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.

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 Winnipeg back in 1995, rode the shift from break-fix to recurring revenue, and decided at 40, sitting at his cabin, that he wanted out by 50. Eight years later he sold to the local telco he'd been quietly courting the whole time, for just over 8X.

David wrote the book Getting to Exit and built a nine-step framework for planning an MSP exit that's actually sellable, not just profitable. Carrie sits down with him to talk about what most MSP owners get wrong about exit planning, and what he'd tell his 40-year-old self.

Read more about David's approach to exit planning on the Fox & Crow blog here.

In this episode:

• Why David picked his buyer eight years before he sold to them
• The nine-step framework for an MSP exit, starting with "figuring out your why"
• Why a legacy exit (selling to family or employees) usually means a lower valuation and a longer wait to get your money
• The classic MSP hiring mistake David made: promoting his best salesperson to sales manager. He calls it a cardinal sin.
• Why five-plus years is the real minimum runway for exit planning, not two or three

Guest: David Reid, author of Getting to Exit.

Find the book and his exit-planning resources at gettingtoexit.com.

If you're an MSP owner thinking about your own exit, or you just want to hear a "Holy moly, that's a big gap I gotta fill" moment turn into an actual plan, subscribe.

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.