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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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
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