An Operationally-Focused CFO’s Guide to Scaling From SMB to Enterprise: Lessons From ServiceNow
Description
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.com ServiceNow: https://www.servicenow.com/ CJ on X (@cjgustafson222): https://x.com/cjgustafson222 Mostly metrics: http://mostlymetrics.com RELATED EPISODES: Gaining Strategic Advantage in Vertical SaaS With Guidewire's CFO, Jeff Cooper — https://www.youtube.com/watch?v=xtyFpz6Jwyk "Steal Your Boss's Job”: Calendly CFO John McCauley on Leadership, Ownership & Growth — https://www.youtube.com/watch?v=VRpTNDIfzPY The Largest Software IPO Ever: How Snowflake Still Left Money on the Table — https://www.youtube.com/watch?v=SWmKtzCEa88 — TIMESTAMPS: (00:00) Preview and Intro (02:40) Sponsor – Tropic | NetSuite | Planful | Tabs (08:48) Becoming an Operationally Focused CFO (11:59) Staying Close to the Customer as a CFO (16:49) Sponsor – Rippling Spend | Pulley | MUFG (20:47) Running Towards a Challenging Market at ServiceNow (24:32) How He Established the Deal Desk at ServiceNow (26:34) Structuring a Deal That Works for Both Sides (29:30) Transparency in Usage-Based Pricing (33:04) A Client’s “Budget Problem”: Cash or Expense Issue (37:13) Lessons From Building Out the Deal Desk at ServiceNow (41:25) Pros and Cons of Multi-Year Deals (44:39) Auto-Renewals: Do This Instead (46:57) Adapting the Go-to-Market Strategy for Enterprise Sales (56:29) Selling to CIOs Whose Jobs Are at Stake (58:17) What Defines “Enterprise” (1:00:45) The Most Important Thing To Get Right in Enterprise Sales (1:02:02) Lessons From Andrew’s Background in Corporate Finance (1:04:19) The Story of How Andrew Got His Job at ServiceNow (1:09:10) Long-Ass Lightning Round: A Big Mistake (1:11:45) Advice to Younger Self (1:12:34) Finance Software Stack (1:16:05) 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 bblee@us.mufg.jp to find out more. #SMBtoEnterprise, #gotomarketstrategy #scalingSaaS #dealdesk #ServiceNow YouTube Music IDs: The Volume up Hip Hop ASQHDXGAVDJMELTR Chopped AAJGXHAZW4KG2A43 Sweet Pieces NLTX9GTXDDZS7AR3 Move Right Now H4CIETKPMEFFJOFC No Body CYYJBWDQDLZY2LQ6 A 90's Baby VG2GJRJYAP5GLFXU Chop Chops by Graceful Movement 5IDN5KSLCGKWOC5I
The key points from the transcript are:
The speaker discusses how they conducted a survey of their sales team at a previous company, ServiceNow, and found that the salespeople were not prioritizing prospecting and opportunity discovery. This led the speaker to realize that the salespeople needed to take more ownership of identifying expansion opportunities with existing customers.
The speaker talks about their experience transitioning companies from a small/mid-market focus to an enterprise focus. This requires changes to the sales process, deal structure, pricing models, and overall go-to-market strategy.
A major part of this transition is aligning the sales team's incentives and behaviors to drive long-term customer success, rather than just short-term deal closure. This includes changes to compensation plans and putting more responsibility on salespeople for renewals and expansions.
The speaker emphasizes the importance of transparency in pricing and contract structures, using examples from their time at Lacework where they moved to a usage-based pricing model tied to cloud resource consumption.
The speaker shares stories of navigating complex reporting structures, such as reporting to both the CFO and CRO at ServiceNow, and how this allowed them to gain a broad operational perspective.
Overall, the discussion highlights the speaker's focus on being a highly operationally-minded CFO, with deep involvement in sales, pricing, and go-to-market strategy, rather than just traditional accounting and finance responsibilities.