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3 Lessons on Managing a Diverse Remote Sales Team

3 Lessons on Managing a Diverse Remote Sales Team

The last six months have been humbling as a sales manager. Overnight, I transitioned from being a 100% IRL manager to being 100% remote. Initially, I was overly confident, thinking how hard can this really be!? Got this in the bag. 🏆  But I quickly realized that managing a team of remote salespeople presented some unique challenges.

Managing sales teams remotely is different than managing any other team for a few reasons:

  1. Sales reps hold extra stress from carrying quota (especially in a volatile market)
  2. Sales reps no longer have the opportunity for real-time social learning
  3. Sales reps miss the motivation of friendly competition

As a sales professional in this new remote world, I realized that I needed to invest in learning how to manage a diverse, measured, social team if I wanted to maintain a high performing team.

These are some of the lessons I’ve learned along the way. If we make it a point to do a better job of understanding and supporting each other within a remote framework, our teams have the freedom to get better, grow stronger, and thrive onward. Not to mention, reduce attrition and decrease ramp time, which helps us hit our numbers.

At Flockjay, we connect top tech companies with diverse, pre-trained sales reps.

Lesson 1: Check in On Your Sales Reps, Their Whole Selves

For salespeople, carrying quota is a double-edged sword. We love it. It gives us clear, measurable goals to hit every day. We know exactly what is expected of us and how we’re tracking against them. That being said, carrying a quota is also stressful!

Now layer on all the added stress of this year. Between social unrest, a global pandemic, and apocalyptic wildfires, I think it’s safe to say 2020 has been a high-stress dumpster fire for everyone. Who couldn’t use an extra check-in from a mental standpoint

More than ever, people have a lot going on besides just work. The added stress of working remotely on top of trying to take care of our communities, family, and friends is unmeasurable. This is going to cause your sales reps to show up differently sometimes.

This is particularly true for folks from underrepresented communities, which is important to recognize because the best sales teams are diverse sales teams. You need all kinds of people to make the dream team.

Some folks reading this might be wondering why they should even care about how their sales reps are doing both personally and professionally. Not only do I think it’s the right thing to do as a person, but from a business perspective, happy people perform better and decrease attrition on your sales team.

If you care about high performance, you should care. The average tenure of a sales rep is less than a year and just 40% of reps consistently hit their quota. That makes it incredibly challenging to build consistently high performing teams. So how are you as a sales manager going to show up in return to support the diverse team you need?

As Brené Brown said of corporate work environments:

“There is a deep yearning for being more wholehearted; people want to be able to show up at work in a meaningful way. They want to lead from the heart.”

Embrace this as a leader by checking in with your sales reps and letting them know it's safe to bring their full selves to work. We're all human.

Deeper Dive on Remote Sales Management Tips

When I first started managing sales teams, I learned that consistency is the key. Anyone can have a good month or quarter but how do you build a team that consistently hits quota quarter-over-quarter? And how do you keep it up remotely? I can offer these remote sales management tips as a place to start.

The worst thing that can happen to you as a sales manager is to have a top performer flame out, out of nowhere. Consider that your quota is the same regardless of if you have a team of 8 high performers or 4 high performers or 4 burned out performers. Part of your job is knowing who you need to speed up and who you need to slow down. I don’t manage any two people on my team the same way.

Your team is unique and diverse and so your management style should follow suit and be flexible from rep-to-rep.

Here are a few tips on how you can start checking in on your sales reps:
  • Open your 1:1s by asking how they are doing (and allowing them time to answer thoughtfully if they so wish) before diving into sales metrics
  • We all wear so many hats. Ask questions to get to know their life outside this one role.
  • Ex: Do they have kids at home that they are homeschooling during the pandemic? Do they live somewhere affected by wildfires?
  • If there was ever a time to be consciously empathetic, is it now. Offer extra support for people in communities particularly affected by police brutality.
  • Ex: “Hey, I know there is a lot going on in the world right now. Please take care of yourself. I am here to support you.”
  • Practice vulnerability as a leader and you will find yourself in more authentic situations.
  • Ex: “I’m actually having a tough time focusing myself this week with the fires and poor air quality here in San Francisco.”

Asking these questions and having a pulse on the answers will help you understand how to better meet the varying needs of your diverse sales team. Create a work environment where people feel safe and encouraged to have these conversations. And when you see signs that someone needs to slow down, or someone needs extra support, show up. Provide solutions.

Resource: Inclusive Leadership Insights to Build Successful Teams in 2020

Resource: One Black employee’s answer to “How can I help?”

Lesson 2: Embrace Social Learning In a Remote World

Picture this: The year is 2011, I’m a Sales Development Representative at Box, and I’m rocking an amazing mullet. I’m blissfully ignorant and have decided I’m ready to run my first discovery call. What I lacked in skill I made up for ambition. So my manager just gave me a knowing smile and said “Sure Kelly, you can take that call. I’ll be on just in case you need anything.”

Me being me, I thought ppssshh sit back and relax, I got this! Almost immediately upon starting the call, I realized I was very underprepared to run a discovery call with the CIO of a Fortune 500 company. Thankfully, my boss, bless his soul, let me flounder for a bit, and in between questions he’d mute the speakerphone, give me some real-time advice and encouragement, and throw me back in the deep end. This social learning exercise taught me a lot.

The reality is that most of today’s sales leaders were taught how to sell in a social setting. Our managers sat in on calls with us. Our teammates would swing by our desks to help craft that 4pm outbound sequence. Everyone would share a laugh when they heard you totally botch a cold call and then offer their unsolicited advice.

Sales reps have to learn in real-time, with real people. In this new world, we must get creative. So much of sales is reading facial cues, voice intonations, body language, and adjusting as you go. The way you get better at that is by practicing with humans in a social environment.

Deeper Dive on Virtual Sales Training Tips

Engineering teams have long practiced pair programming (an agile software development technique in which two programmers work together at one workstation). Working remotely has me wondering, what is the sales equivalent? How do we replicate that in this remote world?

McKinsey found that almost 90% of B2Bs have transitioned to a virtual sales model during COVID-19. The upside? Almost 65% of B2B decision-makers say that remote selling is more effective now than ever before. It can be done! If your team isn’t quite there yet, don’t fret. But since data shows your sales team is most likely to stay remote, it’s important to invest in learning, training, and development now.

Here are a few sales training tips that can help you start supporting your virtual sales team:
  • Overemphasize body language and facial cues when communicating on tools like Zoom
  • Offer real-time feedback by communicating directly with your sales reps daily via Slack
  • Invest in game-changing tools like Gong’s revenue intelligence platform, which allows you to refer back to recorded sales calls that can offer critical insights into what’s happening with your remote sales team, your deals, and your market

Flockjay Tech Fellows turned SDRs have a competitive advantage that allows them to ramp faster, retain longer, and add to the culture of your organization. Our graduates have accepted exciting sales roles at companies that are growing such as Zoom, Gong, Airtable, and Gusto.

Lesson 3: Build Community & Playtime into Your Sales Culture

Sales is inherently competitive and the best teams usually drive each other to succeed in a positive way. While celebrating over Slack is better than nothing, it’s not quite the same as when you’d close a big deal at the end of the quarter and the whole office would celebrate together.

I can’t believe I’m saying this as an introverted salesperson, but now more than ever, we need to make sure we’re building in social time for our teams. By nature, sales is a repetitive job.

The best sales teams have little variability in their sales motion, which means most days should look similar in terms of process. This is intentional, you’re building a well-oiled machine.

That being said, ask any outbound manager, you need to find a way to keep the energy up, keep people engaged, and nurture excitement in order to keep driving revenue.

My suggestion is to:
  • Create your time to socialize, be creative, and bond. If the only time your team sees each other is for sales team meetings, I suggest creating some purely social playtime via Zoom breakout rooms for people to recharge, reinvigorate, and bond with each other.
  • Invite the whole company into the sales team’s competition. This is a great way for other teams to learn about sales and for salespeople to exercise those competitive muscles.

For example, at Flockjay, when the team was eagerly awaiting our debut webinar on diversity leadership with Microsoft Chairman John Thompson, it presented a great opportunity to encourage our collective team to engage and participate. How did we do it?

We announced a company-wide competition via Slack, made unique URL registration codes for each employee, and awarded a prize to whoever pulled in the most leads. By leveraging our employee’s remote network and being inclusive, we were able to pull in close to 400 registrations in a matter of a week.

Give this a try at your organization and explore different events you can rally your team around!

Deeper Diver on Remote Events to Improve Sales Culture

We’re still figuring this out at Flockjay, but here are some examples of what we’re doing:

  • 🚀  Mondays: Our CEO Shaan kicks off our weekly “Liftoff” team meeting with announcements. Then, we dive right into Zoom breakout rooms to share 10 minutes with a smaller, randomized group of teammates to talk about our weekends or answer a suggested prompt before returning to talk business. A recent prompt that was really interesting to explore with teammates was, “What did community look like for you growing up?” At the close of the meeting, we name our weekly MVP (by nomination)
  • 🥗  Tuesdays: We have a recurring Zoom room for an optional team lunch hour for anyone who wants to join, chat, get a little facetime, or you know, eat with an audience.
  • 🍷  Fridays: Our “Wine Down Fridays” quickly became a highlight of my week! Every Friday at 3pm, the whole company jumps on a Zoom call and we play games together. Sometimes it’s trivia, Pictionary, table topics. This is a great way to end the week, build community, relieve some stress, and remind everyone why we’re all here.
  • 🧘🏽‍♀️  Bonus: Our Programs Analyst Ashima recently volunteered to lead a team yoga class (you guessed it, on Zoom). Using a poll on slack, the team voted on the best time slot, and those who could make it gathered for an hour before kicking off the day with a little more mental and physical balance. Look for fun ways to integrate the varying skills and superpowers the people on your team have. What are your superpowers?

Start Now for a Stronger Remote Sales Team in 2020 & Beyond

I encourage you to start today improving your remote sales management strategy today by implementing more communication, connection, and community among your sales team. This remote world is never going to fully grant us the magic of that in-person camaraderie. But if you approach this intentionally and creatively, there will still be plenty of time for the folks on your sales team to rise to the challenge of grinding toward and achieving their quotas.

That said, I’m not done learning. I look forward to sharing more sales and management insights with you and am really interested to hear about the lessons other sales managers have learned.

What have you found the most surprising about managing a remote sales team so far?

Flockjay reps already love to sell. They are trained by the best, onboard faster, perform better, and stay longer. Interested in diversifying your sales team with pre-trained talent?

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