Balancing Risk and Reality: A Cybersecurity Playbook for Businesses with Dutch Schwartz of Side Channel

Welcome to another episode of Mastery Fractional CFO’s Punchy Podcast — the short, sharp show where we bring you impactful insights from leaders across industries. I’m Ryan Chenier, founder and CEO of Mastery Fractional CFO Services, and today’s guest is Dutch Schwartz, VP of Cloud Services and a fractional Chief Information Security Officer (CISO) at Side Channel.

Dutch sits at the intersection of enterprise security and strategic business growth. With a career that spans Fortune 100 giants and nimble startups, Dutch offers clients global expertise in cloud services and cybersecurity risk management — the kind that saves you money and headaches when things go sideways.

From AWS to Advisory: Dutch’s Career Pivot

After a five-year run at Amazon Web Services (AWS), Dutch transitioned into advisory work with Side Channel, a boutique cybersecurity firm that acts as a “parallel channel” of support for growth-minded companies. He now splits his time between leading Side Channel’s cloud services practice and serving as a virtual CISO for engineering and tech-forward organizations.

He describes his role as less about revenue thresholds and more about a company's maturity curve. If you’re not ready for a full-time CISO but are grappling with compliance requirements or cybersecurity challenges, that’s when Dutch steps in.

“We’re typically brought in when a company knows they have a challenge, but they’re not quite ready to hire someone full-time. That’s where fractional leadership shines.”

Who Needs a Fractional CISO?

Dutch works primarily with clients across North America and Southeast Asia — companies that are either facing explicit events (like audits, funding rounds, or IPO prep), or implicit ones (such as building a factory or launching a new product line).

Sometimes the trigger is a private equity firm asking, “When’s the last time you had a security assessment?” Other times, it’s a COO recognizing that the business needs to level up.

Either way, Dutch provides more than a penetration test. He delivers a strategic lens — “alignment, prioritization, focus” — customized to your sector’s specific risks and requirements.

The Cost of Waiting Too Long

When companies delay addressing cybersecurity risks, the costs stack up fast. Dutch shared a real-world scenario involving a small manufacturing firm that believed they were too small to be targeted.

They were wrong.

An attack halted production, caused immense financial strain, and exposed the fallacy of “we’re too small to matter.” Most breaches aren’t about targeted attacks — they’re crimes of opportunity.

“If you make yourself just a little harder to access, attackers move on. They're not targeting you — they’re targeting an easy opportunity.”

That’s why Dutch advocates for early-stage, preventative action. According to data, investing in cybersecurity in the first 12–18 months of growth is when preventative measures yield the most return.

Risk Management Isn’t “No” Anymore

Dutch pushes back against the outdated notion that security professionals are blockers — the so-called “Department of No.” Instead, he sees himself as a strategic advisor who helps boards and CEOs make informed decisions about which risks are acceptable and which aren’t.

He uses tools like:

• Risk appetite assessments (what kind of risk are you willing to take?)

• Tolerance thresholds (how far can we push that risk?)

• Scenario modelling (what does accepting this risk really look like?)

Whether it’s about deploying a new ERP system in Europe or adjusting cyber insurance, his approach is grounded in aligning security with business goals.

What SMBs Can Do Today

If your company isn’t quite ready for a fractional CISO, Dutch recommends checking out the U.S. Cybersecurity & Infrastructure Security Agency (CISA) resources for small businesses.

“Use multi-factor authentication. Use a password manager. Start with basic, effective steps — they make a huge difference.”

For businesses in the $3–10M range, these foundational measures help prevent catastrophic events and prepare you for future growth.

Cross-Functional Synergy: The Bigger Picture

Throughout the conversation, Dutch and I aligned on a core truth: business success is about collaboration across functions. Whether it’s HR, IT, finance, or operations, no one team can carry the load alone.

Dutch summed it up by reflecting on what he’d tell his younger self: talk to your peers in other departments. Understand the whole business, not just your corner of it. That’s how strategic alignment — and growth — really happens.

“We translate strategy into numbers. Dutch translates risk into business impact. That’s the synergy.”

The CFO Question

As part of every Punchy Podcast episode, we flip the mic and let the guest ask a CFO question. Dutch asked what IT and security leaders should be asking sooner.

My answer? Understand the three pillars of business — finance, operations, and sales — and make sure they’re all aligned. That’s the stool your company’s success sits on. And when they’re out of sync, your whole foundation gets shaky.

Final Thoughts

“Sooner is always better. It costs less money. You don’t need to engage me tomorrow, but talk to someone now. It could be a friend, a peer, or even a resource online — just start the conversation.” - Dutch

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📩 Want to work with a fractional CFO? If you’re ready to transform your company’s financial strategy, reach out to Ryan at Mastery Fractional CFO Services — let’s discuss how we can move your business forward here: https://www.masterycfo.com/contactus.

Ryan Chenier is a #FractionalCFO and the Founder of Mastery Fractional CFO Services. Find out more about Mastery Fractional CFO Services and connect with Ryan Chenier on LinkedIn here: https://www.linkedin.com/in/ryanchenier/.

For more on Dutch Schwartz and his business expertise, look at his LinkedIn: Dutch Schwartz

Interested in being a guest? Reach out to us on our contact-us page here: https://www.masterycfo.com/contactus.

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