Chirag Shah on Scaling From $30M to $1B and Prepping Companies for IPOs | Mostly Classics

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, joins CJ to share insights from his experience of scaling businesses from $30 million to nearly $1 billion and tripling ARR. He talks about taking companies public and how he helped take one private again in a $5.2 billion deal. In this episode, he explains what signals indicate that a company is ready to accelerate its growth, the art and science of building sales capacity, and how to balance efficiency and growth in hypergrowth mode. He also covers how to achieve a great valuation without a strong performance, the biggest headache on the road to IPO, and whether you should IPO in the first place or remain private.—SPONSORS:Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—Chirag Shah on LinkedIn: https://www.linkedin.com/in/chirag-shah-787b1b20/Motive: https://gomotive.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:From $30M to Almost $1B: A Guide to Hypergrowth, IPO Prep, and Navigating the Public Markethttps://youtu.be/_pJfdN5p-ik—TIMESTAMPS:00:00:00 Preview and Intro00:02:57 Sponsors – Mercury | RightRev | Tipalti00:06:49 Motiv CFO Intro & Company Background00:07:01 Product Market Fit as a CFO00:09:26 Lessons From Taking Companies Public00:11:04 Preparing for Life as a Public Company00:11:26 Moving From Finance Into a GM Role00:12:50 Learning the Business Beyond Finance00:14:23 Empathy for Sales & Carrying a Quota00:15:51 Sponsors – Aleph | Fidelity Private Shares | Metronome00:19:03 Asking Better Questions After Operating Experience00:21:23 Knowing When to Accelerate Growth00:23:16 High-ROI Capacity Signals00:24:51 Scaling Requires Supporting Functions00:26:19 The Art + Science of Adding Reps00:27:53 Sales Team Buy-In Before Scaling00:29:15 Reading Product-Market Fit Through Sales00:30:08 Where Scaling Breaks First (Enablement)00:31:36 Importance of SE / SC Ratios00:33:13 Timing Supporting Hires00:34:32 Maintaining Momentum While Scaling00:36:33 Longest Pole in IPO Prep: Predictability00:38:47 Building Confidence Through Consistency00:40:45 Large Deals Swing Small Companies00:42:41 Growth Still Drives Quarterly Volatility00:44:43 Investor Education as a Core IPO Task00:46:00 Harder to Make Big Changes Publicly00:47:39 Managing Morale in Volatile Markets00:48:33 Taking Cornerstone Private00:52:32 Advice: Know Why You Want to Go Public00:56:18 Efficiency Without Sacrificing Growth01:00:58 Operating Roles Prepared Him for CFO01:06:23 Finance Software Stack Overview#RunTheNumbersPodcast #Hypergrowth #IPOreadiness #CFOInsights #MostlyClassics This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com