Manage a Large Sales Team Virtually and Build a Kick-Ass Discovery Process

Armand, a recent guest on the Predictable Revenue Podcast, did not take the conventional route from SDR to Director. Rather than doing a 2 year stint as an SDR, then AE, then mid-market AE, etc., he zig-zagged from collegiate wrestler, to top 2% insurance producer, to start-up founder and USC’s Entrepreneur of the Year, to strategy and investments before starting as an AE at Carta. As a top producer there, he quickly climbed through the ranks. Within a year and a half, he had a team of as many as 40 SMB SDRs and AEs under his rigorous guidance. 

So, how does he manage such a big team so effectively? In this post, learn how to run a large sales team virtually – from your cadence as a leader, to the difference between coaching and training, and keeping the sea of faces on your team zoom calls engaged.


Your cadence of training and coaching activities as a sales leader is critical, and three-pronged. You need 1) something to hold people accountable to their commitments, 2) something to keep people motivated, and 3) something to develop people. Note that for Armand – training and coaching are not the same thing. Training activities are one to many, while coaching activities are one on one. Which leads us to his weekly training cadence:


  • (30 mins) Every Monday, Armand and his team start the week off strong with a morning “stand-up”. At this meeting everyone looks at a shared google doc where each individual’s commitments from the week before are outlined. People get check marks if they stick to their commitments – or fun consequences if they don’t (once Armand could only eat Greek yoghurt for an entire day). This meeting also provides an opportunity for Armand to share any announcements. 


  • (30 mins – 1 hr) Every Wednesday morning the team does a “sales builder” with the team. This involves some sort of skill building activity (i.e. cold call reviews, practicing new talk-tracks, breaking down cold emails) and works towards number three in our three-pronged approach – constantly pushing the development of the team.


  • (15 mins – 1 hr) Friday is reserved for one off training sessions like “dial-blitzes”, or quick stand-ups with the team to keep people fresh.

Having a clear cadence gives reps structure, shows them you have a process for developing them, keeps up their momentum, and sets them into a routine which is more important than ever now that they’re working virtually.


While Armand actually does call out every single person on his Monday morning stand-up, he recognizes that it isn’t feasible to get into a deep conversation with all 30 people on the line in every meeting. So he narrows things down a little, and asks himself: What needs to be handled one on one? What needs to be handled one to a few? What can be communicated one to thirty? 

For meetings that do need to involve the whole team, he has reps come prepared with 2 or 3 questions, or 2 or 3 rebuttals before a training session on a certain topic. But for meetings where he wants to get a little more specific (i.e. discovery call reviews with his AEs) Armand introduced a different type of intermittent, rotating training call. He whittles the cohorts down to just 4-6 reps, so that while he’s scaling his time, the group isn’t so large that they can’t get into detailed discussions. 


During his collegiate wrestling days, Armand often attended “open mats”. Open mat gives wrestlers the opportunity to practice and improve on their own time, without the structure of formal practice. At Carta, he offers his reps Thursday morning open mat call reviews – an optional meeting where reps can join with a call recording to work through. While more “lend an ear” and less “cauliflower ear”, his version gives his team the chance to listen to other reps’ calls, and get a little organic back and forth going (something we are sorely missing in our virtual environment). The same concept is true for his 4-6 person discovery call reviews.


Armand’s training cadence seems like a whole lot of meetings when you factor in the other obligations you have as a sales leader (like forecasting, product feedback, maintaining alignment with your company’s top dogs). So where do you find the balance? Of course you want to prioritize the time with your reps without overwhelming them, so the first thing you do is check if they have more than eight hours of team meetings on their calendars and if they do, pull something. Then, you move onto your corporate meetings.

When Armand first started as a Director, he had a one on one meeting with practically the whole company – everybody in marketing, his fellow managers, senior leadership – and he quickly found his calendar so stuffed with meetings that he didn’t have a minute of white space in the day. It’s common to fall victim to the idea that being in meetings means you’re being productive, but another of Armand’s noteworthy cadences suggests you ask yourself: should this meeting fall into my weekly, monthly, quarterly, or my “not at all” cadence? 

Once you’ve thinned out the unnecessary corporate meeting into a cadence that doesn’t conflict with the rest of your calendar, you can leave time blocked for any ad hoc meetings and have the time there for the people who really need it – your reps. 


Another instance where balance is important for a sales leader is dashboard tracking. Some managers live in salesforce, while others totally ignore the data. Armand prefers to distill all metrics down into one simple dashboard he calls “The Inputs Dashboard”.

This dashboard walks him through rep by rep, from beginning to end, what is going on. Data pulled into the dashboard for one rep might include:

  • How many demo requests they get 
  • Where their top of funnel comes from
  • How many meetings they have
  • How many of their meetings convert
  • How much pipeline they create
  • How much pipeline closes
  • What all of this data looks like month over month. 

Armand looks at the dashboard to understand and diagnose any bottlenecks, but then he gets out of the dashboard and into hands on, one on one coaching.


Considering Armand started as an AE for Carta and was promoted to Director of Sales within 18 months, he must have done pretty well for himself in his first role. Let’s fire through the discovery process that helped him do it.


Let the prospect know where the call is headed, and give them an out.

Example: “Sarah, you’re the star today. I don’t have a deck to go through, my goal is just to understand. So I’m going to ask you a couple of questions along the way to understand your business to see exactly what I should show you, and then we’ll leave 5 minutes at the end and you can let me know if you think it’s relevant. Does that work for you?” 

Then see if they have anything to add.

Example: “On that note – you came inbound for x, y, z reason. If you were going to get 2 things out of the call today, what do you want to make sure that I cover?”

To figure out what questions to ask during steps 2-4, you first have to know the common situations of your prospects, the common pains associated with each situation, and the common impacts of each pain (Gap Selling by Keenan can help you come up with these questions).


Get the lay of the land, and keep it quick. 

Example: “How are you managing x process today?” “Who else is involved in that?”


Figure out the pain your prospect has, and then get them to agree.

Example: “Typically when I talk to people who are on spreadsheets it’s either going really    well, or A, B, C things tend to happen. Do any of those sound familiar?”


Once you hone in on the pain, figure out if they even care. 

Example: “Of all the problems you have, is this something worth the time to solve? Or is there something else much more pressing?”


Now that they believe they have a problem, start narrowing them down to specific date, time, and dollar amount. 

Example: “How does this feel from an economic standpoint?” “Do you feel like the ROI is there?” “If you were going to solve this problem, when is the latest that you’d want to have it solved?” “How can I help you get there?”

When you’ve made your way through all these questions and your prospect is still on the line, then, and ONLY then you can do your demo, just to confirm to your prospect that your solution is going to solve their problem.

Running a large sales team isn’t easy at the best of times, and moving to a virtual model adds its own host of challenges and opportunities. From keeping reps accountable, motivated, and honing their skills; to meeting cadences, example dashboards, and balancing your many responsibilities, Armand’s tactics will help you build your own clear system as a newly virtual sales leader. And, if you stick to your commitments, Armand won’t make you eat only Greek yoghurt. *Gratuitous wrestling reference*. 


More on remote sales teams:

075: The ins and outs of managing remote sales teams with upCurve Cloud’s Joey Maller

155: Managing up as an individual contributor on a remote team with Renee Safrata

And a little more on discovery:

061: X Marks the Spot: How Mark Kosoglow’s Sales Team at Outreach Uncovers the Pain Points and Needs of Their Customers

105: The rocket demo: how to effectively sell your product in 30 minutes with veteran entrepreneur and sales coach Dan Martell




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