This Is Not Traditional Consulting.
Cyber Operator Group is an operator-led advisory firm — built by enterprise cybersecurity leaders who have sat in the buyer's chair, led Fortune 500 security organizations, and navigated the complexity of enterprise procurement from the inside.
We don't theorize about enterprise adoption. We have lived it. Our advisors bring decades of hands-on experience building, scaling, and transforming security programs at the highest levels of corporate America.
Operator-Led
Guidance from executives who have run enterprise security organizations — not consultants who have studied them.
Outcome-Focused
Every engagement is structured around measurable results: faster sales cycles, stronger positioning, and enterprise customers won.
Board-Level Perspective
We speak the language of CISOs, boards, and enterprise procurement committees — and we teach you to do the same.
We Have Sat in the Buyer's Chair.
Enterprise security buyers evaluate vendors through a lens that most founders never fully see. They assess organizational fit, procurement risk, long-term vendor viability, and executive trust — often before a single technical evaluation begins.
Cyber Operator Group gives cybersecurity founders rare, unfiltered access to that perspective. We help you understand how enterprise security organizations actually make decisions, and we position your company to win those decisions with confidence.
Advisory Designed for Enterprise-Stage Growth.
Our services are structured around the specific challenges cybersecurity founders face as they move from early product validation into enterprise scale. Each engagement is customized, executive-driven, and built around your specific growth objectives.
Enterprise Strategy
Comprehensive enterprise readiness assessments, go-to-market strategy development, and enterprise sales motion design tailored to Fortune 500 buyers.
Executive Advisory
Ongoing fractional executive leadership and board advisory that elevates your credibility with investors, customers, and strategic partners.
Product Strategy
Enterprise product-market fit analysis, buyer persona development, and product roadmap alignment with enterprise security requirements.
Executive Introductions
Direct access to our network of senior CISOs, security executives, and enterprise decision-makers who can become your first enterprise customers.
Every Stage of the Enterprise Journey.
Go-to-Market & Sales
- Go-to-Market Strategy
- Enterprise Sales Strategy
- Customer Advisory Boards
- Enterprise Procurement Navigation
- Customer Messaging & Positioning
Executive & Board
- Board Advisory
- Investor Readiness
- Fractional Executive Leadership
- Executive Introductions
- Board Meeting Preparation
Product
- Product Strategy & Roadmap
- Enterprise Product-Market Fit
- Competitive Positioning
Built for Cybersecurity Founders Ready to Win Enterprise.
Cyber Operator Group works with a focused set of clients — companies serious about enterprise adoption and growth. Our advisors have limited capacity, and we engage selectively to ensure every client receives genuine executive attention and measurable impact.
Cybersecurity Startups — Series A through D
Growth-stage security companies with proven technology seeking to accelerate enterprise adoption, sharpen positioning, and shorten sales cycles with Fortune 500 buyers.
Founders & Executive Teams
CEOs and founders who need an experienced enterprise operator in their corner — someone who has built, led, and scaled security organizations at the enterprise level.
VC & PE Portfolio Companies
Venture capital and private equity firms seeking enterprise cybersecurity expertise for portfolio companies navigating complex go-to-market challenges.
Boards & Investors
Boards of directors and institutional investors who require an independent, senior cybersecurity advisory perspective on portfolio strategy and enterprise market dynamics.
Shawn Harris
Founder & Principal, Cyber Operator Group
Shawn Harris is an enterprise cybersecurity executive with decades of leadership experience building and scaling security organizations across Fortune 500 enterprises. He has led transformational security programs, advised boards and executive leadership teams, and driven AI and cloud security initiatives at the highest levels of corporate America.
Shawn brings deep experience helping organizations balance aggressive innovation with measurable risk management — and translating that enterprise buyer perspective into actionable guidance for cybersecurity founders. His network spans senior CISOs, enterprise security leaders, venture capital partners, and industry organizations.
What Founders Achieve Working With COG.
Our engagements are structured to deliver measurable, enterprise-scale outcomes — not strategy decks that sit on a shelf. Founders who work with Cyber Operator Group leave with sharper messaging, faster pipelines, and the executive credibility that enterprise buyers require.
Customer Access
Direct introductions to Fortune 500 security executives and enterprise decision-makers in our network.
Years of Experience
Decades of combined enterprise cybersecurity leadership informing every engagement.
Sales Velocity
Clients report significantly faster enterprise sales cycles after enterprise readiness alignment.
Accelerated Enterprise Adoption
Move from proof-of-concept to production deployment faster with enterprise-aligned product positioning and procurement strategy.
Executive Credibility
Walk into every C-suite meeting with messaging that resonates at the board level — not just the technical level.
Revenue Acceleration
Close enterprise deals faster, improve win rates, and build a repeatable enterprise revenue motion that scales.
Investor Confidence
Demonstrate enterprise traction, market credibility, and a board-ready narrative that strengthens investor relationships.
Operator-Led. Outcome-Focused. Enterprise-Proven.
The difference between Cyber Operator Group and traditional consulting is simple: we have been the customer. We have built the security programs that your product is trying to sell into. We understand the organizational dynamics, the internal politics, the procurement requirements, and the executive priorities that drive enterprise security decisions.
That operator perspective is not something that can be learned in a consulting engagement. It is earned through decades of enterprise leadership — and it is precisely what we bring to every founder, every board conversation, and every go-to-market strategy we develop.
Understand the Buyer
Enterprise security buying behavior, procurement cycles, and executive decision-making frameworks.
Align Your Product
Position your product to match enterprise requirements, risk frameworks, and buyer expectations.
Win Enterprise Customers
Execute a go-to-market strategy that earns enterprise trust and accelerates revenue.
Ready to Accelerate Your Enterprise Growth?
Cyber Operator Group works with a select number of cybersecurity companies each year. If you are a founder serious about enterprise adoption, we want to hear from you. Schedule an executive strategy session and let's explore how operator-led advisory can help you win.
Cyber Operator Group
Helping Cybersecurity Startups Win Enterprise Customers.
Shawn Harris
Founder & Principal
Services
- Enterprise Strategy
- Executive Advisory
- Go-to-Market Strategy
- Product Strategy
- Board Advisory
- Investor Readiness
- Fractional Executive Leadership
Who We Help
- Cybersecurity Startups
- Founders & CEOs
- VC Portfolio Companies
- PE Portfolio Companies
- Boards & Investors
Copyright © Cyber Operator Group
Operator-led advisory that helps cybersecurity founders refine product strategy, accelerate enterprise go-to-market, and earn the trust of Fortune 500 security leaders.