TacoBytes: Celebrating the Days That Matter – Introducing HeyTaco Milestones

In this episode of TacoBytes, Una and Doug take you behind the scenes of HeyTaco’s newest feature: Milestones—a fun and effortless way to celebrate your team’s birthdays and work anniversaries, right in Slack.

They explore why recognition on these personal milestones matters more than we often admit, how it used to be done (balloons, cakes, and jackets, anyone?), and how HeyTaco is making these celebrations feel authentic—even when they’re automated.

You’ll hear how customer stories shaped the feature, why it’s more than just a calendar reminder, and how Milestones brings back the joy of being seen—without the spreadsheet chaos or 5:45 AM Slack messages.

Whether you’re part of a remote team or managing culture at scale, this is a fun and thoughtful conversation about celebrating people, not just performance.

👉 Learn more about Milestones and how you can use it to make your team feel valued on the days that matter most.

Key Takeaways

• Why birthdays and work anniversaries matter: These “non-performance” moments are key to making people feel seen and valued.
• The problem with current solutions: Manual reminders and HR-managed celebrations don’t scale—and can feel impersonal.
• HeyTaco’s solution: Milestones lets teammates be recognized automatically, in public or private channels, while keeping the celebration personal.
• The real magic: It’s not just about the automation—it’s about creating a moment that invites everyone to join in with tacos, emojis, and appreciation.
• Recognition is about being seen: Just like a college athlete’s jacket or a 10-year trip to Jamaica, the memories stick when recognition feels earned and visible.
  
  
  

Resources & Links

• Learn more about HeyTaco Milestones
• Try Milestones free in your Slack workspace via the Admin → Milestones tab
• Explore how HeyTaco can help build a culture of gratitude → heytaco.com
  
  
  

Quotes to Remember

• “Recognition isn’t just about big wins. It’s about being seen—and being seen with that jacket on.” – Doug
• “We used to say: automated = bad. But Milestones changed our mind.” – Una

Transcript

Una Japundza (00:01.597)
Hey, everyone. Welcome to the Amazing Teams TacoBytes episode, where Doug and I chat about all things gratitude, Hey Taco, and making work better. Today, we have a special episode where we're going to talk about our newest Hey Taco feature called Milestones. Doug, can you shed some light on this feature? What is Milestones? Why is it called Milestones?

Doug Dosberg (00:24.982)
Of course. Yeah. So In our quest at being the best at peer recognition on this planet, the one thing that we kind of, I guess, overlooked has been celebrating and recognizing people on their special days. And those special days would be their birthdays and their work anniversaries. And so we've taken both of those special dates and we've bundled them up into a new feature for Hey Taco called

Milestones. how was that?

Una Japundza (00:56.669)
Why do think, that's great, but Why do think people care about being recognized on their birthdays and work anniversaries? What's in the human nature that makes that so important?

Doug Dosberg (01:08.236)
Well, mean, most people I think care. There are gonna be some people that are gonna tell you they don't care, but I think most people do care. You know, It's being somewhere for a year, two years, three years, 10 years, that's pretty special, right? Not many people spend a decade working for a company. And the cool thing with Hey Taco is it kind of makes it a fun celebration rather than just an HR duty or, you know,

something that is a calendar reminder, people can now use Hey Taco to let people know that, this is my 10th year at the company. And people can kind of chime in and it creates a bigger moment for people.

Una Japundza (01:54.877)
We didn't talk about this beforehand, but the question came to mind that I have to ask you, how did you use to celebrate birthdays and work anniversaries when you were at the Motley Fool?

Doug Dosberg (02:04.982)
Yeah, so it was, came out of HR and we actually did a really good job. You'd get balloons. Sometimes it was like a big number balloon or it was, you if you're celebrating 10 years or 20 years, you'd get 20 balloons. And birthdays, trying to remember birthdays, birthdays were grouped together. And what we did is we had in the break area, we had cakes delivered.

and it was to recognize and celebrate people for having a birthday within a certain timeframe, usually a month, that tended to be the timeframe that we chose. So birthdays, you're a grouped with other people, we didn't call out people specifically for their birthday. And then, yeah, the work anniversaries, those were kind of personal, tailored to you, and then each year you got a gift and it was based on.

your tenure at the company.

Una Japundza (03:04.114)
Do you remember a gift that you enjoyed, that you can still remember?

Doug Dosberg (03:09.452)
Yeah, I think one of the ones that I really liked was, I think it was maybe my 10th year work-aversary at the Motley Fool, and I got a trip to go somewhere, and where did I go? went, I wanna say, I think we went to, I wanna say I went to Jamaica with my wife. Now, I could be confusing that with.

was a different trip, but I think we went somewhere pretty far and had a great time and the company covered the cost of our flight and our stay. So it was pretty epic.

Una Japundza (03:46.845)
That is quite a 10 year anniversary gift. mean, Your 10 year anniversary with Hey Taco is coming up and the beauty is you get to design your own anniversary gift. Who knows what you're going to pick up? Maybe another trip or something like that. You know, this is not the same, when I played volleyball in college, every single year, our university would give a token of recognition to every student athlete after you make it through the year.

Doug Dosberg (03:54.818)
Yeah.

Doug Dosberg (04:04.462)
Sounds like fun.

Una Japundza (04:16.617)
So the first year it might've been like a really fancy mug or something like that. Don't hold me to it, I forgot. But I remember when you were a junior, when you were finishing your junior year, everyone got this really cool jacket with the logo. And you knew when you saw someone on campus that they're now a senior, right? Because they just got that jacket at the end of the junior year and everyone couldn't wait to get that jacket. It was more important than the senior gift, which was like a watch.

but people love the jacket. So it's a little bit different, but it still kind of marks the milestone of like, I guess a work anniversary at a university, four years, four gifts, you made it through the year, here's something fun. I don't think I have the jacket anymore, but I know exactly what it looks like.

Doug Dosberg (04:54.542)
Yeah, and looking at my notes here, I see a comment, know, recognition isn't just about big wins. It's about being seen and it's about being seen with that jacket on.

Una Japundza (05:05.925)
Exactly. It's a little bit, everyone knows how you got it. You know, how people earn rewards in Hey Taco that are very taco specific. So when you have a t-shirt that says, I earned it with my tacos, everyone knows you earned it with your tacos. wasn't just given to you because you just joined the company. But now back to Milestones. One thing, One reason that we built this feature is that we kept hearing from customers about how they were doing this right now.

A lot of spreadsheets, a lot of calendar reminders. mean, I have a calendar reminder for everyone's birthday, which I don't have to have anymore because Milestones will take care of that for me. And it fell on people's kind of to-do list and it gets cumbersome when you have hundreds of people. Do you remember the one customer we spoke with where she said she's on the West coast and wanted someone's birthday or work anniversary and they're based on the East coast. She'll wake up extra early so she can kick their day off with a message.

She'll wake up at like 5 45 right before their day starts, right? So she can do it. And I'm like, we need to solve that problem.

Doug Dosberg (06:09.452)
Yeah, Yeah, I think there's a lot of stories like that in in there. There have been many emails and a lot of questions about adding birthday celebrations and work anniversary celebrations to Hey Taco for many years. And I'm really excited that we're finally rolling this out. I think it kind of really helps complete the the the picture here of of Hey Taco and being a great peer recognition app. But not only that, but just a great app to celebrate people, not only for

things that people have done or to show appreciation, also those special days like birthdays and anniversaries. So very excited.

Una Japundza (06:49.385)
One thing we always kept coming back to is who gets excited about an automated email from Starbucks telling you it's your birthday. that's a lot of it, what it prevented us from building such a thing because you're thinking about automated can't be good, right? We give tacos authentically, you write a taco message, it's really personal. What makes Milestones special and how did we get over the hump of automated equals bad?

Doug Dosberg (07:11.374)
Mm-hmm.

Doug Dosberg (07:17.378)
Yeah, I think what makes it super special is that you as the user of Hey Taco, you can choose how and where you want to be recognized on your birthday or work anniversary. And the cool thing is, is it can happen right where people are already recognizing one another. So it's really about being seen and rather than, you know, if or unless you choose, you can have Hey Taco send you a direct message to recognize those dates. But really the power is

Hey Taco is going to recognize you on those dates in a public channel so everybody can see that it's your birthday and others can wish you a happy birthday and throw tacos at you and just make it a bigger moment.

Una Japundza (08:00.297)
I think that's my favorite part is that everyone can pile their tacos on together, right? So everyone gets this message for their anniversary or birthdays. There's no grouping necessarily. So people can add confetti and taco emojis and whatever they want. Kind of like the vibe that your HR team was creating of cakes in an office where not everyone joined in and gave you a high five and asked you how your birthday was, right? How do you recreate those taco parties or birthday and work anniversary parties in a virtual setting? And I think Milestones does that really well.

Doug Dosberg (08:31.128)
Agreed.

Una Japundza (08:32.999)
So if you're already using Hey Taco, Milestones makes it even easier to spread joy in your remote or in-person or distributed workplace. And if you're not using Hey Taco, well, what are you waiting for?

Doug Dosberg (08:49.742)
Yeah. There you have it.