Welcome to The Independent Operator, a new blog series from Pavilion featuring insights for GTM leaders navigating fractional and advisory work.
Meet Neil...
Neil Weitzman is a longtime Pavilion Ambassador and the co-leader of our CAF (Consultant, Advisor, Fractional)sub-community. A seasoned fractional CRO and GTM leader and founder of weitzmangtm.com, Neil brings tactical wisdom and unfiltered insights to help independent executives thrive. This article is part of The Independent Operator, Neil’s ongoing series for Pavilion.
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📧 neil@weitzmangtm.com or check out how to work with him at weitzmangtm.com
On June 25, we hosted a Pavilion event titled "What the CEO Really Wants in Fractional Executive Leadership." I had the privilege of moderating the discussion, and I’ll be honest, I think I did more absorbing and learning than moderating. The panel was that good.
We brought together a powerhouse group:
- Shelley Perry and Sean Stephens, two seasoned CEOs
- Jen Burton and Leslie Venetz, respected fractional executives and executive coaches
- Henning Schwinum, a leading matchmaker and one of the most connected voices in the fractional space
Their message was clear: hiring a fractional executive isn’t a plug-and-play engagement. It’s a strategic relationship that hinges on context, clarity, and consistent communication.
Defining “Fractional”
It’s important that when we say, “Fractional Executive” we are all singing from the same song sheet. Here is what we mean.
That being established, here are four of the most critical, do not miss soundbites and insights.
1. Context Is King
“If you drop the same template into five different companies, you’ll get five divergent results. Context shapes everything.” — Sean Stephens
Hiring for frameworks alone is a mistake. Great fractional executives understand that success depends on adapting strategy to the nuances of a company’s culture, workflows, stage, and team dynamics.
Pro Tip: Kick off every engagement with a Context Mapping session. Spend 30 minutes with your client leadership team mapping out processes, cadences, and cultural realities. This will inform how you tailor your approach—and increase the odds of successful execution.
2. Clarity in Scope = Engagement Success
"Nothing sinks a fractional engagement faster than vague scopes. You need deliverables, deadlines, and dependencies spelled out in black and white.” — Shelley Perry
Misaligned expectations remain the #1 cause of failed engagements. Yet many executives don’t take the time upfront to align—verbally or in writing.
Pro Tip: Create a one-page Engagement Charter before day one. Include:
- Objective: What success looks like (e.g., +20% demo conversion by Q3)
- Deliverables: Specific outputs like hiring plans or dashboards
- Stakeholder Commitments: Who owns what internally
- Deadlines: Key milestones with dates and owners
This document should be signed off by both parties. Think of it as your North Star.
3. Over-Communication Is Your Operating System
“I spend more time emailing project updates than actually doing the work. If we’re not on the same page every Monday, small misalignments snowball.” — Leslie Venetz
Executives agreed: communication isn’t a soft skill—it’s a survival skill. Especially in fast-moving, high-impact fractional work.
Pro Tips:
- Send a weekly Win-Risk-Learn email (3 bullets on what you did, what’s at risk, and what you learned)
- Maintain a shared Kanban board for visibility
- Schedule monthly strategy deep-dives to reset or reprioritize
4. Real Expertise Beats a Flashy LinkedIn Title
“I’ve seen seasoned operators slap ‘fractional’ on their resumes and give promises to the moon. But CEOs spot empty pedigrees faster than you can say ‘deliverables.’” — Henning Schwinum
Being fractional isn’t just about availability—it’s about true value. CEOs are savvier than ever, and they’re looking for operators who’ve walked the walk.
Pro Tip: If you’re hiring a fractional leader, validate:
- They share both challenges and wins—not just shiny success stories
- They bring referenceable clients, not just endorsements
- They ask better questions than they answer—showing real learning agility
If this resonated, good. There’s more where that came from.
Watch the full event replay: What the CEO Really Wants in Fractional Executive Leadership
Topics Covered
