7 secrets of sales leadership

Expert insights from leaders at OptimoRoute, Zendesk, UJET, Vidyard and Sales Melon

Sales teams across all industries are facing unexpected changes, including an abrupt move towards remote work. At a time like this, leadership makes all the difference. The LinkedIn State of Sales Report for 2020 found that 70% of sales managers think that being able to navigate change is more important now than it was five years ago.

To help you positively impact your organisation through sales leadership, we’ve asked five sales leaders to share their insights. They emphasised that sales leadership requires a keen ability to discern what strategies are the most effective for building both a great team and great processes. When what’s coming around the corner feels unpredictable, it helps to have these sales leaders’ input on working through adversity.

To encourage top-notch performance from their team, sales leaders have to set reps up for success.

“A sales leader should be there to work cross-functionally to provide the team with the pipeline, enablement and product they need to close more deals,” says Dan Wardle, Vice President of Revenue at Vidyard.

But that doesn’t mean giving reps every possible tool they could possibly need. It means being calculated in how you develop your team’s resources and fostering a healthy team environment.

For Wardle, that means knowing what is essential for the team to function rather than giving your team every shiny tool they ask for.

“We constantly reference the children’s book – If You Give a Pig a Pancake by Laura Numeroff,” he says. “With restricted resources, you will be amazed at how the team steps up and begins to perform at a level exponentially higher than they did when you gave them everything they thought they needed.”

While salespeople may believe they need everything and the kitchen sink to get deals, this doesn’t align with what sales leaders identified as their biggest challenge going into 2020. Richardson's 2019 Selling Challenges Research study found the biggest obstacles included managing change and making strong arguments to prospects.

With restricted resources, you will be amazed at how the team steps up and begins to perform. Dan Wardle, Vidyard

What a rep may perceive as a tech problem may be something that is better solved by another means, like additional training. You don’t necessarily need a new tech suite to improve how you pitch to prospects – you might just need to reevaluate your process and provide more resources about the tools you already have.

For sales leaders and their teams, the best way to cut through the noise is to focus on quality work that helps your bottom line.

“There is an unlimited amount of work in front of you,” says Andrew Hansen, Director of Commercial and Enterprise Sales at Zendesk Sell. “Establish what you’re trying to accomplish, identify what contributes to that goal and don’t be afraid to say no to things that don’t support the goal.”

This insistence on tying everything back to a goal is particularly helpful when assessing your strategy. Todd Caponi, founder, speaker and workshop leader at Sales Melon, encourages managers to scrutinise their process to find weaknesses rather than listening to traditional sales notions about volume making all the difference.

“I see metrics like, it takes 18 dials to connect with a buyer. I still hear of sales leaders who look at that stat and say to themselves, We’re stopping at 10. We need to add 8!” he says.

Rather than jumping to make more calls, ask ‘Why are they rejecting the first 17?’ and use the answer to that question to optimise your pipeline.

Caponi takes a similar attitude towards prospecting emails. Instead of cranking out more cold emails everyday, he recommends finding and fixing the flaws that are keeping your response rate so low.

Mike Chevraux, Vice President of Sales, North America at UJET, agrees and says his key to deal velocity isn’t deluging a potential customer with calls or loading up pipelines with as many leads as possible.

“[When I started,] We took the solid opportunities and focused on what we could do to drive those deals to closure in the quarter. We defined the steps, scheduled the meetings and followed our process. By focusing our efforts on the qualified opportunities, we were able to significantly increase deal velocity,” he says.

The deals he didn’t pursue? Ones that were ‘built on hope’.

Data from high-performing teams backs up Chevraux’s approach. According to FeedStock, high-performers are 1.5 times more likely to forecast with ‘data-driven insights’, which helps teams focus on qualified leads. For example, data about product engagement or gated asset downloads that a lead takes in the discovery and sales process can be valuable for separating serious, potential customers. Emphasising the quality of leads, not the quantity, creates the best chance of success.

Not everyone is cut out for sales. To build a strong team, you must differentiate between those who will sink and those who will swim.

The sales leaders we spoke to agreed that what makes a good salesperson in the long term isn’t speed, enthusiasm or even the number of deals closed. It’s self-motivation.

“Not everyone wants to get better. Recognise this as early as possible,” says Hansen, when asked what he wished he knew when he started as a sales leader.

Wardle adds that even the best managers can’t create that intrinsic inner fire: “No amount of coaching can change that [unmotivated] behaviour.”

A key part of sales management is building the right team, so learning how to identify the best candidates through hiring and training is one of the best things you can do to give your team a strong foundation.

Sales teams have a culture of giving high-performers bonuses and other rewards and perks. While recognising accomplishments is important, dangling carrots won’t actually spur good work across the board.

Wardle puts it bluntly: “Perks and bonuses don’t make your team perform at higher levels.”

Both Wardle and Caponi noted that intrinsic drive helps reps more than any carrot or stick ever could, pointing again to the importance of finding self-motivated salespeople.

Perks and bonuses don’t make your team perform at higher levels. Dan Wardle

But even these sales superstars benefit from being managed. Harvard Business Review says the best way to encourage strong performance is by approaching each rep as an individual and tailoring how you inspire motivation in each team member.

For example, the study found that creating winner-take-all prizes doesn’t make top performers try any harder and can demotivate those at the bottom of the pack. Instead, offering personalised coaching and encouraging reps to complete their own individual goals led to strong performance results.

“If we need external rewards to do a job, the job must suck,” says Caponi. By building a tailored approach to your reps, you can help them reach their own potential and find fulfilment in success, rather than just compete for a separate prize.

Good leaders trust their teams. They build a culture where reps feel supported but able to own their work. That means letting go of micromanaging – especially tempting for newly remote teams – and instead allowing reps to show that they are trustworthy.

Remote setups are a big shift for employees. Micromanaging leaders only make this transition harder for sales reps.

“Add to it the drowning oversight of a manager, who, because the rep is not-in-sight, feels pressure to know exactly what they’re doing all day? It’s less productive, and less effective,” says Caponi. “Those reps are likely keeping an eye out for their next job.”

Gallup’s research backs this up: employees who trust leadership are two times as likely to be with the company for another year than those who don’t. The long-term success of your team and the retention of high-performers hinges on trust.

But according to a 2020 Harvard Business Review study, 40% of managers have low confidence in their ability to manage remotely. If that sounds like you, becoming a helicopter boss might be appealing. Don’t fall into this trap.

Trust needs to be earned, but sales teams need the opportunity to earn that trust and that begins with setting proper expectations with your team from the beginning. Mike Chevraux, UJET

“The sales leader’s job is not to get constant deal updates from the reps and pressure them on closing more deals,” Wardle agrees.

In order to roll with the remote punches and build trust in your workers, HBR suggests that you manage based on results.

Try taking a step back and letting your workers operate more autonomously rather than checking on every step of the sales process. Once you take a step back, see if your direct reports are reaching goals and doing their work on time.

Just make sure that the goals you want reports to reach are clear. That’s key to trust-building, notes Chevraux.

“Trust needs to be earned, but sales teams need the opportunity to earn that trust and that begins with setting proper expectations with your team from the beginning,” says Chevraux.

Giving reps the coaching and resources to improve is key not only to their professional success, but it’s also critical for your team’s success. Hansen says the most important thing a sales leader can do for their team is to “give individualised help to each rep and teach them how to fill their gaps as a sales professional.”

Research backs this up. In fact, in 2019, Marketo found that top sales performers are 1.6 times more likely to have invested in and focused on sales training.

One good way to approach training is to turn everyday problems into coachable moments.

“Encourage action in a safe environment and give space for viewing missteps as growth opportunities,” says Sarah Tracy, Director of Technical Sales and Support at OptimoRoute. This culture should flow from the top-down, so your team becomes a place “where looking out for each other elevates individuals as well as the company overall.”

Wardle recommends leaders coach reps in their sales process as it happens.

“Working some deals side-by-side with the reps helps tremendously,” he says, adding that it’s important that “the team sees you’re there to help, not just to take credit for all their hard work.”

Making adjustments with a rep means they can practice a new process with managerial support before they have to implement learnings on their own, solidifying their development.

Learning about what makes people tick will help you approach your sales strategy better. If you can see things from the prospects’ perspective, you’ll have a much better chance of successfully engaging with them. Understanding human behaviour will also help you empathise with your sales reps and foster teamwork.

Self-guided learning can be a great resource for anyone looking to dig into human psychology or management techniques.

“For me, personally, I pull up my podcast app, do a search for ‘leadership’, then find the ones that speak to me,” says Caponi. He feels they are a good resource to “invest in yourself and your understanding of what drives adult human beings – and how to create environments that maximise engagement.”

Some management-specific podcasts that tackle both the big and small challenges of leadership:

• The Change Management Podcast
• HBR IdeaCast
• The Modern Manager
• People and Projects Podcast

Tracy turns to “any outside-the-box toolkits/playbooks on the value of doing things differently and of paying attention, despite mainstream external pressure”. In particular, she recommends The 7 Habits of Highly Effective People, The 4-Hour Workweek, Outliers and Who Moved My Cheese?

Collaborative learning can be just as valuable for managers who want to understand how they, their teams and their customers are behaving.

“Find a peer group, and it doesn’t need to be local. I’m a member of Sales Assembly as well as the Bessemer Venture Partners CRO groups and it’s been a huge help,” says Wardle. “It gives you a tonne of people to ask questions, feedback, opinions, etc.”

And if you are looking for a more formal experience, Chevraux says, “Consider getting your MBA. It is hard work, but well worth the effort!”

By understanding how humans deal with uncertainty and change, you’ll be able to bolster your effectiveness as a manager and keep your ship level.

Believe in your own sales leadership

Managing a team isn’t easy. Being confident in your leadership is especially hard when facing unprecedented challenges like the ones COVID-19 has caused. But believing in your own leadership is what sets successful sales leaders apart.

“Trusting my instincts is always the way to go, even in uncharted territory. And that I’ve charted more territory than I sometimes give myself credit for,” says Tracy.

Remember, all of these sales leadership secrets are under your control as a manager. You may not be able to change the state of the world, but you can still focus on the decisions that benefit your team – and that is what will get you and your team through any change or challenge.