Get Started
← Member Spotlights
Member Spotlight

Tyson's Tabletop Strategy

Tyson Martin — Transforming Client Relationships with Play.

Tyson Martin
★★★★★
“I turn strategy sessions into play that actually sticks”
Tyson Martin · Fractional CTO · CTOx Accelerator™ Alumni

Key Numbers

20+ years experience
100+ organization knowledge
22k+ followers

Who is Tyson?

Before CTOx Accelerator™
  • Dry, disconnected sessionsTraditional strategy and cybersecurity meetings often left executives bored or disengaged.
  • Limited impactTabletop exercises were technical, one-off events that didn’t influence broader business strategy.
  • Missed alignmentLeaders and teams rarely collaborated effectively, limiting organizational adoption and cultural change.
After CTOx Accelerator™
  • Created gamified tabletop simulationsCo-developed with collaborator Cliff, inspired by Dungeons & Dragons and business strategy games.
  • Built a flexible, interactive platformDynamic, customizable scenarios that evolve over time and reflect real business consequences.
  • Engaged executives at every levelSessions now foster collaboration, competition, and excitement across leadership teams.
  • Enabled broader adoptionIndustry-specific frameworks allow organizations to scale exercises to meet compliance, leadership, and strategic needs.

The Challenge

Many organizations struggle to engage executives and business leaders in strategic technology discussions. Traditional strategy sessions and cybersecurity reviews often feel dry, technical, and disconnected from business outcomes.

Further, most tabletop exercises (simulated drills used in security, compliance, and operational preparedness) focus only on technical teams and lack alignment with broader business strategy. These one-off sessions often fail to build lasting behavior change or cultural alignment.

The CTOx® Approach

Dynamic, customizable scenarios

Covering incidents (like ransomware attacks), strategic shifts (like adopting GenAI), and business transformation.

Industry-specific frameworks

Tailored to regions, compliance requirements, and leadership styles.

Play-driven design

Inspired by Dungeons & Dragons and business strategy games, the platform engages stakeholders at every level.

Progressive simulations

Companies can "save their game" and continue evolving their strategy over months or even a year.

Holistic decision modeling

Each decision affects risk, revenue, investor confidence, and employee and customer sentiment — showing real business impact.

CTOx® Methodologies Used:

CTOx methodologyCTOx methodologyCTOx methodologyCTOx methodologyCTOx methodologyCTOx methodology

The Transformation

High Engagement & Trust

Executives who began skeptical became highly engaged — even competitive — collaborating across functions and leaving sessions energized.

Expanded Market Reach

From the United Nations and defense agencies to Fortune 50 boards and universities, the approach has proven universally appealing and scalable.

Product-Led Growth

Tabletop exercises are used as a “gateway offer” to build trust and generate deeper fractional CTO or advisory engagements.

Strong Differentiation

Instead of selling purely service-based strategy sessions, Tyson offers an interactive, experiential product that sets him apart from other CTO consultants.

Community and Collaboration

Tyson’s platform opens opportunities for other CTOx members to partner, white-label, or co-create industry-specific modules — creating new revenue streams and shared value.

Real Results

High Engagement and Trust

Executives leave energized, collaborating across functions and taking ownership of outcomes.

Expanded Market Reach

From the United Nations to Fortune 50 boards, universities, and defense agencies, the platform is widely adopted.

Community and Collaboration

Enables CTOx members to co-create or white-label modules, generating new revenue streams and shared value.

Product-led Growth

Tabletop exercises act as a “gateway offer,” leading to deeper fractional CTO or advisory engagements.

Strong Differentiation

Provides an interactive, experiential alternative to standard service-based strategy sessions.

What Can You Learn From Tyson?

Make it Memorable

Transform dry topics into engaging, interactive experiences that people actually want to participate in.

Strategic Alignment Matters

Connect technical decisions to business outcomes to ensure lasting impact.

Start with Play

Innovative approaches can break down barriers and inspire collaboration.

Build Scalable Systems

A repeatable, modular platform allows for growth, market expansion, and partnership opportunities.

Differentiation Wins

Offering a product-based experience sets you apart from service-only consultants.

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 advice do successful members share most often?
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 successful members share most often?
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.

Ready to speak with a CTOx® Advisor?

Book A Free Brainstorm Call