Sapling’s first Virtual Company Offsite - here’s what we learned

Sapling held its first virtual company offsite through Zoom break-out rooms last week. While we’ve always operated as a distributed team, historically we had held local company offsites across our different locations.

These always received great feedback, but we knew recent events gave us even more reasons to switch to virtual and bring everyone together. After completing a Virtual Company Offsite, we don’t know what took us so long to give it a try, or if we’ll ever go back to in-person again!

How we learned how to run a Virtual Company Offsite

Like most things we do at Sapling, we’re very much ‘standing on the shoulders of giants’.  Here are three key resources that helped us build a background understanding of virtual offsites.

There is a great HBR article from 2006 that’s stood the test of time - Off-Sites That Work by Bob Frisch and Logan Chandler, however for modern remote and distributed companies, new playbooks are emerging.

Dave Bresci from PagerDuty (that powers their People Ops with Sapling!) wrote Virtual Offsites: A Collaboration Approach for Distributed Teams which provided a great framework for us to use. 

Lastly, Wade Foster - the CEO of Zapier (read their Sapling case study here) - wrote How to Run a Company Retreat for a Remote Team.

The Sapling virtual offsite consisted of two sessions: Leadership offsite (7 people) held on Tuesday from 1pm - 6pm PST Company offsite (40 people) held on Wednesday from 8am - 11am PST. You can find our full agenda as a template here.

Lastly for tooling, we specifically leaned heavily on Zoom, Slack, Sapling, Google Docs and Google Sheets, with screen sharing that allowed our team to co-create quickly and track their thoughts.

Day 1 - The Leadership Offsite
(the warm up)

The leadership offsite focused on a Q1 retrospective, company goal alignment and a candor exercise. We started with a lunch and round table where everyone answered two questions about themselves:

1. What was your biggest influence growing up and why?
2. When was the last time you laughed so hard you were crying and what took you to that point?

There were some incredible personal stories (and great memes) that were shared that brought the team together.

The Q1 retrospective focused on wins and losses in Q1 of 2020 by department, and how that rolled up to our company goals for 2020. 

The candor exercises then focused on two simple questions - I like it when….. I wish you would... which was shared across departments. 

While we did this at a leadership level, we have regularly done this exercise at the team level for recognition and identifying areas we can improve. Here is the Google Form Template you can create a copy of if you’re interested.

Day 2 - The Virtual Company Offsite

The Virtual Company Offsite was held on Wednesday with an agenda focused on building (even) stronger bridges between teams, and connecting individuals across the organization.  

The goal of our offsite was to get 80% of the Sapling team together for a company event, ultimately to build bonds and foster trust among the team and align on our vision.

The agenda for the company offsite that we used was:

1. Kick-Off: 8.00am - 8.20am
2. Session 1: 8.20am - 9.40am - What I need from you (WINFY) exercise by team
3. Break: 9.40am - 10.20am
4. Session 2: 10.20am - 11.10am - Identifying our Emotions
5. Closing: 11.10am - 11.30pm

While historically an offsite is owned by the CEO (or the division head) - we normally share responsibilities across teams to give everyone the opportunity to learn.

With offsites designed to be a safe zone where anyone can share ideas - we only recorded the opening and closing sessions for the few people that couldn’t make it.


The Kick-off session covered three things - a welcome, a walk through agenda, and an icebreaker. We used Zoom to run our offsite, but there are other great tools out there that support the required breakout rooms like BlueJeans.

Sapling’s offsites (physical or virtual) are each centered around one or more of our core values - which we take very seriously (you can find them all on our careers page). 

The two company values that we focused on for this offsite were:

1. Uplift your team
- It’s important for us to maintain a highly collaborative workflow internally. To best support each other across every timezone, each team maintains a shared understanding of each other’s goals and values.

2. Build trust in every interaction - We strive to build trust in every interaction, with our investors, customers, business partners, prospects, and co-workers.

Following a quick overview of the virtual offsite agenda, we used Zoom to get started and break out into random rooms of 5 people each for the icebreaker - Who was your biggest influence growing up and why?


It was our first time using breakout rooms, but it was quite intuitive - the key thing to be aware of is that one person controls the groups, and to over communicate the starting and ending of breakout sessions through the broadcast feature.

Otherwise, people can be caught mid-conversation (which isn’t the best experience while getting to know your peers).

Session 1 - WINFY

Following the opener, the first session we ran was What I Need From You (WINFY). This exercise focuses on helping people working in different functions improve how they ask each other for what they need to be successful.

Building software is a team sport where each function must work together to achieve the company goals. 

For example - our customers can’t be successful (Customer Success team) unless our product is amazing (owned by our Product Team), and our sales development team can’t hit their goals (Sales Team) unless we have a strong brand and leads (Marketing).

At Sapling (a software company) we have many different departments with individual team goals. For the WINFY session, we split into these groups and then each department created a list of three things they needed from each other department to be successful (if they didn’t have an item, they just said thank you). Here is the basic template we used - it’s important to use big fonts so everyone can see clearly on the screen-shares 🤓.

Make sure your breakout rooms are set-up by department - we had to do a bit of shuffling on the fly.


There are two parts to the WINFY exercise:

1. Breaking into groups to prepare the asks for your department
2. Reviewing and answering the asks from the other departments as a team

For the first part of the exercise, each department broke into rooms to discuss and prepare the list of what they need to be successful from each team for 30 minutes.


It’s important that each department has a spokesperson elected (which doesn’t necessarily need to be the department leader) to share their screen with the group, and also present the answers in part three.

Every department lead shared across their list of what they need before breaking out again into department focused rooms for the second part of the exercise.

Most companies say they want an open company culture where everyone feels part of the same campaign, and at Sapling - we’re huge on transparency for the team (which is often reflected in our Glassdoor reviews). Discussing the ‘tough asks’ is something that comes naturally as we have high expectations of each other (and know each of us can get there).


For the second part of the exercise, each department then returned to their room and consolidated the asks that they received from the other teams, discussing the list of what other teams needed from them to be successful. 

Each team had three options for how to reply to each of the asks they received from the other teams:

1. Yes!
2. We will try
3. No (with additional context as to why)

After each department had time to review all of their asks from other departments, we regrouped in the main room and a spokesperson from each team read through each of their team’s asks, replying one by one.

It was a great exercise and highlighted a lot of opportunities across the organization where teams can work better together by understanding what other teams need!

Session 2 - Emotion Identification

After a short break, we then moved to session two of the virtual company offsite - emotion identification.

This exercise focused on illuminating our full self to each other, no matter where we are, and building stronger bonds amongst the team.

In this session, we split the team into randomized Zoom groups who then nominated a leader of the group (who led the share screen) and brainstormed on identifying their emotions:

- Anger (present)
- Fear (future)
- Sadness (past)
- Joy (present and past)
- Excitement (future)
Each team had to put together at least two points for each, and discussion across teams and locations was encouraged. Here is a template you can u

There were a lot of common themes and healthy discussion around the excitement points, focusing on why we were feeling a certain way and what we can do about it.

Closing Session


The closing session covered a recap of the key themes of our offsite, and introduced some new rituals we’ve adopted at Sapling.

We’ve been fans of
15Five’s team, culture, and product for a while, and were recently inspired by a great webinar led by a member of the team, Priscilla Zorrilla - Rituals & Tools of the Trade for Remote Teams.

Three existing rituals we’re proud of at Sapling are: running our company with regular all hands meetings, a strong drum beat of OKRs, and recognition across the org with #wins (we use
heytaco on Slack).

Our #wins slack channel - where team members share recognition of others going above and beyond.


We used our virtual company offsite as a platform to rollout our three new rituals:

1. Gratitude Mondays - 15 min call led by a member of the leadership team. Team joins, breakout rooms split, and each team shares what they are grateful for.

2. Wed Boosts - 30 min call. Shorter format and focused on getting everyone together to 'boost' the mood. This will be department-specific updates or a mini workshop led by a team member.

3. #life on slack - we changed our #random channel to #life, to encourage people to share updates, sites, news, and fun things.



We love feedback at Sapling and constantly seek it from our company events. 

One of our core values is Seek Perpetual Growth and knowing that daily wins and losses are just short term outcomes of the bigger long term goal – improvement.

Following the offsite, we sent out a Google Form to collect feedback from the team about their experience (you can create a copy here). The team’s favorite session was tied between the icebreaker and WINFY.


Planning and running company offsites can be tough, however there is evidently a lot of technology to make things easier. While Sapling is 50 people today, we’re growing rapidly and expect the above playbooks could scale to 100s of people.

We are super proud that many of the companies that we learn from are Sapling customers and use our product to power their People Operations. Thank you to PagerDuty and Zapier for the incredible resources on running virtual offsites, 15Five for empowering our team members from anywhere, and Webflow for helping us share this content with the world.

When we work with our customers, we always encourage them to design employee experience programs that reinforce their unique company values. For Sapling - our first virtual company offsite was a huge success by both uplifting the team and building trust in every interaction through each of the exercises.

The way people connect is changing, and many companies are rapidly shifting to empower their people to work remotely. With that, we expect that virtual company offsites are here to stay and we’re excited to iterate on the process.

In the meantime, we hope this serves as a guide to empower other people leaders to build better companies through their virtual company offsites.

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