Serving SMB mid-market customers is one thing, but when you go upstream to enterprise sales, everything changes: go-to-market strategy, the sales process, how you structure deals, even how you define customer value. Today’s guest, Andrew Casey, has helped scale four SaaS companies: ServiceNow, WalkMe, Lacework, and his current company, Amplitude. At ServiceNow, he worked closely with Snowflake’s Mike Scarpelli and Coatue’s David Schneider, and he was instrumental in establishing the company’s deal desk to support its sales motion. As an operationally focused CFO, he shares a wealth of knowledge on the importance of staying close to the customer, structuring deals that work for both sides, establishing transparency in usage-based pricing, aligning incentives and strategy in sales, the pros and cons of multi-year deals, the problem with auto-renewals and what to do instead, and how to adapt your go-to-market strategy when moving from SMB mid-market to enterprise.

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SPONSORS:

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

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.com

RightRev 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/run

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Andrew Casey on LinkedIn: https://www.linkedin.com/in/andrew-casey-6b14875/

Amplitude: https://amplitude.com

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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RELATED EPISODES:

An Operationally-Focused CFO’s Guide to Scaling From SMB to Enterprise: Lessons From ServiceNow

https://youtu.be/iUpMAQ14YpM

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TIMESTAMPS:

00:00:00 Preview and Intro

00:03:27 Sponsors – Metronome, Mercury, RightRev

00:07:08 Andrew joins the podcast

00:08:10 Becoming an operational CFO

00:09:25 Early customer-empathy beginnings at Sun

00:11:34 How customer-empathy shaped Andrew’s career

00:14:08 Navigating HP’s troubled EDS contracts

00:16:05 Sponsors – Tipalti, Aleph, Fidelity Private Shares

00:19:37 Returning from ads – running toward hard markets

00:20:13 Scaling ServiceNow’s sales operations

00:23:27 Breaking into the trusted circle after the Q1 miss

00:25:26 Building and scaling the ServiceNow deal desk

00:28:11 Principles of transparent, value-aligned pricing

00:30:17 Rethinking metering models and usage alignment

00:33:01 Diagnosing budget constraints vs. cash timing

00:36:14 Incentives, comp plans, and high-trust selling

00:39:21 Training enterprise reps for long-term value

00:40:17 Multi-year deals and when they actually work

00:43:05 Overselling, discount levers, and ZIRP contract bloat

00:45:58 How enterprise scale transforms go-to-market

00:51:03 Pipeline coverage and maturity modeling

00:54:02 Not all pipeline dollars are created equal

00:57:05 Career-risk mindset in enterprise selling

01:00:02 Defining enterprise and moving upmarket

01:01:00 A business-first approach to the CFO role

01:03:10 Getting hired at ServiceNow

01:06:37 Building GTM finance, deal desk, and a 400-person org

01:08:00 Lightning round – biggest mistakes and IR lesson

01:11:10 Advice to his younger self and leading through change

01:13:34 Defining customers, ARR accuracy, and hierarchy pitfalls

01:15:12 The wildest expense attempt ever submitted

#RunTheNumbersPodcast #SaaSFinance #EnterpriseSelling #GTMStrategy #CFOInsights

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

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