#85 Scaling B2B SaaS Growth: Insights from a Smartsheet Expert | Brendan Regan, Senior Director, Lifecycle Marketing at Smartsheet

In this episode, Brendan Regan, Senior Director of Lifestyle/Lifecycle Marketing at Smartsheet, shares his strategic, multi-channel approach to engaging both enterprise and SaaS customers. He explains how Smartsheet blends digital programs with human touchpoints—such as customer success reps and account executives—to optimize acquisition, retention, and monetization. Brendan discusses key growth levers they’ve tested, including freemium conversion, upgrades, seat expansion, and cross-sell/upsell tactics, all rooted in a data-driven, experimental mindset. He also explores the benefits and challenges of Product-Led Growth (PLG) and Product-Led Sales (PLS), highlighting how A/B testing and propensity modeling support smarter decision-making. Among his most surprising learnings: onboarding plays a larger role in expansion than expected, and simple, sales-driven heuristics can be remarkably effective in cross-selling. Brendan wraps up with valuable advice for B2B SaaS companies—avoid silos, don’t fall into copycat marketing, and never underinvest in technology. Mastering your martech stack and integrating it properly, he emphasizes, is essential for impactful customer communication.