Jon's
Long-Term Relationships
Jon Freedman — Building a Fully Booked Fractional CTO Business Through Deep Trust and Long-Term Relationships.
5/5
“I built a fully booked Fractional CTO business without chasing clients”
Key Insights
Who is Jon?
Before CTOx Accelerator™
After CTOx Accelerator™
The Challenge
Jon couldn’t publicly market or engage with clients after April, 2025, due to contractual restrictions. Despite this, he needed to prepare his brand, refine his messaging, and ensure that when the gate opened, he would convert quickly — all without traditional outbound sales pressure.
The CTOx®
Approach
- Leverage a deeply cultivated network: Over 15 years, Jon had unintentionally built a strong, London-centered network by consistently delivering exceptional results, staying visible at FinTech events, and maintaining his reputation as a reliable problem solver.
- Activate trusted relationships: Rather than broad cold outreach, Jon focused on warm, trusted introductions. He knew his niche (hedge funds and wealth managers) rarely engages on LinkedIn and prefers personal, relationship-based connections.
- Pre-build content to demonstrate expertise: While on garden leave, he batch-recorded "mock cast" video content: seven weeks' worth of short, expert-focused videos highlighting his thinking on AI, tech adoption in finance, and modern tooling.
- Showcase as high value, low risk: Jon positioned himself as a “high-value, low-risk” partner: offering deep expertise without requiring a full-time commitment. He deliberately avoided rigid minimum commitments, instead inviting clients to continue only if they saw value after one month.
CTOx® Methodologies Used:
The Transformation
Three Clients In One Month
Client 1: A startup founder introduced by a former employee whom Jon had mentored.
Client 2: A coaching business referral that emerged naturally from a casual discussion about AV equipment.
Client 3: A major hedge fund where Jon initially thought he had no chance — they hired him to oversee a major foundational trading tech buildout.
Target Portfolio Size Hit Quickly
Jon’s approach meant he could be fully booked, on his own terms, without exhausting outbound prospecting or chasing leads.
$20K/month Anchor Client
High-ticket hedge fund engagement validated Jon’s positioning as a strategic, trusted partner rather than a hands-on implementer alone.
Real Results
What Can You Learn From Jon?
FAQs About the CTOx® Journey
Common questions technology leaders ask when exploring the fractional CTO path, answered based on patterns we’ve observed across hundreds of successful members.
What kind of background do successful CTOx Accelerator™ members typically have?
Most successful CTOx Accelerator members are experienced technology leaders with 10+ years in the industry, including current or former CTOs, VPs of Engineering, Technical Directors, and Senior Engineering Managers. They typically have experience leading teams, making strategic technology decisions, and working directly with executive leadership. Many come from startups, scale-ups, or enterprise environments where they’ve been responsible for technology strategy, not just implementation.
How long does it usually take CTOx Accelerator™ members to get their first client?
The most proactive CTOx Accelerator™ members typically land their first client within 30-90 days of joining the program. Some exceptional cases have signed clients within their first week, while others may take longer depending on their network activation efforts and niche focus. The timeline largely depends on how consistently members implement the Network Activation process and execute on the business development activities outlined in the program.
What are the most common challenges people face when transitioning to fractional CTO work?
The three most common challenges are: (1) Overcoming discomfort with business development and “marketing” activities, (2) Shifting from hourly thinking to value-based pricing and retainer models, and (3) Learning to delegate tactical work while focusing exclusively on strategic leadership. Many also struggle initially with positioning themselves in a specific niche rather than trying to serve everyone.
What types of client engagements and revenue models do CTOx Accelerator™ members typically build?
CTOx Accelerator™ members typically build diversified portfolios with two main engagement types: “Engaged” clients (full strategic leadership at $10k-$15k/month) and “Advisor” clients (high-level guidance at $3k-$5k/month). Many also offer strategic intensives or half-day consults as entry points. Successful members often manage 5-8 total clients with a mix of engagement levels, targeting $500,000+ annual revenue through this diversified approach.
What advice do most CTOx Accelerator™ members give to technology leaders considering this transition?
The most consistent advice from CTOx Accelerator™ members is: (1) Start while still employed to reduce financial pressure, (2) Focus on a specific niche rather than trying to serve everyone, (3) Leverage your existing network through the Network Activation process before trying cold outreach, and (4) Embrace relationship-based business development rather than traditional marketing. They also emphasize the importance of following the proven system rather than trying to figure everything out independently.
