Morning coffee, virtual lunches, and gratitude: managing a remote field sales organization

Posted April 15, 2020

Stephen sunshine headshot

By Stephen Sunshine

Director of Sales at Outreach at Outreach

As people across the globe confront COVID-19, we are suddenly all working from home and we’re all remote employees. For many of us in sales management, this new reality brings some unexpected remote management challenges.

At Outreach, here are a few things that are working for us during these times.

1. Remember Your Goals, Objectives and Mission

I remember where I was when I read our CEO Manny’s email announcing we were all going to be working from home for the foreseeable future. It was a Thursday morning in early March and I was wrapping up a forecast review via Zoom with one of my account executives. Ironically, I was working from home that day, but little did I know this was about to become the new normal.

Seemingly overnight, Seattle became the first major metropolitan area in the United States where both state and local authorities recommended strong measures to slow the spread of COVID-19, the novel coronavirus. Schools all around the Seattle area were shutting their doors, and businesses around Puget Sound were telling their employees to stay home.

While I’m no stranger to working from home and being part of and managing large, remote teams, many on my team had never experienced this type of work environment and were not accustomed to some of the inherent challenges that working together, yet apart, creates. Limited interaction with peers and management, feelings of being left out, and technical limitations to name just a few. It’s easy to lose sight of one’s path forward, so now, more than ever, we as managers need to be present, provide a clear path forward for our employees and focus on the goals, objectives and mission.

In their best selling book First Break All The Rules - What the World’s Greatest Managers Do Differently, Marcus Buckingham and Curt Coffman detail how the best managers and companies clearly define the outcomes they want and communicate the specific goals and objectives. In times of crisis, it’s more critical than ever to lean on your goals and objectives to keep your focus tight.

At Outreach, and I speculate at your company too, as the novel coronavirus has spread to every corner of the globe, we have doubled-down to enable our teams to do what they do best: help our customers realize the value in our products and services. From the highest levels of our company down to our field teams, we continuously discuss and remind ourselves of our core company values. “We Are One With Our Customers" and “We Got Your Back” are just two examples.

Keeping your teams centered on sales goals and your organization’s mission can be as simple as reminding the team in the morning to partner with their SDRs, discussing ways your team can reach out to their extended 360 degree internal ecosystem (SCs, Customer Success, Support team, Professional Services, Marketing, etc.) and reminding them that you appreciate them and their hard work.

2. Real-Time Change Management

The other day, my team and I were on Zoom for one of our daily Morning Coffee video calls and we were talking about the wave of happy hour events that we were being invited to attend. After a few minutes of the obligatory alcohol and liver-related jokes, I suggested to my team that instead of a happy hour, it would be cool if they could have virtual lunch meetings with their prospects and customers, and somebody said, “I love it! We can treat them to a lunch delivered by their favorite local restaurant, and we will be able to support their community and the restaurant industry in a time of great need.”

In minutes, we’d begun the process of getting a new “Virtual Customer Lunch Meeting” Sequence and Template into Outreach, and people were excited to begin inviting their customers. The Template integrates with Sendoso, our gift giving platform, and facilitates a simple way to provide a gift card for the customer to use for our lunch meeting.

Using our own platform, we are able to quickly execute new Sequences, proactively take advantage of the new business realities, trigger a variety of tasks and track key metrics. These reports allow managers to consider the efficacy of a particular Sequence or sales playbook, and to then coach our teams in real-time how to adjust for better results based on the replies and progress of individual account executives or teams.

Right now, it is more important than ever to communicate more effectively with our teams, prospects and customers. With these reports I can quickly and easily see what emails are being delivered, how many opens we are getting and, more importantly, gauge the sentiment of the replies.

We continue to adapt daily, updating content and Sequences to match the new rhythm of shelter-in-place. For additional information and some amazing recommendations and thought leadership, please check out my colleague Brooke Simmons’s awesome post on Selling in a COVID-19 World - 4 Immediate Steps to Take as well as my other colleague Brooke Bachesta’s fantastic blog post, Stand-Ups, Slack and SPIFs: Managing a Remote SDR Team at Outreach.

3. Culture, Caring, and Community Building

For many of us, working from home is something that can bring out feelings of fear, trepidation, loneliness, etc. The list goes on, but we as managers have a choice: we can face the unknown together with our colleagues and teams or we can sit back and watch them struggle with the unknown and ever-changing daily events around us.

If you’re anything like me and love your team and your role as a manager, I am certain that you’ve already chosen the first path. We as managers need to be leaders now more than ever and demonstrate to our teams that we “have their backs”, that we'll face the challenges ahead together as one, and that we'll lead them to positive outcomes.

Here are a few ways we’ve tackled the new normal of work from home and how we have fun!

  • Morning Coffee: daily standups with the team, special guests (our COO, CEO, Regional VPs, etc.).
  • SPIFFs: we have created contests rewarding our account executives, sales development reps and solutions consultants to partner together in order to get the word out and set up new logo prospective customer meetings.
  • Happy Hour: BYOB, of course.
  • Book Club (plus Happy Hour!): with the team and respective authors.
  • Virtual Lunch Meetings with Customers and Prospects
  • Fun with Zoom: background images with accompanying costumes (shout out to Craig Henehan - yours are THE BEST! I’m sure that Ireland is still recovering from your virtual St. Patty’s Day visit).
  • Kids, Pets and Significant Others . . . Oh My!: As we rely on video conferencing more and more lately, I love seeing the menagerie of pets, patios, different room venues, artwork, children, significant others, etc. We get a view into the personal lives of those we spend so much time with at the office and learn more about them as individuals.
  • Sales is a Team Sport: Last, but not least, I constantly remind myself of the phenomenal extended team at Outreach who supports my sales team and the customers we serve: sales development representatives, solutions consultants, customer success, support, IT, data science, professional services consultants, finance, the deal desk team, legal team, HR, marketing, engineering, revenue operations, recruiters, our executive team and so on.

Now more than ever, I find that both I, and others on my team, feel the need to take the time to reach out to our internal teams and just say, “Thank you.” There doesn’t have to be a demo forthcoming, an MSA under review and in-redline status, or a new feature we are angling for in an upcoming quarter. We just need to remember that we’re all in this together and we’ll succeed together. We cannot do what we do without any of you. Thank you, thank you, for all that you do each and every day.


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