Welcome Back to This Month’s CFO Mailbag

This week we have the following CFOs answering your reader questions:

Today we’re covering:

  • Favorite business book for a long flight

  • How long can you realistically put off your first audit for?

  • How to run a great weekly pipeline call with your CRO

  • How to structure multi year deals as a seller

  • When should I hire my first head of FP&A

Let’s get into it!

Question #1:

What is your favorite business book? And what’s the #1 lesson that stuck with you? I have a flight to Australia coming up.

Jamie, USA

Chris from Zeta:

It is not a “business book” but it’s a powerful, emotional read about a father’s relationship with his autistic son. Autism has touched our family’s life and it’s a cause we support. The book is called “Born Lucky” by Leland Vittert.

Michiel from Remote:

Since you’re headed to Australia, you need a book that’s as dense as a 10-K but a bit more readable. My pick is "The Signal and the Noise" by Nate Silver. It’s about forecasting, probability, and why humans are generally terrible at predicting the future. The lesson that stuck with me is that adding more data doesn't necessarily lead to better predictions. In the world of finance we are constantly bombarded by noise: a one-off churn event, a weird month of AWS spend, or a competitor’s stunt. The job of a finance leader isn't to report every data point but to filter out the static so the CEO and the Board can see the actual signal. 

Question #2:

We’re about to cross $10M in ARR and my board is asking me to start vetting audit partners. Feels early. Realistically, how long can I delay having an auditor for? I have a biz to build!

Jerry, TX

Chris from Zeta:

While it may seem early to bring on an auditor, I believe it is a worthwhile investment to do it sooner than later. The auditor can be a valuable advisor and business partner in addition to serving their functional duty. Their perspective across industries and seeing how common challenges are overcome is invaluable.

Michiel from Remote:

Audits are about as fun as a root canal, and they cost significantly more. You can delay a formal audit until it’s mandatory or you need it for e.g. a fundraise. But the real question to ask yourself is whether there is anything in the numbers that you feel uncomfortable about. Why is your board asking this now? Is your revenue recognition a little shaky? Are you unsure about your tax strategy? It’s better to get some advice on this now than to have it blow up during due diligence.

CJ from Mostly Metrics:

I’d say after $20 million you’re lucky to get away with any year you don’t have to get an audit done. $10 million is honestly a bit early. I’d try to get away with another 12 months if you can. Buuuut if you are a total mess when it comes to rev rec, then it’s better to take one on the chin now than have an entire additional year of hard re work.

plus, remember - in your first audit they also do an audit on the year before that for a baseline. So it’s 2x the work.

“This is accrual accounting?”

Question #3:

What does a great weekly pipeline review call look like? I’m the closest thing we have to revops (I’m head of finance), and I’ve stumbled into running out Monday pipeline calls. My CEO is technical and isn’t in a position to run the call. And right now, I feel like our VP of sales is running circles around me. For context, we are still sub-$100M and have a field sales force with about 20% coming from self-serve.

Hank, NYC

Chris from Zeta:

The weekly sales pipeline meeting is THE MOST important cadence a company has. To get the highest ROI, I suggest the following:

  1. Ensure there is a single version of truth for sales KPIs.

  2. Prioritize measuring top of funnel metrics as opposed to bottom of funnel metrics. Top of funnel = what are your sales people’s daily activities. Bottom of funnel = pipeline opportunities. Habits are the number one predictor of success.

  3. Cohort the sales team by tenure to have visibility into productivity. This gives visibility into the production of your newest versus most experienced reps. 

  4. Fail fast. The killer of sales productivity is losing “winnable” deals and not removing poor performing quota carriers fast enough.

Michiel from Remote:

If your VP of Sales is running circles around you, it’s because they’re playing ‘Storytime’ and you’re playing ‘Accounting.’ Sales leaders are professional storytellers, that’s why they are more fun at parties than us finance folks… To take back control, you need to turn the pipeline review into a numbers game. Ask AI to build you a dashboard or scorecard specific to your sales process, and require that to be filled in before the meeting. Quantification of each potential deal (size, close date, probability) and pipeline coverage is key… After a few months, you’ll be able to compare this to reality to properly calibrate this meeting.

Question #4:

We just lost a deal to a competitor who offered a 3-year contract with significant Year 1 discounting in exchange for the commitment. Our CEO now wants us to start offering similar structures. I’m nervous about setting a precedent and what it does to unit economics. And to our reputation. I don’t want to be a bargain bin company. How do you think about multi-year deal structures - when do they make sense, what guardrails do you put around the discounting, and how do you make sure sales doesn’t just use it as a crutch to close everything? Send help!

Pat, Austin

Chris from Zeta:

Ultimately, your goal is to land, expand and extend with your customers. I would make the unit economic trade of concessions up front, for the opportunity to retain a customer longer. Customers tend to become more profitable the longer they are on the platform. Your sales incentive structure should be something you leverage by promoting the importance of near term AND long-term value + profitability of the customer over time.

Michiel from Remote:

Multi-year deals are a great tool to prevent customers from shopping around, but "First year free" is a slippery slope. Beyond the revenue recognition headaches and the hit to your working capital, this can indeed signal low quality. Instead of putting hard guardrails around it, you can also change the sales incentives. Put more weight on the first year, and less on the outer years, or cap the commissionable discount. When the "easy win" results in a smaller paycheck, your reps will find ways to defend your premium pricing, and only use this structure when absolutely necessary.

Question #5:

I’m trying to figure out the right time to bring on a Head of FP&A. Right now, I’m doing most of that stuff myself as VP Finance, with a senior analyst supporting me. We’re about 200 people and $30M ARR. Every time I think about hiring for the role, I talk myself out of it because I like owning the modeling and board work. But I’m also drowning. How did you think about when to make that hire, and how did you avoid the trap of hiring someone and then not actually letting go of work?

Terry B., Tennessee

Chris from Zeta:

It’s not too soon to make this hire. The FP&A role you are considering can wear many hats and therefore give you the capacity to do more. You can scope the FP&A role to be the hand and glove with your accounting team, provide dedicated support to your business counterparts, and serve as your center of excellence for KPI/analytics. Each of these tasks you were probably taking on as your 2nd or 3rd shift. You don’t ever want to lose the skill to dig into the work yourself, but this gives you a greater chance of going from spending time “reporting the news” to “making the news.”

Michiel from Remote:

Your most important job is to build a good team. As your team scales, you must keep a high bar for quality, but you’ll have to accept that not everything will be done your way. As a first step, ask the senior analyst to own the model with your supervision. Then afterwards, hiring a head of FP&A should help you in partnering with the rest of the organization. Don’t worry, you’ll still be busy with board decks. That never goes away…

(P.S.: I secretly run my own little model on the side, just to have an alternative view and challenge the FP&A team. Please don’t tell anyone.)

Wishing you don’t get run over by your CRO in the pipeline call this week,

CJ

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