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The Evolution of Product Development at Yesware

One of the reasons I love working at Yesware is that we aren’t afraid of change.

And as Director of Project Management, I’m constantly working to improve what isn’t working so that our Engineering teams can work in the most efficient ways possible.

About two and a half years ago, I wrote a post for our Engineering blog all about Product Development at Yesware. I thought it would be fun to write an updated blog post to describe how we work now. 

Today, I’ll speak about remote employees, our team structure, our project management process, and the three types of meetings.

Remote Employees

First, I wanted to mention the recent work we have done to be more remote-friendly.

Currently, we have three employees who are full-time remote but we are expanding to hire more remote Engineering employees.

We don’t take this lightly.

Recently, we upgraded our video conferencing software to be more remote-friendly. They report less lag and find that it’s easier to have discussions. We are also bringing in an AV specialist to help us get the right setup of microphones in our conference rooms to improve the overall meeting experience.

We are mindful of the benefits of remote work and are constantly looking for ways to improve that experience to create the best possible work environment.

Our Team Structure

We currently have five development teams at Yesware (soon to be six!). Each team is led by a Product Manager, a Team Lead, an Agile Project Manager, and a dedicated Product Designer. There are three to five Engineers per team.

The number of Engineers per team comes down to balance. It’s difficult with less than three Engineers when you take into consideration vacation days or sick days. However, when you have more than five Engineers, it becomes difficult for the Product Manager to maintain a backlog that can sustain that many Engineers and to get through meetings efficiently.

Project Management at Yesware

We do things in an Agile fashion here, but we are pragmatic about all the guidelines we follow. Our process is a hybrid Scrum/Kanban.

I have learned in my nearly five years at Yesware that not everything that has worked for me at other companies works here. We adjust our processes to fit our people and our culture. One thing we are mindful of is making sure that Engineers, Designers, and Product Managers have heads-down time where they can really focus on their work.

This means scheduling meetings that are really necessary. We consider it a big win when we are able to wrap up meetings early. In general, there are only three recurring meetings for the teams.

The Three Types of Product Development Meetings

1. Daily Team Stand-up Meetings

Each morning, our teams get together to sync up on three things:

  1. What everyone is working on;
  2. What progress has been made;
  3. What blockers or areas of dependency need to be addressed

The team uses JIRA work board as a focal point during stand-ups, so that everyone can see what everyone else is working on.

Product Managers attend stand-ups to address any questions that come up around priorities, but Designers are not always necessary unless there are questions regarding mockups.

This meeting lasts 15 minutes. It’s a quick and valuable way to ensure the team is communicating. Some days, it’s the only meeting Engineers have to attend.

2. Planning Meetings

Our planning meetings are scheduled in one-hour increments, twice a week. Teams don’t always use both meetings every week since we focus on our near-term work.

Once the Product Manager and the team feel that we have enough groomed work for the next week or two, we don’t plan out more work. There is too much opportunity for priorities or requirements to change and it’s hard for the team to remember discussions that happened weeks prior.

Product Managers set the agenda for planning meetings and present user stories they have written and deemed a high priority. They also explain what they want to be built, why, and who it’s for. The team has the opportunity to ask questions until they are satisfied and understand the work.

Then, the Team Lead has a technical discussion to determine a plan for building the work and a task breakdown to allow more than one Engineer to work on stories at a time.

3. Retrospective Meetings

Last but certainly not least comes my favorite meeting — retrospective.

We meet about twice a month to talk about how we are feeling about the team, the work, the process, and the company (or anything else on our minds).

We call out recent wins and mention where people went above and beyond but, in true Yesware fashion, we identify the areas that could be improved. Sometimes, we decide it’s been too long since we had a team outing and we should all go to BodaBorg.

The “retros” here are very informal. It’s important that no one’s direct boss is allowed in the meeting so that people should feel comfortable to speak freely. No one is forced to add sticky notes to a board with their top things that went well or poorly. They are really just an opportunity for the team to talk about whatever is on their mind, person-to-person.

Wrapping Up

If Yesware sounds like the kind of place you’d thrive in, you should check out our current job openings.