We had the opportunity to speak with Bob Marsh about B2B SaaS sales. He was the CEO of LevelEleven in Detroit which was a wonderful portfolio company of ours. He also does a lot of public speaking with numerous speeches at Dreamforce as well as at SaaStr and Hubspot’s conferences. Visit his site at meetbobmarsh.com to learn more about his speaking. Our interview is below.
What are you seeing in the market? What are sellers fighting? The world is getting more complicated. Attention spans are shrinking, we suffer from information overload, and so the customer defaults to ‘who is the easiest to work with and who do I trust?’ As a result you have to simplify. Customers buy from those they like and those they trust. Building the latter requires that the customer believes in you as an expert and believes in your confidence. The customer needs to view you as a thought leader.
We’ve all became so data driven and volume oriented with content, but you really need to show deep category and product knowledge. How do you do this? Be a student of the industry. Learn about your customers’ challenges, and what industry knowledge makes you savvier in the eyes of the customer even if that knowledge has nothing to do with selling. You should also seek and share stories; if you’re part of an organization with multiple sellers, those individuals are having conversations with the customer every day. As a group, you should dig into the stories of why you win or why you lose. The idea is that the more your team is armed with real stories, the more powerful you are. Instead of saying “the typical customer has X, Y, and Z,” it’s much better to say, “your situation reminds me of Bob from XYZ company that had a similar problem,” and then delve into that story telling.
In sales, there’s a profound difference between selling a product and being a true expert. The magic happens when you move beyond simply pushing capabilities and systems, and start sharing genuine insights that your clients haven’t even considered.
Imagine asking a question so insightful that it stops your client in their tracks. A question that makes them realize they’re facing challenges they hadn’t fully articulated — or maybe even realized. Suddenly, the conversation shifts. What started as “just another sales meeting” shifts into a strategic discussion. The client starts thinking, “This person isn’t just trying to sell me something — they’re helping me make sure this project is going to be a success.”
This is the moment when something incredible happens. The client doesn’t just see you as another potential supplier to interview and get a price from. They start pulling you “upstairs” — voluntarily introducing you to decision-makers because they recognize the unique value you bring.
What can someone do to show they’re an expert? At Hubspot in the early days, every new sales person was forced to write 3 to 5 blog posts. Forcing yourself to write not only reinforces your knowledge but sets you apart; a simple LinkedIn post can create thought leadership. The fact that you publish content makes you look like more of an expert immediately. Also imagine if you’re talking to a customer, and you could then say “hey here’s a post I wrote that our conversation has reminded me of,” and then sharing it. It amplifies you. Having content out there is powerful in so many ways and has a halo effect on the overall brand. Worst case though, forcing yourself to be an expert by doing research just gets you smarter on your space.
Technology can help. Rather than asking ChatGPT to write a post about a particular topic, tell it you’re writing a blog post, share an outline, and then tell ChatGPT “what questions do you have for me based on the content?” Sharing bullet points or an outline can get you to a post, and it’s authentic because they’re your core concepts which AI is just helping you to write. You can then modify it to the extent it doesn’t sound like you, just to make sure you’re authentic. Building lists and research is also a very valuable use case of ChatGPT. Let’s suppose you’re preparing for a meeting with a client: tell ChatGPT and ask what are common trends or challenges that others in that industry are experiencing. It can position you to quickly be more educated on the customer’s industry.
How do you end up looking like a fake? If you’re just trying to make yourself look smart, it will come through and perhaps wont be received well. Some are into their personal brand just to make themselves look great, versus building a personal brand to help others. The other mistake Bob sees is you’re trying to sell too hard. Your content and persona will wreak of salesmanship, not expertise. Use content and share your expertise that by itself is helpful to someone. Finally, some individuals get lost in the idea that they’re giving too much information to the point where you’re giving away secrets. This is nonsense. Share what you know, all you know, and even if the customer doesn’t buy from you that day, you’re the expert for when they’re ready, and you’ve left a real impression.
What are some practical steps to becoming an expert?
I) Sellers often think of themselves as quota chasers versus true industry experts. But pause and do the math. How many clients have you worked with? How many projects have you talked to clients about — whether you won them or lost them? A client might handle 1–2 projects like yours every few years or annually. You? You’re likely managing 2–5 similar projects every month. Regardless of your industry, odds are your range of experience may go well beyond your typical clients. Start recognizing your wealth of experience. Identify the patterns you’ve observed. What common challenges do you consistently see? These insights are your expertise waiting to be shared.
II) Commit to continuous learning, but make it manageable. Spend a few minutes each day skimming industry headlines. Commit to reading 1–2 in-depth articles weekly. Start considering other key players in your industry: what other suppliers do your clients work with that are tangentially related to your business? Get to know adjacent businesses and the sellers that work for those companies. Maybe even start getting a coffee every few months with the salespeople are your direct competitors.
Your goal isn’t to become an overnight expert, but to develop a curious, learning mindset.
III) Your greatest asset is the collective experience of your team. Stay connected to all projects, not just your own. Interview colleagues. Ask about recent wins, and equally important, about projects they’ve lost. Why did they lose? What could have been done differently? These conversations are gold. They help you spot trends, develop nuanced understanding, and transform your pitch from feature-listing to storytelling.
Big thanks to Bob for sharing his insight. Reach out to Bob directly on his website at the beginning of this post to connect with him directly.
Thank you for your readership. Visit blossomstreetventures.com for more blogs and SaaS data.