WIN

About 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/

Publisher

Carrie Richardson Fox and Crow Group

Category

business · business · business

Language

en

Explicit

No

First episode

28 May 2022

Latest episode

28 Sept 2026

Latest episodes

99 episodes in the feed.

1. 

   28 Sept 2026

   WIN x West McDonald: Closing the AI Readiness Gap in the MSP Channel

   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 Carrie Richardson sits down with West McDonald — founder of GoWest.ai and BizVantage — to unpack why MSPs are so far behind on AI, even though customers are begging for help. West shares why AI hasn't followed the same fast-adoption path as cybersecurity did for MSPs, why "i...

2. 

   17 Sept 2026

   Matt Tomlinson: MSPs will WIN with AI

   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 this exact hesitation play out before with cloud, MDR, EDR, SIEM, and SOC. In this episode, he and Carrie dig into why AI adoption in the MSP channel is following the same slow-then-sudden pattern, and why the real barrier isn't the technology itself. Matt explains the stigma...

3. 

   11 Sept 2026

   Doug Miller at Brightworks Shares on How Sales Coaching Builds WINNING MSP sales teams.

   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 actually worked. In this episode, host Carrie Richardson talks with Doug about why a business built entirely on referrals can't be sold, why cold calling still works in the IT channel, and how stepping back from sales completely helped Brightworks post its best year ever, with...

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

4,537,166

Score snapshot 15 Sept 2025

Apple Podcasts (US)

5.0 / 5

2 ratings

Spotify

5.0 / 5

1 ratings

Podcast Authority Score: 72 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

94

Social presence

0

YouTube

93

Engagement

32

Contact WIN

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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