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Sales rep attrition can cripple your sales team.

When you find good salespeople, you have to keep them motivated. But how?

Most advice points toward team culture. We have even written before about building a Success culture.

Of course you need to treat the sales reps well. And yes, you need to give them an opportunity to earn a great income. The product should be strong. They need support and skills development to get better at their job.

I could go on and on about the table stakes for having a high-performing team. But what happens when you have it all set up and you are still losing reps to other opportunities?

The most important thing we did at Levelset to keep our best salespeople on the team: Build a Career Path for individual contributors.‍

What is a Career Path?

Most ambitious people want to understand how they can move up in their career.

If you don’t provide high-performing sales reps a path within the company, they will find one outside your company.

A career path is just that. It’s a plan that lays out exactly what is required in order for the individual to get more income, more responsibility, or to move up in title.

Nothing is more discouraging than feeling like you don't have control of your career. So give your team control.

Make it clear what performance milestones must be achieved before being eligible for a promotion. Be transparent about the payment structure for each role on the team.

Note: this works for sales teams because pay is often discussed openly and on-target-earnings are largely driven by variable compensation. Be careful about publishing compensation bands for roles outside of sales.

Your SDRs should understand what objective measures to hit in order to be promoted to Account Executive.

Same goes for AE to Senior AE. Or to Enterprise.

‍What should be included in a career path?

For every role on the team, you should outline:

- title

- compensation (base and variable)

- responsibility

- expected tenure

- milestone to hit next level in career path

Put all the roles on one page and share it with the team. Communicate with them how the career pathing works and how they can put them in a position to move up in their career.

Revisit this with the team each quarter and make yourself available for 1:1s with anyone interested in learning more about growing in their career.

This applies to more than just sales. You can build a career path for each function within the organization: Customer Success, Product, Engineering, even Finance.

You should also have a leadership track for those interested in moving into a leadership role. This is a separate type of career path but just as important.

Your rep retention will increase when you are explicit with your team about what it takes to advance in their career.

‍Up The Ante

Everyone wants to make more money. Everyone likes to have a bigger title. Everyone seeks to have more impact and influence, more responsibility in the organization. How can you make the gradual steps even bigger for the team?‍

1. Make it fun

Accompany each milestone with an event or a trophy of some sort.

At Levelset we gave a baseball bat to each person that hit $100k in sales. It was an informal way of saying “welcome to the sales team, you are a real closer now”.

When a rep hit $500k in total bookings, we put a gold vinyl record on the wall with their name and the date that they hit the milestone. At $1MM in total bookings, we put a platinum vinyl record on the wall.

When a rep received a promotion to leadership, we took them to dinner to celebrate.

Find ways to make moments and leave mementos of the reps’ successes. They will emulate the behavior that helped them earn those experiences.

2. Attach skills development to advancement

As sales reps grow in their career, they need to learn new skills. A junior rep closing enterprise deals for the first time needs help navigating larger companies and negotiating contracts. A new sales manager needs to learn how to run 1:1 meetings with their team members. They need to learn how to forecast bookings for the team.

You should already be leaning into the sales enablement for the team, coaching the skills within the individual contributors and managers. You can amplify this skills development by providing the team access to outside coaching at different levels of the career path.

For example, once a rep hits $500k lifetime revenue, you can give them a $2,500 annual budget for professional development to use for whatever they want. They may get a personal sales coach, they may go to a Tony Robbins seminar. It doesn’t really matter what they use the budget for so long as they are spending the time to make themselves a better professional.

Beware of Entitlement Culture

Career Pathing can be a wonderful accelerator for great sales cultures because it gives each person on the team a clear understanding for how they get ahead. One adverse affect on the team is an entitlement that comes with the accomplishments.

I try to keep this very simple for the team with a couple of rules:

1. Promotions are not automatic.

When a rep hits the milestone that is correlated to a promotion within the career path, the natural tendency is to ask their manager “I am going to get promoted now, right?”.

Hitting the milestone makes the person eligible for the promotion, but the promotion is still subject to a manager’s discretion.

First, the role must be available for the individual to receive the promotion. If there aren’t enough seats to move the individual into a new role, then that person needs to wait until a seat is available.

Second, even if the milestone is hit and the role is available, the individual must have the recommendation from their manager to get the promotion.  You don’t want to promote a high performer who has attitude issues, doesn’t play well with others, or who otherwise has a negative impact on the team.

When you roll out your career path, you can communicate that movement within the organization is subject to the recommendation of the manager. Coach the team on how to get promoted beyond simply hitting milestones.

2. Tenure is irrelevant. Only performance and attitude matter.

Another risk with career pathing is that tenured reps sometimes feel they deserve a promotion simply because they have been around for a while. That’s not how this works. There are no participation awards in sales. 

Set the expectation with the team that you must produce and hit milestones in order to move up in the organization. 

‍Put it on the wall

Most sales leaders make the mistake of rolling out their Career Path then never talking about it again.

Don’t keep this thing hidden on the 47th slide of your Annual Kickoff presentation.

Print it out and put it on the wall. Talk about it often. Celebrate the promotions that happen within the organization.

Acknowledge that making professional and financial progress is a key part of the Success culture that you are building.