Life as a Quarterback: Due Diligence from an investor’s perspective

Two things I didn't see coming: that I'd become a football fan — the Lions' 2022 season was the  first I paid any attention to — and that the best description of my job at Straylight would be "quarterback."

For those of you who aren't sports fans, the quarterback is the one who stands back, reads the defense, and calls where the ball goes each play — they don't gain every yard, but they own how the drive ends. That's almost exactly my job at Straylight. Just swap the field for a fundraise, the receivers for the diligence workstreams, and the defense for everything we don't yet know about a company, and the role translates:

Quarterback: the member of the investment team who runs diligence end to end on behalf of the deal leads (the partners who'll own the investment) — keeping every workstream moving, connecting what each one turns up, and owning the single coherent picture we carry into an investment decision.

Recently, I led diligence on Straylight's 11th platform investment out of our current fund — my first time taking the quarterback position. It feels a little odd to admit that out loud, but I'm doing it on purpose: the view from this seat is exactly what I wish founders could see before they're in the middle of their own due diligence process.

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The Quarterback in Action

A few pieces of context before we talk about ‘the plays’. Straylight Capital is a technology-focused fund writing $5M to $25M checks into growth-stage companies — typically those doing $3M to $13M in revenue. That stage is exactly why diligence runs so deep: by the time a company reaches us, it has real revenue, customers, contracts, and operating history — far more to understand, and more that can hide, than at the early stages. The process is built not just to understand the business, but to map how we'll partner the day the deal closes.

A quick look at the field:

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The deal lead, most often a partner or principal, is the coach — they set the strategy and make the call to close. The quarterback — a mid-level role like mine — runs the process day to day and keeps every workstream moving. And the supporting players — a mix of analysts and specialist third-party teams — handle the specific digging.

At Straylight, the majority of diligence is done in house, but we will call on specialty providers for things like technical due diligence — evaluating the code base and security powering the software, an accounting firm to do a quality of earnings analysis, and counsel to perform their own legal diligence and draft the closing documents.

The deal lead, most often a partner or principal, is the coach — they set the strategy and make the call to close. The quarterback — a mid-level role like mine — runs the process day to day and keeps every workstream moving. And the supporting players — a mix of analysts and specialist third-party teams — handle the specific digging.

At Straylight, the majority of diligence is done in house, but we will call on specialty providers for things like technical due diligence — evaluating the code base and security powering the software, an accounting firm to do a quality of earnings analysis, and counsel to perform their own legal diligence and draft the closing documents.

In any round of funding, diligence isn't just one conversation — it's a dozen of them running at once, each its own workstream with its own owner and its own timeline. Those workstreams are the game plan, all designed to understand something specific about the company you are building.

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Diligence, done right, is the first real act of partnership.

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Throughout the process, I decide which thread to pull next, keep any one workstream from sitting blocked on another, and pull that whole moving picture into a single answer to the question every workstream is really asking: should we invest? But that question isn't the whole goal. We're not just deciding whether to write the check — we're working out whether we can help this company become a champion, and how. Done well, diligence doesn't just get us to yes; it earns us the head start to make that yes count.

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That's the job. I'm not the one trying to find a reason to say no. I'm the one making sure that by the time we get to a decision, we understand the business well enough to help it win.

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Why we go this deep

This is the part I'd most want a founder to hear, because it's not obvious from your side of the table.

When you're being diligenced, there’s no question that this is a time-consuming and laborious process – and it can certainly feel like an interrogation. Another data request. A third reference call. A question that seems to be poking at exactly the soft spot you were hoping nobody would notice. It's easy to read all of that as skepticism, a firm building its case for why not to invest.

It's the opposite. By the time we're in diligence, we want to get to yes. The depth isn't us looking for reasons to walk. It's us doing the work of understanding your business nearly as well as you do, because that's the only way we can be useful the day after the money hits your account.

Diligence, done right, is the first real act of partnership.

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The same end zone

Behind every fundraise is a founder's version of the same dream — the day this becomes something, the exit that makes the whole grind worth it. What I don't think founders always realize during diligence is that we're picturing that exact day too. Underneath every data request is one question: do we believe we can help drive this company to that outcome, and if so, how?

That's why the part I care about most isn't the decision itself — it's what the partnership looks like on day one. The exceptional moment years from now isn't won at the term sheet; it's won in the groundwork we lay before the partnership even has a name — and in every play we run together after that.

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What the depth actually buys you

The most impactful thing we did on the 11th platform was map the company's workflows end to end — how the business actually ran, all the employees involved to ship something, step by step, not just how it looked in the financials.

We weren't doing it to find problems. We were doing it to understand the operation. And in the process, we could see plainly what was working, what could be automated, and — most importantly — what kind of person the team needed to hire next.

So by the time we closed, the founder didn't walk into day one with a vague "we should probably build out that function." They walked in with the job descriptions already written and a headhunter already searching for the role. The gap between "we're partners now" and "we're adding value" was basically zero.

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The Outcome We All Hope For: A Capital P Partner

This is the outcome we're all hoping the process leads to: not just an investor who wired the money, but a Partner — capital P. Someone who knows your business well enough to be useful from day one and is still in the huddle years later. Everything I've described is us trying to earn the right to be that.

And it isn't all on us. Founders sometimes ask how to "get through" diligence — wrong question. The ones who get the most out of it use it to start building the partnership early. 

A few things separate the founders who do it well:

1. Be honest, especially about the warts. Surfacing a problem before we find it builds trust fast — and it tells us you see your own business clearly, which is exactly what we're underwriting.
2. Be collaborative, not defensive. Treat the hard questions as a preview of how we'll work together, not a test to pass — the founders who engage openly get a sharper partner on the other side.
3. Be responsive. A tight, transparent process is its own signal: it tells us how you'll operate when something real is on the line, and it gets you to a decision faster.

On the 11th, that's exactly how it went. Diligence confirmed everything we believed going in — but the conviction was never the valuable part, the foundation we built was. Because we went deep, and because the founder met us with openness instead of  offense, we didn't start the partnership from a standstill. We'd already done the work of understanding each other.

That's why we run the process the way we do. The rigor is designed to drive partnership way before close.

So if you're a founder staring down a diligence process that feels endless, try to see it the way I do from across the ball: this isn't the interrogation before a no. It's the opening drive of a long game we're hoping to play together — and the work we put in now is what helps us win it later.

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Caroline Wolanin is an Associate at Straylight Capital, a growth equity firm for “the magnificent middle”, based in Detroit. As an associate, she helps source and vet deals for the firm. Outside of her work, she writes pieces like the one here and was once a pastry chef.