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Four tips from the experts to lead your Customer Success team remotely

CS Leadership
#covid19#teamwork

Imagine a world where a quarter of workers don’t go into the office. That reality is closer than we may think says Kate Lister, President of Global Workplace Analytics.

“Our best estimate is that 25-30% of the workforce will be working from home multiple days a week by the end of 2021.”

- Kate Lister, President of Global Workplace Analytics

For Customer Success teams making the cube-to-kitchen-table migration, there are some questions to answer. How do you share customer insights? How do you maintain a company culture? How do you share knowledge? 

Leading a dispersed Customer Success team isn’t always easy. We talked to top CSMs and CS leaders at companies like Close, Customer.io, and Prezly and got their tips for managing remote Customer Success teams. These are their strategies for making remote work ideal work.

Top Customer Success managers (CSMs) and leaders from successful SaaS companies are navigating the challenges of working from home. Here are their strategies:

  • Be transparent. Transparent communications maintain momentum

  • Host virtual team get-togethers. Virtual get-togethers promote trust and protect productivity

  • Have structured check-ins. Check-ins keep your team motivated and on track

  • Set up a peer-to-peer learning network. Knowledge sharing accelerates team growth

Maintain momentum with transparent communications

It all boils down to prioritizing transparency in every communication channel you use. For example, share uncensored customer feedback with the entire company (not just the team).

Natalie Onions leads a team across three U.S. time zones

“I learned pretty early on that it’s not my call to decide which customer insight is valuable to the rest of the company,” says Natalie Onions, Customer Success Team Lead at Customer.io. “So share everything, and let people pick out what they know to be valuable for them.”

Onions shares that data through several platforms:

  • A dedicated channel for use cases and customer stories

  • Vitally for customer files and notes (plus a link to those Vitally pages on Slack)

  • Public tracking sheets shared with the whole company

“Our public tracking sheets also assign tasks to individual CSMs and give credit to the person responsible for meeting a goal,” Onions says. “This is a great way for a remote team to communicate with the whole company and it opens the floor for people on other teams to reach out with praise or if needed, support.”

The Customer Success team at Close also uses dedicated Slack team channels to share customer data. Liz Stephany, Director of Customer Success at Close, says that’s how they make sure everyone has access to important customer information. Specifically, they use Slack to share:

  • Monthly recurring revenue (MRR)

  • Customer upgrades

  • Customer cancellation updates

  • Net Promoter Scores (NPS)

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Transparency in communication needs to be a team goal, not just the rule for managers, says Jacob. “We encourage everyone to write on a team Slack channel instead of direct messages,” she explains. “This way, we ensure that we are sharing knowledge with everyone on the team. You get a faster response, and this helps us keep momentum.”

When you have CSMs on three continents (like Customer.io does) you don’t get far without good communication. So setting up the right communication tools should be the first order of business.

“If moving remote is a sudden change in your work setup, the main worry will likely be how you’ll work together when you’re not all in the same office,” says Onions. “By getting up and running with things like Zoom and Slack, you’ll be able to ease that worry and create a sense of normalcy.”

Raquel Jacob is a Customer Success Manager at Prezly

TL;DR Here’s how to make sure your communications are transparent

  • Use public Slack channels for questions instead of direct messages

  • Share important customer data and stories on company-wide Slack channels

  • Don’t censor yourself—let other teams decide what’s important to them

  • Automate the sharing of customer notes with a SaaS tool

  • Don’t wait to set up communication tools if you’ve shifted to remote work—it should be the first thing you do!

Promote trust and protect productivity with virtual get-togethers

When your CSMs work in the same location, they get to know each other personally through breakroom chats and organized company functions. That’s not easy when your team never gathers in person.

But does it really matter if your CSMs gel personally? You bet it does. A Gallup poll showed that as team engagement improves, productivity goes up, and mistakes go down. A team that plays together wins together.

“Working remotely means employees don’t build instant rapport with their colleagues,” says Klarissa Djajalie, a Customer Marketing Specialist at Prezly. “So having non-work conversations helps teams get to know each other and bond over shared interests.”

The Close Customer Success team has members in three U.S. time zones, and the company has employees in 12 different countries. But they still manage a regular schedule of virtual get-togethers, including:

  • Team game nights using tools like

  • Social hours every two weeks for informal chats

  • 1-on-1s with different coworkers after each weekly all-hands meeting

Customer.io has a team across three U.S. time zones

When do you start fostering engagement? As soon as a new employee starts, says Natalie Onions.

“I would recommend having someone on your team become the new employee’s ‘buddy,’” she says. “Having someone to chat with or check in with can be really helpful in those early weeks.”

Onions also says that creating connections needs to be intentionally managed like any other part of work. “As a manager, I feel it’s my duty to lead by example here.” She encourages her team to get involved in company-wide activities and makes it a point to introduce their CSMs to as many people as possible.

Although real-time hangouts can help bring a team together, Liz Stephany says that async communications can also help bridge the gap between CSMs. Her team posts often on their internal special-interest Slack channels like #shenanigans, #dogs-of-close, and even a #woodworking channel. “The variety of experience and diversity of thought is such a valuable part of our team experience,” she says.

TL;DR Here’s how to use real-time and async communication to bring your team together:

  • Organize virtual game nights and happy hours

  • Schedule virtual “water cooler” chats between different employees

  • Set new hires up with an onboarding buddy

  • Create special-interest Slack channels

Keep your team on track with structured check-ins

Managing a team of CSMs remotely means you miss out on subjective signs of overwork or productivity bottlenecks.

“When you’re not physically together as a team, you can’t see when someone has piles of work on their desk or see the look on their face through the day,” says Natalie Onions of Customer.io.

How do you make up for that lack of in-person assessment? By tracking their workload and holding abundant check-ins with your team. For example, Onions keeps a tracking sheet and data report on how revenue, as a measure of workload, is distributed across the team. She then holds weekly 1-on-1 meetings and a weekly team call, and leaves two blocks of time open every week to field questions or for a friendly hello.

When things get busy, it’s easy to let these meetings slip off your calendar. Avoid that if you can. “Consistency is key here, so the CSMs know their voice will be heard,” says Onions.

Prezly takes a “results not hours” approach to keeping their Customer Success team on track. They use their Monday stand-up calls to review work from the previous week and define goals for the following week. Then, everything gets put into Asana so the whole team can follow along, no matter when they work. For bigger goals, they keep well-defined company and team objectives and key results (OKRs) for the year and track them monthly.

Those check-ins are also an excellent chance to celebrate your team’s wins. During her weekly stand-up, Onions calls out the team’s progress to make sure everyone is aware of the positive impact they’re having on the entire company. “Making them feel like an integral part of the bigger picture definitely helps to keep CSMs motivated,” she says.

TL;DR Here’s how to keep your team focused with a variety of group and individual check-ins:

  • Set weekly 1-on-1s and team calls

  • Keep all goals in a project management app that’s available to the whole team

  • Create yearly OKRs and track them monthly

  • Celebrate wins in every meeting

  • Prioritize all of these check-ins on your calendar

Accelerate team growth with intentional peer learning

In an office, you can just poke your head into a coworker’s cube to ask how they did something. Or you can sit in a conference room and collaborate over a new workflow. But when everyone is working in the silo of their own home, those countless micro-learning moments never happen.

Liz Stephany is the Director of Customer Success at Close

And CSMs are continually learning on the job: which customer behaviors indicate churn; how best to engage a troubled account. If those instances aren’t shared, each CSM is forced to create their own solutions by trial and error.

Liz Stephany of Close places a premium on breaking down knowledge silos. Here are a few of the steps she takes to make sure everyone benefits from one another’s insight:

  • A portion of team meetings are used for “knowledge bombs,” where CSMs explain how they solved a customer problem or workflow issue.

  • A weekly customer or trial is spotlighted: the team dissects a single customer and talk about what the company does, how they found Close, what delights/frustrates them, etc.

  • Quarterly customer interviews are held on Zoom with CSMs joining to hear the customer’s thoughts live.

For commonly asked questions, Prezly uses Notion as an internal company handbook. That makes it easy for everyone to find answers to commonly asked questions. “Oftentimes, it’s quite easy to feel lost when you’re trying to find a solution for a specific situation,” says Klarissa Djajalie of Prezly. “Having a handbook or guide can really get team members up to speed.”

Djajalie also suggests using an app called Discourse for lengthy discussions. Slack can be an excellent option for a quick Q&A, but it’s not well suited to discussing a project between several team members. Djajalie says they like Discourse because it encourages more in-depth conversations.

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Turn team success into customer success

Close, Customer.io, and Prezly are great examples of how a Customer Success team can work remotely and still communicate well, learn constantly, and even have fun together. It may take a little more intention to get there for a dispersed team, but the payoff is happy employees and delighted customers.

Jamie Davidson
Jamie DavidsonCEO @Vitally

Jamie Davidson is the CEO and founder of Vitally. Formally CTO and Chief Customer Officer @Pathgather, he often treads the line between Product and Customer Success, leveraging one to enhance the other.