The Weekly Briefing

Chorus CEO, Jim Benton, discusses exclusive sales research with GTM executives 

The Weekly Briefing

Chorus CEO, Jim Benton, discusses exclusive sales research with GTM executives 

Best In Sales: Management Tips From Top Sales Leaders

September 26, 2019

Shawn Parrotte

You need a strong personality to succeed in sales - a combination of grittiness under pressure and true smarts makes for the perfect sales rep.

In order to manage a whole team of those personalities, a sales team manager has to have a pretty strong personality themselves. Faultless interpersonal skills, ability to empathize as well as strategize, motivational chops, organizational ability - the list of requirements is daunting.

With that in mind, we decided to ask four top sales leaders how they do it.

We put Intercom’s Dustin Crawford, Hotjar’s Alison Prator and Animalz’s Jimmy Daly, as well as’s very own Grace Tyson on the spot to give their best advice. Here’s what they told us.

What We Learned From Top Leaders About Sales Team Management #

Sales teams are bound to come in all kinds of shapes and sizes - from large and experienced (Intercom) to young and growing (Hotjar & Animalz & Chorus).

While there is no one true philosophy for sales team management, there are a few common takeaways that any sales leader should bear in mind.

Use Your Data #

Across the board, the value of a data-centric approach is unmistakable - whether that’s for evaluating new candidates for your team, or formulating training and performance aims for your sales reps. Data collection and analysis should sit at the forefront of your sales team management approach, and your sales enablement strategy as a whole.

Getting the most out of visibility into your deals, improving your competitive win-rate - it all starts with the right data from the right tools.

Empathy Is Key #

Sales reps don’t come in packets - no two will ever be quite alike, and no two will relate to their jobs in exactly the same way. What distinguishes all of our top sales leaders is not only an ability to empathize, but a real sense of the value of empathizing - particularly when motivating your team, being able to understand their various perspectives is paramount.

You Can Never Train Too Much #

The variety of response among our top sales leaders is instructive - so is the fact that they all agreed on the importance of training.

Consistent review of performance, a perceptive sense of when the right time is to implement training processes, a practical approach towards teaching reps how to evaluate their own performances, and an emphasis on having on having the right tools.

It all amounts to a solid training schema that will allow your sales team to perform to its best.

How Do You Go About Setting Goals For Your Sales Team? #

Grace, When I set goals for my team, I focus on "controlling the controllables". For pipeline creation, for example, I sit down with each team member and run through their pipeline math with them.

Working backwards from their quota and based on their ASP, sales cycle, and win rate, we calculate how much pipeline they need to have in play in order to hit their number.

Then, based on their prospecting conversion rates and inbound vs. outbound pipeline expectations, we agree on activity metrics. The key, though, is holding your team members accountable and remembering to check back on progress week over week.

Dustin, Intercom: Before I start thinking about the goal setting, even for the outbound perspective, I’ve got to really look at the product and where we are in the marketplace.

Say you’re selling a CRM: that’s gonna be high value. So, not only will you have to take into consideration the value that this product has, just in general, but it's also a question of how hard it is to convert people to the new CRM you're selling because most companies do have CRMs, so you're actually going to have to get them off of the one they're using right now.

For Intercom, we started off in the S&P space, and now we kind of have that market. When you first start out, that's more transactional; you don't have as much money to spend on something like this. But, it's a transactional product. So, the goal-setting requires understanding those things first and foremost and then working with your Sales Ops team to understand your company goals. Then you go from there.

Jimmy, Animalz: We extrapolate sales goals from our annual revenue goals. 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. Each month, we look at adding $X in net new MRR, meaning that we’ve accounted for churn but also new customers and upsells/cross-sells.

How Do You Develop Strategies For Your Sales Team? #

Grace: Lots of observation. I believe strong strategies arise from being intimately acquainted with your team's day to day: the roadblocks they're facing, the conversations they're having with prospects, the product feedback they're getting, etc.

I am constantly listening to reps' calls as I coach them, and I use this as an opportunity to listen for common pitfalls/struggle areas as well. When I find a common thread, I formulate a new approach or training or strategy around overcoming that problem. Rinse and repeat.

Jimmy: Because we have a strong inbound pipeline, our sales process is very consultative. The entire sales strategy is 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.

: If you're first starting out, it's really important to have 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].

You have to step back and have a little bit of a structure because hopefully your management team has been there, done that and can give you a starting point: “Hey we're going to be going after this target, and we're going to be using this strategy to do it.” Although this is what worked at previous companies, it's not going to probably work exactly the same for this company. So, what we need to do is come up with a strategy together, and we're going to modify it over time as quickly as possible.

That's why hiring proactive reps who can collaborate and be responsive to strategy is important - it's a team effort to get strategy right.

This is where data is going to play a big part in your strategy and what you do. 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 verticals we go after, the language of each industry, even the locations we're attacking. We start to piece it all together to better understand, "Okay, what is going to be successful?|. Hopefully, within six months, you actually have something very solid for the organization, the first iteration of your playbook.

How Do You Approach Training In Your Sales Team? #

Grace: Consistency is key when it comes to training and continuous development. In our team, we do weekly film reviews focused around a specific skill. This is a time to leverage tribal knowledge sharing so it's not always management's voice only.

I also do 1-1 coaching with each rep. Based on the calls I listen to, I identify 1-2 Coaching Focus Areas (CFAs). If needed, I'll do individual remedial training on that CFA, and once the rep and I are aligned on "what good looks like", we clip examples of the rep exhibiting that skill on actual calls and listen to them together in future sessions.

Alison, Hotjar: Funnily enough, training is our #1 focus right now since we're in the midst of building out our foundation for the team, and the true heart of that, I believe, is getting the training right. One big focus for training is our sales culture in general. We take an educational and helpful approach with our customers, and 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. We are here to help the potential customer understand if Hotjar is the best fit for them, so we must intimately know how they can get value out of our tool or if it can directly solve their problems.

One lesson I learned recently in training new hires is that it's better to learn material when it is relevant, rather than as a wave of information at the start and expect the learner to fully comprehend and store all that knowledge. We've restructured our training materials so that when you are shadowing a call and a topic comes up that you didn't quite understand, then that is the moment where we take the time to explain the concept and apply it in the exact situation they just heard while shadowing. The concept comes from just-in-time learning, which, for a somewhat technical product, is valuable in making the knowledge stick.

Dustin: Once you’re looking at the data, you can start to look at the accounts the reps are going after. So when you're talking about an SDR, it's more of, "Okay, what is the least amount of friction that you're going to face to try to get an appointment?" For an AE, it's more, "What is it going to yield me financially for my pipeline?" It goes back to that stuff, but then you start to look at, "How many accounts do I need to work?"

If you're looking at those two attributes - the value of accounts and how you're looking at accounts - you can answer the question, "How many accounts do I actually need to work?" We found that 80 accounts are the right amount that reps should aim to work each month. And so, what we found is, if reps are not hitting about 20 [new accounts] a week, that means that they're not setting themselves up for success.

You need to show reps how to analyze their own approaches. How many contacts per account are you going after? Are you going after the right industries that we talked about? Do you have the talk tracks? For account executives, how are your phone skills? Active listening skills, objection handling, pivoting conversations and effective questioning - I think, intrinsically, they go hand-in-hand.

How Do You Go About Motivating Your Team? #

Grace: I think it's really important to get to know each team member to discover what makes them tick.

Not every salesperson is the same. People have different motivating factors. I try to understand the individuals on my team first and foremost: what are their backgrounds? Their world views? Their reasons for coming to work each day?

Once you build that foundation, you can work towards authentic motivating factors.

Alison: I genuinely believe that working in a company with a start-up mentality and fully believing in the product we're selling is where motivation begins. 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). We also celebrate our big wins together and with the entire company on our demos; we use 15Five as a means of thank you's and congratulations at a one-on-one level.

Dustin: Motivation is always tricky because everybody gets motivated in different ways. I think that it's more of, as a team, you really have to take a step back and just say, "This is our strategy, and these are the things that we're doing in order to be successful." And being successful is motivating in and of itself because if people are not winning, then they're not going to be motivated. So, it's more of, do they believe in the process and the things that you've put in place? And this is the reason why we actually do things as a group.

When people start to talk about motivation, they always want to throw money at a problem: 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 like, "What really is your number-one motivator?"

I had a rep who I couldn't throw money at because she just really wasn't getting motivated by it. And I was trying different things over and over and over and over again. I even asked like, "Hey, what motivates you?" And, sometimes, people don't even understand what motivates them. Turns out, what really motivated her was not wanting to let down the team. Once you know, you can work that understanding into your wider, whole-team motivational plan.

How Do You Evaluate New Candidates For Your Sales Team?

Grace: I try to take a data-driven approach to evaluating and interviewing new candidates for my sales team. I have a rubric with core capabilities/traits that I'm looking for each new hire to have, and I will score candidates against that rubric throughout the interview process. I've created a list of behavioral interview questions that correspond to those traits so I can consistently assess each candidate.

Finally, we all know salespeople can be masters at the art of deception. To me, it's important to have candidates do a discovery role play. I believe discovery is the most crucial part of the sales process, so I want to verify that the candidate not only has basic sales chops, but also that they have soft skills that are tougher to train: EQ, curiosity, desire for feedback/growth, etc.

Alison: Hotjar is known for having a lengthy application process (five total steps!), and the sales team is no different. In fact, 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. We actually have an open sales role now, so I look for things like:

  1. Did they take the time to understand the Hotjar product?
  2. Do they understand why our sales culture is different from the norm?
  3. Are they scrappy and creative enough to think of process improvements or point out what is going wrong?

The task stage is where we truly understand if the candidate is a good fit because it allows them to work alongside us and the rest of the company. They take calls and use Slack to communicate to find their answers and are encouraged to be brutally honest about what we're doing right or wrong. It takes guts, but that's the point.

Dustin: When I first started out, you could just have grit. You could just hammer the phones. You could just be a complete dummy and just have that grit and be able to persevere because there were not a lot of competitors in the spaces. We evolved. There are competitors popping up all the time because of the web. Now you need to have more.

You still need grit, don’t get me wrong, like when you’ve gone to the last week of the month and you’re 30% down, you need that mindset at that point, but you really need to have the intelligence piece.

You need to be generally curious, that mindset of, "Okay, this did not go well, and I'm actually self-reflecting, and now this is what I'm going to do to get better next time." If you learn something from your manager, that means you need to adopt it now, not later. I find that reps who are generally curious and have that mindset are really, really going to stand out from anyone else because they learn so much quicker.

There are certain skill sets within curiosity and determination that I like to build out - grit, intellect, that growth mindset, the ability to have active listening skills, and being self-aware. I separate them in order to have those individual questions that I ask during interviews to be able to understand: “does this person fit this mold?”

You really have to have this fine balance, and it's very hard to actually have it. But, I see that a lot. 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?“

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