
Revenue recognition shouldn’t slow your business down—but too often, it does. As a CFO, I’ve seen how rigid systems, compliance hurdles, and manual workarounds make closing the books a nightmare.
We put together this free report outlining the biggest revenue recognition challenges CFOs and controllers are facing—and what the right solution should look like. If revenue complexity is holding your team back, this will help you understand how to fix it.

Wiz sold to Google for $32 billion, and suddenly everyone’s doing growth retrospectives like the playbook is right there for the taking. They blitzscaled to a billion dollars in revenue faster than perhaps anyone other than OpenAI. Truly amazing stuff.
I heard this one anecdote, I don't want to be apocryphal here, but I think it was during the time where they went from like $200 million to $400 million in 12 months. Unheard of growth for a predominately field sales company. And they were asking their CRO, “How did you know how many sales reps to add?” And he was like,
“There was nothing to benchmark it against, we were literally just looking at sales rep calendars and being like, ‘Yeah, that person can't take any more meetings’.”
To put it lightly: it was far less mathematical than you’d think.
Wiz figured it out. But a lot of companies never get close to this kind of trajectory; not because of a bad product, but because they’re too hungry to eat.
What I mean is they are primed for hypergrowth, and exhibiting the tell tale signs, yet starve themselves of the supporting resources and bandwidth to make it happen.
They say, “We’re going to double revenue this year,” but don’t hire the people needed to feed the beast. Or they start hiring but forget to hire the people who support the people. Or they hire everybody at once, with no plan for training, onboarding, or even just getting a laptop in their hands.
I’ve seen three specific forms of this self-imposed fasting. They all tie back to hiring great people. Afterall, an org in hypergrowth mode is a living and breathing organism going through growing pains.
1. The Sales Manager Who Can’t Interview Because They’re Too Busy Closing Deals
Here’s the classic convo:
Sales leader: “We need more bodies. Why aren’t we hiring faster?”
Finance leader: “How many interviews have you done this week?”
Sales leader: “One. I’ve been slammed helping my team close Q3.”
Meanwhile, recruiting is waiting for updated scorecards. The candidate pool is getting cold. And the six open headcount slots are still sitting in a spreadsheet with green boxes and no names.
(A message from your local FP&A team: Dale, you asked me to greenlight these heads two months ago. Now you’re destroying my capacity model. WTF??)
This isn’t finger-pointing (OK, maybe a little)… it’s structural. Sales leaders are often expected to carry a bag, manage a team, and hire the future at the same time. I’ve seen a lot of sales leaders get burnt out over the years, and honestly it’s not the sales part that kills them; it’s the people management as their span of control jumps.
This hiring dance between recruiting and sales is very fluid. It gets out of whack on both ends. As an FP&A leader I’ve also sat first row to situations where the recruiting was moving too slow.
Chirag Shah, CFO of Motive, nailed it when we spoke on the podcast:
“You have to constantly ask—where’s the bottleneck? Is it sourcing? Is it the interview load? Is it that no one’s had time to update the job description since 2021?
So it's not easy. It's pretty complex and there's a lot of different elements to it, but, you know, it's one of those things where you just have to continuously stay close to your recruiting team, your sales team, and clear bottlenecks as they pop up.”
Scaling a team is an iterative process. But too often, we treat it like a side quest.
2. Cheaping Out on Support Roles
Here’s a red flag: your $250K AEs are qualifying MQLs, booking their own meetings, and cobbling together demo environments.
That time would be much better spent talking to customers and closing deals.
And timing is everything. Budgeting for system engineers or sales engineers (SEs) is one thing; but actually getting them in place at the right time is where things get dicey.
I’ve been on both ends of the timing spectrum. One year, we were so focused on getting closers in the door that we delayed SE hiring. Suddenly, deals were bottlenecked because no one could handle the technical deep dives.
The next year, we tried to get ahead of it—started hiring SEs two months before the reps showed up, so they’d be trained and ready to roll. And then… nothing. (Expensive) People sitting around waiting for something to do.
It felt inefficient—but it turned out to be the cost of being ready.
Chirag also had a take on this. SEs often take longer to ramp than sales reps. They need to be technical experts, not just pitch-ready. So yeah, having some slack capacity up front isn’t waste - it’s contemplated. As long as you know why you're doing it, a short-term imbalance can be a long-term unlock.
He explained that when you're scaling a sales org, you can't just stare at AE productivity dashboards. You have to think about the whole unit—SEs, ops, enablement—and how it functions together. Because if any one part breaks down, you lose momentum across the board.
The key is knowing your ratios, planning for temporary inefficiencies, and staying proactive enough that you’re not always scrambling to course-correct after the fact.
3. Enablement That’s One Formerly Retired Guy Named Lou in Seattle
Let’s talk about enablement.
SMB reps typically take three months before they can start reliably closing deals. Mid market six months. And it may take up to a YEAR before an enterprise rep gets their feet under them. Part of the process of course is building pipeline. And the speed at which that can be done is often incumbent on marketing, at least to a degree. But the other component is learning the product and the industry.
Reps can’t sell what they don’t understand. And there are two types of understanding that matter:
The product itself
The market and the customer
They are not the same thing. And each comes with its own learning curve.
At one company I worked at—cybersecurity—the product was complex. It scanned code for vulnerabilities, which sounds simple, but in reality meant you needed to understand the entire SDLC (software development lifecycle), talk the talk with really smart DevSecOps leads, and navigate objections that started with, “Well, actually…”
It took time to learn. Technical ramp, API lingo, coding languages that were not Javascript, long-ass acronyms for days.
Then there was another company I worked at that sold to garages—literally. The product was easy to grasp: “We help garages buy brake pads.”
But the customer? Not so much. The auto industry has more layers than an onion. OEMs, aftermarket manufacturers, regional distributors, local suppliers—and then, finally, the garage. And depending on whether it’s a chain or a family-owned joint, the guy ordering parts might be a grizzled owner, or a 17 year old who was working drive-thru at Burger King last week.
Reps needed to learn how garages ran their operations, what a “service writer” did, and how to not get yelled at by a mechanic who had a wrench in one hand and a phone in the other.
In this case, the product wasn’t the problem—the ecosystem was.
If enablement doesn’t help reps get up to speed on both product and customer, you're not doing enablement. In fact, you’re creating a sunk cost that plunges further into the red until you give it the context it needs to thrive.
Everything Is Connected
The sales manager who can’t interview → means you don’t fill headcount
The SE hired too late → means deals stall out on demos
The AE without enablement → means ramp takes twice as long
This is the “not good” type of compounding. It happens silently at first, because remember, you’re doing really well, or you wouldn’t be trying to pour gasoline on the fire in the first place. But then, the cracks start to show. In my experience the “oh shit” realization usually takes 2 quarters to rear its ugly head. Many times the canary in the coal mine is someone who’s great quits out of sheer frustration. And almost always it’s missing revenue targets because your sales capacity model doesn’t reflect the reality of your trained workforce.
Most hypergrowth windows are short. Maybe 18 months. Often less. Especially now, when competitors (and GPT wrappers) can copy you in a weekend.
So if you’re truly hungry—eat.
Don’t skip meals. Don’t save budget for the sake of saving budget. Don’t assume you can out-hustle your own organizational gaps. You can maybe brute force 10% of a plan, but not a 110% growth goal.
Because if you wait too long, the buffet might be closed.
Run the Numbers Podcast
Apple | Spotify | YouTube
How do you know when a company is ready to go public? And what do you do to prepare for this? Chirag Shah, CFO of Motive and former CFO of Kong and Cornerstone OnDemand, joined me to share insights from his experience of scaling businesses from $30 million to nearly $1 billion and tripling ARR. We talked about:
Taking companies public and how he helped take one private again in a $5.2 billion deal.
What signals indicate that a company is ready to accelerate its growth
The art and science of building sales capacity
Tow to balance efficiency and growth in hypergrowth mode
How to achieve a great valuation without a strong performance
The biggest headache on the road to IPO,
Whether you should IPO in the first place or remain private.
The Looking for Leverage Newsletter
The Most Misunderstood Word in Finance is Leverage.
There’s a special kind of side-eye that gets thrown around when someone combines the phrases “leverage” and “private equity.”
In my experience, it’s a similar look to when you combine “children’s birthday party” with “lawn darts.”
To some, it’s shorthand for slashing costs and maxing out debt to juice IRR. The “Dark Arts” of finance.
But the more I’ve sat with seasoned CFOs inside the PE ecosystem, the more I realize: most people are playing checkers while PE is quietly playing capital structure chess…
If you aren’t sick of me yet…(I’d be)
Here are some other great pods I recently went on. Great not because of me, but because the hosts had amazing perspectives and were gracious enough to invite me on.
Lilly Wyden operates at the intersection of tech, finance and creating content. We talk about how I found my first CFO gig through my newsletter, the memefication of finance, if Substacker’s could have agent’s some day, and the value of corporate gossip. Listen here.
Troy Wallace is an HRIS practitioner with over 25 years of experience in the HR space. We discuss the hallmarks of a great HR / CFO partnership, how to ask your CFO for budget, and much more. Listen and follow on Apple | YouTube | Spotify
Quote I’ve Been Pondering
“How do you change what got you everything you’ve got?”
-The Cost of These Dreams by Wright Thompson