Every CFO at an investor-backed company is managing a relationship that is incredibly difficult to navigate: the one with the board and investors. The stakes feel high, the room can get tense, and most finance leaders never get a candid look at how the other side actually thinks.
So for the third episode of our series, I sat down with two people who have lived on both sides of that table. Joe Alie is our CFO here at Charted, and he spent his early career in investment banking and private equity before crossing over to the operator side. Caleb Hill is an Operating Partner at Level Equity, one of our investors, and he got there after fifteen years as a finance operator in growth-stage software. Between them they’ve seen this relationship from every angle, and they kept coming back to the same idea from opposite directions: the divide closes when there’s enough trust in the room to disagree openly, and it widens every time something goes unsaid. Here’s what I walked away with.
Everyone in the room is under pressure
I asked what they got plain wrong about the other side before they lived it, and Caleb’s answer was very helpful in reframing the dynamic of the investor-CFO relationship. As a member of management, it’s easy to feel like the board is thumbs down on you, especially in a tough season. What you forget is that someone is also thumbs down on them. The partner who made the investment stuck their neck out, put their name on the memo that went to the investment committee, and answers to their partners about your performance the same way you answer to the board. Everyone is feeling the heat, just a different version of it.
Joe’s answer came from the other direction. As an investor, he underestimated how hard execution actually is. His example was acquisitions. The math always looks great in the spreadsheet, and as Caleb joked, “it pencils.” But making an acquisition work comes down to things the model never shows, like keeping key employees, retaining the customers you just bought, and consolidating the systems, and all of that consumes the team’s capacity while it happens. So what looks like a slow-moving operator from the investor’s seat is usually a team dealing with the real work the model skipped over.
Healthy relationships have friction in them
When I asked Caleb what a great investor-CFO relationship looks like, his answer didn’t shock me, but it was a good reality check. A strong relationship has a lot of disagreement in it, and the reason for that is trust. If I trust you, I’ll share a half-formed idea on the phone and we’ll work through it together in real time, which makes both of us faster and sharper. If I don’t trust you, I take that idea home, sit on it for a week, and come back with something polished because I don’t want to look bad. So when you see a relationship with no debate and no friction, that’s actually the one to worry about, because it usually means things are going unsaid.
He quoted a chairman he once worked with who put it perfectly: “meeting room silence led to corridor violence.” If you don’t say the thing in the room, and then pull someone aside afterward to say the idea was terrible, you’ve just eroded your ability to execute together.
Credibility is what makes that friction safe, and Caleb’s version of it is what he calls the say-do ratio. Show up, say what you’re going to do, and then a quarter later, deliver it. The more reps you get of doing the things you said you’d do, the more room you earn to go out on a limb when it matters.
Great CFOs live in the drivers, not the outcomes
I asked whether there’s a profile of CFO that investors trust more, and Caleb said he’s seen every background work, from public accounting CPAs to strategic finance people to former bankers. What separates a great CFO is taking accountability for the things that produce the numbers and not just reporting the numbers once they show up on the P&L. A weaker CFO says the revenue number is the number and reports whether it came in above or below budget. A great CFO understands everything that gets you to that number, the pipeline, the customer journey, the data quality behind all of it, and engages at that level first.
Joe added the other half. The best CFOs think like their investors. They know the hold period, the growth targets, the path to profitability, and they anticipate what the investor will care about before the meeting instead of reacting afterwards. As the CEO on the receiving end of Joe’s work, I can tell you how much that forward-looking instinct matters, and I gave him a shout-out for exactly this in our previous episode.
Share the hard stuff early, even when it’s ugly
Both Joe and Caleb told versions of the same regret. Early in his operating career, Caleb held things too close. He wanted every answer buttoned up before the board saw anything, so his communication slowed down and he showed up to board meetings with big, consequential reveals. All backed up with data and pristine slides, and still the wrong move, because a big reveal creates a huge asymmetry. You’ve been living with a problem for a month, and now you’re putting the board on the spot to get up to speed and do their governance job in a single meeting. His lesson was to bring people along for the journey instead. Share news early, say you don’t have all the data yet, ask what they’re seeing. You often end up in the same place, but with a board that was engaged and involved in getting there.
Joe’s example made it more concrete. One of his prior companies had a strong customer base built on older technology, and the plan to move customers to AWS turned out to be far more costly than anyone modeled. He had to recommend to the board that they pause growth and focus on modernization, which is close to the last thing an investor with growth targets and a hold period wants to hear, because a decision like that can extend the hold period itself. But because they raised it early, the company had the room and the capital to make the right call, and they shifted engineering from 75 percent new product work to something closer to 40 while they rebuilt the base.
Define the outcome, not the tool
We spent a good amount of time discussing systems, and this is where my world overlaps most with the conversation. I asked Caleb about the two schools of thought on how prescriptive investors should be, since some PE firms mandate which ERP you’ll run. His answer was that it’s more useful to define the outcomes a finance function should drive at a given scale and stay flexible on the how. His example was the close, which he called the single biggest rate limiter in a finance function, because if you spend 10 to 15 of your 20 business days closing the books, you have no time left to do anything valuable. So, the near mandate is the outcome, work toward a five-day close, and then the firm brings ideas on the systems and processes that get you there.
His reasoning for not mandating the tool made sense to me. When you take the vendor decision away from the CFO, you pull away some of the ownership that drives performance everywhere else, because if the CFO doesn’t believe they own their own tech stack, what else don’t they own? Level Equity runs on what Caleb calls a mutual affinity model, which he described as “we’re on your bus, not the other way around.” As someone whose company they’ve invested in, I can tell you that approach builds a very different kind of trust. Joe agreed from the operator seat, and what he values most is the pattern-matching instead of the mandate, a firm that sees twenty-plus portfolio companies and can say this tool is working well at similar businesses, it’s probably worth a look.
When is too much Excel, too much
I had to ask, because Joe loves Excel. He said Excel becomes a problem when it starts slowing down the close, and when the volume gets big enough that errors creep in. His example was deferred revenue schedules, where at some point nobody can explain why an entry was made seven months ago in row 10,050 of a spreadsheet; it’s the kind of data point that can cause you to start to lose confidence in your own numbers. Caleb works backwards from outcomes here too, and his red flags are simple. If the historic ARR number changes slightly every time he asks for it, or pulling an AR aging report takes until the middle of next week, the process is telling on itself.
Caleb’s caution is that an ERP or FP&A implementation is a big lift that you don’t want to redo, so if the business is still changing quarter to quarter, stay in Excel a little longer and put the system in once things have settled enough. My own view, and Joe backed it up, is that the implementation can also be a healthy forcing function. It pushes you to define things that would otherwise stay fuzzy, and Charted got onto NetSuite earlier than most companies our size, which put structure in place that has paid off ever since. Joe’s experience is that once a comprehensive ERP like NetSuite is in, scaling gets easier because your data lives in one place, and the hardest jump is the first one, going from a one-person finance function where the processes live in someone’s head to real systems, documented processes, and a team. It’s daunting, and you come out the other side going from a 20-day close to a five-day close, which is how you get the buy-in. It matched what I see at Charted every day, and it’s the same cue I mentioned in our last episode: when a prospect wants to implement NetSuite and there’s no controller in place, that’s our signal to ask more questions, because Caleb was clear on this too. The controller is the first big critical hire, and everything else builds off that foundation.
The final takeaway
I closed by asking for advice, and I put myself on the spot first by asking what they’d tell a CEO. Joe’s answer was spot on—know the investor’s roadmap, the growth and profitability targets, and carry that mindset into every decision so you raise things early and stay proactive instead of reactive. Caleb added the piece of advice I keep coming back to; ask your investors what needs to be true about the business for them to realize the return they underwrote. Most of the answers will match what you’re already doing, but there might be one or two blind spots, like an end-market expansion that has to happen in the next three years for the business to recapitalize well, and you want to internalize those early. And whatever the numbers say, keep your reporting consistent even when the story is bad, because the investors will open the last board deck and notice the missing slide anyway. Own the hard stuff.
If there was one thread running through the whole conversation, it’s the divide between investors and CFOs is mostly made of things going unsaid. The finance leaders who close it build enough trust to disagree in the room, own the drivers and not just the results, and bring their board the ugly news early enough to be able to help. Do that consistently and the person across the table stops being a critic and starts being what they wanted to be all along, which is an ally and a partner.
This was the third of several conversations I’ve been having with finance leaders about the things they really wrestle with. If you’re a CFO or senior finance leader who’d want to be part of one, I’d love to hear from you.
To watch our full conversation, view it on YouTube here.
Follow Bernardo Enciso for more insights like this on LinkedIn.
