The WIN: The Weekly Ritual That Keeps HubSpot Connected at Scale

How a little internal newsletter has supported HubSpot culture through a decade of change.

In January 2010, I had the great good fortune to join HubSpot, which was then a little-known tech company still in startup mode. When I joined, there were only about 60 of us at the company, all happily sitting together in rented office space. Back then, it was pretty easy to feel like you knew everyone at HubSpot and what they were up to.

But we were growing incredibly fast. By the time September rolled around, we’d nearly doubled the size of our team, and we were about to move into a much bigger office a few blocks down the street. Instead of being all seated together, we’d be split up into a bunch of different rooms, with hallways and meeting rooms and closed doors in between.

Some of us were getting a little concerned. We’d always had a strong culture at HubSpot, and we all dearly wanted to keep what was special about our company alive. But how could we maintain that small company feel — where we felt like we knew everybody, supported each other, and all pulled together toward a shared goal — when we were growing so fast? How would we still know each other’s faces and names if we weren’t all sitting together in the same room? How could we make sure every new hire got a sense of what made our culture so special, and encourage them to join in?

That’s when we decided to start an internal newsletter. No, it wasn’t exactly a radical idea. Lots of companies have internal newsletters that nobody reads. We wanted ours to be different. Because every company newsletter reflects and enshrines its organization’s values and culture, whether it means to or not. Stuffy and hierarchical? Your company newsletter probably reflects that. Open, exciting, and fun? Same theory applies. So we knew that a company with as remarkable and beloved a culture as HubSpot would need to have a remarkable and beloved internal newsletter, too.

Simplicity WINs

These days, the WIN (that stands for Weekly Internal Newsletter, of course) is a very simple, stripped down email. In fact, as the editor of the WIN I can tell you it only takes a couple of hours each week to compile. But when we started out, it used to include all sorts of things — a list of new hires with links to their profiles, birthdays, promotions, HubSpotiversaries (marking the date you were hired each year), local events, and more. Over the years, most of that has fallen away, and that’s by design.

The list of new hires each month quickly became very long. Ditto for the number of people celebrating their anniversaries as HubSpotters, much as we loved marking that date. People just weren’t reading those sections anymore, we discovered. And as we started opening more global offices, it became more and more important to highlight events that were of interest to people all over the world, not just events that were relevant to our global headquarters in the US.

What’s left is what’s always made the WIN what it is: a lively, inspiring snapshot of the stories and people who make HubSpot such a warm, weird, and worthwhile place to work. It’s a weekly reminder that even if we’re a lot bigger these days, spread out all over the globe, we’re still all in it together. With the WIN, we can all still sit in the same virtual room. Everybody’s invited, everybody’s included, everybody belongs.

The WIN now consists of just two sections: stories and photos. The stories are just a few lines of enticing copy to intrigue the reader enough to click through on the link. Most of the links go to a freshly minted page on our internal wiki.

The Stories

Each story is written in a lighthearted, conversational tone that reflects the company’s personality and internal voice. The copywriting in the WIN subtly reinforces the message that we’re all in this together, that everyone has a remarkable story to tell, and that we’re better and stronger the more we help each other out. It also tries to subtly promote the HubSpot style of writing, so that our brand voice and tone infuses the whole team.

But more than anything, the WIN is just meant to be fun to read. Here are a few examples from some recent editions:

The Photos

The photos — which are really why everybody reads the WIN in the first place, let’s be honest — are of HubSpotters everywhere, doing what they do. Oh, and often, their pets.

In truth, this may be one of the reasons people love reading The WIN. Who doesn’t love looking at pictures of their friends, looking happy, and their friends’ pets, looking cute? Honestly, now.

As you can see above, there’s also always a little snippet of “alt text” hiding behind every image, which only appears when you hover your mouse over the picture for a second or two. Usually, the alt text is just a fun little caption, but on special occasions it’ll take on a life of its own.

Sometimes you’ll hover over each image in order, and find yourself reading the lyrics to a song (generally these are silly parody lyrics, as above, when each image in turn revealed a line of a slightly updated holiday song), or an improvised poem about life in our world that week. It’s all usually pretty silly. Which is really the point.

Everyone’s Invited

Most company newsletters solicit material for each issue from managers and executives only. Sometimes it’s just all about HR. That’s the standard model for an internal company newsletter: Management decides what gets included, and the employees are to (one hopes) dutifully read it each week.

The WIN is different. Every Wednesday, an email goes out to the whole company, asking for pictures and links for that week’s WIN. Absolutely everybody at the company is invited and encouraged to send in pictures — of themselves, their coworkers, their teams, their outings, their deskspace, their houseplants, their cats — and links, usually to something on our internal wiki — about what’s going on in their part of the world. Cultural events, book clubs, new office space, a team project kickoff, a project review. What you learned as an intern. What being a parent at work has taught you.

There’s a fairly arbitrary limit of nine stories per issue, so it’s the editor’s job to curate submissions and ensure there’s a good balance of content that’s of interest to all. The choice of content is vitally important to conveying that message of inclusion and support for every HubSpotter, everywhere — if every story is about the Cambridge office, for instance, how does that make people in other offices feel? If every picture shows people only from a certain team, demographic, or region, what does that say?

That’s why absolutely everybody’s invited and encouraged to submit to the WIN. The mix of links and pictures every week needs to be a true reflection of who we are, how we live, and what’s important to us.

And because everyone at HubSpot submits to the WIN, it’s always had a very open, fun, grassroots feeling. Executives and managers will occasionally submit things as well, but for the most part it’s really always been the people’s newsletter.

It’s All About HEART

When we published the HubSpot Culture Code in 2012, we started expressing our company values in the acronym HEART — Humble, Empathetic, Adaptable, Remarkable, Transparent — it was only a year or two after the WIN got its start. And our little newsletter has always served as an amplifier of those values, and we hope it always will.

Humble: The WIN reinforces the message every week that we’re all in this together. The fact that it’s open to submissions from any HubSpotter, anywhere in the company or their tenure with us, is clearly stated on the call for submissions each week. And the mix of content included is carefully curated to send this message, too. Stories and pictures from every department, every office, every walk of life are included, to keep people aligned on and in tune with who we are in all our various ways.

Empathetic: As our company grows, it can be all too easy to get fractured and siloed into our various teams, offices, and projects. Sharing stories and ideas from every corner of HubSpot helps us all gain insight into the challenges each team faces and the successes we’ve had, and to think proactively about how we can better support each other and understand each other’s lives.

Adaptable: We’ve grown and changed as a company in some significant ways over the last ten years. From 60 to 3,000+ employees, one to nine offices, from small scrappy startup to publicly traded company… But through it all, the WIN has kept arriving in our inboxes, week after week. We hear from readers all the time that the Wednesday call for submissions is their favorite email of the week, and that reading the WIN every Friday is a cherished ritual for them. We think it’s much easier to adapt to constant change when there’s something at your core that everyone can rely on.

Remarkable: It’s pretty unusual to have a company newsletter that’s not just a corporate mouthpiece for leadership, HR, or anyone else. The WIN is truly a grassroots publication, focused on the regular employee and what their life is like. It’s a weird, wild, warm, and wonderful thing, just like the typical HubSpotter.

Transparent: Because we value transparency as a company so highly, we share a ton of information on our internal wiki. But that can be a double-edged sword. It puts the burden of keeping up with this firehose of information on the employee. Offering people a quick, skimmable, curated set of links ensures that everyone’s always on the same page. Most HubSpotters don’t have time to read every little thing on the wiki. But with the WIN, they can be sure they’re not missing a beat.

But what it really comes down to is how people at HubSpot feel about reading The WIN. Is it really the cultural touchstone we all think it is?

Here’s what some HubSpotters have to say:

“When I’m reading the WIN, I feel like HubSpot is an old friend who’s sending a letter just to me. At our size, that’s really special, I think.”

Hannah Fleishman, Senior Manager, Employer Brand, Cambridge

“Once a week, I get to celebrate and enjoy the WIN with HubSpotters from around the world. It makes me appreciate our diversity and the feeling of belonging to an extremely inclusive community. As a global company, it’s easy to work in silos or be absorbed into the daily grind. When I read the WIN, I’m reminded of our collective goal to help customers and each other grow better.”

Mariel Argonza, Customer Success Trainer, APAC, Singapore

“My favorite part of the WIN has to be the photos — it’s the people at HubSpot that make all the difference. At HubSpot it’s not just about work but a team of talented people working happily toward a common goal. I find The WIN an amazing way to stay connected with other offices as we continue to expand. I’m so glad that every HubSpotter can contribute to it in one way or another.”

Derek Pun, Manager, APAC Customer Onboarding Team, Singapore

“Reading the WIN takes me back to how I felt when I first joined the company; excited about things to come and eager to keep learning new things. But more than that, it’s a space where we can share our whole selves. That’s crucial when we want to remain a company where empathy for others and an inclusive environment is a top priority.”

Nicole Zwaaneveld, Product Events & Employee Experience Coordinator, Dublin

“The WIN keeps us connected, no matter how big we grow. It’s always the week’s most captivating reading. Seeing pictures of my team, my kiddo, or even my pup makes me personally feel included and special. The WIN honestly feels like a part of me.”

Jill Fratianne, Channel Account Manager, Remote

Everybody WINs

Since it started, the WIN has been a powerful part of the culture at HubSpot. It reminds us every week who we are, who we’re becoming, and who we hope we will be. Past employees of HubSpot tell us time and time again that one of the things they miss most about working at HubSpot is getting the WIN. It’s a good reminder that even something as simple as an internal company newsletter can have a remarkable impact and lasting legacy.