Free in Cybersecurity: How Founder-Led Offers Win Early Deals

In cybersecurity, enterprise sales don’t follow the typical SaaS playbook. There’s rarely a self-serve signup, no viral usage loop, and very little patience for tools that promise visibility but don’t fix anything. The space is flooded with dashboards and posture management tools that highlight issues — and then leave the solving to someone else.

Security leaders are tired of it. If you want to stand out, you need to go beyond just showing the problem. Startups should find risks for free — and offer to fix them for a fee.

That’s the go-to-market motion behind some of the fastest-growing cybersecurity companies of the last decade. From Wiz to CrowdStrike, from Okta to Abnormal Security, the early traction came not from giving away product features, but from offering focused, frictionless assessments that surfaced serious risks and then proved the value of solving them.

Why Free “Problem Discovery” Usually Beats Traditional Freemium

Freemium and product-led growth work when users can experience value independently. But in security, “value” is often invisible. No breach, no problem. Until something goes wrong, it’s hard to know whether a tool is doing its job.

Free assessment offers flip that script. Instead of waiting for a user to stumble across value, they actively surface real, urgent risks — inside the prospect’s own environment.

Wiz is a standout example. They didn’t build a free tier or open up their UI. Instead, the founders offered a no-cost, agentless scan of a company’s cloud infrastructure. The result? Immediate visibility into misconfigurations, excessive permissions, and sometimes even sensitive data exposed to the internet. One scan might reveal that “85% of your cloud instances are misconfigured” or “200GB of PII is publicly accessible.” No sales pitch required after that.

Zscaler offered a security preview tool that simulated common attacks and showed which ones got through. Abnormal Security made it easy to connect to Microsoft 365 or Gmail and then delivered a crisp report showing phishing attacks that bypassed the company’s current filters — sometimes dozens per month, even in well-defended environments.

CrowdStrike offered compromise assessments that uncovered active threats missed by incumbents. Tanium scanned for unmanaged endpoints and missing patches. Okta leaned into time-to-value by letting prospects roll out SSO in minutes, proving that deployment — not just security — was their wedge. Even Snyk, with its more developer-focused motion, won early traction by offering a CLI tool that surfaced security flaws in open-source codebases, prompting broader platform adoption.

These weren’t just freebies. They were calculated, high-signal offers designed to make a business case instantly clear.

From Zero to Ten: Founder-Led, Problem-First

In the earliest stage, founders are the GTM motion. There’s no marketing funnel, no sales team, and limited trust in the market. The best move? Show up with value.

Wiz’s founders reportedly closed their first several million in ARR personally, offering direct scans and walking customers through what they found. Their early assessments required no setup, just API access. When results showed previously undetected risks, the urgency to act was built-in. That speed and clarity helped close Fortune 100 deals in a single quarter —far faster than normal enterprise cycles.

Early Mandiant built a similar wedge. Their incident response teams would deploy tools mid-breach response, help remediate the issue, and then leave the tooling in place — converting emergency response into recurring SaaS revenue. The value was obvious, proven, and already in production.

Amplifier Security is taking a modern spin on this approach. Their Free User Risk Assessment connects to other tools via read-only APIs — no agents, no disruption. Then they surface which users are most at risk based on device posture, MFA gaps, and policy drift. It’s a fast way to visualize operational blind spots across identity and endpoint — built entirely from the customer’s real environment.

These founder-led sales weren’t about “try our tool” or worse "check out our cool security platform" — they were “let us show you what’s broken.” That subtle shift makes all the difference.

The 10-to-100 Playbook: Productizing Discovery

As companies grow past the first ten customers, the motion has to scale. The discovery offer evolves from founder-driven consulting into a structured playbook.

Here’s how the best teams did it:

• Lower the barrier to participation. The offer must be lightweight, fast, and safe. Think read-only API access, no agents, no risk. Abnormal Security’s assessment takes five minutes to set up. Cyera scans your cloud for exposed sensitive data with minimal effort. This simplicity increases conversion.

• Highlight one killer insight. Don’t overwhelm the prospect with raw data. Point to a specific, uncomfortable fact: “23 phishing emails reached your C-suite last month.” “Sensitive HR data is accessible to 14 developers.” The goal is to create that one stat that drives internal urgency.

• Package results for internal sharing. A well-designed summary — clean visuals, quantifiable risk, and a clear path forward— turns your internal champion into a seller. Abnormal branded their deliverables as CARE (Cybersecurity Assessment Report for Email). Cyera framed risk in terms of business data exposure. These weren’t just scan results. They were sales tools.

• Build a specialized delivery team. Many companies hired dedicated security engineers or consultants to run and present these assessments. These weren’t generic SEs… they were part technical, part advisory, and skilled in storytelling. Some vendors even created “assessment squads” that could deliver dozens of high-quality engagements per quarter.

• Scale through ecosystem partnerships. Microsoft routinely funds partners to deliver free security workshops and assessments, driving adoption of its broader suite. Wiz partnered closely with cloud providers like AWS and Azure, making their discovery offer a value-add in joint sales motions. These partnerships allowed the free assessment model to scale without dramatically increasing CAC.

• Leverage the insights. With 50+ assessments under your belt, you can start publishing trends: “60% of mid-market orgs have dormant admin accounts exposed.” These anonymized insights feed thought leadership and drive inbound interest. They also make buyers wonder: Are we in that 60%?

Why This Works in Security (and PLG is rare)

In security, the absence of a problem isn’t evidence of value. A freemium tool that sits idle and “works” by doing nothing won’t compel a buyer to act.

A well-executed free assessment, on the other hand, surfaces latent pain. It forces internal conversations. It shows a problem that needs solving, now. That clarity shortens sales cycles and elevates urgency.

More importantly, it earns trust. Security buyers are inundated with noise. But if your team shows up, finds a real risk in a safe, consultative way, and offers to fix it? That’s value. That’s credibility. And that’s how you win enterprise trust early.

For Founders: A GTM Motion That Drives Results

If you’re building in cybersecurity today, start with a free offer that reveals a real risk — fast. Before you’ve hired a sales team or scaled a repeatable motion, this is your wedge. The most effective early-stage GTM strategy is a founder-led assessment that surfaces something specific, urgent, and painful inside the customer’s environment. Below is a breakdown of the six essential ingredients that make this kind of offer work. It’s not a gimmick. It’s how you earn trust, trigger urgency, and open the door to your first ten customers.

Of course, having the right ingredients is only half the job - the rest is how you deliver it. Your goal isn’t to show off product features. It’s to walk the customer through the problem with clarity and credibility. Think like a virtual CISO: explain what’s exposed, why it matters, and how to fix it. That’s what makes the risk real. And when your output is packaged in a way your champion can carry forward — concise, visual, and tied to impact — it becomes more than a scan. It becomes a case for action.

This founder-led approach sets the tone for your entire GTM. It creates urgency without pressure, positions you as a partner (not just a vendor), and builds trust from the first meeting. Done well, it leads directly to high-conviction sales. And when the fix maps cleanly to your product, the conversion is natural. That’s why this model works. It’s not just about discovering risk - it’s about becoming the trusted partner who helps solve it.

Because in security, the companies that grow fastest are the ones that help customers see the problem — before selling the solution.