When Should Your Small or Medium-Sized Business Consider a Wingman for Cybersecurity advisory services?
Cybersecurity has become a boardroom conversation for companies of every size. While enterprise organizations have long employed Chief Information Security Officers (CISOs) to steer their security strategies, many small and medium-sized businesses (SMBs) lack the resources for a full-time executive in this role.
That’s where Refoundry ‘s Wingman comes in. Wingman can offer the same expertise, but in a flexible, right-sized model.
If you’re wondering whether a Wingman Cybersecurity Advisory is right for your business, let’s walk through the why, the how, and the benefits.
Why SMBs Hire Wingman Cybersecurity Advisory Today
SMBs are facing many of the same threats as large enterprises. Ransomware, phishing, insider risks, and regulatory requirements are all concerns for SMBs, but often without the same level of in-house expertise. Many hire Wingman because:
- Clients and partners demand stronger security. Business relationships increasingly depend on demonstrating compliance with frameworks like SOC 2, ISO 27001, HIPAA, or GDPR.
- The cost of a breach is devastating. Even a single incident can cripple operations and reputation. The global average cost of breach in 2025 being $4.88 million.
- Cyber insurance requires it. Insurers often expect to see clear leadership in security governance.
- Talent is scarce. Recruiting and retaining a seasoned CISO is out of reach for most SMBs. A full-time CISO can earn over $200,000 per year, with salaries in larger companies or highly regulated industries often reaching the high $200,000s.
How Wingman Differs from a Traditional CISO
Engagement model: A traditional CISO is a full-time executive. Wingman is built for SMBs that need the same caliber of expertise but in a more flexible, right-sized model.
Flexibility: Wingman adapts to your needs, whether that’s strategic guidance a few hours a month, hands-on leadership for a project, or ongoing partnership as your business scales.
Cost: With Wingman, you gain access to top-tier security leadership without the six-figure salary, benefits, or overhead tied to a permanent executive role.
Breadth of experience: Wingman draws on experience across industries and environments, giving you a wider lens than what a single in-house executive might provide.
Benefits of Working with Wingman
- Immediate expertise – Skip the hiring cycle and gain instant access to a proven security leader.
- Right-sized investment – Pay only for the level of involvement your company requires.
- Smarter strategy – Align your security roadmap with business growth, not just IT operations.
- Peace of mind – Take the weight of cybersecurity leadership off overextended IT managers and into expert hands.
Services Wingman Provides to SMBs
Wingman is designed to cover the critical bases SMBs often struggle to resource internally, including:
- Risk assessments and security posture reviews
- Policy and procedure development
- Compliance program design and audits (SOC 2, HIPAA, ISO 27001, etc.)
- Security awareness training programs
- Vendor and supply chain risk management
- Incident response planning and tabletop exercises
- Security awareness training programs
- Board-level reporting and strategic roadmaps
- Security tools rationalization
- Security Guidance
Responsibilities Wingman Owns
When you engage Wingman, you’re not getting advice in a vacuum, you’re getting accountability. Wingman owns:
- Establishing and maintaining your security strategy
- Reporting to executive leadership or the board on risk and readiness
- Overseeing regulatory and industry compliance
- Coordinating with IT staff, MSPs, or internal security teams
- Leading incident response and remediation when issues occur
The goal is to provide true leadership and ensure security gets done.
How to Engage Wingman
- Define your needs – Compliance support, strategic guidance, or ongoing leadership.
- Start small – Kick off with an assessment or targeted project to establish the relationship.
- Scale as needed – Wingman flexes as your business grows, from quarterly check-ins to embedded leadership.
Final Thoughts
For SMBs, a full-time CISO often isn’t realistic. But ignoring cybersecurity leadership isn’t an option. Wingman gives you the strategy, credibility, and accountability of a seasoned security leader, at a scale and cost that fits your business.
In short: Wingman is your copilot when security becomes too complex, too costly, or too critical to leave as a side job.
