The Benefits and Concerns of Free Trials & POVs of Cybersecurity Products

Who is Nick Ryan?

Nick Ryan is an experienced cybersecurity professional currently serving as a Business Information Security Officer (BISO) at RSM US LLP, a position he has held since March 2022.

With over 15 years of experience in the field, Nick has established himself as a leader in information security and risk management.

Prior to his current role, Nick held several significant positions that contributed to his extensive expertise.

He served as the Director of Information Security at Coyote Logistics for nearly four years, where he was responsible for developing and implementing the company's information security strategy.

Before that, he spent over six years at Trustwave, progressing from a Senior Security Consultant to the Director of Security Consulting.

Nick's career also includes roles at organizations such as Discover Financial Services and Accenture, where he honed his skills in various aspects of cybersecurity and risk management.

He has further enhanced his expertise with professional certifications, including CISSP (Certified Information Systems Security Professional) and CISA (Certified Information Systems Auditor).

Throughout his career, Nick has demonstrated a strong ability to align security initiatives with business objectives, manage global teams, and implement effective security programs.

His experience spans multiple industries, including financial services, logistics, and consulting, giving him a broad perspective on information security challenges and solutions.

As a BISO at RSM US LLP, Nick likely plays a crucial role in bridging the gap between business operations and information security, ensuring that security measures support and enable the company's strategic goals while effectively managing risk.

Pro Tip for Connecting with Nick

To effectively connect with Nick, be direct, honest, and prepared.

Start by being upfront about your solution’s capabilities and limitations—Nick appreciates vendors who acknowledge gaps rather than oversell.

He’s interested in real use cases backed by tangible data, so lead with specific metrics and practical examples, not buzzwords.

Respect his time by keeping meetings concise and sending agendas in advance.

Be a resource, not just a salesperson, by offering relevant insights or educational content that aligns with his strategic goals, like compliance updates or industry trends.

On LinkedIn, engage thoughtfully by sharing insights, not pitching directly.

Follow up with personalized emails that reflect his unique challenges and the conversation you’ve had, showing that you’ve listened and tailored your approach.

Demonstrating long-term value is key, so frame your solution’s benefits as part of a broader strategy that aligns with Nick's focus on revenue protection and compliance efficiency.

Insights and Key Takeaways

CISOs Crave Authenticity, Not Buzzwords

Insight: CISOs need more than trendy marketing terms; they want straightforward, genuine communication and practical solutions.

Buzzwords like "zero trust" and "SASE" often dominate sales pitches, but they can come off as disingenuous when not backed by clear explanations or meaningful context.

For CISOs, it’s not about adopting the latest buzzword; it's about understanding how a solution genuinely addresses core security needs.

If vendors fail to demonstrate a clear path to solving problems, trust erodes quickly.

Free Trials and Proofs of Value (POVs) Are Crucial But Risky

Insight: While free trials and POVs are key for evaluating solutions, CISOs are wary of excessive permissions and complex unwinding processes.

Free trials and POVs help vendors showcase their capabilities, but they also introduce risks.

CISOs carefully consider which trials to allow, as some require deep access to environments.

This raises security concerns, especially when vendors request broad permissions.

Additionally, once integrated, some trials are challenging to unwind, which adds friction and potential risk.

Vendors that offer trials with minimal, clear permissions are more likely to gain trust and traction with CISOs.

Data Protection Solutions Are Essential for CISOs

Insight: Protecting data effectively remains the most significant challenge for security leaders, driving their evaluation of tools and strategies.

For CISOs, data management is the bleeding-neck challenge.

Ensuring data is encrypted, secure, and accessible only by authorized users is a top priority.

Solutions like SecureCircle, which offers transparent encryption across all file types, align well with this goal.

They not only protect sensitive data but also offer peace of mind—critical for security teams under constant pressure to prevent breaches.

CISOs Value Transparent and Honest Vendors

Insight: Transparency and honesty from vendors are crucial to building lasting relationships with CISOs.

CISOs appreciate vendors who are upfront about both their strengths and limitations.

They are turned off by vendors who avoid discussing shortcomings or deflect questions about competitors.

Transparency helps CISOs make more informed decisions, as it allows them to understand where vendors might excel and where they might need improvement.

The Sales Process Needs to Be Adapted to a CISO’s Reality

Insight: CISOs have busy schedules, so vendors must be upfront and efficient with their outreach to gain traction.

Security buyers often face packed schedules, making it essential for vendors to respect their time.

Requests for “15 minutes” should be genuine, as overstating the brevity of meetings only adds to distrust.

The most successful vendors are those who prioritize relationship-building over immediate sales and take a long-term view of success.

TL;DR

If there’s one lesson to take away from this episode, it’s that trust isn’t built on buzzwords or flashy demos—it’s built on clarity, transparency, and genuine problem-solving.

CISOs like Nick are not just gatekeepers; they are partners looking for meaningful solutions.

Vendors need to approach the sales process with empathy, honesty, and a deep understanding of the challenges CISOs face.

Selling security solutions isn’t about quick wins; it’s about nurturing relationships over time by delivering real value and standing by your word.

You can’t fake trust—it’s earned through every conversation, every demo, and every follow-up.

Until next time,
Dani