How to discuss AI with your CEO and board

As planning season gets underway, CFOs everywhere are likely getting this question from their CEOs and boards: "How should our company invest in AI?"

In this webinar, Dave Wieseneck (Ramp’s Expert-in-Residence), Brian Gwiazdowski (Primary Venture Partners’ VP in Portfolio Strategic Finance), and Johnnie Walker (Rooled’s Co-founder and Director) discuss how finance leaders can strategically steer the conversation, depending on the personality of their CEO and board and the maturity of their AI implementation.

You’ll hear their thoughts on:

  • Managing expectations with execs who are all in on AI—and ones who are more skeptical
  • Getting critical buy-in from employees for your AI strategy
  • Experimenting with finance AI

About the speakers

Johnnie Walker
Co-Founder and Director, Rooled
Johnnie Walker is a Director of Rooled, which provides outsourced accounting, fractional CFO, and tax services to venture-backed and high-growth companies. Johnnie was previously VP Sales with inDinero, providing fully outsourced accounting solutions to start-up, emerging high-growth, and established companies where he led sales and BD activities nationwide for the company. Prior to inDinero, Johnnie led the East Coast office for tempCFO and provided strategic CFO advisory services to technology ventures and other businesses. Johnnie was also an Adjunct Associate Professor in impact investing at Columbia Business School for over 8 years. He advises several startup businesses, focusing on financial management and investment strategy. Educated in business and engineering, Johnnie has held senior roles in the defense electronics industry, venture capital, and non-profit sectors.
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Brian Gwiazdowski
Vice President, Portfolio Strategic Finance, Primary Venture Partners
Brian is an operating VP at Primary focused on Strategic Finance. In this role, he helps founders and portfolio companies develop financial models and forecasts, analyze and refine KPIs, and allocate and raise capital efficiently. Brian began his career at Vista Equity Partners acquiring enterprise software companies and partnering with management teams to drive operational improvements. He has since held financial and operational leadership roles at software companies including Relias Learning, Wolters Kluwer, and Watermark Insights. In these roles, he managed budgeting and forecasting, KPI reporting, systems implementations, M&A and debt transactions, and other strategic initiatives. Brian graduated from the University of Virginia with a B.S. in Commerce.
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Dave Wieseneck
Expert-in-Residence, Ramp
With 15 years of experience as a finance operator and advisor across 7+ fast-growing tech startups, David’s career has rallied around 1 core purpose: building high-performance teams that scale operations with cutting-edge technology. Having previously ran the finance teams at Demostack, letgo, & Ollie Pets & as an advisor for Carta, Justworks, Navan, and Ironclad, he now serves Ramp as their first-ever Expert-In-Residence. David implemented Ramp with 3 past companies, making him a seasoned authority in their products and workflows. Today, he leads the team by shaping user experiences, both internally and customer-facing, with a unique curiosity and passion for building the future of financial technology.
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