In this episode of Run the Numbers, CJ sits down with Chris Brubaker, SVP of Finance at Postscript, who’s helped build the finance function from the ground up. Chris shares how he partners with sales through deal desks, sets pricing guardrails, and makes sure finance helps close deals instead of slowing them down. They dig into his hands-on approach to automation using AI with limited engineering resources, how Postscript’s metrics evolved as the company scaled, when to trust internal data over benchmarks, and where teams get tripped up. Plus, a private jet accounting story—because of course.

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SPONSORS:

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

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

RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com

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LINKS:

Chris on LinkedIn: https://www.linkedin.com/in/wchrisbrubaker/

Postscript: https://postscript.io/

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

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

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The CFO Case for Probabilistic Forecasting With AI | Bruno Annicq

https://youtu.be/Dl8nDZPJMpE

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:22 Sponsors — Rillet | Tabs | Abacum

00:06:55 Interview Begins

00:07:36 First Finance Hire and Early Scale at Postscript

00:09:02 Usage-Based Margins, COGS, and the Twilio Parallel

00:10:31 Partnering With Sales and Building Deal Desk

00:13:16 Pricing Guardrails, Payback, and Deal Economics

00:15:35 How Deal Desk Evolves Over Time

00:16:01 Sponsors — Brex | Metronome | RightRev

00:19:44 Making Finance a Deal-Closing Partner

00:20:44 Automating Deal Desk With a Slack Bot

00:23:48 How Technical Finance Leaders Need to Be

00:25:17 Automating Without Engineering Help

00:27:12 Why Human Touch Still Matters in SaaS

00:27:53 Postscript’s Finance Tech Stack

00:28:30 ERP Migration and Month-End Efficiency

00:29:42 The Reality of Continuous Close

00:30:34 First Real AI Wins in Accounting

00:31:18 Experimenting With AI Forecasting

00:33:32 Metrics That Matter: Usage as a Leading Indicator

00:35:49 How Metrics Evolve as the Company Scales

00:37:41 Understanding the Product in a Usage-Based Model

00:39:27 Micro-Seasonality and Forecasting Volatility

00:42:21 How to Use Benchmarks Without Misusing Them

00:43:50 Long-Ass Lightning Round: A Costly Modeling Mistake

00:45:45 Advice to a Younger Finance Leader

00:47:05 The Private Jet Accounting Story

00:49:11 Credits

#RunTheNumbersPodcast #FinanceLeadership #DealDesk #UsageBasedSaaS #AIinFinance

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