Selling to the Enterprise From the Start with Sheila Stafford - Ep 50

Sheila Stafford is the Founder and CEO of TeamSense and joins Co-Hosts Matt Amundson and Craig Rosenberg to dig into how to land enterprise clients as a startup, how to build out a B2B sales team from scratch, and why NRR (Net Revenue Retention) is the most important metric for founders to focus on. Shelia also shares why she thinks email is a dead sales channel and why she is betting on modern PR tactics for growing TeamSense.

Also, Craig shares his Instagram Shopping habits, Matt shows off his support for the Dodgers, and Sam the Producer tells a story about a field trip he went on.

Critical Takeaways

•  NRR (Net Revenue Retention) is the most important metric for startup founders because it is a direct reflection of customer love, which is the only real moat in software. When it comes to assessing new opportunities and verticals, founders need to ask themselves if it’s worth taking on a crappy client to get a short-term revenue bump, but a longer-term decrease in NRR. For Sheila and TeamSense, the answer has been a resounding, “No.”
• Discipline is such an important factor for founders in a number of ways, including niching down on a single vertical. This can ensure that your resources are optimally utilized, maintain a strong product-market fit, and ensure long-term sustainability and scalability of your offerings.
• Deep subject matter expertise in the industry you are trying to serve is invaluable. For example, Sheila's extensive experience in manufacturing allowed her to understand and address the unique challenges faced by her customers. This level of insight informed the development and marketing of TeamSense, ensuring the product met real, pressing needs.
• Concentrate all resources on one primary vertical before expanding to adjacent markets. TeamSense initially focused solely on manufacturing and logistics, applying all their efforts there until other verticals started showing interest naturally. This approach ensures a strong foundation before diversification.
• Implement a culture of continuous improvement and maintain active feedback loops. Sheila listens to her team’s Gong calls to ensure messaging remains effective and aligned with customer needs, and she provides direct feedback to her team. This practice ensures that the team continuously refines their approach based on real-time data and feedback.

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Chapters

00:00 - Preview & Craig’s Christmas related-shirt

04:21 - The Sometimes Life-saving Impact Founding a Company Can Have

10:03 - Email is a Mostly Dead Channel

14:17 - How to Get Your First Enterprise SaaS Deal & TeamSense’s Founding Story

20:38 - Learn Your Customers' Native Language & Use It When Communicating Impact

27:24 - Why Building Deep Expertise & Building Something For Someone is Critical for Startups

33:11 - How Do You Measure the Value Your Product Delivers to Customers & Why Founders Need to Focus on NRR 

35:45 - How to Drive Alignment Between Founders and Their Boards

38:53 - How to Build out a Sales Team from Scratch & Growing Beyond Founder-Led Sales

45:16 - Modern Marketing Experiments & Can PR Still Pack A Punch?

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Epic Quotes

• “ Net revenue retention KPIs are probably one of the mo