Are Your Salespeople in the Wrong Roles? How to Match Talent to Revenue Growth
Kevin Lawson and Sean O'Shaughnessy argue that misaligned sales roles—not poor motivation or talent—are a root cause of underperformance. Using sports analogies, they break down archetypes like hunters, farmers, lone wolves, challengers, and trappers, and explain why matching the right seller type to the right business model is essential for revenue growth. They also discuss how sales leaders can audit and restructure teams without wholesale turnover.
Summary
The episode opens with a basketball analogy to introduce the concept of positional roles in sales. Just as basketball positions like point guard or center carry specific responsibilities that cannot be interchanged without consequence, sales archetypes—hunter, farmer, lone wolf, challenger, trapper—each bring distinct strengths and limitations that must be understood by sales leaders before staffing decisions are made.
Kevin Lawson emphasizes the importance of distinguishing between the type of seller and the business model the company operates under. In highly transactional or subscription-based businesses, a farmer or customer service-oriented seller may be the right fit, while an outbound enterprise sales motion demands a hunter. He uses his background selling construction wholesale supplies to illustrate how commodity pricing dynamics can undercut even strong relationships, and how hunters risk burning out in highly relational sales environments if they lack support infrastructure.
Sean O'Shaughnessy builds on this by walking through specific archetypes and the conditions that call for each. He notes that if a product is sold once and never again—like an ERP system—a hunter is appropriate because the relationship is inherently short-lived. Farmers, by contrast, thrive in repeat-purchase environments where long-term relationship maintenance drives revenue. He also addresses lone wolves, describing them as effective in organizations that provide little support infrastructure, and challengers as suited for complex, consultative sales cycles. Sean introduces the concept of the 'trapper'—a seller who can execute across all phases of an enterprise deal, from initial hunting through long-term expansion—as the most complete and difficult-to-find archetype.
Both hosts converge on a central warning for sales leaders: forcing one type of seller into a role designed for another is a structural failure, not a talent failure. Kevin points out that people with call reluctance are often miscast in roles requiring heavy prospecting, and that compensation plans must be aligned to the actual role being performed—account managers and customer service reps should not be compensated like account executives charged with closing new logos.
On the question of fixing a misaligned team without mass turnover, Kevin advocates for upskilling over firing, encouraging leaders to identify behavioral signals—like lone wolves treating customers as personal assets rather than company assets—and address them through coaching, process design, and role clarification. Sean adds that hunters who avoid prospecting likely do so because they were never taught how, not because they are incapable, and that making prospecting goal-oriented and gamified can help bridge the gap.
The episode closes with Sean framing the ideal salesperson as one who can execute proactively across a long sales cycle—planting seeds through pilot projects and working up to enterprise-level deals—and encourages listeners to audit their teams against the actual sales motion their business requires.
About this episode
<p dir="ltr">Two Tall Guys Talking Sales takes a practical look at one of the most common sales management mistakes: assuming all salespeople are built for the same job. Sean O'Shaughnessey and Kevin Lawson use a basketball analogy to unpack the difference between hunters, farmers, lone wolves, challengers, relationship sellers, transactional sellers, and trappers. This episode challenges owners, sales leaders, and frontline sellers to examine whether their sales processes, compensation plans, and revenue management expectations actually match the type of salesperson required for Sales success. If your team is underperforming, the issue may not be a lack of effort. It may be role design.</p> <h2 dir="ltr">Key Topics Discussed</h2> <p dir="ltr">01:00 — Why Sales Roles Need Clear Definitions<br /> Sean opens with a basketball analogy: if you do not understand the positions, the game becomes harder to follow. The same is true in sales. Confusing labels like hunter, farmer, challenger, lone wolf, and trapper can create bad hiring decisions, poor coaching, and broken sales strategies.</p> <p dir="ltr">02:50 — Do Not Confuse Seller Type with Business Model<br /> Kevin draws an important distinction between the kind of salesperson you have and the kind of business you operate. A transactional sales model, a relationship-driven sales model, and an enterprise sales model each require different selling behaviors, messaging, and support structures.</p> <p dir="ltr">06:20 — Hunters, Farmers, and the Cost of Misalignment<br /> Sean explains why a one-time ERP-style sale usually requires a hunter, while repeat-purchase relationships often require a farmer. Asking one type of salesperson to behave like another may be possible, but it is rarely efficient. Sales leaders need Business acumen to know what role the business actually requires.</p> <p dir="ltr">08:25 — Lone Wolves, Challengers, and Unsupported Sales Teams<br /> The discussion turns to lone wolves and challengers, especially in organizations that give salespeople little infrastructure, weak marketing, poor sales processes, or minimal sales enablement. If leadership expects sellers to "just figure it out," they may be selecting for independence while unintentionally creating risk.</p> <p dir="ltr">09:50 — How to Reshape a Sales Team Without Blowing It Up<br /> Kevin warns against the instinct to immediately replace the team. The better move is to take an intellectually honest look at the team's structure, upskill where possible, and decide whether the business needs account managers, customer service support, hunters, or relationship-focused sellers.</p> <p dir="ltr">12:50 — The Trapper: Building Toward Enterprise Revenue Generation<br /> Sean closes by describing the trapper: the salesperson who can hunt, farm, lead, challenge, and plan proactively for larger future opportunities. This is where Value selling becomes more than a technique. It becomes a disciplined approach to expanding from a pilot project to departmental adoption, divisional traction, and eventually enterprise-level revenue generation.</p> <h2 dir="ltr">Key Quotes</h2> <p dir="ltr">Sean O'Shaughnessey — 01:07<br /> "Not knowing what the roles are is a big deal. So that same kind of thing happens in a sales arena, where you may not understand what type of salesperson you have or what type of salesperson you need."</p> <p dir="ltr">Kevin Lawson — 02:51<br /> "It's important to note that just because somebody looks like something doesn't mean that's actually what they are."</p> <p dir="ltr">Kevin Lawson — 03:51<br /> "You, as a seller, need to understand your business model so that you know how to sell."</p> <p dir="ltr">Sean O'Shaughnessey — 08:08<br /> "Asking one type of salesperson to be another is really difficult to do. That's like asking that point guard to be the center."</p> <p dir="ltr">Kevin Lawson — 10:39<br /> "Change people before you have to change people."</p> <p dir="ltr">Sean O'Shaughnessey — 14:15<br /> "How do you become proactive? How do you plan for the deal that's going to happen in nine months?"</p> <h2 dir="ltr">Additional Resources</h2> <p dir="ltr">The Challenger Sale — Referenced during the discussion of lone wolves and challengers, especially the idea that some sellers succeed by taking control of complex customer conversations.</p> <p dir="ltr">Eliminate Your Competition by Sean O'Shaughnessey — Sean refers to the "trapper" concept from his book as the more complete sales archetype for complex, enterprise-level selling.</p> <p dir="ltr">B2B Sales Lab — Kevin mentions that this topic will be explored further in B2B Sales Lab office hours, where sellers and sales leaders can dig into the practical work of assessing team fit, role design, and sales execution.</p> <h2 dir="ltr">A Significant Actionable Item from this Podcast</h2> <p dir="ltr">Audit your current sales team against the sales motion your business actually requires.</p> <p dir="ltr">Do not start with personality labels. Start with the business model. Are you selling once and moving on? Are you expanding accounts over years? Are your deals transactional, relationship-driven, enterprise-level, or a mix? Then map each salesperson against the role the business needs: hunter, farmer, account manager, challenger, lone wolf, or trapper.</p> <p dir="ltr">The decision that follows is the real work. Some people need coaching. Some need a different seat. Some roles need compensation redesign. Some teams need additional support around account management, customer success, prospecting, or CRM discipline. Sales success improves when the revenue management system fits the people, the process, and the customer buying motion.</p> <h2 dir="ltr">Summary</h2> <p dir="ltr">This episode of Two Tall Guys Talking Sales is a useful listen for any owner, VP of Sales, sales manager, or seller who has ever wondered why a capable salesperson still struggles in the wrong role. Kevin Lawson and Sean O'Shaughnessey make the case that sales performance is not only about talent. It is about fit, structure, expectations, and leadership discipline. If your sales strategies are not producing the results you expected, this conversation will help you look beyond activity levels and ask the more important question: Do we have the right people in the right sales roles for how our customers actually buy?</p> <p><strong id="docs-internal-guid-6a72886a-7fff-c312-93ac-9ae1b2d49313"><br /> <br /></strong></p> <p class="p1"><strong>B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory.</strong> It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com</p> <p class="p2"> </p> <p class="p1">You can reach out to Sean at New Sales Expert, LLC - <a href="mailto:[email protected]"><span class="s1">[email protected]</span></a> - <a href="https://www.linkedin.com/in/soshaughnessey/"><span class="s1">https://www.linkedin.com/in/soshaughnessey/</span></a></p> <p class="p2"> </p> <p class="p1">You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - <a href="mailto:[email protected]"><span class="s1">[email protected]</span></a> - <a href="https://www.linkedin.com/in/kwlawson/"><span class="s1">https://www.linkedin.com/in/kwlawson/</span></a></p> <p class="p2"> </p> <p class="p1">You can book time on Kevin's calendar at <a href="https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin"> <span class="s1">https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin</span></a></p> <p class="p2"> </p> <p class="p1">You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/</p>
Key Insights
- Kevin argues that confusing a seller's personality type with the company's business model is a primary source of misalignment—a hunter placed in a highly relational business without account management support is structurally set up to fail, not personally deficient.
- Sean contends that lone wolves are not inherently problematic; they are actually well-suited to organizations that intentionally provide little infrastructure or support, meaning the issue arises only when they are placed in collaborative or process-heavy environments.
- Kevin argues that people with call reluctance are frequently not motivation problems but role-fit problems—they are often farmers or account managers who have been miscast as hunters and are avoiding tasks that were never their natural strength.
- Sean claims that hunters who resist prospecting typically lack the skill rather than the will, and that the organizations that graded them only on closed deals—never on relationship retention—are responsible for allowing that skill gap to persist.
- Kevin asserts that compensation plans that fail to differentiate between account executives hunting new logos and account managers retaining existing customers create misaligned incentives that reward the wrong behaviors and undermine both functions.
Topics
Transcript
In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessy take a hard look at one of the most overlooked causes of poor sales performance, putting the wrong salesperson in the wrong role. Using a basketball analogy, they break down why hunters, farmers, lone wolves, challengers, and trappers all bring different strengths and why sales leaders create problems when they pretend those differences do not matter. You will hear why sales success depends on matching your team structure, compensation plans, and sales processes to the way your customers actually buy. Before you assume you have a motivation problem, a talent problem, or a pipeline problem, this conversation may help you see the real issue, role design.…
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