What 7 Days Of Managing A Remote Sales Team Taught Me 

Like most of you, my stint as a sales professional has defined success in the context of a “business-as-usual” environment: a stable economy, strong product-market fit, predictable supply & demand.

Today’s reality paints a far different picture from that “implied” environment. The world of sales, as we know, is adapting to negligible in-person meetings, postponed decisions, and deal cancellations. Amidst all the chaos, I face a new scenario – virtual sales teams.

I’m a sales manager with Freshworks, managing a remote sales team of under 50 sales development representatives. Honestly, if ‘adversity brings out the best in man’, the past seven days forced me to look at 15 years of sales experience in a relatively new light.

I couldn’t resist sharing what I’ve unlearned, learned, and been utterly knocked off my perch while leading a highly energetic, driven bunch of associates hunkering down from the four walls of a remote location like their homes. Here’s the best out of what the past week taught me:


1. Never Second-Guess Your Team’s Potential: 

It’s natural and human. You’re forced to manage a remote sales team, dramatically different from working together. Phrases like ‘out of sight, out of mind’ could trigger fear or apprehension.

But I have been able to bust certain myths about how to manage a remote sales teams. My entire virtual sales team team, conquering initial hiccups of technology (and work-sickness), quickly adjusted to the new model.

In surprising fashion, they surpassed their targets, rather than hitting them. This happened despite our cautionary note for them to moderate their outreach. I can vouch for this given how we are keeping engagement rates high with our prospects through a shift in communication:

  1. Phone: Conversations through this medium halved to 30% within two weeks, given our prospects are now spending time reworking their business models or balancing work and their personal lives from home.
  2. Email: Interactions jumped 2x to 40% from 20%, given the medium allows for thought-out interactions crucial today with our prospects now analyzing our responses in detail.
  3. LinkedIn: Professional communities are taking center stage, as prospects are trying to gauge market changes from their peers. For us, it is a great tool to research and leverage discussions to find and engage with prospects. Result: Engagement rose by 50%.


2. Find New Ways of Hustling

My account executives noticed inactive accounts turn on the green light, ready to deploy our enterprise software for customer experience, within two months. This, in most part, was due to their need to manage a sudden torrent of customer inquiries or employee resource management through remote working. Others are quietly putting off further discussions until conditions improve.

Here’s a rundown of how we are hustling to sell today:

  1. Investing in hyper-targeted opportunities: We are doubling down on identifying core business challenges of our prospects and applying AI-prediction through tools like ZoomInfo and Freshsales CRM. Subsequently, my team can prioritize and de-prioritize potential accounts. Gradually, our pipeline is being rebuilt.
  2. Reviving conversations with inactive accounts: By comparing historical CRM data with the current selling scope specific to industries and geographies, we are considering targeted approaches to rekindle dormant accounts, shelved during previous quarters.
  3. Reengineering our tech stack: As we push towards improved personalization, we are revisiting our tech stack intending to generate improved data insights, automate mundane tasks, and recommend actions for reps to improve buyer journey experiences.
  4. Experimenting with Seinfeld emails: Everyone is short on time and prospect conversations default to understanding business challenges or finding solutions. In the process, we miss connecting on a common denominator: LIFE. A Seinfeld email is a handy technique to build talk of our now-changed daily lives through storytelling, having an objective of eventually indicating a business solution for them. Gradually arouse their curiosity through an email series and you will see interest grow.

Last week’s rules might not deliver this week. Keep hustling and closing!


Having visually-intuitive software can improve sales results during this period


3. Buyer Insensitivity & Textbook Selling Can Cost You

Turn on any kind of media, and it’s flooded with news of the crisis, but also of a new wave of humanity and common emotion that grips every one of us. Your prospects, just like you, could be going through a rough patch.

With a quickly changing and a slowing economy, you might as well throw the usual prospecting cadence out of the window, or dream of having a predictable sales model.

I’ve learned that this is the best time to develop a lasting bond beyond being a wise consultant or being downright salesy.

I’m on a learning curve, and here are some tips to help you adapt your selling:

  1. Be intentional with buyers: Talk to their fears and hopes during initial conversations. Stay clear of product pushes unless conversations indicate possible interest.
  2. Empathize with them: Enquire how their lives have suddenly changed (kids at home, falling business prospects, remote working challenges, etc.).
  3. Gauge signals and adapt quickly: Know how to prioritize time spent on high vs. low-propensity accounts towards possible closures.
  4. Stop prospects in their tracks: Take an extra day if needed. But create strong value propositions to compel your prospects to re-engage with you.


A response from a prospect reflects the challenging times businesses are facing



4. Your Team Can Unintentionally Burn Themselves Out

Given today’s context, managing a remote sales team can involve a range of variables: managing communication with family members, technology failing, or coping with depressing news. To top that, sales is usually all-consuming.

To chase daily closures, some of my team members were trying to manage their schedules, often working extra to compensate for lost hours. That resulted in less recovery time, fatigue, and a drop in quality. All in Week 1!

I had to act fast. After some research and consultation with the company’s people management function, here’s what we took up:

  1. What we introduced: Best-practice routines, including focused work sprints with regular breaks, coupled with sessions on physical exercises, meditation, and self-motivation.
  2. What we reintroduced: Team bonding activities that were a part of our schedule at the office, such as two daily conversations through our sunrise “Coffee Hour” and sunset “Howdy Hour”. It helps us work as one unit, feed off each other’s learnings, and is a good pressure outlet for us.
  3. Calendarize your calls: Communication can easily be postponed: So, have a handy list of 5 people to call on a daily basis, either from your professional or personal network.


A screengrab of my team’s “Coffee Hour”

5. Discover Hacks to Maintain a Competitive Spirit

A competitive environment is fuel that burns the flame, a.k.a the drive in a sales team. Fanning the flames in a virtual setup is no easy feat. Too little or too much competition is bad for results.

While I am getting on top of managing this, we have gamified our approach by breaking ourselves into smaller teams to compete in:

  1. Sales quizzes
  2. Mock calls
  3. Brown bag sessions – Informal lunch meetings

This is developing healthy competition, and we’re going a step further by comparing results from these games with real-sales results. Then, if we find low-sales performers with high game scores, they are given special attention and vice-versa. We intend to balance individual and team-playing dynamics towards smashing their goals.


A transparent window on peer performance can foster healthy competition


6. Spend Quality Team Time:

As we reorganize how our time is spent in times of crisis, I suddenly notice open windows to reinvest time and effort that was taken up by a ton of meetings or workshops, as we deal with a dip in buyer interactions and increased remote working.

I have begun to reinvest my time to:

  1. Look at individual sales practices of my team
  2. Better shadow low and high performers to cross-pollinate learnings
  3. Make one-on-one meetings purposeful (talk beyond work conversations, if you can). 
  4. Create customized training and enablement programs 

Initial feedback has been tremendous, and they want more. I’m working with my seniors to organize feedback better and quickly make process or team structural changes to improve our outcomes.


My team’s favorite Zoom background


7. Support Leadership Navigate Through Troubled Times

Freshworks has a flat hierarchy, and hierarchy is placed to guide us in the right direction. This is arguably a pivotal point in our company’s history, where our leadership is stressing how important on-ground feedback is carried to them, especially from frontline sales executives gauging word on the street from our buyers.

If you are wondering how to manage sales teams at this time, here is what we are trying to do:

  1. Aggregating key learnings: To optimize our focus through activities like rebuilding our account lists or re-drafting email templates.
  2. A strong feedback mechanism: We are using nifty and customized reporting tools to keep our sales leadership regularly updated, who in turn, share key intel with business heads.

Sales Report


Chase New Rainbows

The clouds are getting darker outside and it looks like our current nature of work will become the new normal for the near future, if not for the long haul. But human agency will prevail if we keep our eyes and ears open to change.

If one week generated tons of learning opportunities, I could only imagine the wonderful things my team and I will come up with to continue driving great conversations and offering value to the market.

What’s more, learnings from managing a remote sales team will spill over into helping manage my personal life. It gives me hope that we will soon turn a corner, and things will look brighter.

Don’t forget, tough times make you and your team stronger. Get off to a great start!