It’s not often a school teacher of over seven years makes the switch to becoming the Head of Marketing and Communications at a leading ed-tech company, but Clinton Milroy proves just how possible this non-linear pathway can be. Read on as we uncover Clinton’s early career story and how his learnings have shaped his approach to hiring early career talent today. 

What is your early career story and how did you end up in your role at Edrolo?

Clinton: My career started out actually as a high school teacher unbelievably for about seven or eight years. Then, I moved into government policy in the Department of Education for state government. I got a lot of exposure to a whole range of different policies and projects through this experience. Then, I slowly made my way to the comms and marketing space. Now working in the education space again, it has been really nice to bring this background and deep empathy and insight for what happens in schools, particularly with teachers and the challenges they face. 

I am now able to look at it all from a very different perspective in terms of the marketing comms lens. It took quite a long windy path to get to where I am now, but I think that’s what it’s all about, right? Try different things until you find something that you like. It’s been a big transition going from community-centric schools very much run on a shoestring to big commonwealth and state government agencies and now to tech startups. 

Just seeing the gamut of different people who work in those workplaces and the way they operate has been really fascinating as well. It’s been something that’s really always interested me in how different organisations function. 

How did you rationalise all of the next steps in your career given they were vastly different to one another and how did you find the confidence to do that?

Clinton: Mm, it’s a good question. Teaching is such an awesome job. It’s so mission-driven, right? It’s what appealed to me, but it’s also really exhausting. It’s a full-on job, and most teachers will tell you that you get to the end of the 12 weeks or whatever and you kind of fall flat. That feeling of constantly being tired and waiting for the holidays as much as you love the teaching and the students. I also found it hard to see a career pathway for myself as a young person at 24 years old. The only pathway I could see was to be an assistant principal, which didn’t really interest me. It was very administration-heavy and away from doing the stuff that drove me to education in the first place. So I think it was that combination of wanting that potential for my career pathway along with thinking there surely must be another job elsewhere, where I can use my skills in a different way and be a bit more energised at the end of the year, not just fall into a heap. 

But you know, I think university degrees, whether it’s science, humanities, education, can open you up to all those kinds of things. It doesn’t mean you have to stay in the one field doing it forever. 

Was there a moment in time that was an inflection point for you for needing to make a change?

Clinton: Look, there wasn’t. I actually had been teaching for around six years when I seriously started to think about my next move. I’d tried to go for roles at publishing companies and tried all sorts of things. However, one of the big challenges is that employers often look for very lateral skills. They won’t take someone into a publishing company unless you’ve done publishing for the last 20 years. At least that was the case when I was 25, that is a while ago now! I had actually tried a few times throughout my teaching to try that, but then I went to London at 27 for a year and actually couldn’t teach over there because it’s so wild and the kids are so full on. I thought to myself, I can’t do this, I have to start looking laterally. 

I ended up getting a job at a publishing company. Then I had a job at Transport London as well. I was able to start moving laterally. This is where I felt the inflection point, I felt confident to be able to do it and I could see how I could sell my skills coming back to Australia in a way that maybe I hadn’t seen before. Plus, also having some of that experience from outside of education I guess it gave me what employers were initially looking for. I was able to make that sideways move with more confidence but also a set of skills that were a bit more transferable. 

How do you compare your experience in a tech startup to some of those more traditional or established industries?

Clinton: So, we call ourselves a startup, but we’ve been around for 10 years. So we’re not four people in a room, we’re 150 staff. I don’t think I would’ve made the step from a very secure, safe job in government to a literal startup of a few people. The move to something so small and uncertain would have honestly scared me. However, the fact that the company has been around and was established but it’s still a startup was really attractive. Particularly in terms of wanting to be in an environment where things move faster at a quicker pace. There’s a bit more of a sense of autonomy and responsibility. Those things are really attractive to me, especially coming from more traditional bigger workplaces, even though I’m in a more senior role, you can still very much be lost in the bureaucracy, right?

In any organisation over a couple of hundred people, even as a senior leader, you are one cog of many. So the opportunity to work autonomously and do things rapidly is fairly limited. So in terms of my advice for a young person - I think startups are a great place where you’re going to get exposed to a whole lot of different things. You might go in thinking your role will be specifically defined but it can very quickly expand out because it’s all about getting stuff done and working together. 

Of course, the flip side to this is that you’re moving so quickly and it’s not as defined, so you have to be comfortable with a level of ambiguity. I think if you’re someone that’s wanting to learn and level up quite quickly, then startups can help you do that. It really just depends on people’s level of comfort learning on the fly and being confident in what you can achieve with a can-do attitude versus wanting to know day in and day out what your job will look like. 

What did you have to do to adjust to this new environment when it is so different to a government role?

Clinton: I think I never fit in government! I kind of always broke the mould and even in school I was always breaking processes and getting in trouble for jumping too far ahead, or I hadn’t been through 55 people to get something signed off. So for me, coming into the startup world felt natural. It’s like ‘Oh great, I can move and get stuff done’, and it fits my modus operandi in terms of being creative. 

I think it’s really about being open to different opportunities and to lean in as much as you can. I know that sounds really cliche, but in big organisations, you can just hang back and let others do the work, whereas, in a startup environment, you have to embrace things that come to you with a can-do attitude. Then, with these immense opportunities, you can just come up with your own processes, and ideas and then execute them. I just find it so much more liberating that you can just get in and do stuff, and if you’re up for the challenges I think you can be really rewarded. Having said that, I found it much more challenging in government to be told from 10 layers above me that I had to do something that had no context in relation to anything. 

I feel now I’ve found the thing that gives me energy and you feel like I’m in a work style and environment that really is well adapted to me. Some people spend their whole careers never finding it. I talk to colleagues and friends who have completely different experiences even within a single organisation. You could just be in a part where it’s really autonomous and high trust and another part that’s micromanaged and not feel any sense of autonomy. 

I think you’ve really got to be looking and deciding what kind of workplace you want to be in and what you are going to be comfortable with. Are you the type of person that wants to go work casual? Or do you want to get suited up? I think about these things in terms of myself. What makes me comfortable in the workplace? So I think it’s a matter of coming up with some of those things you are looking for and then going deeper when exploring job ads and interviews. How do they dress? How do they talk? What’s the kind of demographic of those people? Just looking for all of those signs. Have a good look at their website. Of course, this won’t control who your line manager will be or where you’re going to sit - but it should help. 

I think being able to have a sense of who you are right now, noting that it will also change over time, and does the employer roughly fit that? Then if you’re in a role that doesn’t, don’t hang around for too long. Try something new if you can. Definitely don’t be like, ‘Oh I just want this job because my friend got that job or I want this job for the status’. Actually, think about what’s really purposeful and meaningful for you. Whether it’s flexibility, a city office location or remote working. You want to find an employer that matches. 

Let’s chat about Edrolo. What does your team do to support the company goals?

Clinton: Edrolo is a tech publisher. We are a startup that’s been around for 10 years and we are focused on resources for secondary schools to help with their education. The company started with online self-serve videos for students doing senior secondary school and over the last 10 years we’ve expanded that catalogue to now include Year 7-10 across multiple subjects and print textbooks now too. So we sit somewhere in between a new tech platform and a traditional publisher. We are very much focused on helping teachers unlock learning in every student in every classroom across Australia and globally. 

My team is the marketing team. Prior to me starting Edrolo didn’t have a marketing function. So my job over the last 18 months has been about formally setting that up and building out the team and resourcing around that. The main part of it is obviously brand awareness particularly as we are expanding out across Australia to build awareness in new markets. Then, we also work on retention where we already have a strong presence like in Victoria for example. So that dual focus of new market awareness but also building value with schools that already work with us. 

What does the hiring process look like to join your team for young professionals?

Clinton: The usual recruitment process for us is to post a job ad then the pool is open. We look to shortlist a handful of people based on their responses. Then, there’s a first interview where we often assign a task. Depending on the role, the task is very much related to the day-to-day of the role. So it might be something like creating content for a blog, creating social media posts, etc. I don’t like to put time pressure on the candidate though, I set the task as homework and expect the person to bring it along to the first interview. 

During the interview, we chat about what they’ve done and why, and what work they did to create that piece in terms of the context of the company etc. This gives them a chance to explain their work. Then, depending on the role and the quality of candidates at this stage, there would usually be a second interview where the candidate might meet with a couple of other people, a senior leader etc. Then, at that point, we’ve got enough to be able to make an assessment and appointment. That third stage is usually something more casual like a coffee or catch up to assess cultural fit so that they can ask me any questions they might have. It’s really important to me that if they have any niggling questions they ask them so that we can make sure both parties are super happy. That’s the general process for pretty much any role we recruit for. 

With successful candidates, is there anything that helped differentiate them during the hiring process?

Clinton: I would say particularly in the comms marketing space, quality is paramount. Especially if it’s going to be a role that requires attention to detail. I’m often staggered by how many people have typos or errors in their CVs and cover letters. Also if there’s a task with very clear errors such as a typo in the subject line of a draft email, it’s often sadly a red flag for me in terms of someone’s eye for detail. I’m not so fussed about factual errors about the company like not fully understanding our product catalogue - so long as they’ve had a good go at research. 

I’d also say, don’t underestimate making sure that your CV is top quality. I guess the other part to that is showing that you know the company or at least done some research in responding to the role helps a lot. If it’s a generic cover letter or no cover letter at all, that is very easy for me to pass over unless someone’s got some absolute gun skills or experience that really makes them stand out. Doing that little bit of extra work - like half an hour of work - address the letter to the right person, and have a look at the role in detail on the website, it can go a long way. Then, in terms of the interview, it sounds totally cliche but just do the prep and research beforehand. Obviously, you can’t guess everything the panel will ask you but if you show that company you’ve got a good sense of what they do, it just helps build that connection and makes it seem like you’re already a part of the team. Then the more you can do that, the more it feels hard as a panel to not have you. You want to be basically a part of the team without being too over the top where you’re too many steps ahead. Well, that’s what impresses me anyway. 

What should a candidate be asking when it’s their turn to ask questions?

Clinton: There've been some great ones where I’m like ‘Whoa, that’s such a good question!’ I don’t want candidates to ask a question just to ask a question because they think they have to. I want it to be genuine. You don’t want it to be something especially that’s been covered or talked about that isn’t really relevant. If that’s the case don't ask it because you'll seem disingenuous. I think questions like how would the day be structured and what that would look like over a week is always a good one because the candidate can get a good sense of where the priorities are, how the team is structured, and how they like to work. It also shows that you’re already thinking about what it’d be like to work there. 

Another question might be around team dynamics, like ‘What opportunities are there for collaboration?’ How might you be able to work with others especially if it’s going to be a remote role or you’re not going to be in the office as much? It can help with that connectedness to the team. 

How do you think about developing early career talent that joins your team?

Clinton: Well everyone’s at such a different point, right? You want to think about the individual and what they want. Is it more skill-based exposure? At what level? It could be learning a new tool system or process right through to being exposed to strategy and decision-making. It’s kind of like everything and in between. Or is it about a particular role they’re aiming for? Do they want to go out and meet with clients to build up their interpersonal skills? There’s so much within the space of professional development. It should be embedded into day-to-day that people are feeling challenged, not just one conference a year. 

When I think about young talent coming in wanting to learn and grow and be stretched, it’s always about understanding where they are now and what they would like to do next. Some people don’t even know what they want to do next, but they’ll have a little feeling of where they want to improve or focus. Then it’s about looking at what work you’re currently doing or that you’re going to be doing over the next 12 months to allow for that and if it doesn’t, can we then expand the scope to do that? This means the work becomes more meaningful for the business anyway. 

I think often people can put a lot of focus on formal opportunities and training in roles, but I think when you’re young the most valuable stuff is going to come in your job because that’s the stuff you’re going to be able to put on your CV. 

I think you should be looking at the skills you can work on within your job and working with your line manager to identify how you bake those into what you’re doing. Everyone I think should be feeling slightly stretched and growing at any point in time. If you’re not, you need to have a conversation with someone about that. It can get tricky for young people because often they’re in defined roles. You just have to look creatively within that to find opportunities and then propose to your manager, how about I try this? Don’t create new projects or scare them off with something too radical, but think about expanding the scope a little bit to allow for you to grow. Usually, managers would see value in that because there’s usually business value behind it too (or you need to show them the business value in that case). Learning can be really incremental and small within your role, it doesn’t have to be a wild new project that you’re leading. No one is going to care about your future as much as you do, so if you’re not putting in that reflection, and thinking, documenting and prompting those conversations in a polite professional way, most other people won’t do that because they’re too busy. However, there is a lot of agency to be had, and you’ve got to seek out those opportunities and be purposeful as well in doing that. Show your interest and then hopefully the team will come back with more opportunities for you. You have to drive that yourself. 

Learn more about life at Edrolo 

It is without a doubt that Clinton’s story is far from the average and incredibly inspiring. We also think working at Edrolo in your early career could be a really good decision if you’re looking to learn and grow fast in an agile environment. What will you take from learning more about Clinton’s story and how Edrolo hires talent? We’d love to know! Learn more about life at Edrolo.