Greatest Hits: Building Learning Cultures in Finance with Jessica McClain, CFO at American Staffing Association

In this "Greatest Hits" episode of CFO Weekly, Megan Weis revisits a masterclass in leadership with Jessica McClain, current CFO of the American Staffing Association. Recorded during her tenure as CFO of Girl Scouts Nation's Capital, the 2023 Nonprofit CFO of the Year shares her roadmap for transitioning from public accounting to the C-suite by prioritizing continuous learning, emotional intelligence, and team development. Jessica’s insights offer a timeless guide for navigating technological disruption and mastering the strategic agility required of the modern finance professional.

In this Greatest Hits episode of CFO Weekly, Sara Wyman, CEO & Founder at Stackpack, joins Megan Weis to explore how modern CFOs are transforming vendor management through AI-powered automation and strategic oversight, drawing from her experience as former VP of Strategic Partnerships at Affirm, where she witnessed the chaos of managing hundreds of vendors without proper systems at high-growth companies.

In this Greatest Hits episode of CFO Weekly, Aaron Levine, Chief Financial Officer at Prophix, joins Megan Weis to discuss the challenges and opportunities of being a CFO at a company whose technology is built for CFOs. Aaron shares insights on the evolving role of the CFO in today's tech-driven landscape, the importance of data stewardship, and how innovative financial solutions can enhance collaboration across teams.

In this episode of CFO Weekly, Patrick Villanova, Chief Financial Officer at BlackLine, joins Megan Weis to explore how agentic AI is shifting the office of the CFO from binary, "yes/no" automation to autonomous decision-making. Drawing from a decade of leadership at BlackLine and deep experience in SEC reporting, Patrick discusses the critical need for "deterministic" AI, systems where perfection is the only allowable outcome and how these agents act as a strategic "fifth person in the room". He shares why the future of finance belongs to "data-savvy" professionals who embrace technology to transition from manual doers to high-impact reviewers.

In this episode of CFO Weekly, Hari Sankar, Senior Vice President of Applications Development at Oracle, joins Megan Weis to explore how AI, automation, and cloud technology are transforming finance from a reactive, manual function into an automated, insightful, and connected strategic force, drawing from his fifteen-year journey at the intersection of finance and technology and Oracle’s mission to embed AI directly into core finance platforms.

In this episode of CFO Weekly, Sara Daw, CEO of The CFO Centre Group Limited, joins Megan Weis to talk about the role of a fractional CFO in the growth of modern entrepreneurial businesses. Learn when growing companies should consider bringing on a fractional CFO, how experienced executives can successfully transition to fractional work, and why this flexible model is reshaping the future of executive leadership.

In this episode of CFO Weekly, Todd McElhatton, COO and CFO at Zuora, joins Megan Weis to explore how the CFO-CEO relationship has evolved from reporting history to engineering outcomes, drawing from his three decades of experience leading finance and operations at SAP, Oracle, VMware, HP, and his role guiding Zuora through its $1.7 billion acquisition by Silver Lake and GIC.

In this episode of CFO Weekly, Chris Garber, Chief Financial Officer at Guild, joins Megan Weis to explore how AI and automation are transforming finance leadership from technical specialists to cross-functional business generalists, drawing from his experience leading diverse teams across FP&A, analytics, sales ops, IT, and his fifteen-year journey with a transformational mentor who consistently pushed him into new functional areas to drive company impact.

In this episode of CFO Weekly, Mark Dempster, Founder & Chief People Officer at The Circle by Founders Circle Capital, joins Megan Weis to explore how peer community has become essential infrastructure for CFOs navigating pre-IPO pressure, drawing from his experience building The Circle, a private leadership community serving 350 venture-backed CFOs, and his background as the first non-investor role at Sequoia Capital.

In this episode of CFO Weekly, Kevin Appleby, Head of Partnerships at GrowCFO and host of the GrowCFO Show podcast, joins Megan Weis to explore how new CFOs can successfully navigate their critical first hundred days, drawing from his extensive experience mentoring finance leaders through the challenging transition from technical finance roles to strategic enterprise leadership.