How to Build Your PM Portfolio with Founder

This week our #AskMeAnything session welcomed Chris Gallello, Founder of, to talk about his PM Portfolio!

Meet Chris Gallello

Chris Gallello is a product founder with 7 years of experience across collaboration tools and social. He started his career as a PM on Microsoft Office Online, where his work ranged from onboarding to accessibility to data center infrastructure and helped him bulk up his design, engineering, and public relations skills.

He then joined Imgur as their first PM, where he shipped products and features across every platform. He also learned a lot about hiring, mentoring a team, establishing new processes, roadmapping, and organizational structure.

Finally, with (which he recently announced will be shut down in June), he was the solo-founder with an outsourced engineering team.


Chris is also a big fan of side projects. He created while at Microsoft and it really helped him get his Imgur job, and led to him starting Purple. In the past few years, He has shipped Kitten Cannon VR on Steam, and started the AR/VR design meetup group in SF. You can check out more of his work on his website!

Chris Gallello’s PM Portfolio

How did you get your first role at Microsoft Office Online? What were you doing before that?

I went straight from college. I got an internship at Microsoft the summer after my junior year, and they made me an offer at the end of the summer to come back when I had graduated.

How easy is it for PMs to start a successful side project while fully employed ?

It depends on your skillset. If you can design or code, go build something. If your skillset is with people, go start a meetup group, or even a dinner group with a handful of people who you think will have a really great conversation together about products.

Regarding whether or not you can do this kind of stuff while you have a job, it really depends on your life situation. That’s a really unfortunate side of hiring – side projects look good for employers, but they exclude folks who don’t have time outside of work to commit to additional professional activities.

Ultimately, you’ll have to sacrifice social/fun/homecare type of stuff in order to work on side projects, or actively seek employers who understand that we all come from different situations. I’ve seen employers messaging their values a lot more these days, so I do feel like it’s something you can stay attuned to.

What was it like being a PM at imgur?

It was super fun. Very humbling to have had the opportunity to work on such a big product. Every Friday, our head of community would read us one letter that she received from our users, and it was incredible how life changing a time-wasting app could be for some people. People who were depressed, but found a home and a belonging through the Imgur community, etc.

Even though most of my career has been on the productivity side, I’m considering going back into consumer because it’s a real opportunity to make a lot of people really happy all at once!

What was the experience like that resulted in you deciding to shut down

It was super tough of course – so emotional support was important. It was one of the worst months of my life, despite having people around me to lift me up. And of course, we as a team had to still work on the product and make changes such that it could stay up until (at least) June.

It was tough to keep the team motivated and going to hit that final finish line before we were done for good. Beyond that though, it’s been pretty smooth. Lots of support from people, I’m talking to all sorts of companies to join, and that has been super fun.

We hear so often that a vast majority of ventures fail. What are some of the qualities that increase the odds of success?

To be honest, I’m not sure about the best way to answer this. It really depends on each specific venture. For us personally, I wish we had done more prototyping work early on. We built prototypes, but I know of other companies that will only decide on a direction after being obsessive about it and building like, 10 of them.

It would have helped us iterate on the overall direction of product, and find other designs that could have been beneficial, specifically for non-designers who are coming into the tool. Once again though, this is not generic advice for all startups! Just what was important for us.


Can you talk about exploring other options for Purple? (i.e. acquisition/sale, pivot, etc)

We explored acquisition with a few companies, but ultimately, since the scope of our tool was pretty large, it largely didn’t make sense for those companies to wrap us under one of their products or organizations.

What key takeaways from will help you do things differently in your next venture? Also, will you go back to a big corporate having worked on a startup where most things are done quickly?

One change is prototyping more, which I’ve already discussed in a prior question. Another is building relationships with entire teams of people at a company. My customer outreach included meeting with some teams, but the majority of it was 1:1 meetings with designers or 1:1 video calls. We missed the mark, unfortunately, on building a product that everyone will buy into, not just the designer.

I’m talking to various companies right now, ranging from joining as a co-founder at a new startup to joining on the product side at big companies. To be honest, none of my selection criteria includes how big the company is.

How does one break into the AR/VR domain? From online course perspective, it looks like you may need to be hands-on dev/design for this space. Any advice?

To be honest, there are very few PMs in the AR/VR space. I’d estimate that there are on the order of 100-1000, but it’s not like there are tens of thousands or hundreds of thousands. Many of these PMs will likely come from a background with 3D experience, whether gaming/CAD/simulation/etc.

Not having that, then yes, I would strongly recommend finding a project (hackathons have been great for me) that you could work on to learn either the design or development side, and go deep on that. For me personally, YouTube has been super helpful. I’d search for things like “VR design” and just watch a bunch of videos at 2x speed, then try implementing some of my own ideas based on those videos.

The Product Management Career

What recommendations do you have to make sure I stay relevant in the Product Management industry?

One thing that I’ve done is taken up new technology and done my best to make that part of my brand. VR and AR had nothing to do with Purple, but I knew that it’s a technology that will only become more and more popular, so the faster I get in on the ground floor, the more it will help me down the line.

I’m currently speaking with various AR/VR companies to join them now. Of course, you don’t have to limit it to new technologies. I see others helping to evangelize for new processes/frameworks and writing books about them, or establishing conferences around them. And of course, it doesn’t have to be in the technical domain – it could be on the design side, the VC side, etc!

What are some expectations specific to a Product Manager in the collaboration tools/productivity domain like Microsoft Teams?

Good question. One of the balances that you’ll have to play as a PM on collaboration tools is understanding the lifecycle of how the product works, and who gets involved at each point.

Even if you’re building a tool like Slack for eng/design teams, you’ll need to understand what happens when you throw a marketing or support person into the mix. How does the product work for them? Is it low friction enough for them to dip in and out easily? Etc.

One of the problems I’ve had as a “mentee” is using time with the mentor effectively. Do you have suggestions or resources for how a mentor can come to a meeting with their own set of topics of discussion?

To be honest, I don’t know if I’ve ever come into a first-time mentor meeting with an agenda of my own. I expect mentees to manage their time wisely. If I see that the person is well-intentioned, but not asking the right questions (and hey, it is really hard when you’re starting out to know which are the right questions to ask), I’ll bring up any thoughts on that.

Also, if I see that this person is really hungry, organized, and has the skills needed to do great things, I’ll make that very clear to the mentee and open the door for additional contact. One exception to all of this is if this is a recurring mentorship relationship – then we’ll usually naturally discuss topics that are important or helpful to discuss on a recurring basis, which is a good starting point for our next meeting.

What were some of the surprising difficulties when you first started mentoring (and/or managing) other PMs? Based on that, what advice would you give to someone who’s just starting in a mentoring capacity?

My big surprise with mentoring was realizing how much I knew. There are so many things you pick up on the job that you take for granted, that I was surprised that I was actually able to be helpful to anyone when I first started.

If you’re 2 years into your career, go offer help to people who are just starting. Even though you’re not some super guru, they will still find your experiences helpful.

One other caveat is to try not to push narratives about “specific things that you need to do”. My mentorship relationships are always more “here are stories from my past, that you may find helpful”. It’s dangerous to impose specific strategies or viewpoints on someone without knowing them super well.

Do you use any growth hacking methods to verify users demand or features?

I’m a hard no on using growth hacking prior to understanding user requests. Growth hacking is usually only helpful once a product establishes product market fit. It can inflate metrics if you use these methods earlier on, but they’re only short term metrics like engagement. You’ll likely see them drop off later on though.

Breaking Into Product Management

Can you talk a little more about how you transitioned into the PM role at Imgur? What were some of the hurdles you faced?

I attribute this role to the success of UX Check. I was able to show that not only have I worked on complex software for consumers (at Microsoft), but I’ve also shipped my own stuff, with concrete user numbers and actual retention metrics that I could talk about.

I believe that put me over the edge over other potential hires. I was actually looking around for a solid year and a half before I found something. And I found Imgur just a few weeks after I had shipped UX Check.

I am a Mechanical Engineer and manage a product line for a manufacturing company. Do you have advice on how to demonstrate these skills and fill in my gaps during a PM interview?

You’ll likely need to prove out a lot of the skillset that a software PM takes for granted, unfortunately. But it can be done!

I would heavily encourage you to build/design software on the side and ship it to real users as a way of showing “hey, professionally I have all of these good stories and experiences that you’re looking for”, but in more concrete terms, you actually do have some understanding of how the software world works.

Another thing you could do is write blog posts. For example, compare and contrast PM in the software world vs the hardware world. Interview people to build up interesting stories. That kind of thing is also good evidence that hey, we can totally trust you!

For developers who want to make the switch to Product Management, do you have any advice? How can we position ourselves when every PM job description asks for prior PM experience?

Totally. I’m assuming you’ll want to stay at the same company? In that case, you’ll want to convince the hiring manager that you’ve always been a PM at heart, but with the skillset of a developer. That’s a super compelling story because a PM who understands every facet of development can be super effective.

I’ve seen this done before – I’ll personally take notice of developers who are aggressive on prioritizing work (aka, cutting work as opposed to arguing that everything needs to be built perfectly, which more developers lean towards), speaking about feature decisions from the perspective of a user or how it will impact metrics, and building features with a lot of design polish, animations, and little delighters.


How can one transition from UX role to Product Management? In addition to solid understanding of roadmapping, KPIs, basically the business side, what technical skills are required for the PM role?

You can totally get away with not having solid technical skills, but for the most part, you’ll want to study up on a few concepts. Let’s say you’re trying to get hired as a mobile PM for…Yelp. You’ll want to be familiar, at a high level, with how phones process data, interact with servers, use APIs from other services (like google maps), etc.

For each job you look for you’re going to have different technical needs, but really the point of all of this is so that when you’re in a meeting with your dev team, and you’re trying to decide between a caching solution to minimize network calls from the phone, and a new onboarding interface (just an example), you have the data you need to make a decision.

Any final advice for aspiring Product Managers?

One thing that I don’t think is communicated enough is just how important being an empathetic person is in order to be a great Product Manager. If you look at the people you need to empathize with and convey that empathy to, it’s pretty staggering:

  • New users of a product
  • The vocal demands of your expert users
  • The technical needs of your developers
  • The deep, artistic explorations of your designers
  • The sporadic interest in your work from your management chain
  • Logistical needs of the support team
  • The narrative development that your PR team will need to craft
  • And
  • So
  • Much
  • More

There’s just so many stakeholders that you’re responsible for serving, but not controlling. The role is very deliberately set up this way to ensure that the people who are setting the direction of the ship are also the people who can actually corral everyone to row in the same direction, and head to the right place.

I’m always open to additional questions via Twitter ( Thanks everyone!

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