TLDR
Most MSPs evaluate offensive security partners using the wrong criteria. Certifications and compliance checkboxes don’t predict delivery quality. Real partnership depends on technical depth, communication clarity, and operational experience that only shows up under pressure.
The Partner Evaluation Problem
Ransomware attacks targeting MSPs increased 400% in the past 18 months. Your clients are asking harder questions about offensive security capabilities. Compliance requirements are shifting from checkbox assessments to real adversary simulation. The MSPs winning contracts today offer comprehensive security services, including red team engagements and penetration testing.
Your client needs a red team engagement. You know your vulnerability scanning and compliance work inside out, but offensive security sits outside your core expertise. You need a partner.
The challenge compounds quickly. MSPs face constant pressure to offer comprehensive security services without building every capability in-house. Offensive work requires specialized skills you’ll use occasionally, not daily. Building an internal red team for quarterly engagements makes no financial sense. You need partners who can deliver without damaging the client relationships you’ve spent years building.
The stakes are higher than most vendor decisions. Poor communication creates confusion and project delays. Worst case: the partner tries to poach your client directly. Most evaluation criteria focus on the wrong signals. Certifications matter less than you’d expect. Here’s what actually predicts a successful partnership.
The Business Case for Getting This Right
Before diving into evaluation criteria, understand the economics:
Building Internal Capability:
- Junior penetration tester: $90K-120K salary
- Senior red team operator: $150K-200K salary
- Required certifications and training: $10K-15K annually
- Tooling and infrastructure: $20K-30K annually
- Minimum viable team: 2-3 people
- Annual cost: $250K-450K before utilization concerns
Partnering Model:
- No fixed overhead
- Pay per engagement
- Scale up or down based on demand
- Access to specialized expertise when needed
Revenue Opportunity:
- Average MSP marks up partner services 30-50%
- Offensive security improves client retention by 25-40%
- Cross-sell opportunity to existing vulnerability scanning clients
- Competitive differentiation in proposal responses
- Higher-value client conversations (CISO level vs. IT manager level)
The math favors partnerships for most MSPs. The question becomes: how do you choose the right partner?
Technical Capability: Beyond Certifications
MSPs typically start with the obvious: OSCP, GPEN, CEH certifications. Years in business. Generic claims about “penetration testing services.” Lists of tools and methodology frameworks pulled from vendor websites.
These can matter, but they don’t differentiate. The meaningful signals require deeper investigation.
What You Usually See vs. What Actually Matters
| What You Usually See | What Actually Matters |
| List of certifications | Ability to explain methodology without buzzwords |
| “15 years in business” | Relevant past performance in similar environments |
| “We use industry-standard tools” | Custom capability development for edge cases |
| “Comprehensive testing” | Clear scoping based on technical complexity |
| Generic methodology frameworks | Scenario-based approach tailored to threats |
| Price per IP address | Objective-based pricing with clear deliverables |
Real operational background tells you more than certifications. Military or government offensive cyber experience means someone has worked under actual operational constraints, not just controlled lab environments. Prior work at US Cyber Command or equivalent agencies indicates exposure to sophisticated attack chains and operational security requirements. This experience doesn’t appear in certification exams.
Red team work and penetration testing are different disciplines. Penetration testing typically follows defined methodologies against known vulnerability classes. Red teaming simulates adversary behavior with objectives and constraints. Both have value, but understanding the difference reveals whether a partner can adapt to your client’s specific needs.
Technical depth shows up in conversations, not credential lists. Can they explain their methodology in technical detail without defaulting to framework buzzwords? Do they understand your client’s specific environment (multi-cloud architecture, operational technology systems, industry-specific regulations)? Can they scope accurately based on technical complexity rather than generic “number of IPs” pricing?
Custom capability matters more at the high end. Pre-built tooling enables efficiency, but sophisticated environments require custom exploit development. The question becomes: does this partner understand when automated tools suffice versus when manual analysis becomes necessary?
Watch for red flags. Partners who can’t explain their technical approach without referencing compliance standards probably lack depth. Promises to “find everything” or guarantees about specific vulnerability counts indicate inexperience. Charging purely by time instead of objective-based pricing suggests they don’t understand scoping. Focus on report page count over finding severity means they’re optimizing for the wrong outcome.
Experience That Transfers
Certifications prove someone passed an exam. Past performance predicts actual delivery.
Scenario-based questions reveal real experience faster than credential reviews. Ask about hybrid cloud environments with Active Directory and Azure integration. What’s their attack path approach? When they find remote code execution during the discovery phase, what’s their escalation process? For clients running 24/7 production systems, how do they de-conflict testing activities?
The answers tell you whether they’ve encountered these situations before, how mature their risk management practices are, and what communication protocols they follow under pressure.
Federal government work, particularly defense and intelligence contracts, indicates experience with operational security and complex stakeholder management. Fortune 500 experience suggests capability to work at enterprise scale. Industry-specific work in financial services, healthcare, or critical infrastructure transfers directly to similar clients.
Several factors matter less than conventional wisdom suggests. The number of certifications someone holds doesn’t correlate strongly with delivery quality past a baseline threshold. Firm size often inversely correlates with specialized capability. Small focused teams frequently outperform large generalist practices. Marketing polish and association memberships provide minimal signal about technical depth.
Former military operators from offensive units bring specific advantages. Operational exposure to adversary tactics provides context that certification training cannot replicate. Discipline around rules of engagement and scope management prevents the boundary violations that damage client relationships. Experience with stakeholder communication during sensitive operations translates directly to high-stakes client engagements. Comfort with ambiguity and problem-solving under constraints becomes essential when client environments don’t match documentation.
Delivery & Communication: What Good Looks Like
Technical execution matters, but delivery encompasses more than finding vulnerabilities.
Example: Exceptional Partner Behavior A partner discovers remote code execution on a production system at 2 AM. Within 15 minutes, they’d contacted the MSP with a full brief, recommended immediate actions, and offered to join a client call within the hour. They provided a preliminary technical write-up suitable for the client’s infrastructure team and waited for MSP approval before any client contact. The finding was severe, but the client praised the MSP’s “incredible response capability.”
Pre-engagement practices reveal organizational maturity. Clear scoping that matches client risk profiles versus generic templates. Transparent pricing without surprise add-ons. Realistic timelines (partners who promise unrealistically fast delivery either cut corners or under-scope). Documented rules of engagement and communication protocols prevent misunderstandings under pressure.
During engagements, watch for regular updates without constant hand-holding requirements. Immediate escalation of critical findings instead of waiting for final reports. Flexibility when client environments don’t match documentation. Minimal disruption to client operations.
Deliverables require the most careful evaluation. Reports should match your client’s technical sophistication level, not follow generic templates. Remediation guidance needs business context and prioritization, not just CVSS scores. Debriefs should educate clients about their security posture, not simply review finding lists. Follow-up availability for questions distinguishes true partners from transactional vendors.
Communication style determines whether partnerships succeed. Partners should communicate through you to clients, protecting your relationship rather than trying to establish direct channels. Technical depth belongs in findings sections, but executive summaries need business impact framing. Willingness to adjust report formats to match client needs shows customer focus. Availability for client calls without positioning themselves as the primary contact maintains proper boundaries.
You’re not buying a commodity service. You’re extending your team’s capability. The right partner makes you look good to your clients. The wrong partner competes with you.
Structuring the Partnership
Getting the relationship structure right matters as much as technical capability.
Partnership Models:
White-Label Arrangement
- Partner works under your brand
- All client communication flows through you
- You own the client relationship completely
- Best for maintaining MSP brand strength
Co-Branded Referral
- Both brands visible to client
- Shared communication responsibilities
- Relationship shared but MSP remains primary
- Better for partners with strong technical reputation
Critical Contract Clauses:
Your agreement should explicitly address:
- Client ownership and non-solicitation
- Communication protocols and approval requirements
- Insurance requirements
- Liability limitations and indemnification
- IP ownership of custom tools or methodologies
- Confidentiality and data handling
- Termination conditions and transition procedures
Red Flag Contract Behaviors:
- Partner refuses non-solicitation clause
- Vague language around client ownership
- Inadequate insurance coverage
- Resistance to white-label arrangements
- No clear communication protocols
Transitioning Existing Clients
You’ve chosen the right partner. Now you need to position offensive security to your existing client base.
The Vulnerability Scanning Upsell:
Your vulnerability scanning clients are the natural first targets. They already understand the value of security testing. Position offensive security as the next maturity level:
“Our quarterly vulnerability scans identify known weaknesses. Red team engagements show us how an actual attacker would chain those vulnerabilities together to compromise your environment. Think of vulnerability scanning as a security checklist. Red teaming shows us if someone can actually break in.”
Industry-Specific Triggers:
Healthcare: “HIPAA compliance requires annual risk assessments, but ransomware attackers don’t follow vulnerability scanning methodology. They exploit configuration issues and trust relationships that automated scans miss.”
Financial Services: “Your regulators are asking harder questions about resilience testing. They want to see adversary simulation, not just compliance scanning.”
Manufacturing: “OT environments have different attack surfaces than IT networks. We need to test those operational technology systems the way attackers actually approach them.”
Pilot Engagement Strategy:
Offer your best existing client a pilot engagement at reduced cost in exchange for:
- Detailed feedback on the partner’s performance
- A testimonial if the engagement goes well
- A case study (sanitized) for future marketing
- Introductions to similar companies in their network
This gives you a controlled test of the partner relationship before broader rollout.
Making the Right Choice
The best offensive security partners combine deep technical capability with proven operational experience and understand they exist to support your client relationships. Start with technical conversations, not certification checklists. The partner who can explain their methodology and reference relevant past work provides more value than the one with the longest credential list.
Ask detailed questions about their approach to environments like your clients’. Request references from similar engagements. Pay attention to how they communicate technical concepts. Partners who can’t explain clearly to you won’t communicate well with your clients.
The evaluation takes time, but the alternative costs more. Choose partners based on capability and fit, not credentials and marketing. Your client relationships depend on it.
Quick Reference: 15 Questions for Your First Partner Conversation
Technical Capability
- Walk me through your methodology for a hybrid cloud environment with AD/Azure integration. What’s your typical attack path approach?
- Describe a situation where your standard tooling wasn’t sufficient. How did you adapt?
- How do you scope engagements for technical complexity versus just counting IP addresses or applications?
- What’s the difference between how you approach a red team engagement versus a penetration test?
- What’s your team’s operational background? Any military/government offensive cyber experience?
- Tell me about a similar engagement you’ve done in [relevant industry]. What were the unique challenges?
- Have you worked with MSPs before? How do you structure those relationships?
Experience and Background
- What’s your team’s operational background? Any military/government offensive cyber experience?
- Tell me about a similar engagement you’ve done in [relevant industry]. What were the unique challenges?
- Have you worked with MSPs before? How do you structure those relationships?
Delivery and Communication
- What happens if you discover RCE or another critical vulnerability during testing? What’s your escalation process?
- How do you de-conflict testing in 24/7 production environments?
- Walk me through your typical report structure. How do you balance technical depth with executive communication
- How do you handle communication with the end client? What role do we play?
Business Structure
- Do you offer white-label arrangements? What does your standard partnership structure look like?
- What are your insurance coverage limits for E&O and cyber liability?
- What’s in your standard non-solicitation agreement?
References and Validation
- Can you provide references from other MSPs you’ve partnered with? What would they say about working with you?
Bonus Question for Technical Validation: “Our client runs [specific technology stack]. They’re concerned about [specific threat]. How would you approach testing for that risk?”
Listen for specificity, not generic methodology frameworks. The right partner will give you a detailed technical answer that demonstrates they’ve seen this before.
Use this checklist in initial partner conversations. The partners who can answer these questions clearly and specifically are worth deeper evaluation. The ones who deflect to certifications or generic methodology probably aren’t ready for a serious partnership.