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How to hire the best controller

A take-home questionnaire to de-risk your hiring decision

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How to hire the best controller

How the former CRO of an NBA team was able to steal $13.4 million – and how to protect your business.


CJ Gustafson

Tech CFO

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Tech CFO CJ Gustafson writes Mostly Metrics, a weekly business newsletter for anyone who cares about company performance that’s read by more than 20,000 of your favorite finance leaders, startup operators and VCs. Subscribe to get smarter on business metrics, financial operations, and monetization models today.

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CJ Gustafson

Tech CFO

Twitter LinkedIn

Tech CFO CJ Gustafson writes Mostly Metrics, a weekly business newsletter for anyone who cares about company performance that’s read by more than 20,000 of your favorite finance leaders, startup operators and VCs. Subscribe to get smarter on business metrics, financial operations, and monetization models today.

Brace yourselves for a surprising revelation: I may be a CFO, but don't mistake me for an accountant, and certainly not a CPA. Heck, I'm still trying to figure out what those letters stand for!

Wait, wait, wait! Just kidding about the last one. CPAs are like my ride-or-die crew. They rock the balance sheet like nobody's business.

But in all seriousness, when I ascended to the position of Master of Coin, my mission was crystal clear: find a world-beating controller. I dedicated endless hours concocting interview questions that could separate the smooth talkers from the relentless go-getters. The outcome? A comprehensive set of thought-provoking questions; a veritable case study of sorts for any controller candidate to chew through.

And let me drop some knowledge on you about case studies. I firmly believe that every finance or accounting professional should take the time to complete a written case study. Why? It reveals their written communication skills (a must for virtual teams), their wizardry in Excel modeling, their mastery of PowerPoint, and their overall attention to detail. We can't have someone who can recite blog posts (like this one, lol) but can't deliver top-notch work. And if you lack the willpower or motivation to take on the challenge, well, I guess my screening tactic has done its job. You've self-selected out.

Now, get ready to embark on a journey through my epic "take-home questionnaire" for accountants. Thanks to my collaboration with Brex and their network of controllers, we've injected a wealth of experience from those already rockin' the controller role at lightning-fast startups and enterprises. Buckle up!

But first — a few bullets on how they think about a controller’s responsibilities at Brex:

  • Manage all aspects of accounting incl. accounts payable — owner of all spend management activities and key champion of software solution

  • Own all aspects of the month, quarter, and year-end close process

  • Ensure continued compliance with all federal, state, and local tax requirements

  • Work with employees to collect, review, manage approvals, and troubleshoot expenses and reimbursements

  • Gather data for reports on spending and budgets for the CFO, leadership, and others

Now, on to the interview questions. You can feel free to add your own additional questions as they relate to your monetization model (SaaS, consumption, marketplace, B2B, B2C) as you see fit.

Get to know your candidate

  1. Walk me through your month-end close process.

  2. How many days would you aim to have the books closed by?

  3. What would you accomplish on each of those days?

  4. What’s a check you would perform or implement to ensure you are not moving too fast and sacrificing accuracy?

  5. Which part of accounting do you enjoy the most? The least?

  6. Tell me about a time you helped an employer save money. What was the result?

  7. What will be your number one concern on a day-to-day basis, in a role like this?

  8. Tell me about a system you implemented (other than NetSuite). What was the impact?

  9. Tell me about a mistake you made while implementing a tool, and what did you learn from it?

  10. Do you have any experience in setting up financial reporting controls? If so, please give an example of a control you were able to design and implement.

  11. What governance would you put in place around cash?

  12. Do you have any experience with audits? Please elaborate.

  13. Where do you think hosting costs (AWS, GCP, Azure) belong within the P&L?

  14. If you could only look at one financial statement to evaluate the health of a company, which would it be, and what would you look for?

  15. What do you include within Working Capital?

  16. What is the difference between Accounts Receivable and Deferred Revenue?

  17. Tell me about your current order-to-cash reconciliation process.

  18. How have you dealt with delinquent receivables in the past? What did you do to resolve the issue while keeping the relationship with the vendor intact?

  19. How do you calculate Free Cash Flow?

  20. How does revenue recognition differ for monthly SaaS sales vs. GMV (gross merchandise value) sales through a marketplace platform vs. professional services?

  21. If cash collected from customers is not yet recorded as revenue, what happens to it?

  22. When do you capitalize rather than expense a purchase?

  23. Under what circumstances does goodwill increase?

  24. What overhead expenses would you suggest we allocate between departments?

  25. What would be the first hire you make? What would they do on a day-to-day basis to support you?

  26. What’s a time when you made your accounting team a hero, rather than a blocker?

  27. Tell me about the most important KPIs you tracked and how you used them to drive decision-making.

  28. What was something you solved that used to keep your old CFO up at night?

  29. Stack rank your level of comfort/expertise in the following areas: technical accounting, operational accounting, financial statement reporting, payroll, tax, and treasury.

  30. If you have a choice to pay for something using a wire, ACH, or corporate credit card, what is your thought process?

  31. Have you had any exposure to company equity plans? What impact would increasing an ESOP (Employee Stock Option Plan) have on the financial statements?

  32. What creates an FX gain or loss?

  33. Have you ever had to analyze sales tax obligations (US or internationally)?

  34. The CEO tells you we are launching a new product or expanding into a new country, what do you do?

  35. How do you think about materiality and risk?

  36. How would you describe the differences between management accounting and GAAP accounting?

  37. What spend management systems have you used in the past? What components were you able to automate by relying on a system?

  38. Have you implemented employee spend management programs before? How did you determine who was able to book what?

  39. Attached is a snapshot of our current P&L chart of accounts (using dummy data). What would you change? How could we improve it? Provide at least 5 recommendations [NOTE: attach your QuickBooks or NetSuite export with dummy figures].

Find a long-term strategic partner

When it comes to the art and science of accounting, you need more than just an X's and O's kind of person. You need someone who grasps the underlying theory behind why the business demands certain actions. Sure, managing our financial position is part of the gig, but it's equally crucial to comprehend how it ties into our company's grand strategy. I'm not on the hunt for a mere number cruncher — that's a task we can outsource. I want a strategic partner, someone who sees the bigger picture.

Getting someone who can successfully answer all of these questions, succinctly and accurately, will significantly de-risk your hiring decision.

PS - Interested in joining Brex’s growing controller community? Shoot them an email to get more info on how you can connect with peers, share insights, discuss hiring faux pas, and just talk about your favorite numbers.

This post originally appeared on mostlymetrics.com.


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