When Should a Nonprofit Outsource Compliance?

SPEAKER_01: 0:00

Welcome to the Nonprofit Compliance Brief, where we explain charitable solicitation and multi-state fundraising requirements in clear, practical terms for nonprofit leaders and finance teams. This podcast is produced by Ironwood Registrations.

SPEAKER_00: 0:13

It is uh really great to be here.

SPEAKER_01: 0:15

Yeah, we’re thrilled to have you. So today we’re diving into a subject that I think um, well, it haunts the to-do lists of just about every nonprofit leader I know.

SPEAKER_00: 0:24

Oh, absolutely. It’s a universal stressor.

SPEAKER_01: 0:27

Right. It’s that specific and often really stressful evolution of how an organization handles its legal paperwork. Specifically, we are talking about that tipping point where, you know, handling it in-house stops feeling like a smart, scrappy, cost-saving measure.

SPEAKER_00: 0:42

And starts feeling like a massive liability waiting to happen.

SPEAKER_01: 0:45

Exactly. It just becomes a risk.

SPEAKER_00: 0:47

Right. And I think it’s really about recognizing the life cycle of compliance. Most organizations, they uh they start in one place and they end up in a completely different one.

SPEAKER_01: 0:56

Aaron Powell But they try to use the same systems for both.

SPEAKER_00: 0:58

Yes, exactly. So the mission for this deep dive today is to really map out that life cycle. We want to go from the startup days all the way to multi-state expansion and you know, help you figure out if your internal systems have actually hit a wall.

SPEAKER_01: 1:12

Aaron Powell And what strikes me about this topic is that it’s not really about the paperwork itself.

SPEAKER_00: 1:17

No, not at all.

SPEAKER_01: 1:18

It’s about organizational maturity. It’s about recognizing that what got you here won’t necessarily get you there. So let’s just start at the beginning, the starting line. I think we all have a uh a mental image of the early stage nonprofit.

SPEAKER_00: 1:32

Aaron Powell Oh, for sure. It’s the classic kitchen table phase. Or maybe the, you know, the shared co-working space phase.

SPEAKER_01: 1:38

Right.

SPEAKER_00: 1:38

In this stage, compliance isn’t a department. It isn’t even a specific job title. It’s essentially just a task list.

SPEAKER_01: 1:44

Aaron Powell And who usually ends up holding the bag for that list?

SPEAKER_00: 1:47

Literally everyone. It’s that classic all hands-on-deck reality.

SPEAKER_01: 1:50

Yeah, the executive director is also the HR manager.

SPEAKER_00: 1:53

And the board treasurer is doing the bookkeeping on weekends. The development director is the IT guy. Compliance, which means filing those initial charitable solicitation registrations, just gets added to whoever has the bandwidth on a Tuesday afternoon.

SPEAKER_01: 2:08

And to be fair, at that stage, um, it usually works.

SPEAKER_00: 2:12

It does work. And it is important to acknowledge why it works so we don’t discourage people who are in that phase right now.

SPEAKER_01: 2:17

Right. We’re not saying it’s bad.

SPEAKER_00: 2:18

No, it works because the scope is naturally narrow. If you are a local animal shelter in Ohio, you’re likely only soliciting in Ohio.

SPEAKER_01: 2:27

You file one form once a year.

SPEAKER_00: 2:29

Exactly. The deadline is predictable, it’s manageable.

SPEAKER_01: 2:32

But there is a massive hidden vulnerability in that simplicity, isn’t there? It’s what people in the industry call the bus factor.

SPEAKER_00: 2:39

Yes, the bus factor. That is the single biggest risk in the early stage. Institutional knowledge is concentrated in one, maybe two people.

SPEAKER_01: 2:47

So let’s say you have an incredible office manager who handles the renewals.

SPEAKER_00: 2:51

Right. They know exactly which file cabinet the state credentials are in. They know the login for the state portal. They probably even have the two-factor authentication code sent to their personal cell phone.

SPEAKER_01: 3:01

And if that person gets a new job.

SPEAKER_00: 3:03

The system walks out the door with them. We see this constantly.

SPEAKER_01: 3:06

Just totally vanishes.

SPEAKER_00: 3:08

A nonprofit is humming along, totally compliant for three years. Then the admin person leaves. Six months later, the executive director gets a nasty letter from an attorney general because nobody knew there was a renewal due in May. The organization didn’t have a process, it had a person. And that works fine until it doesn’t.

SPEAKER_01: 3:31

That brings us directly to the core theme of this discussion. And honestly, the part that is most counterintuitive, it’s the growth paradox.

SPEAKER_00: 3:38

Yeah, the growth paradox.

SPEAKER_01: 3:39

Because we tend to think growth is linear.

SPEAKER_00: 3:41

Exactly. This is the concept that trips up so many leaders.

SPEAKER_01: 3:44

The assumption is if I double my fundraising revenue, I double my compliance work. Simple math.

SPEAKER_00: 3:51

But the reality is much messier. It’s exponentially messier.

SPEAKER_01: 3:54

Because compliance tends to expand alongside fundraising growth.

SPEAKER_00: 3:59

Yes. Compliance tends to expand alongside fundraising growth, but it does not scale linearly. It scales with complexity. And complexity has multipliers.

SPEAKER_01: 4:09

Let’s break down those multipliers. Why does adding a few more states create such a headache? Isn’t it just the same form, different address?

SPEAKER_00: 4:17

I wish it were that simple. That is the dream of the unified registration statement, but in practice, the reality is completely fragmented. First off, every state has unique rules. Right. Some states require a wet signature, others are online only.

SPEAKER_01: 4:32

And the financial requirements change too, right?

SPEAKER_00: 4:34

Huge variations there. Some require a specific type of financial audit once you hit$500,000 in revenue, others don’t care until you hit two million.

SPEAKER_01: 4:42

So you really can’t just copy and paste the data into 40 different envelopes.

SPEAKER_00: 4:46

Exactly. But the real killer isn’t even the forms themselves, it is the calendar.

SPEAKER_01: 4:51

The deadlines.

SPEAKER_00: 4:52

This is where the exponential headache kicks in. In the early days, you had one deadline, maybe May 15th. You did the work, you were done for the year.

SPEAKER_01: 4:59

And once you’re nationwide?

SPEAKER_00: 5:00

You’re in a year-round cycle of staggered deadlines. Some states want renewals four and a half months after your fiscal year closes.

SPEAKER_01: 5:07

Four and a half.

SPEAKER_00: 5:09

Right. Others want it six months after. Some operate on a calendar year regardless of your fiscal year. Suddenly you have deadlines in November, February, May, July. It never stops.

SPEAKER_01: 5:19

That shifts the skill set requirement entirely. You aren’t just looking for someone who can read a rule book anymore.

SPEAKER_00: 5:24

Precisely. The challenge shifts from comprehension, understanding how to fill out a form to coordination.

SPEAKER_01: 5:30

You’re managing a massive web.

SPEAKER_00: 5:32

A web of deadlines, data inputs, evolving financial requirements, and doing that while trying to run a fundraising gala, that is where the internal team breaks.

SPEAKER_01: 5:42

Okay, so that is the theory of the growth paradox.

SPEAKER_00: 5:44

Yeah.

SPEAKER_01: 5:44

But I want to get practical for a minute. If I am an executive director or a CFO listening to this, how do I know if I’m there? What does it look like on a random Tuesday morning when the system is actually failing?

SPEAKER_00: 5:56

Well, it usually isn’t a catastrophic explosion. It’s a slow erosion of efficiency. But there are red flags, diagnostic signs that your internal capacity is stretched too thin.

SPEAKER_01: 6:08

What’s the first one?

SPEAKER_00: 6:09

The first one is what I call the scramble.

SPEAKER_01: 6:12

The scramble. I feel like anyone who has worked in a nonprofit knows exactly what that feels like.

SPEAKER_00: 6:17

It is that distinct feeling of panic. If document gathering is always a last-minute emergency, that is a red flag.

SPEAKER_01: 6:24

Like frantically searching email threads.

SPEAKER_00: 6:26

Yes. If every renewal feels like a fire drill where you are frantically emailing the accountant and the board treasurer three hours before the state portal closes, your system is broken.

SPEAKER_01: 6:37

Because compliance should be boring.

SPEAKER_00: 6:38

It should be totally predictable. If it’s exciting, you’re doing it wrong.

SPEAKER_01: 6:41

What about how the data is tracked? I imagine spreadsheets play a big role here.

SPEAKER_00: 6:45

Spreadsheets are great until they aren’t. Right. If your compliance system consists of post-it notes on a monitor, a spreadsheet that hasn’t been updated since the last board meeting, and calendar alerts on someone’s personal iPhone.

SPEAKER_01: 6:58

You are in the danger zone.

SPEAKER_00: 7:00

You really are. Because if that spreadsheet gets corrupted or the person ignores the alert.

SPEAKER_01: 7:05

You miss a filing.

SPEAKER_00: 7:06

And missing a filing isn’t just a small fine. It can mean losing your certificate of good standing.

SPEAKER_01: 7:11

Which brings up the opportunity cost. That’s something we often overlook. The cost isn’t just the late fee, it’s what you can’t do because you aren’t compliant.

SPEAKER_00: 7:19

Exactly. Imagine you have a major grant opportunity. You have done the work, written the proposal, cultivated the relationship, the grantor asks for your certificate of good standing.

SPEAKER_01: 7:31

And you have to say, hold on, we are technically lapsed in that state.

SPEAKER_00: 7:35

Right, because we missed a renewal. You might lose the grant entirely.

SPEAKER_01: 7:38

And there is also the internal drain on talent.

SPEAKER_00: 7:42

This is huge. If your development director, who you hired to build relationships and bring in major gifts, is spending 20% of their week wrestling with the Pennsylvania State Portal.

SPEAKER_01: 7:51

Or trying to figure out why a payment didn’t go through in California.

SPEAKER_00: 7:55

Yes. You are losing money. You are paying a high salary for administrative data entry.

SPEAKER_01: 8:00

I want to pause here because hearing all of this, it can feel like a critique. It can feel like we are saying, you messed up.

SPEAKER_00: 8:06

And it is vital to reframe this. These red flags, the scramble, the complexity, the strain, these are usually symptoms of success.

SPEAKER_01: 8:14

Success.

SPEAKER_00: 8:15

Yes. It means you grew. You have outgrown the startup phase. You are raising enough money to trigger audit requirements. You are attracting donors from enough states to require registration. It is a good thing. It’s a great thing. It is a growing pain, not a failure, but you have to treat it like a growing pain and adjust your treatment plan.

SPEAKER_01: 8:35

So the treatment plan often involves outsourcing, but I know for a lot of leaders, specifically founders or hands-on EDs, that word outsource is terrifying.

SPEAKER_00: 8:45

Oh, absolutely. There is a myth that outsourcing means losing control.

SPEAKER_01: 8:48

It’s the loss of agency fear.

SPEAKER_00: 8:50

Right. People think if I don’t do it myself, how do I know it’s done right? Am I just washing my hands of my legal responsibilities?

SPEAKER_01: 8:56

Is it what happens?

SPEAKER_00: 8:57

No. And we need to draw a very bright line here between execution and governance.

SPEAKER_01: 9:02

Okay. Execution versus governance.

SPEAKER_00: 9:05

Outsourcing changes the execution. It does not remove the governance.

SPEAKER_01: 9:09

Break that down for us. What actually stays in-house?

SPEAKER_00: 9:12

The oversight, the fiduciary responsibility. The board and the executive director are still the captains of the ship. They are responsible for ensuring the organization is compliant. They review the reports. They sign the Form 990.

SPEAKER_01: 9:26

So what are you actually handing off to the external partner?

SPEAKER_00: 9:29

You are handing off the friction, the administrative execution, the filing preparation, the deadline tracking.

SPEAKER_01: 9:36

All the manual stuff. Yes.

SPEAKER_00: 9:37

The regulatory correspondence. Answering those letters from the state asking for clarification on line 17, you are handing off the coordination of documents.

SPEAKER_01: 9:46

There’s a great analogy for this. It’s like the car mechanic.

SPEAKER_00: 9:49

It is the perfect comparison. If you own a car, you are the driver. You decide where the car goes, you decide how fast to drive.

SPEAKER_01: 9:56

But you hire a mechanic to change the oil.

SPEAKER_00: 9:59

Exactly. To check the brakes and ensure the engine doesn’t overheat.

SPEAKER_01: 10:03

You don’t lose control of the car just because you aren’t the one under the hood with a wrench.

SPEAKER_00: 10:07

No. Outsourcing compliance is hiring a mechanic for your fundraising engine. You want to focus on driving on the mission, not on reading the technical manual for the transmission.

SPEAKER_01: 10:18

So let’s talk about the tipping point, the decision matrix. Is there a magic number? Do I wake up one day with$2 million in the bank and say, time to outsource?

SPEAKER_00: 10:29

It is rarely a specific dollar amount, though revenue is a factor. It is more about organizational maturity and geographic footprint. There are specific triggers.

SPEAKER_01: 10:40

What is the first big trigger?

SPEAKER_00: 10:41

The expansion of the fundraising footprint. Usually the rule of thumb is when you start soliciting in five or more states.

SPEAKER_01: 10:47

Five states?

SPEAKER_00: 10:48

Yeah. Once you cross that threshold, the administrative burden of tracking distinct deadlines starts to outweigh the cost of hiring help.

SPEAKER_01: 10:56

Because at five states, you probably have deadlines in different quarters, so it becomes a constant buzz in the background.

SPEAKER_00: 11:01

Right. Another trigger is the audit requirement.

SPEAKER_01: 11:03

Ah, yes.

SPEAKER_00: 11:04

Once your revenue hits the level where states require audited financial statements, usually around the$500K to$1 million mark, depending on the state land, the scrutiny level goes up.

SPEAKER_01: 11:15

You can’t just wing it anymore.

SPEAKER_00: 11:17

No. The filings become much more technical.

SPEAKER_01: 11:20

And I assume staff specialization plays a role here, too.

SPEAKER_00: 11:23

A massive role. When you are small, everyone is a generalist. But as you mature, you hire specialists, you hire a major gifts officer, you hire a program director, you hire a CFO.

SPEAKER_01: 11:35

None of those people should be doing data entry for state registrations.

SPEAKER_00: 11:38

Exactly. It’s about highest and best use of time.

SPEAKER_01: 11:42

Makes total sense.

SPEAKER_00: 11:43

When leaderships start seeking predictable processes rather than celebrating heroic saves by the office manager, that is the moment to look for outside help.

SPEAKER_01: 11:52

Let’s be the devil’s advocate for a moment, though. Let’s weigh it up. The cost-benefit analysis. Because outsourcing isn’t free. There is a line item on the budget.

SPEAKER_00: 11:59

There is. And for a frugal nonprofit board, that can be a hurdle. But let’s look at the gains first. The primary gain is centralized tracking and a single source of truth.

SPEAKER_01: 12:09

You stop wondering if you are compliant.

SPEAKER_00: 12:11

You know?

SPEAKER_01: 12:11

And that continuity piece we touched on earlier.

SPEAKER_00: 12:14

It is insurance against turnover. If you outsource and your internal admin quits, your compliance engine keeps running.

SPEAKER_01: 12:23

You don’t have to panic train the new hire on 40 different state portals on their first day.

SPEAKER_00: 12:28

Exactly. But we have to be balanced.

SPEAKER_01: 12:31

What are the downsides? What is the friction in doing this?

SPEAKER_00: 12:34

The financial cost is real. You are paying for expertise. There is also an onboarding cost, not necessarily money, but time.

SPEAKER_01: 12:44

It’s an investment of energy.

SPEAKER_00: 12:46

You can’t just flip a switch. You have to transfer the knowledge, get the account set up, and grant access. It takes a few weeks of focus to get the external partner up to speed.

SPEAKER_01: 12:54

And communication changes. Yes.

SPEAKER_00: 12:55

You need to establish clear communication structures. You need to know who internally is approving the filings.

SPEAKER_01: 13:01

We can’t just ignore them.

SPEAKER_00: 13:02

Right. You need to be responsive when the partner asks for the audit or the 990. It’s a partnership, not a vending machine.

SPEAKER_01: 13:09

That is a key distinction. You can’t just pay the money and disappear.

SPEAKER_00: 13:12

No. The goal is improving reliability, not removing internal awareness. You still need to read the reports.

SPEAKER_01: 13:20

And it really ties into what we found across the board, which is that organizations that review requirements periodically avoid most problems.

SPEAKER_00: 13:27

Yes. Organizations that review requirements periodically avoid most problems. It is just a fact. It keeps you proactive instead of reactive.

SPEAKER_01: 13:35

So to bring this home to the listener, if you are sitting in your office right now, maybe looking at a stack of mail that you’re afraid to open, what should you be asking yourself? What is the self-evaluation checklist?

SPEAKER_00: 13:48

There are four questions I would ask. First, are compliance tasks delaying your core work? Is fundraising slowing down because you are stuck in paperwork?

SPEAKER_01: 13:56

Second.

SPEAKER_00: 13:57

Do your deadlines feel unpredictable? Do they surprise you? If you are ever surprised by a government deadline, your system is failing. Is your institutional knowledge concentrated in just one person? If Susan leaves tomorrow, are you in trouble?

SPEAKER_01: 14:10

And the last one.

SPEAKER_00: 14:11

Are the filings becoming difficult to coordinate? Are you getting rejection letters or requests for more information because you missed a detail? If the answer to most of those is yes, then it is time to consider a change. And remember, the ones who ignore the friction are the ones who end up with the Attorney General letter.

SPEAKER_01: 14:27

This brings us to a really important closing theme. We talked about reframing earlier. I think there is a deep-seated tendency in the nonprofit world to view outsourcing as admitting defeat. Like we weren’t smart enough or hardworking enough to handle it.

SPEAKER_00: 14:43

That is such a common misconception, and it is completely backwards. Outsourcing isn’t a response to failure, it is a sign of operational maturity. Say more about that. Think about the corporate world. You don’t see the CEO of a Fortune 500 company filing the corporate taxes. Right. You don’t see the head of sales writing the HR handbook. They have specialists. Outsourcing means you have reached a level where your time and your staff’s time is too valuable to be spent on administrative compliance.

SPEAKER_01: 15:10

It’s graduating, not failing.

SPEAKER_00: 15:12

Exactly. It allows your staff to focus on mission-driven work. It creates a system that is structured, predictable, and resilient.

SPEAKER_01: 15:19

And ultimately, this isn’t just about avoiding fines or paperwork. It goes back to the core of what a nonprofit is. It’s about trust.

SPEAKER_00: 15:26

It is.

SPEAKER_01: 15:27

I want to leave our listeners with this thought. The most effective systems are those that create clarity and confidence for donors.

SPEAKER_00: 15:34

Absolutely.

SPEAKER_01: 15:34

Think about that. If your internal system is creating anxiety, if you’re worried about whether you’re legal to ask for money, that anxiety bleeds into the organization. It affects how you write grants, how you speak to donors. But if you have a system that creates confidence, that projects outward. If your internal system is creating anxiety instead of confidence, it might be time to evolve.

SPEAKER_00: 15:58

Well said. Compliance responsibilities evolve alongside fundraising and organizational complexity. Whether you manage it internally or support it externally, the goal is clarity.

SPEAKER_01: 16:09

Absolutely. Well, that wraps up this deep dive into the world of compliance outsourcing. Hopefully, we’ve made the decision a little less daunting for you.

SPEAKER_00: 16:16

Indeed. It’s all about finding the right fit for where you are right now.

SPEAKER_01: 16:20

If you found this discussion helpful, you can find additional compliance guides and visual resources at ironwoodregistrations.com. Thanks for listening.