Caleb Mattingly is the founder and CEO of Secure Cloud Innovations, where he helps SaaS and tech companies simplify compliance and strengthen security without slowing down growth. A CISSP with 7 years of hands-on experience, Caleb blends deep technical expertise with a passion for making audits painless and practical.
I’ve worked with dozens of founders, CTOs, and RevOps leaders who are navigating SOC 2 or ISO 27001 for the first time. Whether it’s a sales blocker or a board directive, compliance becomes a priority real fast.
Over time, I’ve noticed the same five questions always come up so I figured I’d lay out our most honest answers here.
1. “When should we get SOC 2 or ISO 27001?”
This depends entirely on your customers.
Asking your enterprise buyer early, ideally at the start of a POC, shows that you proactively care about security and are serious about protecting their data. It’s one of the easiest ways to build trust fast.
Most teams assume they should wait and hope compliance doesn’t come up during the deal cycle. But the reality is that when you reach the end of a 3-month POC and your customer says, “Great, we’re ready to buy! Just send over your SOC 2 Type II report,” and you don’t have it… panic sets in.
At that point, your competitor who does have a SOC 2 report can swoop in and close the deal while you’re scrambling to start the process.
Getting a full Type II report in hand takes a minimum of 4.5 months:
- 2 weeks to finalize policies and tooling
- 3-month audit window (mandatory minimum observation window for reputable auditors)
- 2–4 weeks for the auditor to finalize and deliver the report
Bottom line: asking up front is a power move. It shows maturity, transparency, and foresight.. and it creates a better customer relationship.
2. “How do we determine which one to get: SOC 2 or ISO 27001?”
I like to tell people this analogy.
SOC 2 is like the Imperial system, built for the U.S. (we like to be unique).
ISO 27001 is like the Metric system, used everywhere else.
If your customers are U.S.-based and SaaS-native, SOC 2 is likely the right move. If you’re selling into Europe or highly regulated industries like healthcare, fintech, or government, ISO 27001 is often preferred, or required.
In some cases, companies pursue both. We’ve helped teams prioritize based on their buyer mix and roadmap, and even run both frameworks in parallel when timelines are tight.
Resource: No BS Guide To Select Your First Compliance Framework
3. “What are all of the costs associated with getting compliant?”
Here’s a full breakdown:
- GRC Tool (Drata, SecureFrame, etc.): $2,400–$25,000/year
- Audit (SOC 2 or ISO): $5,000–$30,000
- Penetration Test: $3,000–$30,000
- Staff Time (DIY): 150–300 hours
- Support Partner (like us): $2,000/month (Embedded Compliance)
To put that staff time into perspective:
If your team’s average loaded hourly rate is $60/hour and they spend 200 hours getting compliant, that’s $12,000 in hidden internal cost, on top of the learning curve, delays, and distractions from product or sales work.
With SCI, we take 98% of that off your plate.
Resource: The Cost of Compliance
4. “Is a penetration test required to be compliant?”
No, it’s technically not required, but it’s highly recommended.
Most enterprise security reviews will specifically ask for a pen test report, and some won’t proceed without one. It’s also just good practice if you’re serious about your security posture.
When you’re evaluating vendors, make sure a retest is included in the price. That way, once you remediate any findings, you can request a clean, customer-facing report.
Resource: Pen Testing for Startups
5. “How much time will this take for my team if we DIY vs. use SCI?”
We track this pretty obsessively. Here’s what we see on average:
- DIY: 150–250+ hours spread across engineering, ops, security, and leadership
- With SCI: 15–40 hours total, mostly in quick async reviews and once-per-week live calls
One of our clients recently told us his founder friend spent 40+ hours in one month just setting up their GRC tool… meanwhile, he’d spent just 3.5 hours and was already halfway done with implementation.
Final Thought
Compliance doesn’t have to be a massive time suck or sales blocker.
With the right strategy, and the right compliance partner, you can use compliance to build trust, move faster, and close bigger deals.
If you’re thinking about SOC 2 or ISO 27001 and want to make it as low-lift as possible, let’s talk.
We’re Secure Cloud Innovations and we’ll get you there.
