Closing Time

Rallying the Troops: How to Lead Remote Sales Teams During Challenging Times

Your team is spread across the country, and the forecasts are looking a bit anemic.

Is it the economy, our industry, or just bad timing?

Regardless, it’s time for leaders to step up and create an environment that attracts, supports, and retains remote sales teams.

For many remote teams, that means dedicating time and resources for consistent in-person meet-ups. For others, it could mean virtual happy hours and flexible PTO policies.

What’s the right mix of information vs. team bonding to maximize your time together, whether in person or online? How do we keep salespeople thriving in times of uncertainty? How does the approach differ with entry-level SDRs/BDRs vs. seasoned enterprise AEs?

Join Mike Weir, CRO of G2 and former sales leader at LinkedIn, as he shares his insights into effectively using off-site team meetups to keep remote teams engaged and shares all the tips for how to lead remote sales teams in this episode of Closing Time.

Watch the video:
Key Moments:
Transitioning to remote-first work

Transitioning from an office to a remote-first setup may be overwhelming for sales leaders. Effective strategies and communication methods, such as increasing communication frequency and utilizing different channels like Slack, can help leaders navigate this shift. Holding leadership meetings more often and meeting monthly for global leadership teams can promote alignment and information dissemination, a strategy that worked well for G2. Over-communicating and reinforcing essential messages through various means ensures the right information reaches the team.

How to retain your A-players

Sales leaders who invest in their people, set realistic benchmarks, and adapt to market conditions create a culture of retention, even during times of uncertainty.

Mike’s advice: flexibility is key. Allowing individuals to connect in ways that make them most comfortable fosters a sense of empowerment and engagement. Sales leaders should listen to their team members’ preferences and adapt accordingly.

Salespeople often get lured away by attractive compensation plans, particularly when the sales forecast is not promising. To retain A-players, leaders need to help them thrive. Success should not be solely defined by exceeding quotas. Sales leaders must communicate that performance metrics are not the only indicators of success. By investing in peak development plans and coaching, sales leaders can show their commitment to their team’s growth and professional advancement.

Sales reps also want to feel a sense of community at their workplace. Encouraging employees to participate in the broader company culture and community activities provides them with additional opportunities for engagement. Regular events, interaction with peers, and guest speakers contribute to their overall experience and job satisfaction. However, compensation remains a significant consideration. To address this, sales leaders should reset expectations and adapt targets to the current selling environment. When the market shifts, so should their quotas. By making quotas more attainable and fair, employees are more likely to achieve success, fostering a sense of fulfillment and loyalty.

Ideal cadence for in-person meetups

How often should your remote sales teams meet up in person? Mike recommends organizing them every six months, such as a beginning-of-year kickoff and a mid-year meetup. These meet-ups provide opportunities for team members to build bonds, especially for those comfortable with in-person interactions.

While in-person meet-ups are valuable, quarterly gatherings may feel excessive and disruptive. By spacing the meet-ups every six months, teams can strike a balance between building relationships and maintaining productivity. Additionally, ad hoc team-level or segment-level meetings can complement these larger gatherings. For companies experiencing growth or welcoming new team members, these events provide an opportunity for new hires to connect with their peers, teams, and cross-functional partners, fostering a sense of inclusion and camaraderie.

In addition to in-person meet-ups, sales leaders should also create virtual forums. However, be sure not to overwhelm team members with excessive internal meetings. Listening to feedback and assessing the effectiveness of virtual gatherings is key. By cutting optional meetings that may impose pressure on attendance, leaders can free up time for team members to focus on customer engagement and prioritize external interactions.

Content agenda for in-person meetups

Finding the right balance between meetings and social connections ensures that these gatherings are memorable and impactful. Sales leaders can follow a few key strategies to achieve this balance:

First, it’s important to acknowledge and address feedback from previous events. Overloading the agenda with back-to-back meetings can leave attendees feeling exhausted and unable to engage fully. By condensing the content agenda and allowing more open time, team members have the opportunity to network, socialize, and address any questions or concerns that arise. For example, a hybrid all-hands session followed by dedicated team sessions allows for important information sharing while providing flexibility for teams to connect, collaborate, or even engage in community service events or fun activities that resonate with them. These events create lasting memories and strengthen relationships among team members, both as individuals and as colleagues.

Keep in mind the needs of introverted team members as well. Providing some downtime during the off-site meet-up allows introverts to recharge and find moments of solitude if desired. This conscious approach to leadership and considering all perspectives contributes to maintaining a healthy balance between extroverted and introverted team members.


How can sales leaders continue to rally the troops remotely during challenging times? We’re giving tactical tips on this episode of Closing Time. Thanks for tuning in to Closing Time, the show for go-to-market leaders. I’ve Val Riley, head of content marketing and Insightly. I’m joined today by Mike Weir. He is the Chief Revenue Officer at G2 and also spent eight years leading sales teams at LinkedIn. Welcome to the show, Mike. Hey, Val.. Thanks for having me back again. So here’s the scene, your team is spread across the country. The forecasts are looking a little bit anemic. This is the time that sales leaders need to step up. How do you coach teams during these times? This is a tough one. And honestly, I, like others, I think probably struggled with this for quite a while, especially the part about the remote aspects going to nearly 100% remote was incredibly challenging. That in and of itself required us to think differently about how to engage with our team, how to engage as a leadership team. And then you throw on top of it really bad global economy, and you’ve got a whole recipe for disaster. For us, we wanted to amp up the amount of communication that we were doing and the means with which we were communicating. So we started layering in additional kind of Slack channels for conversations about specific topics. Some overarching updates from the business to the team so that they were staying really well informed. We changed up some of our leadership meeting cadences to make sure that folks were getting more regular updates. My global leadership team comes together every month now versus less frequently before, more like every other month or quarterly. And the goal within those those forums for the leadership team is to make sure that they have tangible takeaways that they can bring back to their individual team meetings that they can talk about with their teams so that everybody is feeling extremely well informed. As a sales organization, we are also connecting into the broader communications that our employee success team is doing and our CEO does via our global all hands. So we have indexed a lot towards over communicate. Make sure we’re reinforcing the most important messages. Use multiple means of communicating. That includes just sharing the information and open collaborative sessions where it is much more of a discussion.. And so a lot of this has helped us to make sure that the right information is out there, that we’re getting the right feedback, that we’re getting the right pushback on when things need to be changed. For instance, we have changed some policies where the team really did push back on certain things to make sure that we were you know, being responsive to the current environment. For instance, like many people are cutting back on expenses. We have tried to not drastically cut our travel and entertainment expense budgets to make sure that the team, when they have opportunities to be with customers, when they have opportunities to come in for our midyear meet up that we host in Chicago in August, or to come in for bigger trainings, that they are able to do that. I love to hear that flexibility. I think that that’s the key, making people connect the way they feel most comfortable connecting. I think that’s great. One topic we keep hearing on this show from sales leaders is around tenure. So we’re seeing salespeople getting lured away by some really attractive comp plans.. When the forecast isn’t great, How do you retain your a-players? During the great reshuffle, great resignation, whichever, whichever storyline you got behind it was really challenging. I would say that nobody and I talked to dozens and dozens of peers across different companies because every week somebody be reaching out saying, I’m trying to hire for this role and like, yeah, you’re the fourth person. Plus I’m also hiring for the same role. And it was a very difficult time because there was so much opportunity, whether it’s that situation or now, where there is less hiring going on To us, to me, it’s always about helping your employees thrive. And so we don’t just rely on the 100% plus attainment being your definition of success. So one thing I spent time talking about with my global rev org at our mid year meetup in August is like, this is going to be a difficult period.. We’ve had two years of amazing success and growth and everybody, you know, when you look at the averages, nearly 70% of my global team made their number last year. Right? And you look at benchmarks and they say like OK, 35 to 40% of a team usually makes their numbers, it’s like a phenomenal success. Also a lot of folks that are younger in their careers and so you hit a huge economic storm like this all of a sudden their confidence has been shattered. Their morale is starting to dip down because they’ve solely defined themselves and their time here at G2 based on i’m over 100% therefore I’m good at my job. So we’ve actually taken a different approach to remind everybody about what they’re doing right. And it’s not that you forgotten how to sell. It’s not that we’re not on board and supporting you. It’s that we want to create an environment where you continue to do the right thing. So we’re going to focus on the peak development plans, helping coach you to be the best in this job and start planting seeds for what you may want to do in a year or two. So that we’re adding to your skill, your knowledge, your experiences. And that’s not an investment that a lot of other companies make. Plus, we do encourage everybody to be a part of the broader G2 culture and community where we have regular things going on outside of their day jobs that give them an opportunity to engage with their peers, with others across G2, with external guest speakers to add more to their job, to add more to their experience here. And again, just like hitting 101% of your quota. And then, you know, with those mix, we’re trying to create an environment where it is you know, it’s tough to leave because you love the people that you work with. You love the purpose of what G2 is trying to accomplish. And we feel like we’re giving you more than what you would get elsewhere. When it comes to compensation, though, obviously that can be a big deciding factor coming into the second half. We reset expectations, we changed targets, and we adjusted to the current selling environment so that folks would have, you know, a equal shot of getting to 100%. So it’s creating a better experience, but also acknowledging the challenging market conditions and adapting to that to create a more hospitable environment, better quotas, more likelihood of overachieving for the team in the second half. Yeah, so it sounds like you’re continuing to invest in people, you’re growing them and making sure those benchmarks are realistic. And all of that together is leading to a culture of retention. Yep. Great. So you mentioned briefly that you hadn’t cut your budget for meetings for team meetups in this time and in the whole remote world, what do you feel like is the cadence of in-person meetups that is ideal for a remote sales team? Yeah, we do every six months it’s a beginning of year kickoff and then a mid-year meetup.. In between them, And that’s like the whole company, right? With some limitations on international folks being able to fly in. But that gives an opportunity twice a year for us to build bonds in person for those that are comfortable being in person. The teams have flexibility within their budgets where we do really promote just transparency and responsibility to to have my leaders get their budgets, they cascade them to their leaders. That gives the flexibility for at a team level or on a segment level, like all of mid-market sales getting together or just one of the acquisition mid-market teams getting together to create the kind of bigger forum twice a year, which feels really good. I think quarterly does feel excessive. It feels a little disruptive to kind of bring hundreds of people together but every six months paired with ad hoc team level kind of group segment level meetings has been really powerful to keep strong bonds, keep new relationships developing because like many, we hire a lot of folks at the beginning of this last calendar year. So we have a large amount of people that join the company as really difficult economic times started, and we still wanted to provide the opportunity for them to get to know more of their peers, other teams, other cross-functional partners. And then as I’ve talked about before, we got to make sure that we’re creating a lot of virtual forums. Right, but not overbearing. I think that is the one thing we heard as we tried to course correct and start over communicating was, Hey, this is a little too much. I’m spending a lot of my time on internal meetings, and so we then reassessed, cut a few of those, you know, optional meetings out where people felt some level of pressure to show up for them and just said, Nope, take the time back engage customers, help customers and let us know when you have questions and we’ll bring those into the public forums, the open team meetings that we do keep on the schedule. Yeah, striking that balance. I think that’s super brave of your leadership to say, Hey, maybe, maybe we overcorrected and we’re going to pull it back. Some companies may not be that brave to make that shift. So really interesting perspective. I also like how you shared about the cadence of in-person meet ups, because no matter when you get hired, you’re no more than a few months away from meeting people in person.. I think that’s important. So the last time my team did an offsite meeting I know we talked about business, but we went to a baseball game and we played miniature golf, and those are the things that I really remember. So when you guys do get together in person, when you’re gathering your sales people from from all over, what percentage of the time is like meetings and learnings versus like that social connection? Yeah, we definitely try to strike the balance like y’all did at your most recent one. It’s tough. I think the last two events we’ve done have gotten very positive feedback that we’re starting to strike a really good balance. Before there was just so much to cover and so many topics that were being requested to be discussed that we would cram the agenda full, like 9 a.m. to 5 p.m. and, you know, 3 hours in the morning. And it was like everybody together.. Afternoon is choose your own adventure. But like you’re jumping around from topic to topic and different internal speakers and and while that got, you know, a lot of really positive reviews. People are like, Whoa, I am so spent. One, I didn’t have an opportunity to like engage with questions that were coming in to me from partners, customers and so forth. But two, it’s like now the team stuff is starting at night, but I’m like, just ready to take a nap. So we’ve pulled that back and condensed our content agenda down. At our midyear meetup, we did a like a three and a half hour global hybrid all hands. And then all afternoon was free for the teams to do their own activities to just do work if they wanted to. And then we had three and a half hour session with just the revenue organization the day after that. And then 2 hours at a team level. And then all afternoon we had a ten year anniversary for G2 party at the end of that. And so we, we really went from like nine to five over the course of three days with team dinners and outings and fun stuff at night to about, you know, half of the amount of content, roughly 3 to 5 hours a day with 3 to 4 hours that’s just open time to use however you want, to network, to socialize. And a lot of teams did, you know, community service events, scavenger hunts like fun things that they allowed, you know, they voted on and chose what really resonated with them. And then we paired in bigger group outings to create opportunities for everybody to come together and that felt really good. A lot of great content, a lot of great information was shared, but way more networking and socializing time for the team, which as you said, they always come away remembering how awesome it was to be able to just sit there and talk to people and get to know them better as as individuals, as coworkers. As a textbook introvert,. I will say there’s probably a lot of people that appreciate a little bit of downtime in their too, Mike. Yeah, maybe the fact that we do have more introverts in our leadership team helps to balance out the person like me who just loves being out there with the team and could talk business all day long and then go to dinner and have a great conversation. So I think our conscious leadership approach to hearing from everybody, all perspectives, has gotten us to a very good balance. Mike, this was great. Thanks so much for being on the show. Thanks for having me. Remember everybody like this video, subscribe to the channel and ring that bell for notifications so you don’t miss an episode. We’ll see you next time.

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