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How To Build Remote Team Engagement: Real-Life Tips From Shepherd’s Head of People and Culture

Our Head of People and Culture shares tried-and-tested tips on how to build engagement within remote teams.
Back in 2020, Shepherd was only made up of two guys. Today, our team has grown to 117. And we’re still growing.

Like many remote-first companies, scaling team culture was a huge challenge for us. One of the best decisions we’ve ever made was to find a culture leader within the company — someone to champion our values and keep our distributed team engaged. We found an awesome one in Pammy.

Initially in charge of HR, Pammy now heads our People and Culture Team and has played a vital part in keeping our entire organization engaged, motivated, and productive.

In this article, Pammy shares the benefits of team engagement and how we overcame challenges— plus proven tips on building remote workplace culture. If you’re struggling to scale team culture like we did in our early days, get comfy and read on:

What does the Head of People and Culture do?

A photo of Pammy with some of our Shepherd team members
Pammy (top left) with some of our Shepherd team members

First, a little background on Pammy:

She’s a seasoned pro with more than a decade of experience in corporate training. Before joining Shepherd, she conducted leadership and communications training for entry-level employees and executives alike.

As our main HR person, Pammy showed a lot of initiative in keeping our remote team engaged. She planned events, greeted everyone on their birthdays, and essentially took ownership of team engagement on Slack.

Today, Pammy is in charge of 3 main things at Shepherd:

  • Creating company policies - Policies are the backbone of any growing company. We use them to standardize our processes, stay organized, and help team members understand their roles. Pammy did a good job of creating and implementing these policies across our organization.
  • Providing training and growth opportunities to team members - Assigning this task to Pammy was a no-brainer, given her 10+ years of experience in training. She’s responsible for our team’s overall upskilling efforts.
  • Creating fun engagement activities - Lastly, Pammy and her team are responsible for creating engagement activities like our regular Friday catch-ups and in-person townhalls.

If you see a team member showing initiative like Pammy, empower them. They might just be the culture leaders you’re looking for.

Related: Leadership roles you can outsource to remote Filipino employees

Why is it important for remote-first companies to build a strong team culture?

The Shepherd team during one of our townhalls. It was the first time the team met our co-founder, Marshall.

Pammy is passionate about building genuine relationships. For her, team engagement is more than just scheduling Zoom calls to keep people entertained — it’s one of the building blocks of a successful remote company.

She breaks down the importance of remote team engagement into three major points:

It motivates people to stay in your company

According to Pammy, getting your employees to emotionally invest in your company is a great way to boost retention.

"Working in corporate for more than a decade, I've realized that people eventually will stop working for the money and will start hanging on to what's making them come to work everyday," shares Pammy.

So what motivates people to come to work beyond monetary compensation?

Pammy says it’s all about the relationships that team members make along the way. “When there's nothing there for them in that company, it's easier to resign and go. But if you have a lot of emotional investment with the people that you work with, it becomes much more challenging to leave the company.”

Culture helps you gain buy-in from your team

Getting your first few employees to buy into your vision is a huge ask, especially if you’re still figuring things out. Pammy recalls how things were when Shepherd was just starting:

  • We didn’t have a lot of processes in place yet
  • The team was overwhelmed with projects —
  • — and there were lots of clients to attend to

Despite all these growing pains, people stayed — and we were able to grow our team to more than 100 members in under two years. Pammy attributes this success to team engagement. By continuously depositing into our team’s emotional bank accounts, we got them to buy into our vision and stay, even when things were tough.

For Pammy, getting a team to that kind of level of engagement is critical to business success.

It keeps your employees accountable and productive

Lastly, team culture drives productivity. Pammy shares:

"If you have a company where you empower people and let them know that their hard work has a direct impact on the company's success, people will care more."

Engaged team members, according to Pammy, are more likely to show up and take ownership of their work. They carry their own weight and make sure that the project is successful.

Related: 9 ways to retain talent — according to actual remote employees

Tried-and-tested engagement activities for remote teams

Shepherd's leadership team during our year end party

Pammy admits that getting everyone to participate in engagement activities is a major challenge for remote teams. It’s easy when you’re on the same floor or building, but it’s a different ball game when everyone’s all over the globe.

To make sure that everyone has an opportunity to get to know each other, she and her team put in extra effort to plan fun and purposeful activities throughout the year. These activities range from simple Slack messages to big annual team-building trips — and they’ve been crucial in keeping engagement high across our organization.

Here’s a quick look at some of Pammy’s tried-and-tested engagement strategies:

Daily activities

Every Wednesday, Pammy sends out wellness tips like these on Slack and Gmail

Pammy and her team send out “engagement blasts” like tips, reminders, and check-in prompts all throughout the week. These messages are usually delivered with simple graphics via Slack and Gmail.

To keep things interesting, Pammy follows a different theme each day:

  • Monday HR Tips - Mondays are for reminders and best practices from HR. This is a great way to share company policies and to remind employees of the environment that we wanna promote within the team
  • Smart Shepherd Tuesday - On Tuesdays, they send tips on how to save, invest, and spend money wisely.
  • Wellness Wednesday - These blasts are all about health, wellness, and self-care. Pammy and her team share tips on mental health, stress reduction, and physical fitness.
  • Thursday Watch and Learn - Thursdays are dedicated to learning something new. The team sends out short clips that feature interesting facts, new skills, or cool trivia.
  • Feel Good Friday - Feel-good quotes to cap the week off!

  • A little goes a long way. Schedule simple check-in prompts to touch base with your team.
  • Use automation to make your job easier. You can schedule these messages on Slack, Gmail, and project management apps like Basecamp.

Weekly activities

The People and Culture team also hosts a company-wide hangout session on Zoom called Fridays At Shepherd. It’s where people shoot the breeze and catch up before winding down for the weekend.

Pammy also prepares fun games, customized Zoom backgrounds, quizzes, and themed Friday nights for a more exciting experience. Prizes and perks await winning participants!


Give your team something to look forward to at the end of each week. Incentivize attendance to get everyone to participate.

Monthly Activities

Internal newsletter

Once a month, the People and Culture team sends out an internal newsletter that recaps the month’s highlights. This newsletter usually includes:

  • photos from the past month’s Friday activities
  • top performers
  • announcements
  • birthday celebrants
  • contributed articles and artwork —
  • — and a lot of other cool stuff

Monthly themes

Just like the daily engagement blasts, the team follows a fun theme each month. For example, all December activities are holiday-themed: Christmas Zoom backgrounds, sharing Christmas wishlists, a company-wide Secret Santa event, and a virtual caroling contest.

  • Invest in internal branding. This helps you communicate your core values while making your employees feel like they’re part of something bigger.
  • Following a monthly theme makes it easier for the engagement team to create content and plan activities.

Annual and Semi-Annual Events

The Shepherd team out and about playing water sports during our annual team building and retreat

Once a year, the team meets up for an on-site team-building activity. Since we’ve got limited opportunities to interact with each other in person, Pammy and her team go all-out to make the activity memorable for everyone. This year’s team-building activity involved an obstacle course, mini-ziplines, and a giant volleyball game. It was pretty epic.

Year-end party

Parties are the perfect way to cap off the year. It’s a special time when people get to dress up, receive awards, and showcase their talents. This year, Pammy and her team threw a fabulous gala night that everyone enjoyed.

Semi-annual employee satisfaction survey

Twice a year, Pammy sends out an employee satisfaction survey to get feedback from our team. This gives her a good idea of what activities to continue, stop, or start. She also sends out a feedback form after a major event, like our team-building activity.

  • Plan in-person meetups at least once a year. Real-life interactions will only make your team stronger. They’re more memorable, too.
  • Listen to your team. Encourage them to give honest feedback about your engagement activities and implement accordingly.

What are the best tools for remote team engagement?

As far as tools go, Pammy believes in using the resources you have on hand. “Be creative! There's no limit to what you can do if you’re creative about it.”

Here are some of the tools she uses to make sure that her engagement activities are a success:


Pammy loves using Zoom for engagement activities. She says she finds it much easier to navigate than MS Teams. Here are some of her favorite features:

  • Breakout rooms to send people into smaller groups. It’s a great way for everyone to interact and get to know each other at a more granular level.
  • The “Annotate” feature to create notes on her screen
  • Whiteboard feature for games like online Pictionary

Google Jamboard

Google Jamboard is mostly used by students, but it’s also a huge hit for Pammy. They use it for Friday night games that involve writing or drawing. Bonus: it’s also a great platform to visually brainstorm ideas!


If you’ve got a few extra bucks to spend on engagement, Pammy recommends Kahoot. She uses it for interactive games, announcements, polls, and quizzes.

Online buzzers and games

A great online buzzer is your best friend when hosting competitive multiplayer games and quizzes.

As for games, Pammy says that there are endless options for online games available. The key is choosing one that best fits your overall theme or activity.

Learn more: 7 Fun virtual Friday activities

Google Forms

Google Forms is another underrated engagement tool that you can take advantage of. Pammy says it’s great for gathering data, creating polls, and planning big events.

Pammy’s best practices on remote team culture and engagement

A happy team gathers around a laptop

We asked Pammy if she’s got any secret sauce when it comes to developing remote workplace culture and engagement. Here are her best nuggets of wisdom:

Change your mindset

“I understand why it would be a challenge to engage people in a remote setting but I think having the right mindset definitely helps.”

Instead of seeing remote work as a constraint, Pammy says that viewing it as an opportunity to experiment can make engagement easier. It can be your testing ground for new ideas. You can use tech to bring your team together. You can share inside jokes on chat and build a remote culture even when you’re not physically together. The options are endless! The key is to shift your mindset and enjoy the process.

Know your audience

Pammy says that knowing your demographic helps you pick the right activities and engagement channels.

In Shepherd’s case, she observed that younger team members loved turning on videos during engagement activities. They also seemed to enjoy using voice calls and Slack huddles. Millennials, on the other hand, preferred talking through chat and email.

This information helped Pammy and her team plan activities that fit the preferences of various age groups.

Stay organized but be flexible to change

Shepherd’s People and Culture team don’t do things on the fly. Instead of just shooting off the hip, they stay organized by plotting activities at least a year ahead. They also take advantage of automation tools and workflows to schedule recurring weekly events.

But staying organized doesn’t mean you can’t be flexible to change. Sometimes your ideas work, sometimes they don’t. Pammy says that being open to feedback — and adjusting your plans accordingly— is key to creating successful engagement activities.

Bottomline: be organized, but stay agile.

Keep up with the trends and themes

Speaking of staying agile, Pammy says that creating activities and engagement content based on something recent and viral is a surefire way to grab your team’s attention.

Based on her experience, it’s easier to get a reaction out of your team if you plan something that’s easy to recall or relate to. This increases the chances of participation and, in turn, boosts your chances of success.

For example, at the height of the pandemic, a lot of remote teams played the viral game Among Us during their hangout sessions. Others recreated popular social media challenges and incorporated them into their team activities. Incorporate activities like these into your own schedule to get everyone to participate.

You can also plan around monthly themes. Pammy and her team, for example, do lots of summer-themed activities around April-May and create spooky content all throughout October-November.

Consistency is key!

For Pammy, team engagement is all about consistency. It’s something that you have to do with purpose and intention.

“Make engagement a habit. Gain momentum by being a constant presence in your team’s online lives.”

Pammy says that when your team starts expecting activities from you, it’s easier to get them to participate. Give them something to look forward to — whether it’s prizes, quality time with office friends, or bragging rights after a friendly competition.

Doing these activities on a consistent schedule also helps your team to plan their days ahead. Lastly, having a routine makes engagement activities scalable. Just like any other aspect of business, having an engagement routine allows you to build processes that will help you scale remote team culture as you expand.

Scale remote team culture like a pro

Scaling remote culture takes a village. And to motivate that village, you'll need a leader. Someone who:

  • embodies your company values
  • is passionate about building genuine relationships
  • can balance process with spontaneity
  • is full of great ideas and knows how to execute them

You need someone like Pammy. If you see a team member showing the same drive — empower them. Provide them with room to grow and the resources to do a great job. That's the real key to scaling remote team culture.

FAQs about remote workplace culture and engagement

Why is team engagement important?

Team engagement is important because it helps you build strong, motivated teams. It also boosts employee retention, helps you gain buy-in from your team, and keeps everyone productive.

How do you build team engagement virtually?

There are lots of ways to build team engagement virtually. You can:

  • send simple check-in messages on Slack
  • plan weekly activities like games and virtual hangout sessions
  • create monthly events based on fun themes
  • send out a company newsletter
  • plan in-person meetups
How does remote work affect culture?

Remote work affects how employees interact, collaborate, and make decisions. Remote teams have to create processes to make communication smooth and efficient. Since there are limited opportunities to interact in-person, remote teams also have to put in extra effort to build team culture and engagement.

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