This post is an oldie, but a goodie.
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 sellers really challenged with? 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.
If stakeholders are being added to the sales process, what do you do? Salespeople become involved with their key contact but other decision makers are most definitely involved in the decision. If you discover more constituents are involved, ask the buyer “I know others are involved in this process, what resistance are you getting from some of these individuals.” This will reveal what others are saying, but also what’s on the mind of the customer that they’ve hesitated to share. Additionally suppose one of the constituents you need to convince is the CIO or CRO of the prospect. One technique is to have your own CIO or CRO reach out and greet them, acknowledge them, mention you and your hard work, and build that social connection with their CIO or CRO. This is part of the emotional connection in the Surround Sound process.
How do you find the ICP? First off, when you identify the ICP, it doesn’t mean you say no to everyone else. It means you identify who is the perfect customer so that’s where you spend your marketing and direct outreach resources. You should still take those inbounds even if they don’t match your ICP initially. In order to identify the ICP, you need to figure out how the buyer thinks. Ask yourself how would a successful buying experience would feel with a perfect customer, who are you engaged with, how often do you talk, etc. The more quantitative way to identify the ICP is to do a win/loss analysis: on your wins, where did the lead come from, at what point in the sales cycle did we have confidence in the close, what did the customer love about the product and the process. On your losses, ask similar questions: where did the lead come from, how did they behave, what were their objections, and if you can identify the things that could have turned a loss into a win, what would those things have been. No doubt, patterns will emerge which will help you further refine your ICP.
When do you make the investment in an outbound program with SDR’s? You do it right away, if you can. In the early days you’re naturally outbounding because no one knows about you, so technically your outbounding program came first. To scale it, when you can clearly articulate the ICP and you can afford the cost of the SDR team, that’s a good time. Note that a typical SDR is someone earlier in their career, so you only bring the SDR on when you clearly understand the customer profile and sales cycle yourself because these individuals will need hand-holding. Bob does see companies build SDR teams too soon. Building an SDR program is a serious investment in time and capital, so you need to have a very clear understanding of your own business and process.
How do you hire the right VP of Sales? Don’t do this too soon. The CEO should be the defacto VP of Sales for as long as possible, especially if they’re a sales oriented CEO. If you’re a customer minded, sales driven CEO, you should act as the VP as long as you can. No one will do as good a job as you, and you have the benefit of being the CEO in the eyes of the customer. Otherwise, you bring a VP of Sales onboard when you know who the customer is, what your process is like, etc. You’re likely at $3mm+ ARR. When you bring on a VP of Sales, avoid individuals that have big corporate logos; they wont be used to startup life. You’ll be better served finding a young up-and-coming sales manager, let them sell your product on their own, and then bring sales talent below them. Bringing in a good strong sales person in your industry and letting them evolve into the sales leader is the way to go.
What do you look for when you hire an AE? They have to take initiative. They’re not waiting for others to lead a conversation or run a process. They need to be personable; that doesn’t mean they’re super outgoing rather it means they can have a conversation easily. They also need to be humble and curious. When Bob interviews a potential AE, when they first sit down, he literally doesn’t say anything. He lets it get awkward because he wants the candidate to take control of the situation. The second thing he does is to open up with “tell me about yourself.” It’s a very open ended generic question. Bob wants to see if they launch into their career or their personal life. In an ideal world, they blend both and tell a story, not just give facts. It’s amazing what people will say. Bob looks for cultural fits and sales acumen, moreso than industry expertise and years in the business. Bob also asks “what questions do you have for me.” Having no questions is a very bad answer. They’ve got to have questions about the company, strategy, or even Bob personally. They need to show curiosity. At the end, Bob just says “ok great” and ends the conversation with no clear next steps. He wants to see if the candidate takes initiative and says “alright so what are the next steps.”
Bob Marsh is as experienced a sales leader as it gets. Visit his website meetbobmarsh.com to learn more about his speaking engagements for your team.
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