It's 2 AM. You Have a Critical Decision to Make.

Stressed founder at desk late at night

You can't call your board. Your team can't know you're uncertain. Your co-founder is too close to see clearly.

You Don't Have to Make It Alone

Talk it through with 25 years of SaaS scaling experience. Available 24/7.

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First Session Free

The $500K Mistake I Watched a CEO Make Alone

Friday board meeting: "Why is engineering so slow?"

Saturday morning: CEO started doubting his VP of Engineering.

Sunday evening: Convinced himself it was a people problem.

Tuesday 2 AM: Couldn't sleep. Made the decision alone. Fired the VP.

The result?

→ 3 months to find replacement
→ 2 months to onboard new VP
→ Same problems still there
→ $500K+ in cost and lost momentum
→ Team trust damaged

The real problem?

It was never the person. It was:
→ Misaligned expectations between leadership and engineering
→ Measuring velocity instead of customer outcomes
→ No cross-functional collaboration framework
→ Product and engineering working in silos

He made a critical decision alone. And he was wrong.

That's when I realized: The most expensive mistakes happen when leaders have no one with real experience to talk decisions through with.

I've watched this pattern repeat dozens of times in 25 years. That's why I built something different.

The Conversations You Can't Have Anywhere Else

These are the late-night, high-stakes, trajectory-changing conversations that determine whether you scale successfully or burn out trying.

"Should We Rebuild or Refactor?"

The bicycle-to-race-car decision. How to evaluate technical debt vs. new features. When rebuilding is actually the right answer (and when it's a $2M mistake).

"Why Is Engineering So Slow?"

Understanding the gap between executive expectations and engineering reality. How to measure what actually matters. Customer-centric metrics that drive results.

"How Do I Align Product and Engineering?"

Cross-functional pod structure vs. departmental silos. Building trust and ownership across teams. Creating shared accountability for outcomes.

"Am I the Problem?"

First-time executive transitions (engineer → leader). What got you here won't get you there. Optimizing for strengths vs. fixing weaknesses.

"Should I Fire This Person?"

People problem vs. process problem. When to fix and when to part ways. How to know if you're about to make a $500K mistake.

"How Do I Talk to My Board?"

Translating technical complexity to business impact. Setting realistic expectations. Showing progress when velocity is down.

These Aren't Hypothetical Questions

These are the decisions that determine your company's trajectory. And you shouldn't have to make them alone.

Start Your Free Coaching Session

Why This Actually Works

1

Available When You Need It

Critical decisions don't wait for scheduled meetings. My Digital Protégé is available 24/7—at 2 AM, on Sunday, whenever that decision can't wait.

2

25 Years of Real Experience

Not generic advice from ChatGPT. Actual frameworks I developed scaling QuantumDelta, working with dozens of fractional CTO clients, and making expensive mistakes so you don't have to.

3

Coaching, Not Cheerleading

I ask the questions you haven't thought of. Challenge your assumptions. Help you see blind spots. This isn't validation—it's strategic thinking.

4

Completely Private & Confidential

Your Digital Protégé conversations are 100% confidential—never shared publicly or with third parties. I review sessions to better serve you, which means when you're ready to upgrade to coaching or discovery, I already understand your situation deeply. It's private, purposeful, and personalized.

5

No Commitment Required

First session is completely free. No credit card. No scheduling. No pressure. Just a conversation when you need one.

Strategic Guidance When You Need It

Different tools for different needs. All designed to help you make better decisions.

Digital Protégé

First Session Free
  • Available 24/7 when you need it
  • First session free
  • Then $120/hour ($2/minute)
  • My 25 years of experience in every session
  • Private & confidential (I review to serve you better)
  • No scheduling, no commitment

Monthly Coaching

$2K/mo
  • Weekly 1-hour sessions with Drew
  • Community support from peer leaders
  • Digital Protégé access at member rate
  • Ongoing strategic partnership
  • Cancel anytime with 30-day notice

Fractional CTO/CPTO

$10K Discovery
  • Start with free fit call
  • $10K for 4-hour discovery + data analysis
  • Then roadmap design & implementation
  • Typical implementation: $15K/month
  • Systematic organizational transformation

Here's my philosophy:

My Digital Protégé is better than me for 24/7 availability—it's trained on my 25 years of experience and always ready when you need it most. I review sessions so when you upgrade to coaching or discovery, I already understand your situation. Sometimes you need immediate guidance at 2 AM. Sometimes you need full engagement with data analysis and transformation. Sometimes you need ongoing partnership with weekly check-ins. Start with Digital Protégé (free first session), then choose the path that fits your needs.

Why Trust Drew's Guidance?

Former SaaS CEO

Founded and led QuantumDelta for over a decade. Built scalable solutions for hundreds of customers.

Scaling Expert

Helped scale a SaaS company to $100M+ ARR and successful IPO. Guided franchise from 1 to 100+ locations.

Fractional CTO/CPTO

Currently serving multiple SaaS companies with data-driven transformation and systematic scaling.

Podcast Host

Host of "SaaS Growth: Scaling with a Fractional CTO" sharing insights on leadership and scaling.

After 25 years in the SaaS industry, I've learned that scaling is like transitioning from riding a bicycle to driving a race car. The fundamentals change, the speed increases, and what got you here won't get you there.

I've been both CEO and CTO. I've made the expensive mistakes. I've felt the 2 AM anxiety of critical decisions with no one to call. I've experienced the loneliness of leadership.

That's why I built this. Because every SaaS leader deserves access to experienced guidance at the moments that matter most—without the 6-month commitment or $300K price tag.

My methodology centers on three core elements: Exploring (understanding through data), Guiding (providing clear roadmaps), and Coaching (developing your capabilities).

I believe deeply that "if you take care of your customers, they will take care of you." That's why I measure success by reduced customer support tickets, improved product adoption, and genuine customer satisfaction—not velocity or story points.

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Don't Make That Decision Alone

Your next critical decision deserves strategic thinking, not anxiety and overthinking.

Available 24/7. First session completely free. No credit card required.

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