Best in Sales: Top Sales Leaders Answer Your Questions

March 17, 2021

Jackie Goudreault

Whether you’re trying to figure out how to climb a mountain, dunk a basketball, or bake a world-class apple pie, it pays to talk to the experts. The same rule applies when you’re trying to figure out how to build an elite sales organization.

Successful leaders can coach junior salespeople into rockstar reps. They can identify prime candidates for roles their team structure requires. They can develop a killer sales strategy and fire their team up with actionable motivational tactics to go out there and execute that strategy.

“How do I do all that?”

We brought together three of the best sales leaders in SaaS — DocuSign’s Dustin Crawford, Hotjar's Alison Prator, and Superpath's Jimmy Daly — to answer that question, and plenty more, that new sales leaders inevitably find themselves asking.

“How do I go about setting goals for my sales team?” #

Sales leadership begins with the ability to set effective goals for your sales team — how much revenue do you expect your individual sales reps and your sales organization as a whole to bring in during the coming period? Sales goals require careful planning and assessing how your sales reps’ individual sales quotas and personal targets relate to your business’s overall revenue or sales goals.

Jimmy is a proponent of this ‘murder-mystery' approach — start from the end, then work backward. “We extrapolate sales goals from our annual revenue goals,” he told us. “Once we know our annual goal, we break it down by month, do our best to forecast churn rates, and set a monthly revenue goal [that will get us to that annual goal].”

By basing sales goals on the amount of MRR they expect to bring in during the coming month, front-line sales managers can get an excellent overview of predictable revenue for the coming period. They can also accommodate for potential complications. After all, not all sales deals end with a closed-won outcome. In a given month, you’ll have to face the prospect of churning customers. You’ll also have the chance to make the most of unexpected opportunities for upsells and cross-sells.

Elite sales management requires you to look at the state of play in your market and adjust your sales goals accordingly. Is one particular buyer segment churning/upselling more than usual? Has the sales cycle slowed down across your industry in this past quarter? Are you coming up to any seasonal periods (e.g., summer slowdown or holiday-season rush) that are likely to affect sales? Consult with your vice president of sales, CFO, or (if you’re a new startup) your co-founders to ensure you’re in sync on sales goals and the wider company goals they need to suit.

For Dustin, an assessment of product and the marketplace comes first. “Say you’re selling a CRM: that’s gonna be high value. Not only will you have to take into consideration the value that this product has but...also how hard it is to convert people to the new CRM you're selling. Most companies do have CRMs, so you're going to have to get them off of the one they're using right now.”

“How do I develop a sales strategy?” #

Even seasoned sales professionals get anxious about sales strategy during a market downturn — but a clearly developed sales strategy can secure both your cash flows and your business itself. However, figuring out how to approach your sales strategy depends on your company’s maturity.

For example, well-established companies are more likely to have a stronger inbound pipeline. They have a reputation, the public is aware of the pain points their product addresses, and prospects come to them. This was the case at Jimmy’s previous company Animalz, where, “[because we had] a strong inbound pipeline, our sales process was very consultative. The entire sales strategy was focused on clearly identifying the prospect’s challenges, ensuring we have a plan to address it, and aligning all parties on that solution. It’s part sales, part consulting.”

On the other hand, if your business is just starting out, Dustin stresses the importance “[of having] that Wild Wild West mentality, because you really don't know what's working. You don't know what's working for each individual, vertically through your company, as well [as within the team].”

Dustin encourages younger companies to begin by strengthening their understanding of buyer personas and building out their data reserves. “I actually build out a lot of data. And so it's a little bit tiresome for the reps, but it actually helps the reps better understand what it's going to take for them to be successful in the role: the [b2b sales] verticals we go after, the language of each industry, even the locations we're attacking.”

From there, Dustin encourages a focus on low friction and careful analysis of the value of prospective accounts. “You need to show reps how to analyze their own approaches,” he suggests. “How many contacts per account are your reps going after? Are they going after the right industries that you talked about? Do they have the talk tracks? For account execs, how are their phone skills? Active listening skills, objection handling, pivoting conversations, and effective questioning - I think, intrinsically, they [all] go hand-in-hand.”

“How do I train my sales team?” #

Here at Chorus, we like to think we know a thing or two about the importance of sales coaching — it’s the foundation of our entire business. In fact, proper sales training is the foundation of any business. It allows your sales professionals to stay ahead of the curve as the sales landscape develops and best practices change.

Alison is a major acolyte of a training-first approach. “Training is our #1 focus [whenever] we're building out our foundation for the team.” She stresses an approach to sales coaching that is oriented around your company's objectives and the services it provides for clients. For Alison and Hotjar, “[we] take an educational and helpful approach with our customers. To do this, we must be experts of our own product as well as understand our ideal customer personas, so we can predict their needs and goals.”

However, it’s not practical to expect your sales reps to develop a tech-lead level of comprehensive product know-how. Alison believes great sales leaders take a targeted approach when educating their sales professionals. “We've restructured our training materials,” she explains, “so that when you are shadowing a call and a topic comes up that you didn't quite understand, that is the moment where we take the time to explain the concept and apply [that sales advice] in the exact situation...The concept comes from just-in-time learning, which, for a somewhat technical product, is valuable in making the knowledge stick.”

“How do I motivate my sales team?” #

Motivation is the key to sales success, whether times are good or bad. Our sales leaders were unanimous in their belief that, whatever the size of your business, strong motivation and a startup mentality are fundamental.

“I genuinely believe that working in a company with a startup mentality and fully believing in the product we're selling is where motivation begins,” Alison said. “We're not just a number on a board, but we get to make a direct impact on sales, and on top of that, we're selling a product that helps people build better websites. It's easy to be motivated when we're helping people achieve their goals, no matter how large or small they might be.”

No motivational playbook should be without a chapter on toasting victory, either. Success is profoundly motivating, so celebrate it. “[At Hotjar] we also celebrate our big wins together and with the entire company on our demos,” Alison told us. “We use 15Five as a means of thank-yous and congratulations at a one-on-one level.”

Of course, a good sales team is composed of a variety of personalities. It’s your job as a sales leader to find out how to motivate each of those personalities. Dustin expressed his belief that motivating a sales team begins with the recognition that “...everybody gets motivated in different ways. It's [also] super important for us to agree and align on what we're doing so that the sales team already feel motivated. If the team doesn't believe in the plan, they're not motivated.”

He also gave particular emphasis on building motivational strategies that focus on the human aspect. “When people start to talk about motivation, they always want to throw money at a problem,” he said, shaking his head. “The starting point is to actually just get the buy-in from the individuals, first and foremost. You don't even know if money even motivates half of the people, so you actually need to have your one-on-ones and say, 'What really is your number-one motivator?' One person's number-one motivator can be money, another's is just getting promoted, another's is just being competitive.”

In Dustin’s experience, successful sales leaders show considerable persistence in getting the most out of their team members. “A lot of times,” he said, “people don't even understand what motivates them. Turns out, what really [motivates some people is not wanting to let down the team. Once you know, you can work that understanding into your wider, whole-team motivational plan.”

“How do I evaluate new candidates for my sales team?” #

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Photo by visuals on Unsplash

Knowing who to hire to strengthen your sales team is a key skill for sales leaders. You might decide to bring in more sales rep talent. You might be looking to build a sales development pod or expand into customer success or sales enablement. Either way, as a sales leader, a lot of responsibility for choosing the right candidate with the right sales skills will fall to you. And a great candidate has much more than a well-crafted LinkedIn profile.

At Hotjar, Alison looks for sales team candidates whose personality matches the team’s priorities. “Because we look for candidates who are empathetic and have experience educating others, it is even more important that we have strict criteria for who would fit with our sales culture. Did they take the time to understand the Hotjar product? Do they understand why our sales culture is different from the norm? Are they scrappy and creative enough to think of process improvements or point out what is going wrong?”

You may wish to incorporate a task stage into your interviewing process, allowing candidates to work alongside their future teammates like Alison does at Hotjar. “It takes guts,” Alison admits, “but that's the point.”

Dustin has a very particular combination of traits he looks for when making a sales rep hire. “When I first started out, you could just have grit and be able to persevere because there were not a lot of competitors in the spaces. Now, there are competitors popping up all the time because of the web. Now you need to have more than just grit.”

Dustin still believes passionately in the value of grit in a sales rep, “[especially] when you’ve gone to the last week of the month and you’re 30% down. Then, you need that mindset at that point. But,” he adds, “you need to be generally curious and self-reflective to keep improving. Those are the areas that I really, really focus on grit, intellect, curiosity, that growth mindset, the ability to have active listening skills, and being self-aware.”

The key to building a sales team that just won’t quit, therefore, is to not over-rely on either guts or brains. “[A suitable sales rep] really have to have this fine balance, and it's very hard to actually have it. People are trying to be like, 'Oh, you know what, this person was a psych major, and they're super smart,' but it's like, 'Have they ever showed grit before?'”

The Sales Leader’s Playbook #

Being a sales leader can be a daunting prospect. You are responsible for the performance, make-up, and well-being of your entire sales squad. Issues of all kinds will fall on your shoulders. Your three top reps might find themselves sitting 20% below quota with three days of the month left. Professionals new and veteran might suffer a crisis of confidence. Your sales strategy might hit a market- or global-event-shaped hitch.

Of course, the flip side is that sales leaders can provide inestimable value to their company and their team. Just as a combination of grit and smarts makes for the ideal sales rep, a combination of winning empathy and strategic intelligence makes for a perfect sales leader.

And the best sales leaders know what tools will help them get there.

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