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The Product Management Blog

Tips and Free Resources to become a Great Product Manager
Tips and Free Resources to become a Great Product Manager

How to Transition into Product with former Shutterstock PM

Does a product manager need a technical background? And where does one get inspiration for product ideas? Former PM at Shutterstock offered her valuable insights in our recent live chat – keep scrolling to get answers to questions you didn’t know you had and lots more!

Holly Hester-Reilly spent 2 years at Shutterstock, where she led the launch of the Shutterstock Editor, from prototype to successful public beta in 3 months. By the end of its first year, the product usage had grown 10x!

Since then, Holly has helped several businesses determine when to invest, persevere, pivot, or kill everything, from feature ideas to business units. She believes that the best product leaders are not only good at building new products, but also at recognizing when resources would be better spent elsewhere.

Before her role at Shutterstock, she was a product manager at Media Math and Rip Road and she holds a Bachelor’s Degree and Master’s in Chemical Engineering. She also teaches figure skating to girls in Harlem, educating and empowering them to aim high and pursue their goals!

Table of Contents

How did you start your career and what are the most important skills as a PM?

Like many product managers, I took a winding path here. For me, it started with an interest in startups. In college, lots of people around me founded startups and when I got out, it stuck with me. So I started reading and learning about how to build products…

How do you start adding layers of being a product manager as a current project manager?

…And then I started as a project manager, just like some of you. I got comfortable working in the environment and then found my way to influencing some product decisions. Ask good questions! If others weren’t approaching something in a way that I thought was good product practice, I’d offer my thoughts and ideas. I found a team that was willing to let me run with it, once I’d shown them I could do more than just project management.

What supplementary education have you had – online learning or certificate programs outside of your related experience in the business environment?

I started with reading a lot. I had a Safari online bookshelf, so I read agile product management. This was before the “Lean Startup” series was out, but nowadays I’d probably go straight to that. I started in a low-level project job at a small startup – I was hire number 4. I was cheap compared to today, but I wanted in. So I convinced them I could do the work as a project manager, then started influencing the direction of their business…over time. It’s always a slow build – you can’t win trust in a day!

What are your thoughts on the increase in APM programs at different organizations?

If you can get into an APM program, great. But don’t wait for it. If you’re not working on a scrum team in some capacity yet, just get as close to it as you can. Sales, support, account management, marketing, training…all are valid ways to get in. I’ve helped people from those functions start to build their vocabulary and exposure, so that they can make the case down the road that they could be a product manager.

What was the biggest challenge you’ve had going from prototype to beta in such a short period of time?

There were a lot of challenges…but the biggest one was team morale. Everyone was working so very hard and felt that the ask was huge. It was tough to keep ourselves grounded. At the time, I had a 1-year-old, so that was my way, but for many of my colleagues, they were thinking of work all the time. We had to remind each other that life is important too. And still deliver the best we could possibly do for the company and our vision.

Did or does being a female PM increase your chances of getting job opportunities?

Not when I started a decade ago…and it made it hard to get promotions. I know many leading product managers who don’t have the title that the males have. But things are changing and it’s best to keep going forward and fight for what you can do and what you can control. Many of us got what we could out of the opportunities and then moved on to more friendly companies. On the other hand, I find that I am a more balanced and collaborative product leader than some of my peers…

What are some Dos and Don’ts in the first few months of a new PM job, when coming from a project management background?

The biggest thing I’d keep in mind is that it’s all a learning process. You don’t have to wow them off the bat. You want to build trust over time. People love to be listened to, so the best way to get started is to do a lot of listening. Ask the people you meet – what do you wish the product manager was doing?

What should be taken into account when thinking about a PM role in a hardware vs software or SaaS company?

Product and software roles can be pretty different, primarily because software is more agile and iterative. These days, hardware can be produced more iteratively than before, but it will still generally require a more waterfall approach compared to software. SaaS vs eCommerce can also have differences – SaaS is very, very continuous. You need feedback models and loops and continuous improvement and service for your subscription customers.

What type of technical knowledge is key to have as a PM in SaaS and software companies?

The technical knowledge needed can vary a lot depending on the product and the culture of the organization. You don’t have to be able to code, but you have to be able to gain the trust of the engineers. You have to learn to speak their language. I think of it as speaking pseudo-code. I don’t write Javascript, but I can talk about logic trees, databases, system architectures. I know what someone is referring to when they say monolith vs service-oriented architecture or what it means to make an API call, what should happen on the front-end vs the application or back-end, etc. You can get this knowledge in multiple ways and you don’t have to know it all to start. If you try some little coding projects, that can definitely help you gain some credibility with the engineers.

Do you think that having a strong technical understanding of software development is paramount to being a good PM? Or should you leave the details to the engineers and keep yourself at a user’s level?

There’s a lot wrapped up in there… you definitely want to leave the details to the engineers. They won’t like it if you get in their area. But if they come to you saying that your practices are building up tech debt and you’re not giving them room to keep the lights on, they won’t like that either (and neither should you). So you have to strike a balance. At the end of the day, you need to understand your users first, but have a sense of the business and the tech capabilities too. This often comes into play when talking with traditional business people – I see so many people who have lots of ideas and may be good at finding market opportunities, but just have no sense of the relative difficulty in the solutions they are asking for. If I had a dollar for every time someone said “that should be easy, right?” to the engineers…don’t be that person. They won’t trust you. If they don’t trust you, you won’t get good quality work from them. Show them your value – that you can identify a good product opportunity, sit in the meetings with the business people that they’d rather avoid, talk to the customers, and learn enough of their world to get them to want to build with you.

PMs run long-term projects and there’s not always a solid deliverable to show on a regular basis. How do you cope with this ambiguity?

Are you tracking key metrics? What would success look like for the long-term project? Sometimes we get asked to do big things and we try not to show any of it until we’re proud and ready, but that’s a recipe for trouble. You want to show things along the way as much as you possibly can. If it’s not shipped product, show what you learned. My recommendation on that is in this piece I wrote: https://h2rproductscience.com/built-learned-planning-demo-in-product-management-insider.

Will an “Agile Certified Practitioner” certificate or any similar certification give you preference when applying for PM roles?

Depends on the company. In general, the larger and more traditional the organization, the more credit they’ll put on certifications – think Fortune 500 companies. The smaller, faster-growing companies put more value on experience. If you don’t have the experience, try to do a side project or show your skill in other ways.

What’s your way of getting product ideas?

Listen to everyone, customers first. The best products solve real people’s pains. So go out and talk to people in the area you are thinking of building a product in. Also, listen to the people inside your company, especially the ones on the front lines – support, sales, etc. Share the problems you want to solve with the designers, engineers and builders that you work with and ideate solutions together.

I am a PM at a large bank but wish to move to a smaller company. What resources would you suggest to learn some of the technical skills required to be a PM at a tech company?

I’ve spoken to others in your situation – there’s a lot of them here in NYC. In terms of understanding the technical side, you could do some free coding classes online to get a sense of the basics – Team Treehouse is a great online coding school. Another thing that changes when you go from large to small is the influence on the product direction that you get to have, and the need for building good customer experiences. So you may also want to work on your design and user experience understanding.

How do you scope projects and set realistic schedules, particularly when there is uncertainty involved?

This is one of my favorite topics, because it causes so much stress for product and engineering teams. I talked with an author about it for this article. I also love my friend Dillon’s piece on it!

I’m a software engineer, current Product School student and looking for a job. What do you think would be the right career move – a software engineering role to transition into product later or a junior PM role directly?

If you’re trying to transition to product, the best would be a junior PM role. At most companies you won’t get a lot of exposure to the user research, design, and business side of the role if your title is engineer. That said, if you need a job, you might want to apply yourself to both paths, take what you find first and then keep moving towards where you want to be. If you do go for an engineer role, one thing to know is that the smaller the company, the better the chance that you can get exposure to all the elements of their business.

What methods do you use to test assumptions?

I can tell you’ve been reading “Lean Startup”! It depends on the assumption. First, look at what are the riskiest assumptions – I try to uncover them with a pre-mortem. What are the reasons this initiative could fail? What assumption would be false? Then think about it like a scientist – how can we see if that is true or false? You might talk to users, you might set up a prototype, you might gather data from an existing product, you might do a landing page test, a usability test, an engineering research spike…

Sometimes people don’t know what they want – how do you build products keeping this in mind?

Look for their pains, and then talk with your development team about how you could solve them. People don’t know what they want, but if you talk to them about how they live today, you will find opportunities – areas where it’s painful, tedious, hard, or boring. Also, I have an article coming out this week on this – how to talk to users without asking them what they want. Look for it!

Any final advice for aspiring product managers?

Final advice, there is so much growth in tech and products – so don’t give up. Everything comes in small pieces – get a little closer here, a little stronger there, try things yourself if your company won’t give you a chance. Build up your experiences and listen, ask, and learn as much as you can.