I’m in San Diego the week of September 21, and I’m hosting three informal meetups for MSP owners, sales leaders, marketers, and anyone who wants an honest conversation about MSP growth. There is no agenda, slide deck, badge scan, or sales presentation.
This Jackdaw edition of the invitation has a sharper question: how much do you really know about the MSPs you compete against? Not what you have heard in passing. Not what one salesperson remembers. What can you actually see, compare, and use when you make a marketing decision?
Three MSP Sales and Marketing Meetups in San Diego
Pick the setting that works for you, or come to all three. Food, drinks, coffee, and cigars are cash and carry. The conversation is free.
MONDAY, SEPTEMBER 21
Happy Hour at Pacific Beach Hideaway
Time: 3:00–6:00 p.m.
Location: 4474 Mission Blvd, San Diego, CA 92109
Bring the competitor claim you keep hearing in sales calls, the referral channel that has slowed down, or the pipeline question your current reporting cannot answer.
Get directions to Pacific Beach HideawayTUESDAY, SEPTEMBER 22
Coffee at Lofty Coffee Co.
Time: 7:00–10:00 a.m.
Location: 444 W Cedar St, San Diego, CA 92101
Bring the MSP marketing decision you are trying to make: which market to pursue, which message to lead with, or why a competitor appears more visible to local buyers.
Get directions to Lofty Coffee Co.WEDNESDAY, SEPTEMBER 23
Cigars at Churchill Cigar Lounge
Time: 2:00–6:00 p.m.
Location: 2415 San Diego Ave, Suite 102, San Diego, CA 92110
Bring the longer strategic question: where your MSP is actually differentiated, whether your pricing position is defensible, or what buyers can verify before they ever contact you.
Get directions to Churchill Cigar LoungeCompetitive Intelligence Questions Worth Bringing
Competitive intelligence is not gossip and it is not a list of company names. It is structured evidence that helps an MSP understand the market buyers can see. If you are not sure where to begin, bring one of these questions:
- Which competitors are most visible in the geographic markets we want to win?
- Do buyers see a meaningful difference between our MSP and the alternatives?
- Which industries, services, and promises are competitors emphasizing?
- Where are competitors demonstrating trust with reviews, proof, and clear positioning?
- Are we competing against firms of a similar size, maturity, and market reach?
- What are we claiming that every other MSP in the market also claims?
- Which marketing gaps deserve action, and which are simply noise?
How 24 Real San Diego MSPs Compare
The comparison below is not sample data. It is an actual, anonymized representation of 24 MSPs serving the San Diego market, organized side by side so differences and recurring patterns are visible. Each row represents one real provider. The numbered, color-coded cells show how those providers compare across the same set of competitive market signals.
The analysis was produced using Fox & Crow Instinct, the same technology Jackdaw uses to build MSP competitive intelligence reports in minutes. The point is not to crown one MSP the winner from a single score. It is to replace assumptions with a consistent market view and identify the questions an MSP should investigate before changing its positioning, message, or marketing priorities.
What a Jackdaw Report Adds to the Conversation
A Jackdaw Report organizes public competitive signals so an MSP can compare its market position without pretending one metric tells the whole story. The report is a starting point for better decisions: which audience to prioritize, which message needs proof, where visibility is weak, and what deserves the next marketing dollar.
You do not need a report to attend. Bring your questions, your uncertainty, and the marketing decision you need to make next. If you are the first qualifying attendee at your meetup, the report is free with no strings attached.
In San Diego for ScaleCon26?
I’ll be in San Diego throughout the event and connecting with friends from last year’s conference. If you have not seen my ScaleCon25 talk, you can watch it below before we meet.
Prefer YouTube directly? Watch Carrie Richardson’s ScaleCon25 talk on YouTube.
RSVP Without a Form or Mailing List
Email carrie@foxcrowgroup.com or call 517-243-3516. Include the meetup you plan to attend. There is no registration form and your RSVP will not add you to a marketing list.
Can’t make one of these times? I’ll be in San Diego all week. Email me and we’ll find another time and place that works.
Event details are adapted from the original Fox & Crow San Diego MSP sales meetup announcement.