Navigating Leadership Challenges and Financial Solutions

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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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

"Steal Your Boss's Job”: Calendly CFO John McCauley on Leadership, Ownership & Growth

The Largest Software IPO Ever: How Snowflake Still Left Money on the Table

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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

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#SMBtoEnterprise, #gotomarketstrategy #scalingSaaS #dealdesk #ServiceNow