The Challenges of Selling vCISO Services

As cybersecurity threats grow more complex and regulatory requirements become stricter, MSPs and MSSPs face increasing pressure to help clients manage risk, ensure compliance, and strengthen their security posture. While offering vCISO services presents a valuable opportunity, many providers struggle with positioning, pricing, and delivering these services effectively. As businesses seek strategic security leadership without the cost of a full-time CISO, MSPs and MSSPs must navigate these challenges to build scalable, profitable vCISO offerings. 

Here are the top 5 challenges of selling and structuring vCISO services and tips for how to overcome them. For more information on how to sell vCISO services, check out our: Ultimate Guide to Structuring and Selling vCISO Services.

We’ll first cover challenges around effectively selling vCISO services then challenges around structuring the services.

1. Educating Clients on the Value of vCISO Services

Many organizations don’t fully understand the role of a vCISO and may not immediately see the difference between basic cybersecurity support and the strategic guidance a vCISO provides. The reality? Clients don’t want a vCISO—they want to be more efficient, attract more customers, and grow their business while reducing risk.

To bridge this gap, MSPs and MSSPs need to take a consultative approach, showing how a vCISO aligns cybersecurity with business goals. Instead of leading with security jargon, focus on tangible outcomes. A vCISO helps organizations navigate regulatory compliance, scale securely, and make informed risk decisions.

For example, in financial services, where compliance with PCI DSS and SEC regulations is critical, a vCISO can do more than just help maintain compliance. They can build a long-term security strategy that protects sensitive data, streamlines operations, and enhances trust with customers.

By positioning vCISO services as a business enabler rather than a technical necessity, MSPs can demonstrate real value—helping clients not just avoid breaches, but accelerate growth and resilience. Want to refine your vCISO offering for maximum impact? Drop me a DM with the word “Outcomes,” and let’s talk strategy.

2. Handling Client Objections

Client objections are a natural part of the sales process, and selling vCISO services is no exception. One of the most common objections when selling vCISO services to organizations is the belief that “I’m too small to be hacked” or “I don’t have any valuable data; cybercriminals only target big companies.” To handle this objection, MSPs and MSSPs must reframe the conversation. Jesse Miller, founder of PowerPSA Consulting and a vCISO expert, recommends asking, “As a business owner, how do you think about revenue? Do you aim to diversify across multiple customers, shorten sales cycles, and minimize risks?” 

Once they agree, explain that attackers operate in a similar manner, seeking diversified revenue and quick returns. Small businesses are often ideal targets for cybercriminals due to shorter transactional cycles and easier entry points. This approach shifts the conversation from fear to proactive risk management and resilience, making cybersecurity a top priority for clients of all sizes.

To further emphasize the point, highlight relevant statistics—such as the fact that 46% of small businesses reported experiencing a ransomware attack in 2023 – to show small businesses are frequently targeted by cybercriminals, which helps reinforce the urgency to act and provides factual evidence to support the conversation.

3. Overcoming Price Sensitivity

Price sensitivity is another common obstacle when selling vCISO services. For many clients, the idea of paying for strategic cybersecurity leadership can be daunting, especially when compared to the costs of traditional IT services or in-house hires. In many cases, clients may see the cost of a vCISO as an unnecessary expense, particularly if they already have internal IT staff or security measures in place.

To overcome this challenge, MSPs and MSSPs must emphasize both the long-term financial benefits of vCISO services and the potential costs of lacking strategic cybersecurity leadership. While the upfront investment may seem high, the ROI can be significant. A vCISO helps businesses reduce the risk of costly data breaches, avoid regulatory fines, and prevent operational disruptions that could impact revenue and reputation. By framing cybersecurity as a business enabler rather than just a cost center, MSPs can better communicate the value of vCISO services in driving long-term stability and growth.

For example, many small and medium-sized organizations only realize the importance of cybersecurity after experiencing one or more attacks. Once they’ve gone through the costly remediation process, they often recognize that investing in preventive cybersecurity would have been far less expensive than dealing with the aftermath of an attack. This shift in perspective is becoming increasingly common as businesses face the high costs of cyber incidents.

Additionally, vCISO services can help optimize existing security efforts, potentially lowering costs by identifying inefficiencies, addressing gaps in coverage, and streamlining processes. For example, one financial services client may have avoided a costly acquisition due to a vCISO’s early detection of potential security risks. Without this oversight, the company could have moved forward with the acquisition, only to discover later that the target company’s systems were compromised. The cost of the acquisition, legal fees, and reputational damage could far outweigh the cost of vCISO services. By presenting these real-world scenarios, MSPs and MSSPs can effectively counter price objections and demonstrate that investing in vCISO services is an investment in risk prevention and business continuity.

Beyond selling, many vCISOs struggle with structuring their services effectively. Here are key challenges they often encounter:

4. Addressing Diverse Client Needs and Expectations

When it comes to structuring services, different clients have different expectations when it comes to vCISO offerings. A one-size-fits-all approach will not work for every client, as organizations vary in size, complexity, and security maturity. For MSPs and MSSPs offering vCISO services, it is essential to tailor the service offering to meet the unique needs of each client.

Segmenting clients based on factors such as industry, company size, and security maturity can help MSPs and MSSPs craft the right solution. For example, small businesses with low security maturity may need basic risk assessments and compliance assistance, while larger organizations with more advanced security needs may require ongoing strategic oversight, incident response planning, and board-level security discussions.

5. Scaling Efficiently

Efficiently scaling vCISO services is essential for long-term success, as these services offer a lucrative opportunity to generate recurring revenue for service providers. In addition, many MSPs and MSSPs struggle to keep up with client needs due to reliance on inefficient manual processes, inconsistent service delivery, and a lack of standardized frameworks. Without a scalable approach, service providers face operational bottlenecks, resource strain, and missed opportunities for growth. Jesse Miller emphasizes that having a standardized approach helps deliver consistent results and manage growth without adding unnecessary complexity. 

By developing repeatable processes, MSPs and MSSPs can serve a larger client base while still maintaining high-quality service. Standardizing your offerings and leveraging frameworks helps meet client needs faster, reduces operational obstacles, and streamlines the sales process, all while ensuring profitability and a positive client experience.

• Focus on scaling services you are already proficient in, rather than reinventing your offerings.
• Develop pre-built templates and frameworks tailored to each client segment. This minimizes the need for customization and accelerates the sales process.
• Ensure your messaging resonates with client needs, emphasizing that you understand their industry, challenges, and objectives.

Additionally, the right tools – such as the Cynomi vCISO platform – are essential to automate many of these activities—especially in risk assessments, compliance checks, and reporting—so that you can manage and scale your offerings efficiently. With automation and standardized frameworks, you not only ensure consistency but also enhance the client experience and reduce the operational complexity of running a vCISO service.

Conclusion

Selling vCISO services offers MSPs and MSSPs an excellent opportunity to strengthen customer relationships, drive revenue growth, and scale their operations. However, it also comes with its own set of challenges, including educating clients on the value of these services, addressing price sensitivity, and meeting the diverse needs of various clients. 

By adopting a consultative approach, handling common objections, and emphasizing long-term ROI, MSPs and MSSPs can overcome these hurdles. Moreover, scaling vCISO services efficiently requires standardizing offerings and leveraging automation tools to streamline processes and maintain consistency. By overcoming these challenges, MSPs and MSSPs can successfully launch vCISO services, stand out in the market, and build lasting, profitable relationships with clients.