In this episode, CJ is joined by Jeff Cooper, the CFO of Guidewire, a publicly traded vertical software company serving the insurance industry. Jeff explains the strategic advantage Guidewire has in owning the control point within a customer's tech infrastructure and how they achieved this. He sheds light on the challenges and benefits of Guidewire's industry-specific business model, including long sales cycles, non-standard fiscal years, and the risks of burning through their market. He also discusses ARR as the most important metric, how he decides on the metrics he reports on, and how to think about the value of professional services within your valuation and value proposition.

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@cjgustafson222 (CJ)

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TIMESTAMPS:(00:00) Preview and Intro

(01:57) Sponsor - Maxio | Mercury

(04:20) How Guidewire Monetizes Its Business

(08:48) Guidewire’s Strategic High Ground and How They Earned It

(13:53) The Benefits of Owning the Control Point in a Customer's Tech Stack

(16:09) Guidewire’s Long Deal Cycles and Sales Capacity Model

(18:47) Sponsor - NetSuite

(20:09) Navigating Big Deals, Long Sales Cycles, and Seasonality

(22:33) Guiding to ARR

(24:38) The Pros and Cons of Having Fiscal Year End in July

(28:27) Concerns Over Burning Through Your Market

(31:39) Professional Services: In-house Versus Outsourcing

(36:11) The Nature of a Good Partner Ecosystem

(38:44) Communicating the Most Important Metrics

(42:03) Long-ass Lightning Round: One of Jeff’s Biggest Metric Mistakes

(44:33) The Advice Jeff Would Give His Younger Self

(45:53) Jeff’s Finance Software Stack

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Gaining Strategic Advantage in Vertical SaaS With Guidewire's CFO, Jeff Cooper

Run the Numbers