The Modern Operators Discovery With CREW

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Hi Bob and Jeff,
Quick refresher before Monday so we can hit the ground running.
Last meeting: April 6, 2026
Next meeting: May 18, 2026 at 3:30 PM CT
 

Here's what we talked about last time we met:

  • Walked through what Modern Operators does and what a Company OS actually looks like.
  • You shared where Crew is today. Around 350 to 400 members, three events a year, and a team that's still growing.
  • Mapped the current stack: Circle, Copper, Stripe, Cvent, Asana, Slack, and a handful of others held together with Zapier and Make.
  • Talked through the friction. Info lives in too many places, the same questions keep getting asked, and member data is hard to pull on demand.
  • Retention came up as a top focus. Engagement signals could flag renewal risk before it's too late.
  • Sales cycles run anywhere from 10 days to 3 months, with different personas needing different prep.
  • Showed a few quick examples: AI newsletter drafting, annual planning that takes minutes instead of 50+ hours, and meetings you can search after the fact.
 

What we heard from you:

  • You want growth with a lean team. More members, better retention, smoother events, without burning anyone out.
  • The "duct tape" feeling between tools is the main drag.
  • Bob wants to keep what works (Copper, Asana, Circle, Cvent) and connect them, not rip them out.
  • Retention is the biggest unlock. Members who join, get what they need, then don't renew is a real pattern.
  • Events are a heavy lift. There's no shared playbook or run-of-show yet.
  • Marketing today is mostly LinkedIn new-member posts. SEO is weak. Referrals have no template or process.
  • Hub Ambassadors are coming and you want their info feeding back to one central place.
If any of this is off, tell us and we'll adjust.
 

Here's what we'll talk about on our upcoming meeting:

Bob set the agenda in his May 14 email. The job for Monday is to narrow the list down to 1 or 2 places to start so Crew gets a fast win.
Bob's shortlist:
  • Sales Planning (use the Copper pipeline to drive weekly plans)
  • Event Planning and Status (end the "where is the info" loop)
  • Project Plans (tie back to Asana so projects house full context)
  • Marketing (start with warehousing assets and calendars)
  • Systems Integration (Circle, Copper, Asana talking to each other)
  • Customer Success (Hub Ambassadors feeding a central intelligence source)
  • Finance (skip for now)
Jeff's adds:
  • Social media marketing
  • SEO and AI for the website and lead gen
  • Referral programs tied to membership base, geography, and competitor view
What we want to walk out with:
  • A rough picture of what the install looks like (phases, timeline)
  • Clarity on who owns what on Crew's side
 

A few things to think about before we meet:

  • If we could only fix one thing in the next 30 days, which one gives Crew the biggest unlock?
  • Who owns the renewal number, event success, and pipeline health today?
  • Are Andy and Adam part of this decision, or is it Bob's call?
  • How close are Hub Ambassadors to going live? That changes which module we install first.
  • Of the current tools (Cvent, Copper, Circle, Asana), are any on the chopping block, or are we integrating around all of them?
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