Episode TwoHundredNine

5 Keys to To Successful Remote Sales Leadership

Guest: John Jenkins, Senior Director of Customer Experience at Realtor.com

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About This Episode

By now, we’ve all heard stories about the incredible agility teams have displayed in response to the wild ride we are on together waiting for the pandemic to resolve. 

Every department can be painted as the hero. 

IT deserves a tropical vacation when those are a thing again; the C-Suite can take a tasteful bow. 

Even customers have been a part of the pivot process with their adaptability and patience.

As everything was shifting like the elusive staircases at Hogwarts, guess who was responsible for keeping the gears oiled, ie: bringing in revenue in the face of some seriously unstable stuff!

You guessed it; Sales! 

The phone slayers, the goal smashers, your friendly neighborhood sales stars, and the leadership teams that guide them.

Sales star wrangler, and Senior Director, Customer Experience at Realtor.com, John Jenkins,  sat down for a much-needed break to share the ups, downs, successes, and challenges of moving his 300 plus sales team to a fully remote environment as the pandemic unfolded. 

Everything isn’t going to go perfectly. That’s ok!

I think it was very appropriate that across the board, the day that stands out for most people as things pivoted from “I wonder whats going one here”” to WE ARE IN CRISIS MODE PEOPLE!” was a Friday the 13th. 

Instincts take over, fight or flight kicks in and you are running on adrenaline and instinct. 

Our view from the sales floor was pretty intense, and everyone had to keep the machine running. John had a few things he would have done using 20/20 hindsight. We all have our version I’m guessing. These 5 things seem to resonate across the board:

  • Breathe– Stop and exhale. Running around with your hair on fire isn’t going to help. 
  • Messaging-Your people need to know where things stand. Don’t live in a leadership bubble. Lead with strength and empathy.
  •  Just get everyone set up– One thing that definitely needs to happen is shifting everyone over to a remote environment. Put your head down and get it done.
  • Settle in-Everyone is up and running? Fantastic. Take a minute to observe your new team environment.
  • Back to focusing on performance- Congratulations, you have made it past the first level of Jumanji! Time to get those numbers back up.

There is no “I (work from home)” in TEAM

Work environment

Salespeople are unique individuals who generally thrive in an energetic, competitive team-centric environment. It’s nearly impossible to replicate the energy they feed off of when they are all scattered and sheltering in place. 

It’s challenging enough for sales leaders to motivate and keep their reps fired up. Having them in quarantine is not ideal. Take actions that support and encourage the camaraderie your team thrived in at the office.

  • Make sure the tech platforms you are using have ways to interact and communicate.
  • Build trust. Your team needs to trust in leadership right now, and just as importantly, leadership needs to trust the team.
  • Keep the social stuff coming! Schedule virtual happy hours! Set up a live farm experience and hang out with some llamas. Host a virtual poker game. There are tons of great options right now. Go Team!

Finding your remote groove

Productivity may very well dip. Don’t be surprised or be caught off guard.

Your team needs to adjust to remote life, the tech needs to bake in, and leadership needs to adjust the sales experience to accommodate new norms for the reps as well as for the customers. 

Keep going, and balance as well as you can. Adapt and pivot with your team. 


Keep your new expectations clear, and give your team the opportunity to express their needs and expectations. 

Keeping the lines of communications open, while laying out what is expected of everyone will put you back, and keep you and your team on the right path. 

Know when to transition your thinking

All of the things we laid out here depend on you understanding when to transition to next steps. 

Trust in yourself and your team.

Know when it’s time to let go and trust in the work you’ve all done.

Remember, it’s a 100% guarantee that this whole process will not be perfect! 

Know when it’s time to accept things as the best possible scenario and when to keep pushing.

Empathize and support, but stay in tune with your role as a leader. Recognize when it’s time to transition from giving tons of leeway, to when you need to step in and make sure everyone is the productive rock stars they can be!

For more engaging sales conversations, subscribe to The Sales Engagement Podcast on Apple Podcasts, on Spotify, or on our website.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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