How to Lead a Remote Sales Team
A new, scaling startup sales team requires hyper-attention under the best of circumstances. Add in the challenge of going remote overnight—as so many of us did earlier this year—and leading a team might feel like treading water.
If you’ve been struggling with leading your remote sales team remotely, you’re not alone—it requires a lot of different skills and adaptability. But you’ve got this. Follow these tips below to improve communication, increase productivity and collaboration, and help your team feel more supported.
1. Hold a video standup every morning
Have your team meet every morning for a 15-minute standup (video on, always!). If the team has more than 10 people, break it up into specialized standups: one for enterprise reps, one for SDRs, etc.
Here’s the agenda I use:
- 2–3 minutes: Highlight news that came in overnight (a big deal that closed after hours, a new product release, a hard-to-pin-down prospect who confirmed a meeting, etc).
- 8 minutes: Each person shares what they commit to for the day—this will vary based on roll (number of calls they will make, number of new appointments they will set, number of deals they will close).
- 3–5 minutes: Ask one question a day, and vary what you ask. Try these questions: What are you most excited about today? What’s a new technique you are going to try today? What’s one thing you want to do better today than yesterday? What’s one thing you learned yesterday? Your goal is to stimulate open communication.
These morning standups are a great time for quick skill refreshers or sharing company news. Then ensure every team member makes a commitment to the group. A daily standup creates a culture of community, accountability and collaboration.
2. Hold another video standup in the afternoon
In the afternoon, have your team assemble once more for another brief standup to discuss the day, report on commitments and share accomplishments. You can also use the time to share tips or new talk tracks and offer to help with anything that came up during their workday.
My agenda includes:
- 10 minutes: Everyone reports on their commits—did they hit their goal for the day? Why or why not? Make sure this is an open sharing, not just a read-out on their results. This transparency around activity and outcomes is important for a new sales team.
- 5 minutes: Open the floor for someone to share something they heard on the phone that day, or a new talk track they tried. If nobody shares, be prepared to do a quick role play or to review a page from your sales playbook together. Even just five minutes of skill development or discussion every day helps your whole team improve—and it signals what’s important.
This ritual of consistent morning and afternoon standups is essential for a new sales team working remotely. Since the team is at home, they don’t get the benefit of the collaboration, discussion and ad hoc coaching that naturally happens in an office.
Over time, when your team is performing predictably, move to a once-per-day or every-other-day standup. But in the beginning, while your team is ramping up and you’re building your sales machine, twice-a-day standups are worth the time investment.
3. Have the right meetings
Don’t skip important team meetings just because everyone is working from home.
You really do need to “see” your team often and maintain discipline about your meeting schedule since you don’t have the on-the-floor energy and feedback loop that you would in an office.
A typical sales team follows a cadence of meetings like this, which work just as well when held remotely:
- Daily standups, as outlined above
- Monday morning forecast and pipeline review (one hour, entire team)
- Deal strategy lunch (one hour, every other week, entire team)
- Afternoon role play session (one hour, alternating weeks with deal strategy, entire team)
- Weekly opportunity huddles and coaching with your ramping reps, bi-weekly for your fully ramped reps (45–60 minutes)
- Weekly coaching sessions for your SDRs (individually)
You might feel like these meetings will bog down your team and take away from valuable selling time. But there aren’t really any meetings here that wouldn’t have been happening in a traditional office environment anyway. And when everyone is working apart from each other, it’s important to get together—selling is a team sport!
4. Make your expectations clear and measure them daily
New sales teams might not yet have benchmarks, but that’s not a reason to be vague about your expectations for results. Set goals and then measure against it every day.
For some roles or ramping levels, you may need to set goals for activity. When things get a bit more predictable and quantifiable, set goals for outcomes.
For example, you may need to set goals for activities like:
- Number of accounts worked
- Calls per day
- Social touches
- Emails sent
It’s even better when you can measure outcomes (results), such as:
- Number of opportunities created
- Appointments set
- Deals won
- Pipeline generated
Measuring outcomes is always the best approach because what you really care about isn’t activity, it’s results. But it’s hard to set outcome-based goals in the early days, so you have to create goals around activity.
Either way, make sure you’re measuring, reporting on it, sharing results and holding people accountable. Have each team member share activities and/or results every day. You can also automate notifications to be posted into Slack via your CRM or gamification platform.
A Slack channel filled with updates on revenue booked, opportunities opened, or deals won is a great source of encouragement and excitement for everyone. It almost replicates the energy of an office sales floor and keeps everyone accountable to their number. And daily team updates on activities and results keeps everyone accountable to hitting important goals.
5. Get the right tools in place
You can’t manage a sales team without the right tools. That’s even more true when you have a sales team working from home.
Here’s the absolute minimum you’ll need:
- Zoom for video conferencing
- Discover.org for list building and prospect intelligence
- Slack for team communication
- Salesforce or similar CRM
- Chorus.ai or Gon.io for call recording
- Spiff or Xactly for commission tracking
- InsightSquared for real-time dashboards and KPI tracking
- Confluence Highspot or equivalent for your sales playbook
- Outreach or SalesLoft for communication cadences
- Gamification tool like Hoopla or LevelEleven
If you don’t already have these tools in place, it’s time to get them set them up.
6. Create playbooks. ASAP.
If your sales team doesn’t have sales playbooks already, create some—fast. Playbooks offer a common reference point, help maintain uniformity and consistency, and ramp your reps faster. I’ve posted my sales playbook outline online and links to other playbook resources to get you started here.
If and when you do have playbooks ready, update them often. Your sales team is learning every day—new ways to handle a question, overcome an objection or get a prospect to sign up for a trial account.
So make sure your playbook stays up to date. Give it a quick refresh on a bi-weekly basis.
Throughout all of your meetings and conversations, keep the playbook front and center. Refer to it, pull it up, use it. Every time you do, you’re building great habits for your team and setting an example for everyone. The team will get used to having the playbook as a resource and everyone will improve faster. A playbook is a central part of creating a predictable, scalable sales machine.
7. Foster the right culture
Your sales culture is incredibly important. Your team must be clear on what your culture is and how best to embody it. That starts with you modeling it yourself and reinforcing it in front of others. Transparency, accountability and communication are essential in any sales team, but especially so when everyone is working remotely.
Set a shining example and lead your team toward the culture you want to promote. Here are some culture examples and how to demonstrate them remotely:
- Accountability. By having everyone make commitments each day and then report on their attainment in the standups, you create a culture of accountability. Share your own commits for the day or week and report back to the team how you did.
- Collaboration. Conducting meetings like deal strategy allows everyone to share and support each other. Encourage your reps to help each other. Sometimes that means you need to pull back and let the team solve problems together, versus being overly prescriptive or opinionated.
- Authenticity. Be real, vulnerable and honest with your team in all of your interactions and they will follow suit. Share what’s on your mind, what’s working, what’s not, what your goals and hopes are. Honor your word and your commitments to your team, and be yourself. Your team will respond to it—and so will your customers. Being authentic sets a great tone and helps build trust quickly.
8. Implement some fun rituals and traditions
Some offices have fun little rituals like hitting a gong whenever a rep makes a sale. Find a way to replicate these rituals even when working remotely. Pick things that don’t feel artificial and are true to your culture.
A few examples to consider:
- Record a short, funny video of yourself hitting a gong (or banging on pots and pans). Every time a deal closes, have a Slackbot post the video to your sales channel.
- Once a week, conduct one of your daily standups as a walking meeting—everyone grabs their headphones and heads out to take a walk “together” for 15 minutes.
- Send special care packages for certain milestones—a small token of appreciation to the SDR team, a piece of company swag for the first deal a sales person closes, etc.
- Give a small weekly award, rotating what you celebrate. You can give an award for the most creative objection handling, or the most effective voicemail. The changing nature of the award keeps things spontaneous and helps everyone stay on their toes, too.
- Consider hosting a virtual happy hour each week the team hits quota.
If you don’t have any rituals already, don’t let it fall to the wayside. Rituals help unite a team and give a deeper sense of community. Get creative!
9. Keep the lines of communication wide open
Communication is key. I’m sure you already know that, but even in a traditional office, it can be hard to get communication just right. For a remote sales team, there will be a whole new wave of challenges. You’ll have to stress communication all the more.
Get used to repeating yourself. If you say something important in a meeting, reinforce it with an email after, then post it on Slack and pin it to your sales channel to make sure it gets noticed. Bring it up again a few days or weeks later. Ask questions to make sure your message was heard and received.
Does this sound like overkill? It isn’t. Different people retain information in different ways, and someone could easily be distracted when you say something in a meeting. They might miss your Slack message. Your email might end up unintentionally buried in their inbox.
Make sure you over-communicate, repeat everything and make it stick.
10. Shadow and record calls
If you’re managing a new sales team, you probably have ramping reps. If so, shadow their calls. It helps you get a feel for their talk tracks and lets you jump in if things get a little over their heads.
But you can’t listen to every call live, so put some call recording software to work for you. You can listen while you’re in the shower, going for a jog or eating a snack.
Plus, your team can listen to each other’s calls and learn. That kind of transparency is powerful—you can diagnose problems and optimize the best practices for your playbook, and everyone can learn from each other on an ongoing basis.
Call recording is a powerful training tool and the best way to keep your finger on the pulse of reps skills, customer sentiment, and talk tracks.
11. Do a lot of role-play sessions
And I mean a lot. Role play is great for training up a team and building confidence. I often role play topics such as qualification, appointment setting, objection handling and discovery. Everyone involved learns from each other while practicing in a safe space.
These sessions don’t have to be very long, either. Even just 5–10 minutes can make a big difference. A new sales team should spend time role playing daily—especially when working from home. A formal role-play session every other week is a great way to reinforce how important it is to keep skills sharp and refined.
12. Manage for process compliance
Don’t leave room for reps to go their own way—this isn’t the time for a free-for-all. You need everyone sticking to the same processes and using the same cadences and sales methodology.
That’s the only way you’ll be able to measure and improve with consistency and certainty. With everyone working from home, you have to go the extra mile to avoid confusion and inefficiency. Expect your reps to follow the playbook, leverage the sales tools and align to your process and hold them accountable to do so.
13. Hire the right people
I can’t emphasize this enough: hire well. You always want to have a good team, but in a remote context, you really need to have people you can trust, people who will hustle independently and communicate well. You need people with plenty of grit and drive.
If you can’t trust someone, you have bigger problems than just remote work. But if you just doubt their skill, work with them until you’re certain that they can improve—or that they can’t. If you think they might not be pulling their weight, increase your oversight of that person so that you can judge fairly and accurately.
Above all: Hire a team of professionals you can trust and hone their productivity, transparency, communication and results. That’s always true, and it’s even more true in a remote situation.
14. Focus on what you know
When you’re managing a remote sales team, there are a lot of unknowns. That means you’ll have to zero-in on what you do know. If you follow my other tips, you should have a solid grasp on:
Know what’s working and what isn’t, and optimize based on that knowledge. Don’t get distracted by what you don’t know—pay attention to what you do know and the rest will become clearer with time.
Managing a remote sales team for the first time can feel impossible, but it’s not
Your sales team isn’t a well-oiled machine yet, and now you have to manage it remotely. That’s okay. It just means things are going to have to be more prescriptive and black-and-white than they would normally be.
Focus on what can be measured and what you know, then be clear and consistent in your communication and expectations. Remember: It will be a work in progress. If something isn’t working, fix it. If something is working, do more of that.
Most of all, lend your team plenty of attention, guidance and coaching. Together you’ll make it work.
More posts on remote leadership
In just five years, she’s helped grow Stripe’s sales team to about 200 folks in the U.S. and 500 globally—that’s bigger than the entire company was when she first came on board.
We all get those terrible sales messages on LinkedIn that sound like they were written by a bot. Well, turns out that’s exactly what’s happening.