Podcast Summary: Always Be Testing #85 – Scaling B2B SaaS Growth with Brendan Regan of Smartsheet

Release Date: May 20, 2025

In episode #85 of "Always Be Testing," host Tye DeGrange dives deep into the intricacies of scaling B2B SaaS growth with Brendan Regan, Senior Director of Lifecycle Marketing at Smartsheet. This episode offers a wealth of insights into growth strategies, performance marketing, customer acquisition, and the nuanced balance between product-led and sales-led approaches. Below is a comprehensive summary capturing the key discussions, insights, and conclusions from their engaging conversation.

1. Introduction to Brendan Regan and His Role at Smartsheet

The episode kicks off with Tye introducing Brendan Regan, emphasizing his expertise in growth and marketing. Brendan provides an overview of his role at Smartsheet:

Brendan Regan [00:56]: "I look after a team that is called the Lifecycle marketing team. We sit within a broader demand generation function and then that goes up to an even broader go-to-market organization. So we focus a lot on nurturing prospects and customers multi-channel to try to get them to various growth outcomes along their customer journey."

Brendan highlights the dual focus on Product-Led Growth (PLG) and Product-Led Sales (PLS), leveraging Smartsheet's diverse customer base—from high-end enterprise clients to low-tier monthly subscribers.

2. Balancing Acquisition, Retention, and Monetization

The conversation transitions to how Brendan and his team address the three pillars of growth: acquisition, retention, and monetization. Brendan introduces a "layer cake" or pyramid model to illustrate the balance between digital interactions and human touchpoints based on customer value.

Brendan Regan [02:03]: "I tend to think about things in kind of a layer cake or almost a pyramid where what you apply and how much human touch you apply versus how much digital programming you run really can vary based on the known value of a customer or the potential value of a customer in the future."

This approach ensures that less mature, lower-value customers receive primarily automated digital interactions, while higher-value, more sophisticated customers benefit from personalized human engagement.

3. Experimentation Insights and Growth Levers

Brendan shares critical insights from Smartsheet's experimentation processes, emphasizing the importance of not operating in silos. By integrating digital programs with human-led initiatives, Smartsheet achieved compounded growth outcomes.

Brendan Regan [03:21]: "We did see compounding gains. So once you realize that, then you can start sort of fine-tuning for those different segments. And that's for me, when it started to get really fun."

He outlines several macro growth levers they have tested over the years, including:

• Freemium to Paid Conversions: Encouraging free users to upgrade.
• Subscription Level Upgrades: Moving customers from lower-tier to higher-tier plans.
• Seat Expansion: Increasing the number of seats/licenses a customer holds.
• Service Attach and Cross-Selling: Promoting additional services or products.
• Onboarding and Win-Back Campaigns: Enhancing initial user experiences and re-engaging churned customers.

4. Strategies for User Expansion

Delving deeper into user expansion, Brendan discusses the challenges and successes of moving customers to higher subscription levels. Initial attempts using purely marketing campaigns were less effective, leading to a shift towards integrating product-led strategies.

Brendan Regan [05:56]: "What we found the flywheel there which is you prepay for a certain number of seats... messaging around, 'Hey, you can add more right in the app.'"

This strategy leverages real-time data on license usage to trigger timely and relevant messaging, thereby facilitating seamless seat expansions. Additionally, Brendan emphasizes the pivotal role of onboarding in driving long-term expansion:

Brendan Regan [07:00]: "I would argue very strongly from my experience, onboarding is expansion."

5. Data-Driven Marketing Strategies and Propensity Models

Brendan advocates for a data-driven approach to marketing, starting with simple strategies before advancing to complex models. He underscores the value of leveraging both internal insights from sales teams and sophisticated machine learning propensity models.

Brendan Regan [09:30]: "We really started simple with what I think of as affinity marketing... you can start really simple and then, yeah, you can get really sophisticated with product qualified account signals..."

He advises marketers to begin with straightforward heuristics derived from sales insights and gradually incorporate more intricate data models as needed.

6. Balancing Qualitative and Quantitative Insights

The discussion highlights the importance of blending qualitative insights from sales teams with quantitative data analysis. Brendan explains how initial qualitative findings can set the stage for deeper quantitative exploration.

Brendan Regan [12:13]: "Sales teams are very tribal knowledge... Perfect time to hit them with some marketing."

This balanced approach ensures that growth strategies are both informed by frontline experience and validated through data.

7. Incrementality and A/B Testing

Addressing the hot topic of incrementality, Brendan emphasizes the effectiveness of A/B testing in measuring the true impact of marketing initiatives. He shares innovative methods Smartsheet employs to visualize and assess incrementality:

Brendan Regan [16:59]: "Here's where we turned it off, the line went down. Here's where we turned it back on, lines back up."

By temporarily disabling marketing programs and monitoring performance dips and recoveries, Brendan illustrates a clear and compelling way to gauge incrementality.

8. Overcoming Challenges in Marketing Experimentation

Brendan candidly discusses the challenges encountered in running marketing experiments, such as:

• Resistance to Holdout Groups: Convincing stakeholders to exclude certain customer segments for accurate testing.
• Alignment with Product Teams: Ensuring that marketing experiments do not clash with ongoing product developments.
• Philosophical Differences: Distinguishing between A/B testing and feature flagging.
• KPI Selection and Stakeholder Buy-In: Selecting appropriate metrics and securing executive acceptance of experiment outcomes.

Brendan Regan [19:55]: "The worst case scenario for an experiment is one where your senior executives will not abide by the results."

He emphasizes the necessity of clear communication and alignment with stakeholders to navigate these challenges successfully.

9. Understanding and Implementing Product-Led Growth (PLG)

Brendan delves into the concept of PLG, offering his nuanced definition:

Brendan Regan [20:51]: "Someone could go through an entire customer lifecycle... without human intervention."

He highlights the importance of a seamless product experience that guides users to discover and utilize advanced features independently, fostering deeper engagement and value realization.

10. Combining PLG with Product-Led Sales (PLS)

The conversation explores the synergy between PLG and PLS, debating the optimal sequence and integration of these strategies.

Brendan Regan [22:58]: "I think it's easier to start PLG and then add PLS."

He suggests that establishing a solid PLG foundation—including robust data infrastructure—facilitates the later addition of PLS strategies, enabling comprehensive growth management.

11. Perspectives on Marketing Mix Modeling (MMM)

Brendan shares his thoughts on Marketing Mix Modeling, acknowledging its growing importance in acquisition strategies while noting its limited application in expansion-focused activities.

Brendan Regan [25:41]: "There's going to be something that's going to be super powerful, that using it will be table stakes."

He anticipates the evolution of MMM and similar methodologies, emphasizing the need for marketers to stay adaptable and integrate advanced analytical tools.

12. Favorite Learnings from Smartsheet's Marketing Tests

Brendan recounts two significant learnings from Smartsheet's marketing experiments:

1. Onboarding as Expansion:

   Brendan Regan [28:15]: "Onboarding is expansion... Those who had the winning test onboarding experience, there was net growth there that was more and faster and sustained over a one-year time frame."

2. Effective Cross-Selling Strategies:

   Brendan Regan [29:35]: "Seeing that play out, like, yeah, wow. We don't need to build a data science propensity model yet... that can really backfire on you in experimentation, but sometimes it gives you a great start out of the gate."

These insights underscore the critical role of initial user experiences and simple, yet strategic, cross-selling tactics in driving sustained growth.

13. Common Growth Pitfalls in B2B SaaS

Brendan identifies several common mistakes B2B SaaS companies make regarding growth:

• Operating in Silos: Failing to integrate efforts across departments, leading to fragmented strategies.
• Copycat Marketing: Blindly mimicking competitors without considering unique customer profiles or needs.
• Underinvestment in Tech Stack: Neglecting the importance of a robust, integrated marketing technology infrastructure.

Brendan Regan [30:20]: "There's just so much important stuff happening [in the tech stack]. If you want to really surround the customer on these channels in real time with really relevant communications, it's super important."

He stresses that a well-maintained and strategically aligned tech stack is essential for executing real-time, personalized marketing initiatives effectively.

14. Personal Insights: Brendan's Musical Passion and Hobbies

Beyond professional insights, Brendan shares personal aspects of his life, revealing his passion for music:

Brendan Regan [32:11]: "Outside of my marketing day job, I'm a musician. So write songs, play guitar, sing. I've made a couple albums over the years..."

He reminisces about recording near the iconic Seattle band Pearl Jam, adding a personal and relatable dimension to the conversation.

Additionally, Brendan recommends a book:

Brendan Regan [33:08]: "The Eyes and the Impossible by Dave Eggers. We read it aloud to our 4 and 9-year-old. They loved it."

He also shares his fondness for 80s movies like "Footloose" and "Red Dawn," emphasizing his appreciation for their nostalgic and entertaining qualities.

15. Conclusion and How to Connect with Brendan

As the episode wraps up, Tye commends Brendan for his valuable insights and encourages listeners to connect with him professionally and musically.

Brendan Regan [35:36]: "Professionally, I'm on LinkedIn... Musically, I'm on Bandcamp and the streaming platforms of your choice."

Brendan expresses his hope that sharing his experiences can help others navigate the complex landscape of B2B SaaS growth without facing unnecessary hurdles.

Key Takeaways

• Integrated Marketing Approaches: Combining digital automation with human touchpoints based on customer value can lead to compounded growth outcomes.

• Start Simple, Scale Smart: Begin with straightforward marketing strategies and gradually incorporate complex data models and machine learning as your understanding deepens.

• Onboarding Equals Expansion: A seamless and effective onboarding process is crucial for long-term customer growth and retention.

• Balance Qualitative Insights with Data: Leveraging insights from sales teams alongside quantitative data analysis leads to more informed and effective growth strategies.

• Invest in Your Tech Stack: A robust and well-integrated marketing technology infrastructure is foundational for executing real-time, personalized marketing initiatives.

• Avoid Common Pitfalls: Steer clear of siloed operations, copycat marketing, and underinvestment in essential technologies to ensure sustainable growth.

Connecting with Brendan Regan

• LinkedIn: Brendan Regan on LinkedIn
• Musical Endeavors: Available on Bandcamp and various streaming platforms.

This episode of "Always Be Testing" offers a treasure trove of strategies and lessons for B2B SaaS marketers aiming to scale growth effectively. Brendan Regan's blend of practical experience and thoughtful insights provides listeners with actionable guidance to enhance their marketing efforts and drive sustained business success.