Postmortem: Deputy

When you interview for a new role, often you’ll get asked: What makes you want to leave your current role? Answering politely is a good professional decision. This is a blog post and not an interview, so I don’t have to be polite.

I’ll do the opposite: I’m going to be brutally honest about why I knew I had to leave Deputy, possibly upsetting some individuals in the process.

Don’t get me wrong, my opinion of team members at Deputy is overwhelmingly positive, but this criticism is necessary for me; a kind of catharsis. I need to get this off my chest.

My Manager Created a Bad Work Environment

Sorry Paul, overall I was not a fan of your management style1 (project management and people management). I had 4 other managers, whom I got along with splendidly, until you.

My few good memories of Paul are eclipsed by one particularly bad 1:1. I wanted to discuss a PDP (professional development plan) that I was trying to put together. So I raised this in our 1:1, shared my google doc and everything. I made it clear that I was trying to grow, find new opportunities, and increase my impact. My PDP was right in front of him.

No feedback, no support. To put it bluntly: my PDP was completely ignored.

How am I meant to grow? I really had to lean into vulnerability by bringing that up. He didn’t even care!

Another time, he did actually give me some feedback. It was negative. He had asked me to look into an incident that was already being taken care of by our principal eng. I could see that I wasn’t needed, so I went to my scheduled morning appointment. The negative feedback was: “Where did you go? You should have more urgency… don’t leave principal eng to do all the work, they are very busy…”

Firstly, principal eng is an adult, he can hand over if he needs to. Secondly, I’m not on call, yes we all have responsibility, but we have to handle unplanned work with some kind of discipline. Thirdly, what are you trying to teach me here? Is it “if I ask you to do something, cancel whatever you had planned”?

I’ll just go ahead and say it: I had a brilliant team of engineering, design, product, and QA, that was suffocated like a flame under a wet blanket.

The Pay Was Below Market

As a so called “Senior Software Engineer” or later a “Software Engineer 3” I was on $135K base. I’m not even going to mention how many worthless2 share options I had — all of which expire after 60 days of departing the business.

I reckon someone with my competency, and with my impact, could easily land a fulfilling role at another company, with a 15-25% salary increase.

I even overheard that my coworker was openly being paid on a junior contract despite her impact being mid-senior, likely because she started as an intern.

On one hand, it’s a great opportunity for early career workers to get into the industry, just don’t be surprised when you outgrow the role.

Too Many Rituals

Standup, sprint planning, backlog grooming, retro. These took up several hours of my week, every week. In my opinion they weren’t useful.

Standup doesn’t work when you have 15 people. It really doesn’t work when you have it at 1pm every day. Multiple people raised this as an issue and nothing was changed.

If you want to plan the sprint, plan the sprint. That’s not the same thing as getting 15 people into a meeting, only to have 1 person move tickets around Jira while everyone watches (and zones out).

Why is it so important for all 15 people to join one big backlog grooming meeting? We do not all need to be there. I’m starting to question whether I even had to attend? Maybe I could have just given my tickets some arbitrary points beforehand and shoved them into Ready for Sprint.

Finally, retro: why even have this at all? 1 hour of my afternoon to have my concerns ignored?

Looking back, I wish I had declined more meetings.

Closing Thoughts: Are the Good People Jumping Ship?

In the 6 months following my departure I’ve seen (via LinkedIn) a number of my former colleagues find new roles at other companies. Through the grapevine I’ve heard of some other big departures outside of engineering as well. Don’t even get me started on how miserable the sales team seems, my condolences to them.

I’m thinking the state of the engineering org is caused by lack of strong engineering leadership, which might improve now that Deputy has a new CTO. The Head of Engineering is a good hands-on engineer, but a CTO is needed to improve the team topology. As for the wider org, I have no idea.

Ah well, I’ll keep moving forward, and I still wish all the best to the current team.


  1. Maybe I’m a coward because I never said this to his face, and I chose to avoid the discomfort of providing negative feedback. Frankly I don’t care. ↩︎

  2. Good luck on IPO if that ever happens. Until then, enjoy putting coins into the poker machine. ↩︎