The SMB Cybersecurity Checklist: What a $50M Company Actually Needs

If you run a $10M–$100M company, cybersecurity probably feels like it's designed for someone else. The products are enterprise-priced. The advice assumes you have a security team. The compliance frameworks read like they were written for banks.

But the threats don't care about your size. Nearly 50% of US small businesses have experienced a cyber attack. Ransomware demands average over $100,000 for companies under 500 employees. And 57% of SMB leaders now say cybersecurity is their top priority — up from 43% just a year ago.

The good news: you don't need enterprise-grade everything. You need the right things in the right order. This checklist is what we recommend to every client based on what we've seen actually work.

1. Multi-factor authentication (MFA) on everything. Email, cloud apps, VPN, financial systems. This single step blocks 99% of credential-based attacks. If you do nothing else, do this.

2. Endpoint protection on every device. Every laptop, desktop, and phone that touches company data needs modern endpoint protection — not the antivirus you installed in 2019. Microsoft Defender for Business or CrowdStrike Falcon Go are solid options under $10/device/month.

3. Automated backups with tested recovery. Backups that you've never tested aren't backups — they're hopes. Set up automated daily backups to a separate location (cloud or offsite), and test a full restore at least quarterly.

4. Email security and phishing protection. 90% of successful attacks start with email. Advanced email filtering, anti-phishing protection, and DMARC/SPF/DKIM configuration are non-negotiable.

5. Access control — least privilege. Every person should have access only to what they need for their job. Review permissions quarterly. Remove access immediately when someone leaves.

6. Patch management. Automate operating system and application updates. Unpatched software is one of the easiest attack vectors. If you can't automate, schedule a monthly patch window and don't skip it.

7. Incident response plan. A one-page document: who do we call, what do we shut down, how do we communicate. You'll never think clearly during an actual incident — this is the document that thinks for you.

8. Cyber insurance. A standalone cyber insurance policy costs $1,000–$5,000/year for most small businesses and covers incident response costs, business interruption, and liability. Your general liability policy almost certainly doesn't cover cyber incidents.

9. Vendor and third-party review. Your security is only as good as your weakest vendor. Know which vendors have access to your data, and ask them basic security questions annually.

10. Employee security awareness training. Not a one-time presentation — quarterly training with simulated phishing tests. Your team is your last line of defense. Make sure they know what a phishing email looks like.

For a company with 25–200 employees, a cybersecurity assessment typically falls into one of three tiers:

Basic vulnerability scan and policy review: $3,000–$5,000 Automated vulnerability scanning of your network and cloud environment, review of your security policies (or creation of basic ones if they don't exist), and a prioritized list of findings. Timeline: 1–2 weeks.

Comprehensive assessment: $7,000–$10,000 Everything above plus manual penetration testing, compliance gap analysis (HIPAA, SOC 2, PCI DSS as applicable), employee security awareness evaluation, and a detailed remediation roadmap. Timeline: 3–4 weeks.

Ongoing managed security: $3,000–$8,000/month 24/7 monitoring, threat detection, incident response, and regular vulnerability management. This replaces the need for a full-time security hire at a fraction of the cost.

Most of our clients start with a comprehensive assessment, remediate the critical findings, and then decide whether ongoing managed security makes sense for their risk profile.

Ransomware remains the most damaging threat. Attackers encrypt your data and demand payment. Average demands for companies under 500 employees now exceed $100,000, and total recovery costs (downtime, remediation, lost business) average $150,000–$300,000. Prevention is dramatically cheaper than recovery.

Business email compromise (BEC) is the most profitable attack. Attackers impersonate your CEO, CFO, or a vendor and request a wire transfer or payment redirect. The FBI reports BEC caused $2.9 billion in losses in 2023 alone. The fix is simple: verify any payment change request by phone using a known number.

Credential stuffing is the most common attack. Automated tools try username/password combinations leaked from other breaches against your systems. MFA stops this completely — which is why it's item #1 on the checklist.

Supply chain attacks are the hardest to prevent. Malware delivered through software updates from trusted vendors. The best defense: keep software updated (patches often close these vulnerabilities), limit vendor access to what's necessary, and monitor for unusual behavior.

Outsource if you have fewer than 200 employees. A full-time senior security engineer costs $150,000–$200,000+ in salary alone — and one person can't provide 24/7 coverage. A managed security provider gives you a team of specialists, 24/7 monitoring, established tools, and shared threat intelligence for $3,000–$8,000/month.

Consider a fractional CISO for strategic oversight. If you need someone to own your security program, drive compliance initiatives, and interface with your board — but can't justify a full-time CISO at $250,000+ — a fractional CISO at $3,000–$8,000/month fills the gap.

Hire in-house when: You have regulatory requirements demanding dedicated security staff, your technology environment is complex enough to require specialized knowledge, or you've grown past 200 employees and need dedicated program ownership.

The hybrid model works best for most SMBs: A fractional CISO for strategy and oversight, plus a managed security provider for day-to-day monitoring and response. Total cost: $6,000–$15,000/month — still less than one full-time security engineer.