode of the WIN Podcast, host Carrie Richardson talks with Andrew Mora from...
Send us Fan Mail From “Who’s Who” to “Who’s He?” – Reinventing Yourself After Leaving Your Business After 40 years in high-tech leadership, Mark Chamberlin found himself at an unexpected crossroads—let go at 61.5 and...
WIN
Send us Fan Mail Are you leaving money on the table when offboarding MSP clients? Matt Yesbeck and his son Gage saw a massive gap in the MSP industry —no structured way to transition low-value or misfit clients without...
Recent guests on WIN. Study who booked and why before you pitch.
pioneer, pastor, educator, author, Richardson and Richardson Consulting
visionary entrepreneur, former journalist, author of Epic Journey, BrEpic Communications, LLC
political science professor at Rhodes College, The Instructional Leadership Collective
CEO, Beltway Air Conditioning
PitchCentric classifies WIN under these industries. Guests from them are the closest fit, and each links to the best podcasts in that industry.
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