How to Hire the Right vCISO for Your Business

Security is a revenue driver. When you can answer security questionnaires in hours instead of weeks and pass compliance audits on the first try, you can close deals faster. But for many organizations, hiring a full-time Chief Information Security Officer may not be feasible. 

That's why virtual CISOs (vCISOs) have gone mainstream. Helping businesses do more than check security boxes, vCISOs can build security programs that unlock growth

This guide shows you how to find and hire a vCISO who delivers measurable results: faster audit cycles, higher questionnaire pass rates, and security that scales with your business.

What is a vCISO? 

A virtual Chief Information Security Officer (vCISO) is a senior security leader hired on a flexible basis, usually part-time or contractual. They perform the same tasks as a full-time Chief Information Officer (CISO) or CIO, but with more flexibility and less overhead costs. 

A vCISO can: 

• Deliver continuous security leadership
• Design and execute security initiatives 
• Accelerate compliance
• Complete risk assessments 
• Prepare audits 
• Improve incident response to cyber threats 
• Plan, mitigate, and review third-party risk management
• Free up key staff members to focus on critical work

A good vCISO will combine hands-on technical expertise, executive-level vision, and cutting-edge tools to strengthen your company’s security posture—making them valuable for many startups and hypergrowth companies in 2025. 

Dig deeper: vCISO vs. CISO: How to Make the Right Choice (From Someone Who Operates as Both)

What are the Benefits of Hiring a vCISO?  

• Specialized cybersecurity tools and resources: If you work with a vCISO firm like Workstreet, you will get access to a range of cutting-edge tools, like advanced analytics and automation tools that you may not have had access to otherwise.
• External perspective: If you hire an experienced vCISO, they will have lots of experience working with a range of clients across industries. This makes it easier for them to identify potential vulnerabilities, mitigate cyber attacks, offer fresh insights, and problem-solve to improve your security posture.
• Cost savings: Hiring a full-time CISO can come with constant turnover, and rehiring for an executive-level role is a time-consuming and expensive process. Many vCISOs have ongoing business relationships with their clients, making them a reliable “interim CISO” option.
• Flexibility and scalability: vCISOs offer flexibility and scalability compared to traditional CISOs, making them useful for various organizations. Do you need surge capacity for an audit? Need more help with vendor questionnaires? vCISOs can be brought on to work based on your needs. 

When Do I Need a vCISO? 

Before you select and hire a vCISO, it’s important to evaluate your company’s needs and determine whether a vCISO would be a good fit. Here are some situations where you could benefit from hiring a vCISO: 

• Your internal team requires guidance around security risks. 
• You need to complete complex vendor security questionnaires.
• You need to comply with regulations like SOC 2, HIPAA, or GDPR, but lack the expertise for full regulatory compliance. 
• You want to hire a security leader, but have budget constraints. 
• You’ve bought security and compliance automation software but need help with setup and implementation.
• You are between CISOs and need an interim CISO as soon as possible. 
• You have experienced an increased number of security incidents and concerns and need expert guidance. 
• Your key team members are spending time focusing on manual security tasks instead of critical work or driving sales. 

What To Look For in a vCISO

Here’s what you should consider before hiring a vCISO: 

1. Industry Certifications and Credibility

Any vCISO should have relevant certifications. Common certifications include CISSP, CISM, CCSP, and CISA. But alongside these certifications, you want someone who has extensive experience guiding security teams, passing audits, and driving ROI. 

2. Strategic and Hands-on Expertise 

You don’t want to hand the keys to your security team to someone who hasn’t been there and done it before. When hiring a vCISO you should look for someone who has experience leading security strategy and operations at other similar companies. 

3. Understanding of Industry Requirements 

A vCISO should be familiar with industry-specific regulations as well as important compliance frameworks like SOC 2, HIPAA, GDPR, and ISO 27001.

4. Strong Communication Skills 

vCISO is a leadership role. Whomever you bring in will need to be comfortable and confident commuting tasks, updates, and complex security issues and strategies to your wider team. 

5. Availability and Flexibility 

One of the key reasons for hiring a vCISO is flexibility. You want someone who can scale with your needs without the need for internal executive overhead or oversight. 

Where To Find a vCISO

Security companies: Businesses like Workstreet provide vCISOs services, providing a dedicated security team that scales with your needs. When you hire a business like Workstreet, you’re getting a whole team, not just one person. 

Direct referrals: Speak to founders and CEOs you know at companies in a similar stage to you. If you know anyone who’s just passed SOC 2 or ISO 27001 you could also know who they used. Many board members and investors will also know vCISOs from their portfolio companies. 

LinkedIn search: If you can’t find any referrals from your network, LinkedIn may be a great place to head next. Search for people with "vCISO" or "fractional CISO" in their profiles. You could also post the role on LinkedIn as a job listing to attract the right talent. 

How to hire the right vCISO

Skip the generic interview questions, you’re hiring fractional security leadership for your business, not an entry level graduate. Instead, speak with candidates about real security scenarios your business is facing—this could be upcoming audits, challenges scaling security questionnaire responses, or scaling your tech stack and ask how they approach the challenge. You want to get a sense of how they approach real issues, not just what qualifications they have. 

It’s also worth getting them to connect with both your engineering team and your C-suite leadership team to see if they can effectively communicate with both. 

And finally, make sure you’re crystal clear on the role, how it fits into your business and what your expected outcomes from the partnership are. 

How to Build a Successful Partnership

Give your vCISO one main internal point of contact, not a committee. You don’t want your vCISO getting stuck in endless loops of approvals or dealing with internal admin, you want them fully focused on generating the results you hired them for. 

Also figure out what matters most and ensure it gets tracked—for example: questionnaires answered per week, audit findings closed, time to complete vendor assessments. You want to make sure your vCISO is held accountable to targets and delivering on what you hired them for. 

Hire Workstreet as a vCISO

Workstreet provides a dedicated security team that scales with your needs without the need for internal oversight—perfect for startups and hypergrowth companies that aren’t ready for a full-time CISO.

Why SaaS and AI leaders choose Workstreet as a vCISO:

• Comprehensive security tools and expertise 
• Flexible engagement to scale when you need
• Zero onboarding required

Ready to elevate your security program with Workstreet? Schedule a call.   

Hiring a vCISO FAQs

How much does a vCISO typically cost?

Depending on their scope, a vCISO will cost $3,000 - $8,000 per month. This is more cost-effective when hiring a full-time CISO, which costs over six figures annually (plus benefits).

How long does it take to onboard a vCISO?

Typically, a new vCISO will take anywhere from 1-4 weeks to successfully onboard. This includes integrations, knowledge transfer, stakeholder introductions, and current security posture evaluations. 

What’s the biggest mistake companies make when hiring a vCISO?

Many companies wait too long before hiring a vCISO. Bring in a vCISO early to ensure audit-readiness, prevent data breaches, and set the foundation for scalable security growth.