WIN

Carrie Richardson Fox and Crow Group
  • 5.0 (2)
  • Entrepreneurship
  • Updated Weekly

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/

  1. 1d ago

    Matt Koenig shares winning MSP event strategies for new IT channel vendors

    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. This episode kicks off WIN's Fall 2026 relaunch with Matt Koenig, the channel sales veteran who built a 45-person team at RapidFire Tools, spent years as VP of Sales at Nodeware, and just launched his own practice, White Tiger Consulting. Matt and Carrie get into what a brand-new IT channel vendor actually needs before committing sponsorship dollars: which shows are for branding versus lead generation, what belongs on a banner nobody's going to read anyway, how to build a $50,000 first-year event budget, why swag is either worth doing well or not worth doing, and how to avoid showing up with your booth stuck in customs. Read more on the Fox & Crow Group website here. In this episode: CHAPTERS 00:00:00 Welcome Back to WIN 00:00:43 Catching Up Before ChannelCon 00:00:59 Launching White Tiger Consulting 00:03:01 What Vendors Can Expect From White Tiger 00:05:15 Where New Vendors Should Start 00:06:32 Event Logistics and Shipping Timelines 00:10:00 Getting Ready to Commit Sponsorship Dollars 00:12:32 Bare-Bones Budget: Booth Basics and Banners 00:14:26 Crafting Your Talk Track and Slides 00:15:21 Stage Presence and Public Speaking Lessons 00:17:02 Building a Marketing Budget and Picking Shows 00:18:20 Working the Show Floor Between Booth Time 00:20:23 Off-Site Dinners and Vendor Politics 00:20:55 Swag Strategy That Actually Works 00:23:50 Attracting Booth Traffic Without Swag 00:24:43 Wrapping Up and Where to Find White Tiger Matt is offering a free 30-minute consultation to vendors and MSPs, no strings attached. Learn more at White Tiger Consulting. 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   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.

  2. 06/08/2025

    Why SASE is a WINNING part of the Modern MSP Security Stack

    Send us Fan Mail 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   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.

  3. 05/30/2025

    How Do I WIN the Attention of Larger MSPs? Jennifer Roy, CEO of Nucleus Networks, Gives You The Cheat Codes

    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 from her leadership at Nucleus Networks, a multi-location MSP within the Lyra Technology Group family, and breaks down how her team prepares for events like Pax8 Beyond. Roy discusses what catches her attention at vendor booths, how her team prioritizes discovery calls, and why follow-up matters more than flash. She emphasizes the importance of being informed, respectful of time zones, and strategically aligned with an MSP’s operational goals.  Vendors who come prepared—and stay professional—are the ones who make it onto her calendar. If you're an IT channel vendor trying to land a meaningful partnership with a large MSP, or a new MSP owner wondering how operationally mature MSP owners prioritize their time at industry conferences, this episode is packed with unfiltered guidance from someone who receives hundreds of outreach attempts per quarter—and still takes the time to coach the channel on how to do it better. Read the article inspired by the podcast on the Fox & Crow Group blog here. 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   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.

  4. 05/28/2025

    Len DiCostanzo Has Been Building Winning MSP Event Strategies for Over 40 Years. Tune In!

    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 40+ years in the IT channel, including leadership roles at Autotask, Kaseya, and Datto. Now leading the coaching and consulting practice at MSP Toolkit, Len helps vendors and MSPs alike improve their partner programs and sales performance—and in this conversation, he breaks down what it really takes to make an event worth the investment. You’ll learn: The top mistakes vendors make when exhibiting at trade showsWhat to do instead of hiding behind your booth tableHow to evaluate your event ROI—and what metrics actually matterWhy relationships, not branding, drive long-term valueTips for making every handshake, hallway chat, and happy hour countWhether you're a first-time sponsor or a seasoned exhibitor, this episode delivers real-world advice to help you turn event spend into sales results. Find Fox & Crow Group at booth 929 at Pax 8 Beyond.   Read the blog post inspired by the interview here. 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   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.

  5. 05/20/2025

    Rex Frank - Winning MSPs Follow A Process

    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 the dangers of hero culture to the strategic misuse of vCIOs, Rex shares decades of insight on what separates mature MSPs from the rest. He doesn’t pull punches—and he doesn’t believe talent alone is enough. If you're tired of duct-taping your business together with hustle, this conversation is your roadmap to building a resilient, scalable MSP. Topics Covered: Why “doing it all yourself” is holding your MSP backHow to reposition the vCIO role for long-term client impactThe one thing your org chart says about your growth ceilingWhy PAX8 Academy is reengineering the MSP maturity modelFind Rex Frank onsite at Pax8 Beyond!  Read the article inspired by this interview on the Fox and Crow Group blog. 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   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.

  6. 05/14/2025

    Nick Wolf Shares MSP Event Engagement Strategies

    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 17 at Datto...) through to his current role with Cork.   Nick shares his pre-event process, his on-site tips and his follow-up expertise. At 32, Nick is already a channel veteran, having spent ten years with Datto, then another 2 years with Scout Security prior to their exit.  Now Nick is bringing his expertise to a whole new category of MSP solutions: cyber-warranty. Don't miss this one! 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   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.

  7. 05/14/2025

    Eric Roach and Dropsuite - Winning Through Strategic Partnerships

    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, to explore how strategic partnerships can supercharge growth. With PAX8 Beyond on the horizon, Eric shares how Dropsuite leverages major events not just for exposure—but for creating deep, scalable engagement with MSP partners. You’ll learn how Dropsuite transforms post-event reflections into proactive planning, how they equip their teams for meaningful conversations on the show floor, and why true alignment with vendor partners starts long before the booth setup. Whether you’re prepping for your next event or evaluating your vendor ecosystem, this conversation will help you make your next move intentionally—and strategically. Learn more about strategic vendor partnerships in this Fox & Crow Group article. 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   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.

  8. 05/10/2025

    Will Ominky and Nerdio's Winning Approach to MSP Events Like Pax 8 Beyond

    Send us Fan Mail 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   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.

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Ratings & Reviews

5
out of 5
2 Ratings

About

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/

Information

  • Creator
    Carrie Richardson Fox and Crow Group
  • Years Active
    2022 - 2026
  • Episodes
    93
  • Rating
    Clean
  • Copyright
    © 2026 Fox and Crow Group
  • Show Website
    WIN