Sales Recognition

5 Sales leaders share secrets for a healthier sales culture, part I

It’s no secret that sales cultures can be notoriously problematic. In fact, nearly half of sales reps believe they work in a toxic environment.

And while the industry is beginning to move away from the traditional coin-operated approach, many leaders still maintain a single-minded focus on sales goals. This total fixation on “the numbers” can quickly create a highly toxic environment—one where sellers push themselves to the brink to close deals and hit quotas and end up burning out or leaving when they can’t keep up. 

Fortunately, a new era of forward-thinking sales leaders is proving that the industry doesn’t have to operate this way. Their teams are beating the odds, fostering healthy sales cultures, and redefining what sales success means in 2022.

To learn more about how they’re doing it, we went straight to the source. We spoke to:

All five of these leaders hail from organizations with top-ranked company cultures and sales teams. We sat down with each of them to learn how they’ve nurtured a healthy sales culture and sustained seller motivation at their companies, and unsurprisingly, there were some common threads and themes.

Here’s how they’re rewriting the narrative on sales leadership and how you can take a page from their playbook.

(Editor's note: This is part one of our two-part series on sales leadership, culture, and motivation. Stay tuned for part two where we’ll dive into sales culture trends and how our subjects' approach to sales leadership has changed over their careers.)

Q: Why do so many sales cultures turn toxic?

Sales is a numbers game. 

No matter where you sit in the sales cycle, from sales development to closing the deal, most sales professionals have a number that they need to hit every day, week, month, and year. While many sales professionals thrive in this kind of environment, it can also be stressful. 

“You are constantly measured by number attainment, and number attainment is not always within your control,” says Steph. 

Adds Thomas: “When there's always a quota to hit and a number over your head, there's a lot of pressure.” 

This is especially true in startup environments with lofty revenue projections and valuations. “If founders start to see that revenue projections aren't adding up with the valuation, a lot of pressure will come down on the sales team, and specifically on the sales leader,” explains Thomas. “Then you get people who are worried about job security, nervous about performance, and end up doing and saying things that in a different setting they otherwise wouldn't.”

Culture starts at the top.

According to many of the sales leaders, a toxic culture tends to trickle down from management. 

“If you’ve got a founder that’s stressed about hitting revenue projections, and you've got a sales leader that's worried about their performance and job, then that trickles down and creates this kind of nervous energy in this environment of ‘Don't make a mistake,’” explains Thomas. 

On top of this pressure to perform, toxic cultures can form when there are mismatched priorities between leadership, middle management, and the rest of the organization.

“I think [culture] is often a representation of how leadership and middle management treat their employees. As a result, there's often a lot of misalignment on compensation, career path, and work-life balance,” says Jason. 

Hiring for performance over culture. 

Last but certainly not least, all the sales leaders agreed that prioritizing performance over culture add can quickly tank a sales organization’s culture.

“You need to make sure you hire the right person who will add to a culture, a culture other than sales, and not just somebody who's cutthroat and does whatever it takes to get that sale,” says Odi. 

Adds Jason, “Reed Hastings, [the CEO of Netflix], once said, ‘There's no tolerance for brilliant jerks. The cost to teamwork is too high.’ For me personally, I know that one toxic person can absolutely infect a lot of other people and an organization.” 

To prevent a bad apple from spoiling the bunch, Steph recommends that all sales leaders look at the balance of skill set, potential, and culture add when evaluating a potential candidate. 

“What makes somebody an amazing seller in one organization does not make them an amazing seller in your organization. So be acutely aware of the skills and the personality traits that drive your company,” says Steph.

Q: What makes for a solid and healthy sales culture?

Understanding the factors that can lead a sales team down the wrong path is one thing, but how can you get back on course? Our expert interviews identified four essential building blocks of a strong, healthy sales culture: 

  1. Intentional culture building, 
  2. Healthy competition, 
  3. Team alignment, and 
  4. Learning and development opportunities. 

1. Intentional sales culture building.

As Thomas says, “Whether or not your culture’s defined, you'll end up having one, so it's better to be intentional about it.” 

Three words guide Meltwater’s culture: moro, enere, and respekt, which are the Norwegian words for “fun,” “number one,” and “respect.” These values are communicated to candidates and new hires and are a part of the company’s day-to-day, so every team feels connected to the culture and is responsible for upholding it.

From there, they’ve built a culture-first approach to management and sales. As Thomas explains: “Culture is the foundation, people development is our rocket fuel, and sales results are the grades on how well we do the first two.”

Adam takes a similar approach to leading his sales team at Thinkific. “It's the right team serving the right customers to generate revenue. In that order. It's not revenue at the forefront of everything.”

2. Healthy competition.

Healthy competition came up a lot in our talks with the sales leaders. While there is a naturally competitive element to sales, what sets a healthy sales culture is how its people compete. Namely, it’s not about competing against your fellow teammates, but with them. 

Steph explains, “It's not that they want to knock down the person beside them. They want to be on the best team. You don't want to be a superstar on a C-league team. If you're playing basketball, you want to play with Steph Curry, right? That is where you want to be.”

What might this look like? You could take a page from Adam’s book: This VP of Sales rewards his team with prizes when they achieve goals collectively, so recognition isn’t purely tied to individual performance. For reps that might not hit their quota that month, competing as a team keeps everybody engaged and morale high. 

3. Team alignment.

There’s a pervasive idea that sales reps are very individualistic, lone-wolf types. Still, many of our sales leaders cite their healthy team dynamics as a significant factor in their success. 

“Sales is only successful if you don't think of it as just an individual contributor to the role, but how do I work with my broader teams to get that success?” says Odi. 

Jason and Adam have a similar team-building focus and use their current staff as a blueprint for future hires. Jason based his hiring blueprint on the qualities he likes in his current team, while Adam took a slightly different approach—working with his team of 10 at the time to answer questions that would eventually become his sales teams’ guiding principles. 

Some of the questions Adam’s team considered include:

  • What do we like about our team right now? 
  • What makes it good? 
  • What are some of the challenges that we're facing with the team?
  • If we fast forward a couple of years, what are the things we're worried about? 
  • What is that future state that we want to avoid?
  • What are our fears about how the sales team could go if we're not careful?
  • How do we want to be viewed in the world?
  • What type of team do we want to be a part of?

4. Learning and development opportunities

While sales reps tend to be money-motivated, the lure of another commission check will only work for so long. 

“We see people get stuck in sales roles where leadership tells them, ‘You're making us millions. You're making lots of money. Aren't you happy?’ While on the inside, they want more,” says Steph.

Your salespeople want growth opportunities just like any other employee, so it’s essential to understand what advancement looks like to them so you can help them develop. Maybe you have a salesperson who wants to lead people, coach, or transition into a new role. Maybe they want to sharpen their skills by going to sales workshops and conferences. 

Whatever the case may be, providing learning and development opportunities is critical to the individual seller’s experience and their ability to feed that momentum back into your team.

Q: How do you motivate your salespeople?

Newsflash: it’s not just about the comp plan. Our leaders agree that the key to sales motivation is ensuring that each team member feels valued, both as an individual and as part of the collective. Offering a variety of personal and team-based rewards and recognition can help you achieve this much-needed balance.

Discover how experiential sales rewards can boost sales team performance and morale

Explore our platformLearn more

Rewards for efforts and outcomes.

Rewarding outcomes and behaviors can keep your salespeople from hyper-fixating on the numbers, especially if they’re having a slow month. For example, accelerators can encourage high performers to push beyond their quotas, but Adam suggests also running competitions around pipeline generation, customer stories, or other behaviors that are less revenue-driven but still support the customer journey. 

Opportunities to learn and grow.

Some of your staff may be comfortable in an individual contributor role, but others may have their eyes on leadership. For those who are more career-focused, helping them connect the dots from the work they’re doing today to the work they want to do in the future can help keep them more engaged.  

As Steph explains, “It's not just about getting promoted up. Sometimes it's getting to work in a different market or with a different product line or segment. Giving people a mix-up to their day and career will help them feel more motivated.”

Meaningful recognition.

As Steph says, “The difference between recognition and feeling valued is subtle. And that comes down to connecting with the individual.”

Not everybody wants to be recognized in the same way. Jason explains, “Some people are motivated by public recognition. Some people hate public recognition. Some people just want to be told that they're doing a great job.”

As a sales leader, it's your responsibility to get to know the people on your team and understand what forms of recognition make them feel valued. For instance, Adam shared that Thinkific has annual sales awards, but they also make space for recognition during their weekly sales meetings. Team members can nominate their colleagues for living out their team principles. Additionally, one of the enterprise team leads makes a ‘five-minute wins’ video every week where she shares a win from each person on the team and explains why it’s important. 

“We express a lot of gratitude as a team, and we earn a ton of recognition,” says Adam.

Team-based goals. 

In addition to individual goals, many of the sales leaders we spoke with have team-based targets to help support a healthy sense of competition and bring their teams together around a shared cause.

“We work in close-knit teams,” says Thomas. “We have bonuses tied to team goals, so you're truly rooting for one another because everyone gets the bonus. We feel like that motivates salespeople more when you feel like you're in it together.”

Odi has even started a buddy program for new people who join his team to help bring them into the fold. 

“I think it's really easy as salespeople, especially in this new virtual world, to go off in their own world, and I think it's part of my responsibility to bring everybody back together and make sure that they're incorporating the bigger part of the team,” he explains.

Q: What are some key challenges or obstacles sales leaders face when building culture?

It’s one thing to come up with a bunch of nice adjectives and vision statements—and another to truly live it, day in and day out. Our sales leaders have built thriving sales cultures, but it wasn’t all sunshine and rainbows. Here are some of the key challenges they’ve faced, and how they’re reframing those challenges into opportunities.

Navigating a tight job market.

As Steph explains, “Tech has had a huge influx in financing. During the last two years, there's been a lot of IPOs, a lot of investments. Many companies have had huge increases in their revenue and have suddenly had a lot of money to suck up a lot of the top salespeople in the market. So yes, attracting qualified talent is tough right now.” 

But rather than focusing on the barriers, Steph prefers to focus on attracting the right talent, which, as we’ve already touched on, goes a lot further than a person’s rolodex. 

“Somebody may have all the skills, they might have great experience, they might have the aptitude, the ability to learn everything they need to do, but is the attitude right? On the flip side, there's a lot of stuff you can teach. You can't change some of these inherent drivers of their personality,” explains Steph.

Feeling connected in a virtual world.

Before COVID, Odi’s team worked primarily in person. Now, they’re entirely virtual and most are in a different state. “When all we do is see each other on screens and sometimes not even that because we're on phone calls? That's a huge challenge,” says Odi.

To combat this, Odi works hard to bring his team together. He plans virtual happy hours, and treasure hunts and coordinated in-person meet-ups and local conferences and trade shows.

“​It doesn’t need to be this big, elaborate plan with a huge agenda. Sometimes people just want to take some time, and not talk shop with the people they typically talk shop with,” says Odi.

Maintaining culture as you grow.

When you’re leading a sales team of 10, it’s not hard to connect with your team members individually and personally uphold the culture. But this work gets tougher to do as your team grows.

To preserve the culture and vision, Jason advises sales leaders to enable the layers of management beneath them and trust them to continue the work that they’ve started. Both Jason and Odi also shared that they continue to prioritize one-on-one time with their teams. 

“A lot of general information can be conveyed in a group setting. But I think that it's really important that you take the time to have one-on-ones with individuals to understand if things are resonating, or missing, and how to fill those gaps,” says Odi.

“Never, never [become] too far removed from being able to work directly with,” adds Jason.

The top secret to building a healthy sales culture? Be intentional.

One theme that kept coming up over and over again was the idea of intentionality. Building a healthy sales culture doesn’t happen passively or by accident. All five leaders are extremely intentional about designing team culture, from clarifying why culture matters to sketching how it should look.

If you want to build a strong sales culture, focus on the following four elements:

  1. Intentional culture building. Bring your sellers into your sales team’s mission, vision, and purpose from day one. Define team principles and embed them into day-to-day work. 
  2. Healthy competition. Develop shared team goals and consider bonus structures to help support a strong team dynamic.  
  3. Team alignment. Attitude is just as important, if not more, than aptitude.
  4. Learning and development opportunities. Compensation is key, but it’s not everything. Think about how you can help your people grow into the people they want to be—not just pad their bank account. 

Ultimately, effective sales leadership boils down to understanding your people as individuals and ensuring their personal motivations line up with the goals of your team and organization as a whole. 

“If you understand what someone's definition of success is in five years, you can work backwards to the work that they do today, and how it's going to get them there,” says Thomas.

(ICYMI: This is part one of our two-part series on sales leadership, culture, and motivation. Stay tuned for part two where we’ll dive into sales culture trends and how our subjects' approach to sales leadership has changed over their careers.)

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