The Top Reasons Why Sales People Leave

Are struggling to retain your software sales talent? 

There are a number of common reasons why sales professionals leave their jobs—and many of them are preventable. Unfortunately, in the hustle of day to day, many startups and early-stage companies miss the signals of an unhappy sales force. 

To generalize—sales professionals want to make money. They’ve chosen to work in sales because it incentivizes success, fuels their thirst for competition, and gives them the opportunity to tie their income directly to the effort they expend. When circumstances get in the way of allowing them to achieve their goals, they start looking elsewhere. This is bad news for organizations who need to retain their top performers—successful sales people are always in demand, and will always have options for where they choose to use their skills. 

If you’re struggling to retain your sales team, have a look at these critical elements of the way your sales team is structured: 

Account assignments and territory re-carving 

Territory re-carves are common in high-growth companies—and handling them poorly is a sure-fire way to demoralize your sales team. Here’s a common scenario: a group of new sales reps are hired immediately following an injection of VC cash. Leadership needs to re-carve the territories so those new reps have people to sell to (fair enough), and the territories for existing reps get smaller. 

Those existing reps are expected to give up accounts that they may have been chasing and nurturing for months. All that time they invested—diligently following up, delivering demos, answering questions, navigating the internal politics at the client’s organization—is now lost to them. They have to hand over accounts that may be just on the cusp of closing to someone new, and end up missing out on the commission. 


Most sales professionals will recognize that territory re-carves are a necessary evil—they’re probably never going to like them, but will understand the business need. The key is to make them as fair and transparent as possible, and to clearly communicate the rationale for approaching them the way you do. This helps to bolster trust in the leadership team—if you’re constantly re-carving territory with little to no forethought, your sales force will start to feel a disconnect with leadership. 

Good leaders will understand that it’s important to have reasonable holdovers—allowing reps to hold on to key accounts for a set period of time. You can also introduce a stepped transition, where incoming reps split key accounts with existing reps with increasing percentages over time (i.e. commission is split 70/30 between the existing rep and the incumbent for the first month, 50/50 for the second, 30/70 for the third month, and then allowing the incumbent to fully take over the account). 


Sales Hiring Checklist

Compensation plans are convoluted, or not competitive

Another common challenge happens when HR and finance starts looking at the numbers, and decides that the sales folks are making too much money. The go in and implement a cap on commissions, effectively de-incentivizing the sales team. 

Other common mistakes include: tying quota to an underperforming product, increasing quota while decreasing the territory, or crafting a comp plan that is so convoluted (with accelerators, higher payout on certain products, etc.) that the sales team has to either keep track of a complicated spreadsheet or just guess at the size of their commission check. 


Understand that you’ll lose your best salespeople if you implement caps on commission. If your reps are exceeding their targets, that’s more than you’ve forecasted for, and the revenue is gravy for your organization. You want to incentivize that! If you’re capping commission, you’re also creating an environment where the sales force is tempted to sandbag—hold off on closing deals until the next year/quarter. 

Make sure that you’re checking in with your sales team often—are they struggling to sell specific products? Do they need more training on that product, or is it that their clients don’t need that particular solution? Are they frustrated that their quota has increased while their territory is shrinking? Are they clear on the accelerators that affect their compensation? Make space for open and honest discussions, and be prepared to listen to their concerns. 


Reduced support/access to Subject Matter Experts 

When budgets get tight, most organizations stay away from cutting sales roles—sales is most closely tied to revenue. Instead, they look to reducing sales support functions as a cost saving measure. Roles like admins, pre-sales consultants, and subject matter experts who support the sales teams get cut. 

As a result, sales professionals are doing way more administrative work. In addition to selling, they now have to generate quotes, scope of work agreements, non-disclosure agreements, master service agreements, create and run their own demos and proof of concept programs. The demands on their time increase drastically, but their quota remains the same. 


If you’re growing or reducing the size of your sales team, be thoughtful about balancing sales and sales support roles. Your team will start to question the efficacy of leadership if you’re hiring a ton of salespeople without scaling the support team—they will recognize that it’s a shortsighted way of bringing in revenue. 

If you absolutely have to reduce support, be thoughtful about the rules of engagement—create a transparent system for scheduling time with your support resources, and weight it according to the potential size of the account. You should also be realistic about how limited support affects the time of your salespeople—think about some quota relief or adjustment so that they don’t feel that they are being asked to do the impossible. 

Of course, you need to hire curious, capable salespeople who are willing to jump in and do what needs to be done to get the sale—and in some organizations sales support becomes a crutch for lazy sales professionals, so you need to understand your product and your team to understand what an effective balance looks like. The most important thing is to be deliberate, thoughtful, and transparent with your team. 

Sales Hiring Checklist

Micromanagement and busy work

Most sales professionals will power through the administrative work they need to do if it means getting the sale. It’s not ideal, but they’ll do what needs to be done. 

But the quickest way to annoy and demoralize a sales team is to occupy their time with work that won’t help them close a sale, or actively pulls them away from selling. How many weekly, monthly, and quarterly meetings do you require your sales team to attend? Pipeline meetings, one-on-ones, training sessions, sales enablement meetings, Quarterly Business Review meetings, all hands, etc. can add up into a lot of hours that are not spent selling. 

Toss in some micromanagement and an over emphasis on management by metrics, and you’ve got a recipe for a frustrated sales team. Of course, organizations need visibility into pipeline status, number of calls, deals that are set to close, and deals that are held up in process—but when your sales team is drowning in the busy work of updating the CRM, you can count on them being frustrated. 


In order to combat this problem, you need mature leaders who are able to be in tune with what their team really needs. It’s common for leaders who are insecure to lead by meetings and micro-management—they’re insecure about their abilities, so they fill their days with busy work, as if to say “see, I’m a great leader! Look at how many meetings I schedule!” Secure and effective leaders know how to strike the right balance between building a sense of community and teamwork, and trusting professionals to do their jobs. 

Take a look at your meeting schedule, and cut it down as much as possible. Do you need to do a one-on-one pipeline review and a team pipeline review? Are you scheduling meetings to share information that could be covered in an email? Is your team able to decline a meeting invite (without being penalized for it) if there’s something else that would be a better use of their time? Do what you can to reduce the hours each week that your team is occupied doing activities that aren’t selling. 

* * * * *

Sales can be a demanding and thankless profession. If you blow out your quota, then it’s often assumed that your quota was set too low—if you miss quota, then you’re ineffective. You have to be adept at navigating change and uncertainty, deal with internal politics, and balance your own results with the objectives and health of the business. It can also be incredibly rewarding—to help clients solve critical problems, to be rewarded for hitting results, and to make a lot of money. 

Effective sales professionals will always be in demand, and if they feel undervalued, disrespected, or concerned about the efficacy of leadership, it’s safe to assume that they’re looking elsewhere. Retaining an effective sales team ultimately comes down to the efficacy of your leadership. Thoughtful, engaged, and supportive leaders are critical for retaining your top performers. If you’re routinely losing your best people, then take a look at these 4 areas, and commit to improving—for the sake of your team, and for your bottom line. 


Are you getting ready to grow your sales team? We've created a free checklist to help you refine your requirements, plan the interview process, and get aligned on competitive compensation. 

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