PJ · SideGuy Solutions · Solana Beach
Compliance is a routing problem before it's a paperwork problem. Tell me who's asking you to be compliant — I'll tell you exactly what to do next.
Most companies waste the first month chasing the wrong framework because a salesperson scared them into it. The honest decision tree is short: SOC 2 if enterprise buyers are blocking deals, HIPAA if you touch patient data, FedRAMP for federal contracts, PCI if you handle cards directly, ISO 27001 if your buyers are international. Pick one, finish it, then add the next — never run two cold-starts at once.
Every framework below links to a real SideGuy guide. The "Who needs it" and "Typical first-year cost" columns are operator estimates for a small-to-midsize software company — your scope can move them.
| Framework | Who needs it | Typical first-year cost | Start here |
|---|---|---|---|
| SOC 2 Type II | SaaS selling to enterprise; deals blocked by security questionnaires | ~$5K–$15K (platform + auditor) | SOC 2 software guide |
| HIPAA | Anyone touching PHI — health apps, telehealth, medical-adjacent SaaS | ~$3K–$10K (controls + BAAs) | HIPAA SaaS check |
| HITRUST | Healthcare vendors whose customers demand HITRUST over plain HIPAA | ~$15K–$60K (assessor + remediation) | HITRUST e1 vs i1 |
| FedRAMP | Cloud vendors selling to U.S. federal agencies | $$$ — six figures, multi-month | FedRAMP ConMon tools |
| PCI DSS | Anyone handling cardholder data outside a hosted processor | ~$2K–$20K (depends on SAQ level) | PCI compliance software |
| ISO 27001 | Companies with international / European enterprise buyers | ~$10K–$30K (often overlaps SOC 2) | Compliance automation tools |
For 80% of software companies that land here, the answer is SOC 2 Type II first, on Vanta or Drata, with one independent auditor — because enterprise procurement is what actually blocks your revenue, and SOC 2 controls overlap heavily with ISO 27001 and HIPAA if you grow into them. The exception is anyone touching PHI: HIPAA is the floor and comes first, no matter how the deal pressure looks.
Do not buy a multi-framework bundle on day one, and do not let an audit firm sell you the platform, the audit, and the pentest as one opaque number — those should be three separate, comparable line items. SideGuy sits in the operator seat: we help you pick, configure, and prep so the audit is boring. We are not the auditor (that has to be independent), and we will tell you when you do not need a framework yet at all.
Once you know the framework, the next decision is the automation platform and the auditor. These guides compare the real options and flag the contract traps — payout haircuts, lock-in clauses, and "compliance" tools that are really just dashboards.
SideGuy is anchored in North County San Diego. If you want a real human who can sit down with your team in Encinitas, Carlsbad, or Solana Beach, these are the local compliance entry points.
It depends on who is asking you to be compliant. If enterprise SaaS buyers and their security questionnaires are blocking your deals, start with SOC 2 Type II. If you touch protected health information (patient data, PHI), HIPAA is the floor and is non-negotiable. If you sell to the federal government, FedRAMP is the gate. If you take card payments directly, PCI DSS applies. Most software companies should not chase multiple frameworks at once — pick the one your customers actually require and finish it before adding the next. See HIPAA vs SOC 2 — which first.
For a solo founder or small team, expect roughly $5,000–$15,000 in the first year once you add an automation platform (Vanta or Drata, ~$8,000–$12,000/yr), a licensed auditor for the report ($8,000–$20,000 depending on scope and Type I vs Type II), and a penetration test if your buyers require one ($4,000–$10,000). The platform subscription is the recurring line item; the audit recurs annually. Beware quotes that bundle everything into one opaque number — break it into platform, auditor, and pentest so you can see what you are paying for. The solo-founder cost breakdown walks through every line.
If you are pursuing SOC 2, ISO 27001, or HIPAA at any real scale, yes — these tools automate evidence collection, monitor your cloud configuration continuously, and map controls to the framework so the audit goes faster. They do not make you compliant by themselves; they reduce the manual evidence work from weeks to days. For very early-stage companies with one cloud account, you can defer the tool and document controls manually until a buyer forces the timeline. Compare them on Vanta vs Drata.
SideGuy is the operator layer between you and the framework — we help you choose the framework, pick and configure the right vendor (Vanta, Drata, or manual), write the policies, and prep evidence so the audit is boring. We are not a licensed audit firm and do not issue the SOC 2 report or HIPAA attestation — an independent CPA or assessor does that, which is correct because the auditor must be independent. We get you ready; the auditor signs off. That separation protects the validity of your report. Text PJ to scope it, or start at the compliance department.