TryHackMe is a bootstrapped, founder-led, scale-up company, which also works completely remote across many timezones. The environment here may be quite different to what you’ve experienced before.

The role of a Product Manager is a pivotal one that touches all areas of the business, so it’s important to be aligned with how we expect that role to work.

• Managing Jira and writing tickets
  • We expect PMs to write the majority of tickets in Jira. This is to save engineers time - we really want engineers doing what they do best, building. It’s also to ensure clarity on what we’re building. In some cases the engineers may prefer to write tickets, or collaborate on them with you. But the default is that PMs are responsible.
  • Not everybody likes creating tickets. It can feel like a laborious task to break the work down into smaller pieces, write the definition of done, and clearly state the work.
• Product manager not product owner
  • People consider those terms in different ways. Typically a PO is more of a process driver - they manage the backlog, do refinement, run the team rituals. A PM is typically more external facing, close to the customer, working with stakeholders, doing discovery work. We want our PMs to be more of the latter, but also cover all the parts of the PO role.
  • We keep teams small so that the PM can manage the development process parts. It’s roughly expected that you’ll spend 20% of the time on this kind of process/product owner type work, and ideally 80% on the other PM aspects.
  • We don’t want to see product team bloat by having delivery managers, scrum masters, and product owners; just a single PM that covers it all with no fuss, and a small nimble squad to make this feasible.
• Autonomy comes with trust
  • Everybody wants more autonomy: to decide what to build, how to build it, and more control over strategic decisions.
  • The reality in a fast moving smaller company is that you must first develop very strong trust with stakeholders before this is feasible.
  • Trust comes from developing a solid understanding of the market, our users, competitors, the product, and having alignment with the founders’ vision and goals. Trust also comes from making an impact and demonstrating good judgement. Both of those take time.
  • Until we reach this point, you may find there is a lot of direction provided about what to do, and sometimes even how to do it. But you’ll always have the chance to give your input - we are highly collaborative across every area of the company.
• Things can change, and quickly
  • We have product squads aligned to our main priorities, but we’re more than happy to change them based on the goals and initiatives we want to pursue. This could mean changing your entire focus from one area of the product to another.
  • We see this as a positive: you get to do more, see more, building up experience in more areas. But this kind of change can be unsettling for some.
  • We also change engineers and designers around. Sometimes we have to shift priorities, moving engineers onto projects that need their skills. We recognise this is not ideal, so we try to avoid it and keep teams stable. But you’ll want to embrace this kind of change and be sure to adapt quickly.
• Founder involvement

  • Our founders built the original product, saw it rapidly evolve and turn into the growth machine that it is today. They are super passionate and involved in everything about the product … and we mean everything. From pixels being slightly out of place, to the wording of a button, to the next big thing to build.

  • This means one or both of the founders will very likely be engaging with you on a frequent basis. Sometimes directing what we should do.

    The PM role itself varies a lot between companies. What you may expect in one company can be vastly different to another, based on the company age, stage of growth, culture, etc. We have a way of operating that works for us in our current stage, so it’s important you know what that looks like, as it may not be for everyone. The last thing we want to do is bring you on board, only for you to be frustrated and misaligned with how we work.

  • This makes a lot of sense for a company at our stage: the founders still know more than anyone about customer needs and market trends. We want their insights to make good decisions. In most cases they probably have a better view on it than you, so it’s good to embrace that.

  • Over time, this might change. It’s up to you to develop really strong intuition about our product, users, and market, and demonstrate sound judgement over a period of time.

• Founder led initiatives
  • Some of our initiatives are personally sponsored by a founder. You might be working on one of these. If so, you can expect an even higher degree of involvement.
  • But the flip side is that it means this initiative is probably very important and high profile within the company. For some PMs this is a golden opportunity to showcase their skills, learn from the founders, and have a big impact.
• Prioritise for speed
  • Speed is important at TryHackMe. We’d rather go fast wherever possible. There’s so much opportunity for us, the faster we move the more opportunity we can capture.
  • PMs are key for setting pace, so we really want our PMs to be leading the way in terms of speed and expectations. Are you comfortable being the one who is always pushing, asking for decisions today rather than next week, and driving your team to go as fast as they can? This is something we want to see consistently in our PMs.
  • The book Amp It Up by Frank Slootman is recommended reading.
• Remote work - being visible
  • We are fully remote. This means we rely on great communication. We expect people to be present and available on Slack. It’s just an important aspect for remote work.
  • As a PM it’s even more so. We want our PMs to be on top of everything in their domain. If bugs are being raised in your area, we really want you to step in and handle the issues to avoid others having to do so. PMs should be easily contactable, highly visible, and always engaged in discussions in their area.
  • At the same time, we do value deep work and staying focused. This sounds like a contradiction, but there’s a balance to strike here, we just want you to figure that balance out and make it work.
• Remote work - silos
  • We don’t tend to host large meetings or regular company presentations. Meetings are mostly in small groups of people, but more frequent. You’ll be communicating a lot within your direct team and with the stakeholders relevant to your work.
  • This can sometimes create the feeling of being siloed to the rest of the company. It’s just a side effect of remote work and everyone being focused on what they need to do. Slack is very open, you can check out the channels for any team. OKRs are visible to everyone, so you can easily find out the priorities of other teams. Notion is full of updates and documentation for every department.
  • If you want to know what’s happening, it’s just a case of being proactive to find out.
• Really good communication
  • Everybody will say that communication skills are crucial. At TryHackMe they really are. Poor communication can slow people down and waste time. Being fully remote means poor communication also significantly increases the risk of misalignment. Misalignment is kryptonite to effective product teams. To avoid that we need to strive for clarity and coherence in our communication.
  • It’s not just about speaking clearly, it’s in all areas of communication, such as writing things down to clarify what you intend, responding in a timely and concise way on Slack, summarising analysis of data in a digestible way, giving frequent but brief progress updates.
  • People across the business rely on information and updates from product, as a PM your communication skills will determine how well this works. And to stress this point a little more, it’s very obvious when it’s not working well, which can be a reason why people don’t work out as a PM at TryHackMe. For a PM, communication is the job, we want this to be the foundation upon which other skills are built.
• Constant engagement with users and data
  • The cybersecurity space is evolving rapidly. This means the perception and needs from our users is also evolving. It’s really important that all of our PMs are constantly engaging with the user base - this means taking regular calls with users, running surveys, reading Reddit posts, hopping on our Discord server, and looking at the findings from other team members’ research.
  • We also have a lot of data to look at, from product usage, to subscription renewals, and we make it available for all PMs. In some companies you have analysts or researchers support you when looking at data, but here we expect PMs to do a lot of that themselves.
  • So on top of the day-to-day job of getting work shipped to users, we also expect you to find time to speak to users and check in on analytics. But this hard work builds trust with stakeholders, you will know how our users think, and you’ll be able to champion your ideas more effectively.
• Shipping
  • We run a 2-week sprint cycle. That means each team has 26 chances a year to get something out the door to users and make an impact. It’s very important that you maximise those 26 chances. A year at TryHackMe goes by very fast; you’ll want to get as much out the door as possible, with as much learning as you can.
  • As a PM you need to be setting your team up to deliver value every sprint, this means breaking work down, ensuring it can be done in the 2 week cycle, and working with your engineers daily to keep things on track.
  • Every 2 weeks we run a company wide product briefing, where PMs show the value their team has shipped. The PM is ultimately responsible for ensuring that happens.
• Execution > strategy
  • Strategy is an important topic. We do care about longer term thinking, creating differentiation, figuring out how to win. As we grow, it will likely become more important. But in a rapidly growing market like ours, where the timing is so important, execution is going to win most of the time.
  • If you prefer spending lots of time strategising, this probably isn’t the role for you. We really value PMs that are focused on velocity, putting ideas into action as fast as possible.
    • “The bottom line is that great execution can make a moderately successful strategy go a long way, but poor execution will fail even the most brilliant strategy. That’s why, in an amped up company, execution is king.” - Amp It Up
• Personal development
  • Some companies, particularly larger ones, will have lots of structure around career levels and progression. You’ll find some of that here, we have a PM levels framework, and you’ll also get a £2,500 annual allowance for training (courses, workshops, books, etc). But it won’t be as extensive as other places.
  • The reality is, your career development is really your responsibility. As a PM, we imagine you are already a high agency person who takes care of their own development. And we know that the best thing for your development is to create tangible impact - we want to offer a platform for you to achieve that.

So that’s a taste of life as a PM at TryHackMe. It sounds intense, and it is. But you’re going to be part of a great team that is there to support you whenever you need it. You’ll be working with founders who are great collaborators, who only want the best for the company and our users. You’ll get the chance to move fast and ship work that directly impacts the lives of millions of cybersecurity enthusiasts worldwide.