Selling to the Enterprise from the Start with Sheila Stafford - Ep 50
Plus, can PR still Pack a Punch?
Welcome to the latest weekly edition of The Transaction newsletter & podcast. Every Thursday, we share resources you should check out, what we’ve found insightful recently, and tactical ways you can improve your go-to-market today. For more: Podcast | YouTube
In a shocking twist, Craig has been having internet issues… So, he asked me, Sam the Producer, to fill out parts of this edition of the newsletter. So, sit down, strap in, and enjoy your journey on Sam’s wild ride - Full of ‘insights’ from a 26-year-old ‘marketer’.
Here’s what’s on deck this week:
What Craig, Sam, & Everyone on LinkedIn’s Reading
A little something fun
Recent Insights from Past Guests
Latest Episode: Selling to the Enterprise from the Start with Sheila Stafford - Ep 50
Did someone forward you this newsletter? I’m sorry about that, but since you’re here you might as well subscribe…
What Craig, Sam, & Everyone on LinkedIn’s Reading: Courageous Marketing by Udi Ledergor
From the Director of marketing leader behind the explosive growth of Gong comes a new film unlike anything you’ve seen before 204 pages of distilled marketing insights curated from over twenty years of B2B marketing experience to help you, “[t]ake the boring out of B2B marketing.”
My copy is unfortunately still stuck in Kentucky-based Amazon warehouse, but I can’t wait to dig into this book.
In case that wasn’t a compelling enough pitch, here’s what the professionals put on Amazon:
“Courageous Marketing is your guide to grabbing attention, creating loyal fans, and crafting messages that connect with your audience (before turning them into buyers). Through practical examples from Udi Ledergor’s journey building an iconic brand at Gong and invaluable advice from marketing leaders at companies like Salesforce, Oracle, and Atlassian, you’ll learn how to:
Punch above your weight with guerrilla marketing stunts to make your company appear bigger than it is.
Create content marketing so good that people are willing to pay for it.
Successfully build a new product category (but only if you really need to).
If you want to intentionally advance your marketing career, build a highly effective team, and impactfully collaborate with your peers, you’re in the right place.”
A little something fun
Recent Insights from Past Guest
Chris Orlob, Chris’s Episode on The Transaction
Great tip for sellers about looking for a big problem, rather than a myriad of smaller problems.
Sam McKenna, Sam’s Episode on The Transaction
Sam shows a cool way for sellers to use LinkedIn Sales Nav to connect with new leaders within their own org and build out a larger network.
Ray Rike, Ray’s Episode on The Transaction
Some of the good, bad, and ugly of the latest SaaS revenue benchmarks…
Psst. Ray also has a great SubStack
Latest Episode: Selling to the Enterprise from the Start with Sheila Stafford - Ep 50
YouTube | Spotify | Apple Podcasts | GoodPods | OverCast | Snipd | More Options
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.
Epic Quotes
“ Net revenue retention KPIs are probably one of the most important things that you should pay attention to as a founder.” - Sheila Stafford
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?
Connect with Sheila
Shoutouts
Fortive
Vanta
Christina Cacioppo: https://www.linkedin.com/in/ccacioppo/
Brett Queener: https://www.linkedin.com/in/brettqueener/
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Follow the Hosts
Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/
Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/
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