When to Hire Your First Compliance Person

One of the most common questions I get from fintech founders: "When do I need to hire a compliance person?" The answer, like most things in compliance, is "it depends" — but there are some useful frameworks.

Signs You're Too Early

Hiring a full-time compliance professional when you don't need one is expensive and counterproductive. Signs you might be jumping the gun:

• You're pre-product — You don't even know what you're building yet. Compliance needs follow from business model; nail the model first.
• You're pre-revenue with no regulatory obligations — If you're building pure software with no money movement, you may not need dedicated compliance staff for a while.
• Your compliance work is <10 hours/week — At this stage, a founder or ops person can handle it, supplemented by external advisors.
• You want compliance to "figure it out" — If you don't understand your compliance obligations yourself, a hire won't fix that. Get educated first.

Signs You're Too Late

Waiting too long creates different problems — usually harder to fix. Red flags:

• Compliance is blocking deals — Partners, banks, or investors are asking questions you can't answer.
• The founder is drowning — Compliance is taking 20+ hours/week from someone who should be doing other things.
• You're reacting instead of planning — Every compliance question is a fire drill because there's no systematic approach.
• You've received regulatory inquiries — If a regulator has reached out, you needed compliance help yesterday.
• You're about to scale — Going from 100 to 10,000 customers requires different compliance infrastructure.

The Decision Framework

Here's a more structured way to think about it:

Customer count is just one variable. Other triggers that accelerate the timeline:

• High-risk business model (crypto, lending, payments)
• Multi-state or international operations
• Significant transaction volumes
• Complex partnerships (banks, networks, sponsors)
• Pending regulatory exam or inquiry

What to Look For in Your First Hire

When you do hire, what matters most?

Adaptability Over Pedigree

Your first compliance hire will wear many hats. Someone who's spent 15 years in a large bank's compliance department might struggle with the ambiguity and breadth of a startup. Look for people who've worked in dynamic environments and can context-switch.

Commercial Awareness

The worst compliance hires are pure "no" people. Your first compliance person needs to understand the business and find ways to enable growth while managing risk. "We can't do that" should always be followed by "but here's what we could do instead."

Relevant Experience (But Not Too Narrow)

Experience in your specific domain is valuable, but don't over-optimize. Someone who's built compliance programs across fintech, payments, and crypto might be more valuable than someone who's only ever worked at companies exactly like yours.

Communication Skills

Compliance touches every part of the company. Your first hire needs to explain complex requirements to non-compliance audiences, push back on business demands when necessary, and represent the company to regulators and partners.

Alternatives to Hiring

Full-time isn't the only option. Consider:

• Fractional compliance officers — Experienced professionals working part-time across multiple companies
• Compliance-as-a-service — Outsourced teams handling operational compliance
• Advisory retainers — Ongoing access to expertise without full employment

These can bridge the gap between founder-led compliance and your first full-time hire, often at lower cost and with more flexibility.