Mismatched leadership styles can derail your SaaS sales strategy
Two terms I hear (often incorrectly) are transactional and strategic. As it relates to selling, transactional generally refers to commodity sales, where speeds, feeds and price are the drivers of the deal (emphasis on price); strategic selling generally refers to a more enterprise (cross-department) focus that requires top/down decision making.
But what about sales leadership? Can we categorize leadership approaches into transactional and strategic? How many sales leaders focus specifically on tactical activities and how many focus on the overall process (forest and trees metaphor seems to fit here). Does it even matter?
I think it does matter, particularly for organizational change SaaS deals (ERP and CRM are good examples).
Drive-by deals (transactional one-call closes) don’t require much strategy other than understanding the competition and having a crisp message, so a sales leader for transactional sellers needs to only focus on volume of calls by the salespeople and some basic product positioning. Buyers of transactional products typically have a specific budget and know the specific functionality they need even if they don’t know from which supplier they will buy.
Strategic deals are quite different, which is why it is so difficult for salespeople or sales leaders who have focused on transactional deals to transition to more strategic deals.
Strategic deals are different primarily due to the need for a compelling business case to withstand the four sales cycles it takes to win and the bureaucratic method of the purchasing process; therefore, sales leadership must be different as well.
Sales leadership for strategic sellers needs to focus on making the business case the central selling theme and focusing on the customer’s behaviors, including understanding the reason for the deal timing (why now and what happens if you don’t — also known as the compelling event). Because sales cycles tend to be longer for more strategic deals, the sales process that is reinforced by the sales leader must be consistent and prepared at any moment to withdraw from the deal, if the timing or business case lack urgency.
Mismatching sales leadership with the deal type (transactional vs. strategic) can have devastating effects on a sales team, including hiring the wrong salespeople and employing the wrong sales process. Are you sure you’ve hired the right sales leader for your type of SaaS deal?
But what about sales leadership? Can we categorize leadership approaches into transactional and strategic? How many sales leaders focus specifically on tactical activities and how many focus on the overall process (forest and trees metaphor seems to fit here). Does it even matter?
I think it does matter, particularly for organizational change SaaS deals (ERP and CRM are good examples).
Drive-by deals (transactional one-call closes) don’t require much strategy other than understanding the competition and having a crisp message, so a sales leader for transactional sellers needs to only focus on volume of calls by the salespeople and some basic product positioning. Buyers of transactional products typically have a specific budget and know the specific functionality they need even if they don’t know from which supplier they will buy.
Strategic deals are quite different, which is why it is so difficult for salespeople or sales leaders who have focused on transactional deals to transition to more strategic deals.
Strategic deals are different primarily due to the need for a compelling business case to withstand the four sales cycles it takes to win and the bureaucratic method of the purchasing process; therefore, sales leadership must be different as well.
Sales leadership for strategic sellers needs to focus on making the business case the central selling theme and focusing on the customer’s behaviors, including understanding the reason for the deal timing (why now and what happens if you don’t — also known as the compelling event). Because sales cycles tend to be longer for more strategic deals, the sales process that is reinforced by the sales leader must be consistent and prepared at any moment to withdraw from the deal, if the timing or business case lack urgency.
Mismatching sales leadership with the deal type (transactional vs. strategic) can have devastating effects on a sales team, including hiring the wrong salespeople and employing the wrong sales process. Are you sure you’ve hired the right sales leader for your type of SaaS deal?
That’s exactly the kind of misalignment we built Pipeline Grader to uncover. It helps you evaluate whether your sales process and leadership approach are actually suited to the type of deals your team is working — transactional or strategic. By grading your sales pipeline against critical criteria like deal complexity, cycle length, and buyer behavior, you get clarity on whether your team is running the right plays — or just running in place.
