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What Our Team Learned From a "Surprise and Delight" Hack Week

Surprise and delight can be just as fun for a team as the customers. Here are some valuable lessons we learned about improving product.

Camilla Velasquez, head of product at Justworks
Camilla Velasquez
Mar 18, 20165 minutes
What the Justworks Team Learned From a "Surprise and Delight" Hack Week

When you’re part of a growing company, it’s easy to get caught up in the day to day tasks and projects that need to get done. Although that’s important for success and growth, it’s just as important to take a step back and look at the bigger picture.

Our customers are the reason we’re here — to help their businesses run health care, payroll, and compliance smoothly.

That’s why we decided to do a customer-focused, “Surprise and Delight” hack week this March. So, what did that mean for the Justworks’ team and customers? For the Product team — engineers, product managers, and designers — it meant taking a week to focus 100% on coming up with unexpected but delightful projects and executing them. For customers, it meant some new features, which you can see here.

Approaching Hack Week

Why Did We Decide on “Surprise and Delight” Hack Week?

When done right, hack week has the ability to stimulate creative juices, enhance team camaraderie, and allow people to take risks  — all with fairly low stakes. It’s a chance to take some time to focus on the projects we don’t always get to do because of our individual domain focus, or top level business priorities.

How Did We Organize Hack Week Ideas?

Overall, we wanted to focus on employees, who are often underserved in HR software — the people who regularly use Justworks to enroll in and check their benefits, view the directory and company calendar, and/or review pay stubs. The product works for these users, but rarely delights.

Decreasing meetings during hack week was pivotal for completing projects on time.

So, the week before hack week, we met up and had a comprehensive brainstorming session to get the creative juices flowing — and it involved a lot of ideas posted on the wall.

Then, we analyzed those ideas for feasibility. That is, based on how long it would take to execute coupled with the delight it would bring to users. As a fellow teammate Tom put it, “It was pretty subjective,” but it still offered a loose qualitative metric by which to select hack week projects. Now, we were ready to get started!

Team members got an option to work alone, or tag onto other team members’ proposed projects if they found them more appealing to work on.


Justworks made sure to mark the occasion with some fitting decor.

Make Every Week Hack Week

For us, the Surprise and Delight hack week reinforced and introduced some important ways we want to continue working as a cross functional Product team. Here are some major learnings that came out of the experience.

1. Weekly Milestones Are Crucial

Having the whole team work towards a company-wide awards ceremony for the hack week on Friday encouraged the team to ensure their features were ready to be launched. This really motivated the team and forced the team to think about projects in manageable chunks.

This reinforced that while our Product team has monthly and quarterly goals, weekly deployable milestones allows us to celebrate small wins and reduce risks in our projects.

2. Demoing More Often Means More to Celebrate

By hitting more weekly and biweekly milestones, we’ll also have more to demo to our entire company - which means more to celebrate and most importantly, more for other teams (like Sales, Marketing, and CX) to talk about with customers, and sooner. Demoing all the projects for the entire company was a huge morale boost and energized every team across the company. Everyone could not wait to get to their desks to play with the new features.

3. Transparency Across the Entire Product Team Makes the Most of Tight Resources

Transparency is one of our company values and it’s something we take seriously. As Product ‘pods’ (what we call our PM-developer-designer groupings by domain area) cross-communicate more about each other's roadmaps, they’ll also be more available to help each other and minimize conflicting priorities. During the hack week, as some projects wrapped up, people jumped onto new projects to help them meet the deadline at the end of the week.

4. Unnecessary Meetings Kill Productivity

It’s no secret that too many meetings kill productivity. Removing meetings during the hack week was crucial to increasing the likelihood of projects being finished by the end of the week.  If it can be communicated well in an email, we’ll keep choosing that over meetings going forward.


Nathan and Laura receive the “People’s Choice Award” award for building Face/Off, a game within Justworks’ app that helps you match your coworkers’ faces and names. You can see the details of the new feature in this blog post.

Takeaways for Next Hack Week

1. Different Themes (or None)

This time around, our theme was “Surprise and Delight”, which was a nice way to package the projects and keep the brainstorming tight. However, themes can also constrain projects. It’s worth considering whether those or open-ended projects are a better direction to take. Going forward, we’ll probably test hack weeks with and without themes.

2. Organize the Company Voting System

When we demo’d in front of the whole company, we voted for our favorites through claps and cheers. Although crowd-based responses are fun, a more organized company voting system will give a better idea of what’s bringing the most delight.

3. Ship as Much as Possible

Minimizing spillover from hack week is ideal. By shipping as much as possible during the week, we’ll be able to keep up with day to day priorities also.

4. More Design Critiques

The design team has weekly critique meetings, but that usually only includes other designers. During the hack week, we included more people who weren’t on the design team in on the meeting. It helped people to give constructive feedback and seek outside perspectives.

5. Involving the Whole Company

Not only is it fun to include the whole company, but it helps us to continually build product with transparency and helpful feedback from all sides of the business. Next time we might consider a company-wide hack week.


An up-close of the two prizes up for grabs after the Surprise and Delight hackathon. The Isaac Award, in which CEO Isaac Oates chooses his favorite finished feature, and The People’s Choice Award, voted by fellow Justworks employees.

Overall, diving into a customer delight hack week proved both productive and fun, and we can’t wait to do it again! Until then, check out all the new product features we shipped by weeks’ end.

This material has been prepared for informational purposes only, and is not intended to provide, and should not be relied on for, legal or tax advice. If you have any legal or tax questions regarding this content or related issues, then you should consult with your professional legal or tax advisor.