Fractional Executive Leadership for MSPs

I held the CIO/CISO seat at a PE-backed MSP. Built a $5M security practice. Integrated security for 8 acquisitions. 25+ incidents as incident commander. I know what keeps you up at night.

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A female engineer using a laptop while monitoring data servers in a modern server room.

The MSP Founder’s Dilemma

MSP founders are excellent technicians who built successful businesses through heroic effort and technical skill. But the skills that got you to $5M don’t scale to $25M. You’re acting as de facto COO, CIO, and CISO while trying to grow the business, leading to chronic firefighting, reactive operations, and revenue plateaus.

Operations, governance, and security require a different muscle, one most founders never developed because you were busy delivering for clients. The frameworks exist (TruMethods, Service Leadership, ConnectWise best practices), but most MSPs fail to implement them consistently because the founder doesn’t have the bandwidth or operational muscle to execute.

I’ve Held Your Seat

CIO/CISO at Anatomy IT

Held the CISO and CIO seats at a PE-backed healthcare MSP (2021-2025)

$5M Security Practice

Built managed security portfolio generating ~$5M annual revenue

1,700+ Clients Protected

Security programs protecting 1,700+ healthcare clients across the continuum of care

8 Acquisitions

Integrated security for 8 acquisitions, designed integration playbooks

25+ Incidents

Served as incident commander for 25+ critical security events

How I Help MSPs

  • Build the security practice that becomes a revenue driver, not a cost center
  • Create the operating model that scales without proportional pain
  • Develop governance rhythms so decisions happen without you in the room
  • Prepare for transaction with security posture that survives diligence
  • Lead incident response when things go wrong (and they will)
  • Coach your technical leaders into operational leaders

“I had the privilege of working under Rick for three years in my role as a vCISO, and I can confidently say he’s one of the most capable and inspiring security leaders I’ve worked with. As CISO, Rick brought deep technical expertise, strategic foresight, and a take-charge attitude that elevated every aspect of our security operations. What truly set him apart was his willingness to jump in, whether it was guiding a complex incident response, mentoring junior staff, or rolling up his sleeves to troubleshoot with the team. He led by example, blending decisiveness with collaboration. His knowledge of cybersecurity frameworks, risk management, and MSP dynamics is unmatched, and he consistently turned challenges into opportunities for innovation. Any organization would be lucky to have Rick at the helm of their security program.”

Juan Bernardo, Vice President Information Technology, TEG Federal Credit Union

Frequently Asked Questions

No. I help MSPs build their own capabilities, not compete with them for clients. My work is helping MSP founders like you build the operational and security infrastructure that lets you scale. I’m not selling managed services to your clients; I’m helping you sell better services to your clients.

Having technical security talent is different from having security leadership. Your engineers can implement controls; a CISO builds the program, governance, and strategy that makes those controls coherent. Most MSPs have a talented engineer who “knows some security” but no one asking whether the program is actually mature or just reactive.

Peer groups give you frameworks and community, which is valuable. But they don’t execute for you. I’ve seen dozens of MSPs buy the methodology, attend the peer group, then go back to firefighting because they don’t have the bandwidth to implement. I actually run the play, not just hand you the playbook.

That’s one of the situations I know best. I’ve done security diligence on 40+ acquisition targets and integrated 8 acquisitions. I know what buyers look for, what kills deals, and what drives valuation. Getting transaction-ready is one of the highest-value things I do for MSP founders.

Yes. I built a managed security portfolio to $5M revenue at Anatomy IT. I know how to productize security services, price them for margin, and train your team to deliver them consistently. Security as a revenue driver, not a cost center, is exactly what most MSPs need.

I’ve Been in Your Seat

I know what it’s like to be the MSP founder who’s drowning in operations while trying to grow. The Operator’s Take is a complimentary 20-30 minute conversation where I’ll give you a senior-level read on whether your structure is aligned with where you’re headed.

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