Ongoing Strategic Partnership for SaaS Leaders
For leaders who need consistent strategic guidance and a trusted advisor in their corner, this monthly coaching program provides weekly touchpoints with Drew plus unlimited access to your Digital Protégé.
What You Get
Weekly 1-Hour Sync with Drew
Direct access to 25 years of SaaS scaling experience. We’ll work through your toughest decisions, strategic challenges, and leadership development together.
Community Support
Connect with other SaaS leaders facing similar challenges. Peer learning, shared experiences, and a network that extends beyond our sessions.
24/7 Digital Protégé Access
Between sessions or for after-hours guidance, use the Digital Protégé at the discounted rate of $2/minute (vs. standard $2/minute for non-members).
Investment
$2,000 per month
- Weekly 1-hour coaching sessions with Drew
- Access to community of SaaS leaders
- Unlimited Digital Protégé access at member rate ($2/minute)
- Cancel anytime with 30-day notice
Who This Is For
This program is perfect for:
- SaaS Founders/CEOs navigating scaling challenges
- First-time executives (VP Eng, CTO, CPO) stepping into leadership
- Technical leaders who need strategic business perspective
- Anyone who’s made critical decisions alone at 2 AM and wants that to stop
How It Works
- Start with Digital Protégé - Begin your free first session
- Experience the value - Use Digital Protégé for strategic conversations ($2/minute after first free session)
- Upgrade to coaching - When you’re ready for deeper partnership, transition to monthly coaching
- Get both - Continue using Digital Protégé for immediate needs, plus weekly sessions with Drew for strategic work
The Drew Harris Approach
After 25 years in the SaaS industry as both CEO and CTO, I’ve learned that scaling yourself as a leader is just as important as scaling your organization.
My methodology centers on three core elements:
- Exploring: Understanding through data and reflection
- Guiding: Providing clear roadmaps and frameworks
- Coaching: Developing your capabilities for long-term success
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.
Alternative: Deep Transformation Work
If you need comprehensive organizational transformation rather than ongoing coaching, consider Fractional CTO/CPTO Services starting with a $10K discovery phase.
Ready to Start?
Step 1: Experience the Digital Protégé (first session free)
Step 2: When you’re ready for ongoing partnership, book your coaching kickoff call
Questions? Use the Digital Protégé to discuss whether coaching or fractional leadership is the right fit for your situation.