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How to build a Career as a Product Manager: Jess Shorland

Jess Shorland is the co-founder of Stax and Product manager at Hover. She has over 12 years of experience as a product manager. In an exhaustive presentation, Jess shares with us her personal journey to becoming a product manager. She also shares with us steps to becoming a product manager. If you’re interested in building a career as a product manager, this article is for you. 

I started off my first job as a founder, starting my own company, which was a firm that actually invested in more brick-and-mortar businesses across Kenya, and East Africa. I did that for about two years, just as a founder of a startup, doing pretty much everything.

However, I gravitated toward building the product itself and the technology platform that we were building. That project ended in a co-founder split. The co-foundership just didn’t really work and I learned a lot from that experience. I ended up staying in Nairobi and working for a company called One Africa Media, which at the time was about one of the largest companies doing online marketplaces. We had three verticals across most of Sub Saharan Africa. We did cars, real estate, and jobs. Some of you might be familiar with some of their brands that were around Jobberman and BrighterMonday in Kenya. I managed their product. After that founder experience, it made a lot of sense to go into product management.

I spent about two years at One Africa Medial, and then shifted into a nonprofit called Ushahidi. Ushahidi does open-source technology for crowdsourcing data, specifically in crisis situations, crisis response, election monitoring, community driven events, organizing, etc. That was really interesting, because it really introduced me to the open-source world, and allowed me to get involved in community-based products, and how you build a community-driven product for growth.

Presently, I am at Hover, which I am a co-founder of and now head of product. I’ve been at Hover for about five years. It’s been a wild ride so far. We originally started building USSD for developers. This wasused by more than a billion people across the world. We started building that as an API-like experience for developers. In 2021, we pivoted a little bit and ended up building an app on top of that technology and developed the core technology. We had to figure out how to programmatically control a USSD session on behalf of the user. The next step in our go to market strategy was actually to build the app on top of that.

Right now I’m leading a product for Stax, which is a universal money app where you can host all of your accounts, and manage all of your financial accounts in one app. That’s where we’re starting and hopefully it becomes a universal payment app.

Steps to Learning Product Management

There are so many different variations of what people consider a product manager or product owner; those two are differentiated based on the type of project management style that you’re using or your organization uses.

First of all, I wish I hadn’t gotten so bogged down in the details of those nuances when I was first learning. At some point or another, they all can converge and have similar underlying fundamentals. For me learning, I learned by doing. I love product management, because I get to learn so many new things just by diving into the deep end and doing them. That said, not everybody learns that way. You have to begin by discovering and understanding how you learn best, and then going from there and devising your learning plan based on that.

No matter your preferred style of learning, these are three steps that would come in handy for everyone.

Step 1 Experimentation

I learned a lot by experimentation. This is important because you’re going to fail a lot in the beginning. You have to reframe failure as an experience to learn from, and reduce the risk and impact of those failures.  

When experimenting, Make it small. This is where scoping comes in. Reduce the scope. You’ll hear a lot of product people talking about how we can narrow the scope of products. This is because if you’re not sure how it’s going to play out, you’re making a risky bet.

Discover how you can experiment in the real world with it, and build products. Try to get a sense for wireframes or talk to users and try to figure out whether there’s a market opportunity for something that you’re thinking about. If it’s in a huge company where you just got your first entry level product management job and you need to come up with a product roadmap for a particular feature or use case, start with the smallest experiments possible. Learn from those and increase the frequency, as much as possible, of how quickly you’re able to run those experiments.

It’s all about building. At first, it’s going to feel very slow. I was very frustrated in the very beginning of my career. But experimentation is key. Just do it wisely. Taking precautions and reducing the risk of negative impact can really help you learn quickly and fast and refine your skills.

Step 2: Seek for apprenticeship and mentorship opportunities

Apprenticeship style is another really important thing about learning product management. Learning under someone and watching someone work and asking them questions is important. That was really helpful for me as a founder in my first job because I was new to the work force and was fresh out of university. I worked directly with the CEO. He had two decades of experience in both products and C level executive suite management. That was really helpful because I was able to learn from someone else’s mistakes. I was also able to learn from him the craft itself.

Step 3: Use Resources

There’s just so many great resources out there now around. There are templates and online courses. A lot of companies now are, are also writing and uploading blog posts publishing their notion templates and things like this around just building the community, the product management community and building the resources within that community. So, I think that’s also another way to learn. Think of products you really love using and go find out who the product manager is. What’s the company that’s building it? Have they published any blog posts about how they work? Do they publish blog posts? Do they publish their templates? Anything like that and being part of their user research, if they have a way to sign up to participate in their user research. You can learn from some of the greatest product managers that way.

Getting Started as a product manager

Once you get to a baseline and you feel ready to try to start your career and enter the workforce, first, I would recommend that you solidify and write down your values and principles. As a product person, what type of products do you want to build? How do you want to build them, and why do you want to build them?

Your clarity on product building is going to evolve all the time. It is not something that’s set-in-stone. You’re going to grow as a person, as a product manager, as a teammate, as a human, and therefore your principles will grow as well. However, writing these key values down and getting a little bit more clarity on that will help you better find an organization that matches what you want to do with your career, and what kind of products you want to work with and what type of culture you want to work within.

Having gained clarity on what you want from yourself as a product manager, here are some things you can do.

1. Research Companies that interest you

Afterwards, you can research the companies that you would like to work with or organizations and try to find the best match for you. I think there are a lot of other options besides just applying to entry level product management jobs. Like I said, apprenticeship is always something I recommend. So, if you are in a position of privilege to take an internship, I do recommend it. 

2. Research on a specific niche in an auxiliary field

Another option is going into an auxiliary field. So, look within your learning experience of the fundamentals of product management and find a particular niche within that you are really drawn to and excited about. For instance, product design, user centered design, user research, engineering, data, operations, project management, Scrum, any of those different roles within the circle of product management. You can go really deep into one of those and become more of an expert in one of those contributor fields rather than the management route.

Summarily, find the right match for you, products you really admire and love, set out your values and find organizations and companies that match those values and principles, and that you think you’d be a good fit for.

3. Get users to use your product

As much as you can, get some experience under your belt in terms of actually shipping products to end users and having those end users use that product.  Having some data to put onto your resume is going to be useful. So, even if it’s just experiments, you’re running by yourself, through that, you can show someone in a product interview that you designed a solution for a problem. 

You can design an experiment to test that hypothesis for solving a problem, get results from it and iterate on those results to do something better. That is a feedback loop that anyone is going to be looking for in a product manager. If there’s any way for you to get that experience of people actually interacting with and using and giving feedback on one of your ideas or solutions, and then implementing the changes based on that feedback. That is a full circle feedback loop and a very great experience to have as you’re transitioning into the workforce.

Additionally, I think product management skills are very transferrable to other fields. Fundamentally, product skills are problem solving skills. Product requires a lot of emotional intelligence and analyzing cause and effect. That’s transferable to science, journalism, engineering, design, etc.

Earning from Products Developed

Personally, I have never been great at earning a salary. Money is not particularly motivating to me. So, I haven’t gone after high paying jobs. But that said, I am very aware of the industry itself, and basically, the tech industry. It is unparalleled in terms of what you can earn. Especially with the rise of remote work on a global scale, salaries are very much normalizing to a global baseline.

We’ll look at three ways to start earning in Product Management; Working for existing companies, building your own business and entrepreneurship

1. Working for existing companies

When you consider the big companies, Microsoft’s of the world, Spotify, Google etc., you are going to really have a comfortable, steady paycheck. That said, they’re not the norm and it doesn’t have to be the norm. I think a lot of people aspire to that but that doesn’t have to be your aspiration. There are a lot of other clever, creative ways to make a living with these skills. 

2. Building your own business

Building your own kind of lifestyle business is really smart. I build products with entrepreneurs who have set up a machine that earns them money, without them really having to be full time on it. I think that’s quite amazing to be able to use those product skills, and just build great products, which are really fundamentally based in identifying and solving a problem for somebody else. Using that skill, and then all these auxiliary skills that I previously talked about, just enough to be dangerous.

Having known enough about technology, get your website set up and running, and maybe do an API integration and automate some stuff. With that, you’ve gotten yourself something that you can get up and running for relatively little money and little time. If you choose to go that route, the most important part of that is making sure that you’ve really identified the right problem. Be sure that people want what you’re trying to sell. 

Otherwise, there are a lot of projects out there that also people set up and they just go into the web, the internet graveyard, and they become unmaintained sites. So focus on identifying the right problem based on the skills you’ve acquired and product.

3. Entrepreneurship

You can also try out entrepreneurship. You can go the route of tech startup, trying to be a high growth tech startup .It’s probably the riskiest of the three options I’ve laid out here. In terms of jsuccess rates, the probability that it will be successful is very low, and the probability of financial success from it is even lower.

So, it’s not the best option if you need to start and want to start earning a more significant amount of money sooner. But like I said, as well, these skills are all transferable. So, I think highlighting the problem-solving skills that you have, the emotional intelligence, and the analytical skills will really be transferable to other jobs as well.


In terms of mentorship, I was not great at this in the beginning of my career, and I do have some regret about that. I think I could have advanced a lot faster if I was more open to putting myself, asking for what I needed and asking for help. Mentorship requires the skill of asking for help and I didn’t have that at first. 

I do recommend getting comfortable asking for help if you’re not already. And then, in terms of finding mentors, it’s been tough for sure, and I don’t have great suggestions here. But I’ll tell you what has worked for me. One is reading a lot of stuff outside of the tech world. My brain gets very curious; I’m a very curious person and sometimes I get sucked into rabbit holes of things that have nothing to do with my job. At first, I tried to avoid that a lot. But as I leaned into it more and more and fed those curiosities, I discovered parallels between,

I am particularly interested in forests, and environmental ecosystems and how those work. I also studied game theory in college, so, am very fascinated by war. Seeing the parallels between those two fields and product management and building a tech product was pretty incredible. Just to see the connections that I was able to make, once I started feeding my curiosities, and the people I was able to uncover who I really respect, who are mission driven, like me. I liked that they shared some of my same values, and had a different perspective than me and different experiences and different backgrounds. 

By opening myself up to industries outside of tech and building software, I really opened up the people that I could access and the people that I could learn from.Ultimately, the lessons I was able to learn were in depth, and it sparked a lot of creativity in terms of how to solve some of the challenges that I was going through in my career at the time.

I think the other thing that I’ve been able to do is trying to connect with people, colleagues or friends, who I really respect their work, and love working with. I try to connect with people they’ve learned from as well. And so my peers have always been a great resource for connecting me to mentors. As a product manager, it’s really important to love negotiating with people. Because it’s a role that requires a lot of empathy, compromise and boundary setting. 

The last thing I’ll say on mentorship, is that it’s important to show up to the mentor, whatever that relationship looks like. Carve out time for it, structure it, lead on that, and show up even when you don’t necessarily want to or you don’t have anything particularly challenging, because as you build that relationship over time, you learn from it in unexpected ways, and you benefit from it in unexpected ways. And so, I think with mentorship, it’s like a long-term game with long term people who are willing to see you as a full person and help you as a full person, whether it’s inside of your career or not.

Q. What are some entry level roles to look for?   

A. For entry level roles, I recommend looking for anything under the product umbrella. If you can’t find something that specifically, I think the title would be product owner, or entry level product manager or associate PM, there’s a couple of different titles that people use, again, just to plant pending on their flavor of agile Product Management. But if you can’t find an entry level role specifically for a product, I recommend looking for user research roles.

User research is one of the best ways to really hone that problem solving skills and be front facing with the users. That’s going to be something that fundamentally just investing in that skill as a product manager, is one of the best investments you can make, learning how to create psychologically safe spaces for users, learning how to structure questions and interviews, and then learning how to analyze that data. So, entry level research positions are all I always recommend looking for in terms of that. The other side of that is not only just qualitative, but also data, entry level data position. So, if you see a data analyst position, that’s always helpful as well.

Q. I would love to ask. Can a product manager also be a product designer? Or will these two roles be overwhelming for one person?

A. Yes, product managers are often product designers as well. In larger well-resourced companies, absolutely these two roles will be split. And I do recommend, if you do want to be in a product management role, I think having those functions divided is actually quite beneficial for the end user. But that said, I currently am doing a lot of the designs on our product, just because it’s what we have, we’re working under constraints and so constraints are always existent. And I think that’s why we need to know enough as product people about the design, about UX, about research, about technology that we can fill in those gaps.

Q. What advice do you have for someone transitioning to PM from an insurance industry?

A. In terms of transitioning to PM from an insurance industry, I am not sure what specific role you have in that industry. But I like to think of products as being as industry agnostic as possible. So I do think obviously, there are specific industries that you may personally have passion and interest and curiosity about more than others. But the product itself should be transitional transferable from industry to industry. And so I think that when you’re looking at other industries for product roles in other industries, think about how you can show examples, hard data around, how you identified problems, how you discovered evidence, how you know that’s a problem and you proved that it’s a problem, and then how you solved the problem and how your solution actually impacted the problem going forward. So, as much data as you can find around that feedback loop that is the fundamental thing that people will be looking for.

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