Looking for a fractional strategic planning facilitator — SaaS/CS ops background preferred
I'm the Lead Business Ops Manager for a Customer Support & Adoption org (SaaS, ~mid-size company). We're planning our FY2027 strategic planning offsite for our 5-person leadership team (VP + 3 Directors + me) in Chicago, and I'm looking for a facilitator to run two focused half-day sessions.
What we need:
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Someone who's been an operator (ideally VP/Director-level in CS, Support, or Ops) who now does fractional/independent facilitation — we want pattern-matched experience, not a generic team-building exercise
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Pre-work-driven: comfortable running short discovery interviews/video pre-work with our leaders ahead of time so the live time is spent on hard trade-offs, not brainstorming from scratch
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Focused on execution, not ideation — we want to walk away with something tactical (priorities, owners, milestones) we can drop into Jira, not a deck of ideas we have to prioritize ourselves afterward
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Comfortable with a lean scope: two half-days live, we handle the rest of the onsite content ourselves
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Budget-conscious — this is a small-department engagement, not an enterprise consulting spend
If you've used someone like this (or you are someone like this), I'd love a name or a DM. Happy to share more context! Thanks so much!