If you’re on the hook for keeping your company’s email safe, you know it’s not just about blocking spam anymore. Ransomware, phishing, business email compromise—attackers keep changing the rules, and every vendor promises their tool is the silver bullet. It’s enough to make your head spin. This guide is for B2B teams who need to pick an email security tool that actually works for them, not just what looks shiny in a sales demo.
Here’s how to cut through the noise, figure out what matters, and choose a solution you won’t regret.
1. Start With Your Real-World Threats and Needs
Don’t get distracted by features you’ll never use. Start by asking:
- What kinds of email attacks have actually hit us (or companies like us) in the past year?
- Are we mostly worried about phishing? Ransomware? Internal threats?
- What email platform do we use (Microsoft 365, Google Workspace, on-prem Exchange)? Some tools work better with certain setups.
- How big is our team? Do we have in-house IT/security, or is this someone's side gig?
Pro tip: Pull up your last few incident reports or talk to a few users. Real pain points beat vague “industry concerns” every time.
2. Decide What You Actually Need the Tool to Do
Vendors love to tout AI, machine learning, and “next-gen” everything. Here’s a no-nonsense list of what most B2B orgs actually need:
- Spam and malware filtering: Table stakes. Every product does this, but not all do it well.
- Phishing detection: Look for real-world accuracy, not just “99% protection” claims.
- Attachment and URL scanning: Stops malware hidden in files or links.
- Impersonation/BEC protection: Protects against CEO fraud and invoice scams.
- User training or warning banners: Some tools help users spot threats, not just block emails.
- Incident response features: Can you quickly find out what happened, and who got hit?
- Reporting and alerting: Clear, actionable info—not just endless logs.
Nice-to-haves: - Data loss prevention (DLP): Useful if you handle sensitive info, but can be noisy. - Integration with SIEM/SOAR: Only if you already use these tools. - Mobile device coverage: If your team lives on their phones.
Ignore the hype: AI is everywhere, but it’s only as good as the data and tuning behind it. Focus on what the tool actually catches, not buzzwords.
3. Shortlist Real Options—And Weed Out the Overkill
There are dozens of tools out there, from cloud add-ons to full-blown secure email gateways. Some big names: Proofpoint, Mimecast, Barracuda, Microsoft Defender, and newer players like Emailguard.
Here’s how to whittle the list:
- Cloud vs. on-prem: If you’re on Office 365 or Google, a cloud-native tool is usually simpler and cheaper.
- Company size: Some tools are built for Fortune 500s and feel like it—overkill for a 50-person team.
- Budget: Email security isn’t the place to go bargain-basement, but you don’t need a Ferrari to drive to the grocery store, either.
- Support quality: If you need help, will you talk to a human or a bot?
- Customer base: Are they protecting companies like yours, or just selling to everyone?
Red flag: If a tool takes weeks to deploy or needs a dedicated admin, it’s probably too much for most B2B teams.
4. Put Claims to the Test With a Real-World Trial
Don’t buy anything based on a demo or a nicely formatted PDF. The only way to know if a tool works for you is to see it in action.
Here’s how to run a proper trial:
- Pilot with real users: Don’t just let IT test it—let a few normal users experience the filters, warnings, and alerts.
- Send test attacks: Use tools like Gophish or your own red team to simulate phishing and see what slips through.
- Monitor false positives: If legit emails get blocked or land in quarantine, users will hate you (and the tool).
- Check reporting: Can you quickly see what threats were stopped? Or is it a data swamp?
- Test support: File a ticket with a fake issue. See how fast and how well the vendor responds.
Pro tip: Vendors love to hand-hold during the trial. That’s fine, but ask yourself—will you get that level of attention after you sign the contract?
5. Dig Into Pricing—And the Hidden Gotchas
Email security pricing is famously opaque. Here’s what to watch for:
- Per-user vs. per-domain: Make sure you’re not paying for unused accounts or aliases.
- Add-ons: Some “core” features cost extra (like archiving, DLP, or advanced threat protection).
- Long-term contracts: Don’t lock yourself in for three years unless you’re sure.
- Hidden costs: Ask about migration, support, and integration fees.
Watch out: Some vendors make it easy to get started, but hard (and expensive) to leave. Ask about export and data portability up front.
6. Check Integration and Maintenance Burden
A tool is only as good as your ability to keep it running and tuned.
Questions to ask:
- How does it integrate with your email system? Does it require DNS changes, connectors, or agents on devices?
- Who will manage it? If you don’t have a full-time security person, avoid anything that needs constant tuning.
- Updates and tuning: Does it update itself automatically, or will you be on the hook for manual rule changes?
- User experience: Will your team get flooded with confusing warnings, or does it stay out of their way unless something’s really wrong?
Pro tip: Ask for references from similar-sized companies. Find out what everyday life with the tool is actually like.
7. Get Honest About What You Won’t Use
It’s tempting to buy the tool with the most features, but in reality:
- Most B2B orgs never use half the bells and whistles.
- “Advanced” features often sit idle because no one has time to set them up.
- Simpler tools are often easier to maintain and less likely to break.
If you’re not sure you’ll use something (like DLP, encryption, or deep compliance features), don’t pay extra for it. You can always revisit later if your needs change.
8. Make the Call—And Plan for Regular Reviews
Once you’ve narrowed it down, pick the tool that:
- Actually stops the threats you care about
- Fits your team’s size, skills, and budget
- Won’t be a maintenance nightmare in six months
Don’t sweat perfection. No tool is magic. Set a calendar reminder to review how it’s going in six months, and be ready to make a change if it’s not working out.
Keep It Simple and Iterate
Picking an email security tool isn’t glamorous, but it matters. Focus on what you really need, ignore the hype, and don’t get bullied into buying more than you’ll use. Start simple, get feedback from real users, and don’t be afraid to switch things up if something better comes along.
Most importantly: You’re not aiming for “perfect”—just “good enough to keep the bad guys out and the team happy.” That’s a win.