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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 "imposter syndrome" is holding channel partners back from owning AI conversations, and why he believes the answer isn't to lead with the technology at all — it's to start with the client's actual pain points. He also walks through GoWest.ai's human-centric philosophy (AI augments people, it doesn't replace them), a real example of an AI inbox-triage agent built for a client, and why agentic search is starting to reshape SEO — including the story behind an $80 million inbound MSP lead that found Fox & Crow Group through an AI answer engine instead of Google.

In this episode:

• Why under 250 of 110,000 MSPs are publicly talking about AI (Fox & Crow Instinct data)
• The "imposter syndrome" keeping MSPs from claiming AI as part of their stack
• Why West starts every AI engagement with the client's workflow, not the technology
• A real-world AI agent example: inbox triage for executives buried in email
• How agentic search is changing SEO — and how it landed an $80M inbound lead

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.

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 MSPs are up against: the fear that using AI contradicts the personal-touch pitch they've built their businesses on, even though most customers just want their ticket solved quickly. He shares a story about spending twenty minutes on the phone with a hotel chatbot he thought was human, and explains why guardrails, not capability, are what separate a useful AI deployment from a viral horror story.

Carrie and Matt also cover sentiment analysis and CSAT, the difference between selling AI and selling automation, why private-equity-backed platforms are positioned to move first on pricing, and what Matt expects to happen when homegrown AI builds start hitting their maintenance ceiling around 2027.

They close with concrete advice on what MSPs should actually be publishing if they want to compete for the AI-advisory conversation instead of sitting it out.

Matt Tomlinson, Senior Director of MSP Partnerships, Fixify

Fixify is an AI solution built to resolve tier-one MSP tickets start to finish. Before joining Fixify, Matt spent years working inside the MSP world himself. Find him at IT Nation this year, or learn more at fixify.com, where an AI assistant named Fiona can answer questions about fit.

Chapters

0:00 – Welcome and Introductions

1:10 – Why MSPs Hesitate on AI

2:18 – Stigma and Guardrails

4:25 – Sentiment Analysis and CSAT Insights

6:41 – Adoption Barriers and the Content Gap

8:55 – AI vs. Automation: Two Different Sales Motions

11:18 – The Coming Messaging Shift

14:54 – Future Trends and Homegrown AI Risks

16:44 – Risk Mitigation and Token Costs

18:42 – Content Ideas for MSPs

21:15 – Where to Learn More

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.

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 an internal sale to his son and COO already in motion.

Topics covered:

• Why an MSP built on referrals can't actually be sold
• Why owners can't just teach their own sales playbook to a rep
• Why cold calling isn't dead for MSPs
• How Brightworks built and supported a top-performing sales rep
• Red flags for disqualifying the wrong-fit client
• Doug's exit plan, and what he's doing to prepare for it

Watch the video here.

Read the blog post 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.