Hiring Sales “Explorers” versus “Settlers” versus “Prospectors”; Mark Birch’s super insightful AND actionable advice

We all receive a lot of ideas and content, only a minority of which grabs us as super insightful AND actionable.

Mark Birch’s recent Enterprise Sales Forum release meets the criteria.

I am personally most impacted by Mark’s informing us of the distinction between sales “Explorers” versus “Settlers” versus “Prospectors”, and each role’s importance depending upon the maturity of your company and sales organization. He makes it simple to understand the behaviors of each and why each may succeed vs. fail, depending on the stage of your company.  The costs vs. opportunities of getting it right are nicely outlined.

Check it out. Great stuff!!!


Mark Birch, Founder of Enterprise Sales ForumGreetings from the Enterprise Sales Forum community and thanks for all your support for our mission to help elevate the craft of the sales profession!

The Dance Between Sales and Product

How sales can be a huge asset in shaping product, market & messaging

Enterprise Sales

Oct 14

“The product is just not good enough!”

How many times has that phrase passed the lips of beleaguered sales reps? Maybe you have even said this yourself in times when selling hits a roadblock. Those times when every prospect brings up features your competitors have but you don’t or when they tell you while the product is interesting, it does not fill an important enough need.

There is no one that has sold anything for any length of time that has not heard some version of these objections before. In fact we expect this whenever we cast our nets wide. For some percentage of customers, the paths of your product and their priorities will never cross. When you hear these objections over and over again however, we begin to wonder. Is it me or is there something going on here?

Much of this depends on the context of the situation. There are three scenarios to consider:

1.  New rep in a company with an established market and track record

2.  Veteran rep with solid track record at company and is now missing targets

3.  Sales reps in a new company without an established market and track record

If there are no wide-scale team issues, the first two scenarios can generally be chalked up to individual performance issues. Not every rep is going to work out at a new company even if they come in with solid past performances from previous roles. Veteran reps can hit rough patches for various reasons including burnout which happens to more of us than is discussed. Both of these are big enough topics that I will discuss them in later posts.

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When it comes to sales at early stage companies however, it is harder to lay fault on individual performance. By early stage, those can be startups that have not reached clear product-market fit, or companies established in one market launching an entirely new product or entering a new market. All assumptions about prior marketing strategies and sales motions can be thrown out the window. The company is writing the playbook on the fly.

This was true of my time at Stack Overflow. Up until I joined, the company made money from monetizing their wildly successful website for software developers through job postings and banner ads. The buyers were recruiters and digital marketers, and the sales cycle was more transactional.

Building an enterprise SaaS business was an entirely new proposition. The problems we were solving were completely different in that we were helping software development teams be more effective through the sharing of knowledge. The buyers were senior IT leaders. The sales cycles were anywhere from 6 to 12 months. The first year of launching the business was mostly about figuring out customer needs, messaging, and buying motions rather than selling.

There were plenty of mistakes I made early on in building the business. The messaging was too low-level and seemed to confuse our value with that of other existing tools like Confluence or Slack. While developers and engineering managers were enthusiastic, we needed to establish visibility and credibility with senior IT leaders. We had little to no demand generation activities to help scale our reach to generate legitimate leads.

As we figured things out about our sales and marketing approach, we also started capturing things prospects and customers wanted from the product. They wanted more features, greater configurability, deeper out-of-the-box integrations, and more flexible deployment options. Our early customer development efforts enabled us to move faster on delivering a fully self-service SaaS offering for smaller companies, something that would not have been possible without the confirmation from sales prospecting and asking detailed sales qualifying questions.

The feedback of sales can often fall on deaf ears inside companies. Whether startup founders and product teams that are too attached and prideful of their creation or existing companies that are too narrowly focused to see emerging market trends, sales teams complaining about the product can seem like whining. But the truth is that sales is often the closest to the customer and the best team on understanding the problems and struggles customers are facing.

This theme came up again in a conversation with a serial startup founder last week. In preparing for our upcoming Clubhouse talk on the AWS Startups Show, he shared a story of how a snippet from a sales call recorded in Chorus AI led the company to revisit their messaging. Another founder mentioned to me a month back that reviewing win-loss data on deals led the startup to speed up delivery of a much desired reporting feature.

So why don’t more companies listen to the feedback from sales. Startup founders and business leaders that did not come out of sales will be more likely to support and trust the things they know best, like product and engineering. The type of sales team also plays a role.

If you have a team of reps motivated mostly to make a quick buck, they will push the proverbial square peg in a round hole. These are process driven reps and if they cannot make sales, they will complain the product sucks and eventually leave.

If you have a team motivated to do what it takes to succeed, they will experiment, test, and prod different audiences, messaging, and markets. Eventually however, they run into the same uphill battle and return to point the finger at the product.

If you have a team motivated to solve customer problems, they will seek to understand the core challenges and what motivates them to change. They explore different ideas, pose questions, challenge assumptions, and view the product from the customer perspective. Instead of complaining to leadership, they work to shape the solutions and guide the product story.

Which begs the question, what sales reps are best for early stage startups and businesses launching new products? I framed three types of reps above and that fact is that you need all of them, but in stages:

·     First you need the Explorers

·     Then you need the Settlers

·     Last you need the Prospectors

The Explorers are trying to find the path to the sale. Often the first explorer is the founder of the business as they do customer discovery in the earliest stages. Adding explorers can be useful because it marries sales skills and experience with the entrepreneurial mindset needed to be patient with developing the sale, solution, and messaging to connect the two. Keep in mind though that Explorers are the hardest type of sales reps to find and often do not stick around long once they have figured out the sale and move onto a new challenge.

The Settlers take what is learned from the Explorers and refine the initial sales process to get to one that is repeatable and scalable. They will tinker and try things, but need a starting point to work from otherwise they become scattered and ineffective. This is the stage when the best reps will quickly rise to the forefront and later on become the management layer as the sales team starts increasing headcount and account coverage.


The Prospectors come after the Settlers have worked out all the kinks in the sales process. Now the process is well understood and allows sales to scale. Prospectors will then come with their tools and determination to focus on pure sales execution. Just like the prospectors of the mid 1800’s California Gold Rush, these reps come to make their big commission payday. When you need to accelerate revenue growth, these are the best reps to have on the team.

Can sales reps switch between these different roles and play another part? Not usually, there are specific skills and behaviors for each role that are not easily transferable nor would they lead to success. Also note that the order you bring in each type of role is critical. If you bring on Prospectors before you have a well-established sales process, you will set up the Prospectors for failure. Likewise Explorers usually do not gel well when selling alongside a team that is mostly Prospectors given the culture and vibe is different.

Next week I will talk about exceptions and scenarios on the Explorers, Settlers, Prospectors concept. For now, let me know if what I shared reflects your experience as a rep or sales leader in the companies you have been in that are scaling quickly.

Mark Birch, Founder of Enterprise Sales Forum




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