Strategic Advisory Services

Focused on growth, governance, and building sustainable enterprise value

How I Work With Founders & Leaders

Growth Strategy & Execution

For founders and CEOs who need to identify and execute high-impact opportunities

What this includes:

  • Market & opportunity assessment: Honest evaluation of where you can win and why, based on your actual competitive advantages
  • Go-to-market architecture: Design scalable, repeatable processes for how you'll reach and win customers
  • Partnership strategy: Identify and design partnerships that multiply impact vs. those that dilute focus
  • Revenue model clarity: Align pricing, packaging, and GTM approach with your actual business model and unit economics
  • Execution support: Working alongside you (or your team) to navigate the hard decisions that arise during implementation

Recent work: Positioning strategy for Breach Warranty, GTM architecture for portfolio companies at Trusted.Associates

Risk Governance & Compliance Alignment

For founders and portfolio leaders where governance and compliance directly impact revenue and underwriting

What this includes:

  • Governance assessment: Understand your current cybersecurity and compliance posture—what's strong, what's at risk, and what impacts revenue
  • Framework alignment: CMMC, NIST 800-171, SOC 2, and how these impact GovCon contracts and cyber insurance underwriting
  • Insurance strategy: Align your governance investments with your insurance and risk transfer strategy so they work together instead of separately
  • AI governance: Navigate increasingly complex AI oversight in environments where it directly impacts compliance and investor confidence
  • Remediation prioritization: When there are gaps, help you prioritize what to fix first based on impact to revenue, contracts, and underwriting

Recent work: Portfolio risk governance at Freeman Clarke, cyber insurance strategy alignment across regulated SaaS platforms

Operating Partnership During Critical Periods

For founders and CEOs navigating transition, scale, market entry, or competitive repositioning

What this includes:

  • Strategic clarity: Help leadership get aligned on where you're going and why, before executing
  • Organizational alignment: Support navigating the people and culture implications of significant change
  • Stakeholder management: Work with boards, investors, partners, and teams to manage expectations and maintain confidence during transition
  • Decision support: Serve as a sounding board when you're facing difficult tradeoffs with no obvious right answer
  • Execution discipline: Help maintain momentum and accountability on strategic commitments even when competing priorities emerge

Model: Fractional engagement as operating partner—typically 10-20 hours/month, flexible based on what's needed during critical periods

Portfolio-Level Growth & Risk Architecture

For portfolio leaders and PE sponsors managing multiple companies across regulated markets

What this includes:

  • Cross-portfolio GTM strategy: Design growth architecture that works across multiple companies without forcing a one-size-fits-all approach
  • Standardized governance: Establish risk frameworks and governance discipline that scale across portfolio while respecting company-specific realities
  • Revenue performance tracking: Support investor reporting on growth, with clear line of sight to pipeline, execution, and underwriting/risk factors
  • Channel and partnership alignment: Build ecosystems spanning MSPs, carriers, vendors, and SaaS platforms where each benefits and relationships deepen
  • Alternative risk transfer: Integrate cyber insurance, breach warranty, and other risk transfer mechanisms into operating model

Current work: Trusted.Associates portfolio growth strategy, Freeman Clarke portfolio risk governance

My Approach

What I Do

  • Listen to understand the real situation before proposing solutions
  • Ask hard questions about what you're optimizing for and why
  • Provide honest assessment—not what I think you want to hear
  • Help you think through implications before you commit
  • Support you through execution, not just hand off a plan
  • Build your capability to navigate these issues independently over time

What I Don't Do

  • Pretend to know more than I do or venture into areas outside my expertise
  • Tell you what you want to hear when I think it's wrong
  • Create dependency on my involvement—goal is your capability
  • Deploy generic playbooks without customizing to your situation
  • Work with organizations where I don't believe in the mission or team
  • Do the work for you—advise on how you and your team should do it

Who I Work With

Founders & CEOs

Growing SaaS, cybersecurity, insurance, or technology companies where you're navigating scale, new markets, or competitive transition.

Typical engagement: Fractional operating partner or strategic advisor; 10-20 hours/month or project-based

Portfolio Leaders & PE Sponsors

Managing multiple companies in regulated markets (cybersecurity, AI, SaaS, insurance) where growth and governance must be aligned.

Typical engagement: Portfolio-level growth or risk strategy; ongoing or cyclical involvement

Regulated SaaS & Cybersecurity

Companies where CMMC, NIST, SOC 2, or other compliance requirements directly impact contracts and revenue.

Typical engagement: Governance alignment or risk strategy; usually 6-12 month projects

Insurance & Risk Transfer

Teams designing cyber insurance, breach warranty, or alternative risk transfer products and solutions.

Typical engagement: Product strategy, GTM, or underwriting alignment; project or ongoing

Getting Started

First Conversation

We'll have a real conversation about what you're working on, what the hard problems are, and what you think could help. I'll share perspective on whether this is an area where I can genuinely add value.

If It's a Good Fit

We'll agree on what success looks like, how we'll work together, and what engagement makes sense—whether that's fractional partnership, project work, or ongoing advisory. I'm flexible on structure based on what you actually need.

What You Can Expect

  • Honest perspective, even when it's not what you hoped to hear
  • Respect for your time and mine—meetings have purpose and agenda
  • Confidentiality and discretion about your business and strategy
  • Focus on building your capability, not creating dependency
  • Support through implementation, not just strategy

Ready to Explore Working Together?

Let's have a conversation about your situation and whether I can help you navigate what's ahead.

Schedule a Call