Drew Schiller

What I do

I work with leadership teams and boards at inflection points—when mission, culture, product, and growth need to stay aligned under pressure.

My experience is deepest in healthcare, data infrastructure, enterprise software, and products that require adoption across complex organizations.

That often looks like:

• A new product or technology that needs to support the mission and the market
• 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 as a founder and operator.

At Validic, I’ve helped build category-defining infrastructure connecting personal health data into clinical and enterprise workflows across health systems, payers, health tech, and life sciences.

I’ve led the company through multiple rounds of venture and strategic financing and driven key channel partnerships.

I’ve held board and advisory roles with digital health companies, payers, and providers.

How I think

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

• Is the mission clear enough to guide decisions?
  A strong mission should shape what the company builds, how it operates, and what it refuses to become.
• Are decisions and incentives aligned with that mission?
  Governance and culture show up in how work gets done, how tradeoffs are decided, and what behaviors are rewarded.
• Is the product value real and urgent?
  Not just “interesting,” but something customers actually need right now.
• Can this team execute under pressure?
  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

Growth that pulls a company away from its mission will not hold.

You can generate real excitement, strong bookings, and early growth inside a market that isn’t big enough, urgent enough, or ready enough to sustain the company.

I’ve seen:

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

Sustained growth only happens when the mission, market timing, and execution align.

That requires:

• A large, viable market
• A clear and urgent value proposition
• Sustained product utilization and growth
• An intellectually curious, customer-obsessed team

Where I’m most useful

I help mission-driven companies 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

• A strong mission guides the company’s actions, governance, and culture
• Every team member reinforces the mission or breaks it
• Trust people to succeed—support them when they don’t
• 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.

Beyond the Boardroom

Outside of work, I write fiction and screenplays—mostly exploring systems, collapse, and what people do under constraint.