AI-Powered Finance Transformation with Billy Newman, CFO at Redwood Software

Oct 14, 2025

Billy Newman, CFO of Redwood Software, brings over 25 years of finance expertise, including transformative roles at Cvent. In this discussion, he explores how modern CFOs use AI for automation and predictive analytics to elevate finance teams. Billy discusses the importance of balancing automation with human oversight to ensure strong controls and compliance. He shares insights on identifying processes ideal for automation and the critical success factors for scaling AI initiatives, all while emphasizing the cultural preparation needed for finance teams.

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ANECDOTE

Quote-To-Cash Breakdown Sparked Automation

Billy Newman recounts a 2017 quote-to-cash failure that forced automation after manual processes overwhelmed the team.
The crisis prompted a strategic shift to build automation into processes early to avoid firefighting later.

INSIGHT

AI Frees Finance For Strategic Work

AI enables predictive analytics, anomaly detection, and real-time dashboards that improve forecast accuracy and agility.
These capabilities free finance teams for higher-value strategic work and faster executive decision-making.

ADVICE

Build Strong Governance Around Automation

Implement robust governance: audit trails, segregation of duties, access controls, and continuous monitoring for automated processes.
Maintain human oversight to validate outputs and update rules as business conditions change.

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In this episode of CFO Weekly, Billy Newman, CFO at Redwood Software, joins Megan Weis to explore how modern CFOs are revolutionizing finance operations through AI-powered automation and strategic oversight. Billy brings extensive experience from his tenure as CFO at Cvent, where he navigated the company through a pandemic, two public offerings, and private equity transactions while implementing transformative automation initiatives.

With his deep background in FP&A and financial transformation across SaaS companies, Billy shares how finance teams can leverage AI to automate repetitive processes, implement predictive analytics, and position finance as a strategic partner rather than a task master. Currently serving as CFO of Redwood Software, Billy oversees the financial operations of a workload automation company while applying lessons learned from successfully transforming broken manual processes into automated, scalable systems.

What You'll Learn:

How to identify which finance processes are prime candidates for automation versus those requiring human expertise
The "Clean Data Framework" for ensuring AI implementations deliver accurate, reliable results
Why AI enhances rather than replaces finance talent by enabling more strategic work
How to balance automation with human oversight to maintain strong financial controls
The critical success factors for implementing automation at scale in fast-moving organizations
How to transform quote-to-cash processes through strategic automation and system integration
Why AI strengthens compliance and risk management through continuous monitoring and anomaly detection
How to prepare finance teams culturally and technically for the AI transformation journey
The importance of establishing clear KPIs and governance frameworks for automation initiatives
Why cross-departmental collaboration improves when manual data sharing is automated

Learn more about Billy:

Billy Newman on LinkedIn
Redwood Software Website

Episode resources:

Personiv's Website
Personiv on LinkedIn
Personiv on Facebook
Personiv on Twitter

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Previous guests include: Tom McDermott, CFO at Career Certified, Claire Bramley, CFO at Teradata, Chris Miles, Founder of Money Ripples, Ranil DeSilva, CFO & COO at CARE, Jordan Grumet, Financial Independence Expert & Host of Earn & Invest & William Washington, Global CFO at Baker McKenzie

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