Hi all - curious to get input on what you’ve seen in the past few years for legal transaction fees on the sell-side. Generally looking for input on low/middle market companies in the $10m-25m revenue range (or even up to $50m revenue). Any input would be greatly appreciated. Thanks
We are drowning in manual AR work at our mid-sized company. Our team spends hours chasing payments and reconciling accounts and I am tired of hearing "that is just how it has always been done." Anynoe who have implemented AR automation, what tangible outcomes have you realised? Looking for real metrics, time savings, DSO impact and the assessments of whether the ROI was worth it.
We have a supplier offering 2% net 10 instead of our normal net 30 terms and on paper taking the discount seems like the obvious choice. I'm trying to figure out is how people think about this when you have a decent amount of AP going out every month. Cash isn't particularly tight for us but paying 20 days earlier across multiple vendors obviously starts pulling forward a meaningful amount of cash.
Right now this is only one supplier but it got me wondering whether we should have an actual rule for these discounts instead of deciding invoice by invoice so for any of you guys who regularly get early payment terms are you generally taking 2% net 10 whenever liquidity allows or is there a point where you'd rather hold onto the cash until the normal due date?
I recently started an Assistant Controller role, and I’m trying to figure out the best way to accelerate my learning while also building a strong foundation.
The role has been a big step up for me. I’m dealing with areas like consolidations, financial reporting, IFRS, intercompany activity, internal controls, and processes that are much broader and more complex than what I was responsible for in previous accounting roles. On top of that, there are a lot of company-specific processes, systems, and historical knowledge that you can only really learn over time.
One thing that has helped me tremendously is AI. I use it to help break down concepts, explain accounting topics in simpler terms, brainstorm questions to ask, analyze processes, and even help me understand the “why” behind certain things. Honestly, I feel like I've learned a great deal faster because of it.
At the same time, I worry about becoming too dependent on AI. I don't want to get into the habit of asking AI every time I encounter something unfamiliar instead of developing my own judgment, technical knowledge, and problem-solving skills. Eventually, I want to be able to look at an issue, understand what matters, know where to research, and form my own conclusions.
For those of you who have moved into Controller, Assistant Controller, or other senior accounting roles:
How did you get up to speed when you first started?
What did you focus on learning during your first 6–12 months?
How did you build confidence in areas you initially didn't understand?
How do you use AI or other resources without becoming overly reliant on them?
What habits helped you transition from being someone who completes accounting tasks to someone who understands the bigger picture and can exercise judgment?
I'm willing to put in the work, take notes, study, and ask questions. I just want to make sure I'm learning in a way that will make me genuinely better—not just better at finding answers.
Would really appreciate any advice from people who have been through a similar transition. (Yes, I did use AI to write this post lol)
Going through renewals for next year's budget and it's the same list as always: three tools that all do some version of reporting, a $60K/year platform renewal nobody's fully using, and what would actually break if we don't renew.
New wrinkle this year: our head of ops keeps asking why we're paying for some of this when we could probably just build a lightweight version in-house using Claude, since our one technical hire can apparently spin up something functional in a couple weeks. I don't have a good answer. I can't tell if that's a real option or if we'd be trading a known cost for a maintenance headache nobody's priced out. So now every renewal conversation has this extra question hanging over it that we didn't used to have to answer.
Anyone actually gone through this calculation seriously? Curious what made you decide to keep paying vs. build it yourselves and what was the impact of it.
I’m reviewing a workforce model for IT and the Innovation Function with an Innovation manager and an additional engineer (new role) have a note that says discretionary.
What does this mean or how is that used in planning?
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I work with a voluntary Section 125 and fixed-indemnity structure, and I am looking for candid CFO feedback on how to introduce something like this credibly. I am not looking for leads.
For a workforce-heavy company, the employer-side impact can be material. Using a company with roughly a thousand employees as an example, the annual financial improvement can approach seven figures and flow directly to EBITDA.
Employees who participate can see a meaningful increase in take-home pay, along with additional health-related value. The existing medical plan is not replaced. The carrier administers the claims side, and the employer is not expected to administer individual claims.
The business case is that it can create recurring financial improvement without raising prices, cutting staff, reducing wages, or asking operations to do more. The work is funded from the financial performance created rather than added as another operating expense.
The specific structure I work with is already in use within Fortune 500 companies and major university systems and is backed by a well-known private equity firm.
I also understand why this category can trigger skepticism. There have been badly presented and badly structured versions in the market. That is precisely why I am asking.
If you had never encountered this category and someone reached out cold, would you dismiss it immediately, or would you be open to reviewing a short brief if the structure, economics, and implementation process were explained clearly?
If you have seen something similar before, what made you reject it, table it, or move forward?
What would you need to see before deciding it was worth a serious conversation?
Feel free to be blunt. I am trying to understand how CFOs distinguish a real financial opportunity from a pitch that sounds too good to be true.
Trying to get a sense of real-world timing vs. generic VC advice.
If you are a full-time CFO/VP of Finance: What hire number were you
Has anyone used or implemented Paylocity into their technology stack? I am looking for opinions on how it has been going or if there are any issues I should be aware of before we sign on with them. At face value they seem to be great but the more i dig into some of their reviews on customer service and invasive Terms and Conditions, the more nervous I get.
Currently we are with a PEO and are not happy with the service we are getting.
I have noticed that as the business grows, bookkeeping can start feeling less sufficient, cash flow gets harder to predict, and hiring decisions become more expensive.
So, I wanna know at what point a business needs more than a bookkeeper or CPA?
Is it revenue, cash flow issues, growth, debt or something else?
Hi! I’m building my own bookkeeping business and doing some market research around fractional CFOs.
Before starting my business, I spent about 4 years working in accounting, and one of my favorite roles was working alongside a fractional CFO as her assistant/bookkeeper.
For the fractional CFOs here — how do you typically handle the bookkeeping side of your client engagements?
Do you prefer to work with a bookkeeper you know and trust so you have reliable numbers to work from? Or do you generally leave bookkeeping entirely up to the client and work with whatever they provide?
I’m curious if there’s a real need for bookkeepers who specifically support fractional CFOs behind the scenes, or if this isn’t much of a pain point in practice.
Would love to hear how you handle it!
I have been deciding between multiple options and wondering about the experiences of the community. I have historically used Mercury.
We're at the point where cash is spread across a few accounts for operating expenses/payroll and reserves and I'm spending more time than I'd like figuring out what our available cash position is. Each account on its own is easy enough to manage but once you factor in upcoming vendor payments and transfers we've intentionally set aside the total bank balance isn't useful.
I usually end up checking a few different places and doing the math myself before making any larger cash decision. If any of you manage a similar setup how are you getting a reliable view of cash without manually pulling balances together and are you consolidating more of the banking or keeping separate accounts and solving the visibility/reporting side instead?
Would love to hear from people who have actually worked in PE-backed companies. I’m currently being heavily recruited by two PE-backed companies. Taking compensation out because financially, it’s not a motivation of mine to put it lightly, I’m more interested in hearing about people’s experiences actually surviving and possibly surviving an exit in the PE-backed world.
One of the opportunities is a platform CFO role. After speaking with both the PE firm and the platform CEO, I’m almost skeptical because I’m surprisingly aligned with how they think about the business, where they want to take it, and what needs to be fixed. I also have a pretty good understanding of the problems I’d be inheriting, the expectations for the role, and the eventual exit strategy. Most of these issues, I know I can succeed in fixing. The others are a good area for myself to get challenged in. I’m not particularly worried about pace or workload during genuinely busy periods. Without doxxing myself, I’m already at a company that has been growing aggressively so operating in a changing environment isn’t new to me.
If the rest of my due diligence doesn’t uncover major red flags, this could be a rare opportunity to jump directly into my first CFO role. At the same time, I’m perfectly willing to walk away if I decide the fit or risk isn’t right.
For those who have worked in PE-backed companies, does getting that first CFO seat materially change the risk/reward equation?
And for those who have made the jump, what ended up being the biggest risk in reality: the workload, sponsor expectations, CEO relationship, unrealistic growth targets, exit pressure, lack of resources, getting replaced, something else? My biggest worry is that this role just seems to be too good to be true for a first-time CFO.
I'm dreading another upcoming reaming by the President of my company and their inner circle of AI evangelists. The bi-monthly chest thumping is more about non-technical leaders yelling about why what they see on their LinkedIn feed isn't being done at our company.
How are y'all holding the line on reasonableness without flying off the handle these days?
We're using AI as one of several automation opportunities to improve productivity across the CFO org, under the spirit that AI is not the right solution for every problem. Apparently, it's not enough.
One of the demands is for AI generated board decks with immediate delivery and a built in digital CFO to chat with about results. I haven't been impressed with the consistency or accuracy from the LLMs enough to think that's not a HORRIBLE idea, especially for a publicly traded company.
Have y'all copitulated on this, or are you successfully holding back the flood of AI influencers, hollow vendor promises, etc.?
Please send help.
We've been manually matching Stripe payouts to our bank statement. every month there's at least one payout that's off because of a refund or chargeback that got netted out weird and our bookkeeper keeps missing it. Looking for a software or bookkeeping service that handles Stripe payout reconciliation end to end, ideally something built for a SaaS or ecommerce setup where the payout timing doesn't line up cleanly with the transaction dates. We're on QuickBooks Online so whatever it is needs to play nice with that. (Also dealing with deferred revenue recognition which our current setup just ignores completely, so that's a bonus pain point.) Budget is probably fine up to around $1k/mo if it actually solves the problem. Anyone found something that does this well without requiring us to babysit it every close cycle?
I’m sure many here are familiar with the concept of Ben Horowitz’s peacetime CEO / wartime CEO concept, which is often extended to CFOs too.
Leaders in peacetime environments have predictability over their trajectory, which is often backed up by periods of macro economic growth which can lead to hyperscaling. Whereas leaders in wartime environments are in a much more challenging environment where their focus should just be on survival through managing cash flow and expenses tightly.
Feels like the last couple of years are leading to violent swings between optimism about economic growth and fear related to geopolitics concerns.
Most CFOs will fall into one of these two buckets based on their expertise and experience so my question is it better for companies to have a peacetime or wartime CFO in 2026?
Genuinely curious how other teams handle this, because at every place I've seen it works differently and mostly badly.
The bill comes in, someone says it's too high, and then... what? Is there one person whose job it is to dig in? Does it fall on whoever is least busy that week? Does it just get ignored until finance escalates?
Specifically wondering:
- Is anyone on your team formally responsible for cloud spend, or does it float?
- When the bill jumps 20% month over month, how do you find out why? Dashboards, a tool, or someone manually clicking through Cost Explorer for two hours?
- Do you review it on a schedule, or only when someone panics?
- Has anyone actually done a proper line-by-line audit, and did it stick or did spend creep back up in six months?
Mostly asking because I keep seeing the same pattern — everyone knows the bill is too high, nobody owns it, so nothing happens. Curious whether that's universal or whether some teams have solved it.