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

Listen to this episode from Run the Numbers on Spotify. 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.—LINKS:Andrew Casey on LinkedIn: https://www.linkedin.com/in/andrew-casey-6b14875/Amplitude: https://amplitude.comServiceNow: https://www.servicenow.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:Gaining Strategic Advantage in Vertical SaaS With Guidewire's CFO, Jeff Cooper"Steal Your Boss's Job”: Calendly CFO John McCauley on Leadership, Ownership & GrowthThe Largest Software IPO Ever: How Snowflake Still Left Money on the Table —TIMESTAMPS:(00:00) Preview and Intro(02:40) Sponsor – Tropic | NetSuite | Planful | Tabs(08:45) Becoming an Operationally Focused CFO(11:50) Staying Close to the Customer as a CFO(16:37) Sponsor – Rippling Spend | Pulley | MUFG(20:34) Running Towards a Challenging Market at ServiceNow(24:15) How He Established the Deal Desk at ServiceNow(26:13) Structuring a Deal That Works for Both Sides(29:08) Transparency in Usage-Based Pricing(32:39) A Client’s “Budget Problem”: Cash or Expense Issue(36:42) Lessons From Building Out the Deal Desk at ServiceNow(40:53) Pros and Cons of Multi-Year Deals(43:57) Auto-Renewals: Do This Instead(46:10) Adapting the Go-to-Market Strategy for Enterprise Sales(55:33) Selling to CIOs Whose Jobs Are at Stake(58:18) What Defines “Enterprise”(59:43) The Most Important Thing To Get Right in Enterprise Sales(1:01:01) Lessons From Andrew’s Background in Corporate Finance(1:03:12) The Story of How Andrew Got His Job at ServiceNow(1:07:57) Long-Ass Lightning Round: A Big Mistake(1:10:31) Advice to Younger Self(1:11:17) Finance Software Stack(1:14:47) Craziest Expense Story—SPONSORS:Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. Take control of your spend with intelligent spend management at tropicapp.io/mostlymetrics.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.Planful’s financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you’ll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.MUFG is a global banking powerhouse that provides comprehensive banking services for VC-backed, PE-backed, and public companies with revenues starting at $40M. Accelerate your growth trajectory. Contact group head Bob Blee at [email protected] to find out more.#SMBtoEnterprise, #gotomarketstrategy #scalingSaaS #dealdesk #ServiceNow Get full access to Mostly metrics at www.mostlymetrics.com/subscribe