I just spent the last three hours reviewing 1,627 fractional leader applications for Shepherd.
Twenty minutes in, they all started blending together.
Here's what hit me: these aren't bad executives. Most have genuinely impressive track records—unicorn exits, massive revenue growth, teams they've built from scratch. But their bios? Completely forgettable.
The problem isn't what they've done. It's how they're talking about it.
What I actually saw (it wasn't pretty)
The History Dump: "20+ years experience across SaaS, fintech, and e-commerce. Previously VP Sales at Company X, scaled team from 8 to 22 reps, achieved 176% YoY growth at Company Y, implemented CRM systems at Company Z..."
I get it. You've done impressive stuff. But this reads like a LinkedIn timeline, not a reason to hire you.
The Swiss Army Knife Problem: "I help with GTM strategy, sales operations, team building, CRM implementation, pricing strategy, market expansion, customer success, revenue operations, and strategic partnerships."
When you're good at everything, you're memorable for nothing. I literally cannot tell what you actually do differently than the 47 other "full-stack revenue leaders" I just read about.
The Buried Gold: Your best result—the one that would make me pick up the phone—is mentioned casually in paragraph three. "Also grew a business from $500k to $2.5M ARR" gets the same weight as "extensive experience in stakeholder management."
Why this drives me crazy (as someone who positions things for a living)
Look, I spent the last twenty years helping technical founders position complex B2B software that nobody understands (and I still do it alongside building Shepherd). I know what good positioning looks like, and this isn't it.
Here's what most fractional leaders are missing: your experience isn't your product. The outcome you deliver is your product.
Think about it like this. When I'm positioning a new SaaS tool, I don't lead with "Our development team has 47 years of combined experience using React and Python." I lead with "Cut your customer onboarding time from 3 weeks to 3 days."
Same principle applies to you.
The stuff that actually works follows a pattern:
Get Specific About Who You Help: Not "all businesses" or "startups and scale-ups." Get narrow. "I help technical founders who've hit $1M ARR but can't scale sales beyond themselves." That's a person with a specific problem, not a category.
Lead With the Change, Not the Credentials: Instead of "Experienced CRO with proven track record" try "I turn chaotic early sales into predictable revenue systems." One tells me what you've been. The other tells me what I get.
Make Your Proof Points Specific and Strategic: Don't scatter your wins throughout paragraphs. Pick the 2-3 results that best demonstrate your unique value and put them front and centre. "In my last three fractional engagements, I built sales systems that generated $2.3M in new pipeline within 90 days" hits different than "extensive experience in pipeline development."
The positioning framework for fractional leaders
Here's the framework I recommend for fractional leaders:
Opening Hook (One sentence): "I help [specific ICP] [achieve specific outcome] by [unique approach/method]."
Proof Section (2-3 bullets maximum):
- Specific metric that demonstrates your unique value
- Named client/company result (if permissible)
- Transformation story that reinforces positioning
Methodology Insight (1-2 sentences): What's your philosophy or framework that creates these results?
Professional Context (1 sentence): Brief credential that establishes authority without listing everything
Call to Action: Clear invitation for the right prospects to engage
A before and after example
Before (Generic Achievement List):"Experienced CRO with 15+ years in B2B SaaS sales leadership. Previously VP Sales at three successful startups, scaled teams, implemented CRM systems, achieved consistent revenue growth. Expert in sales operations, team building, and go-to-market strategy across multiple industries."
After (Positioned for Value):"I help technical founders scale from $1M to $10M ARR without burning cash on premature sales hiring. In my last three fractional engagements, I've built repeatable sales systems that generated $2.3M in new pipeline within 90 days. My framework focuses on founder-friendly sales processes that work before you hire your first AE. Former VP Sales with three successful exits."
Why this matters for fractional leaders
The fractional market is increasingly crowded (no, seriously). Almost every 10th person you talk to is wanting to break into the fractional business. Buyers aren't choosing between good and bad anymore—they're choosing between good and good. Your positioning becomes the tie-breaker.
When your bio clearly articulates who you help and what transformation you deliver, three things happen:
- The right prospects self-select into conversations with you
- You can command premium pricing because you're solving a specific problem
- Your referral network knows exactly who to send you
The meta lesson
The fractional leaders who get the best engagements understand something crucial: they're not selling their experience (or time) —they're selling an outcome. Their bio isn't a retrospective of what they've accomplished; it's a preview of what you'll accomplish together.
Your experience is proof, not product. They're the money shots that make it to the homepage. The product is the transformation you deliver to a specific type of client facing a specific type of challenge.
So, what next?
If you're a fractional leader struggling to convert conversations into engagements, audit your positioning:
- Can someone read your bio and immediately know whether they're your ICP?
- Is your unique value clear in the first sentence?
- Are your proof points connected to a specific outcome you deliver?
The market doesn't need another experienced executive. It needs someone who can solve its specific problem better than anyone else.
That's positioning. That's how you stand out in a crowded market.
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