“Annual Planning Is So Last Year” – Ross Grainger, CFO of Paradox, on What He Does Instead

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Dec 26, 2024

Ross Grainger, CFO of Paradox, shares his unconventional career journey and emphasizes the importance of work-life integration over balance. He explains why the corporate ladder resembles a jungle gym, highlighting the value of lateral moves for career advancement. Grainger discusses the need for strong relationships across departments, particularly in finance, and shares his skepticism towards annual planning, advocating for dynamic financial strategies. His insights on expanding internationally and investing in team relationships provide a fresh perspective for tech companies.

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ADVICE

Work-Life Integration

View work-life balance as integration, acknowledging that perfect balance is unattainable.
Embrace seasons of life, prioritizing work or family as needed without guilt.

ANECDOTE

Prioritizing Family Time

Ross prioritized attending his children's activities, even if it meant working late.
He coached his kids' sports teams, emphasizing the importance of early involvement.

INSIGHT

The Importance of Hustle

Hustle is a strong predictor of success, not just working hard, but working smart.
Don't be afraid to hustle; find tools for efficiency, but hard work is essential.

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In this episode, CJ interviews Ross Grainger, the CFO of Paradox, to discuss work-life integration (instead of balance), why the corporate ladder is less like a ladder and more like a jungle gym, and the hallmarks of a great CFO/FP&A/controller relationship. He starts by sharing his own unconventional career journey and talks about the importance of the hustle, giving examples from his own life of periods when things were weighted towards life or work and how this benefited him. He also describes why the career ladder is more like a jungle gym and gives examples of times when he had to step backwards or sideways to get ahead. He sheds light on the value of investing in work relationships outside of finance, such as product marketing and sales, before discussing the hallmarks of a good CFO/controller/FP&A relationship. With a team in Vietnam, he gives advice on how to expand internationally. The episode includes an explanation of why Ross doesn’t believe in annual planning, what he does instead, and how he justifies this to the board.

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@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:08) Sponsor – Operators Guild | Maxio

(06:00) Work-Life Integration Versus Work-Life Balance

(09:15) The Importance of the Hustle

(10:53) Periods of Ross’s Life That Were Weighted Towards Life or Work

(12:54) Why It’s Not a Career Ladder but a Jungle Gym

(16:38) Sponsor – RemoFirst | Mercury | NetSuite

(20:27) Examples of Downward Career Moves That Got Ross Ahead

(25:17) The Value of Work Relationships Outside of Finance

(29:30) The Hallmarks of a Good CFO/Controller/FP&A Relationship

(32:38) Paradox’s Team in Vietnam and How to Expand Internationally

(37:11) Ross’s Views on R&D Spend and Advice on Payback Periods

(39:27) Why Ross Doesn’t Believe in Annual Planning

(42:18) Justifying This Flexibility to the Board

(43:51) Communicating Bad News

(45:20) Long-Ass Lightning Round: Career Regrets

(46:41) Advice to Younger Self on the Hustle

(47:12) Finance Software Stack

(47:46) Craziest Expense Story

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