Drew Schiller

What I do

I work with leadership teams and boards at inflection points—often when there’s real momentum, but no clear path to sustaining it.

• A new product or technology to reignite growth
• Fresh capital without the operating experience to deploy it well
• Executive turnover, including founder transitions
• Early traction that may or may not translate into something durable

I’ve sat in the CEO seat from founding through exit.
I know what breaks as companies scale—and what holds.

How I think

In the first few conversations, I’m pressure-testing three things:

• Is the value real and urgent?
  Not just “interesting,” but something customers actually need right now
• Can the product deliver on that promise?
  We need real-world proof, or we need a plan to get it
• Can this team execute at the level required?
  Because if the team isn’t right, nothing else matters

If any one of these is off, the company won’t scale the way it expects.

What I see that others miss

Most teams confuse activity with durable demand.
The result is growth that looks real, but won’t last.

You can generate real excitement, strong pipeline, even early growth—inside a market that isn’t big enough, urgent enough, or ready enough to sustain it.

I’ve seen:

• Record bookings quarters while pipeline quietly stalls
• First client adoptions that struggle to find a second client
• Customers excited at close that never adopt post-sale
• Successful implementations that never launch in production

Growth only matters if it compounds over time.

That requires:

• A large, viable market
• A clear and urgent value proposition
• Sustained usage after the deal is signed
• An intellectually curious, customer-obsessed team

Where I’m most useful

I’m most helpful when:

• The company has strong technology but an unclear path to adoption
• Growth has stalled or is at risk of stalling
• The team hasn’t yet built through this phase before
• There’s a need for honest, experience-backed judgment

Typical engagements:

• Board roles
• CEO / founder advisory
• Growth-stage companies navigating scale

What I believe

• Every team member reinforces the culture or breaks it
• Trust people to succeed—support them when they don’t
• Leadership is knowing when—and when not—to step in
• Complacency is a company killer

Most companies don’t fail because of lack of effort.
They fail because energy is spent in the wrong places.