Ashton Tuckerman, Managing Director at TwentyTwo Digital, joined the Women in Digital community for a masterclass on what it really takes to move from specialist to strategist, and why doing great work is not, on its own, a career strategy.

We have all seen it happen. Two people are equally skilled at their job. One gets promoted into the senior leadership team. The other stays exactly where they are, wondering why the quality of their work was not enough. What is the difference?

In her session, From Specialist to Strategist: Elevating Your Digital Career and Personal Brand, Ashton drew on more than 14 years building brands and leading marketing teams across organisations including Flight Centre, Youfoodz and Havas, along with an MBA from the University of Queensland that took her all the way to Harvard Business School for leadership training, to unpack exactly what changes as you move up. Her message was clear: what got you here will not get you there, and levelling up is not about leaving your specialist expertise behind: it’s about adding another gear on top of it.

Strategic Thinking Means Knowing What Altitude You’re Operating At

Ashton’s first lesson was about learning to zoom out, and she was quick to clarify what that does not mean. Zooming out is not about becoming a permanent big-picture thinker. It is the skill of recognising what altitude a situation actually requires, whether that is staying zoomed in on the detail, connecting the work to the people executing it, or stepping right back to ask what is happening across the business, the industry and the market.

Different levels of a business care about different things. A specialist asks which channels and audiences to optimise. A manager asks whether a campaign is on track. A business leader asks whether the function is delivering the growth the business needs. Knowing who your stakeholder is and what they are accountable for is what lets you connect your work to what they actually care about.

This builds towards what Ashton calls being commercially curious: understanding how the business makes money, what a customer is worth, where the business is investing its time, and what its biggest constraints are right now. You do not need to become a finance expert. You need to keep asking the questions that a business leader asks.

That curiosity also changes how you show up in a room. Ashton’s advice was to shift from feeling like you need to have the answers to feeling confident in the questions you ask: what are we actually trying to achieve, what happens if we do nothing, and what are we saying no to if we say yes to this. Good strategists work backwards from the outcome rather than jumping straight into tactics, and they bring a recommendation, not just a list of options. As Ashton put it, “based on what I know, my recommendation is this, because of these reasons” builds far more trust than laying out the pros and cons and stepping back.

None of this requires perfect information. Ashton’s team uses a simple test for making decisions under ambiguity: is this a door you can walk back through, or does it close behind you? Reversible decisions do not need to wait for certainty.

Strategy Is a People Skill

The second shift is about looking around you. Past a certain point, your impact is no longer determined purely by the quality of your own work. It is determined by your relationships, your trust and your ability to read the room.

Ashton’s advice here was blunt: don’t ask, don’t get. Do not assume people know what you want. If you want to be more commercial, ask to see the numbers. If you want exposure to senior stakeholders, ask to sit in on the meeting. If you want the opportunity, say so. The worst outcome is a no, and a no tells you something useful too: whether the people around you are willing to bring you into the rooms you need to be in.

This extends to your network, which Ashton described as building over time through small, consistent connections rather than grand gestures. One solid networking event a quarter, a message when someone changes roles, a coffee catch-up here and there. Quality over quantity, sustained over years, turns a network into a genuine opportunity.

Be Deliberate About Where You’re Going

The final shift is about looking forward. Ashton does not believe in rigid five-year plans, which she finds restrictive and limiting to opportunities you have not thought of yet. Instead, she recommended setting thematic goals: what industry excites you, what kind of work environment suits you, and importantly, what gives you energy versus what drains it.

A practical way to get deliberate is to look at job ads and position descriptions for roles that interest you, and to talk to the people already doing them. Ask your manager directly what the gap looks like between where you are and where you want to be. Then make it tangible: what does that role actually own, what decisions does it make, and what is it known for?

That last question points to the real work of career progression: closing the gap between what you are known for now and what you want to be known for. You do not stop being the person who is great at ‘Google Ads’ for example. You build the layer on top so that, eventually, people say you know how to turn complex data into business decisions.

Keep Your Receipts

Ashton’s practical toolkit for building a personal brand starts long before you need it. Keep a running record of your wins, your feedback and your results, so you are never caught with a mental blank in an interview or a promotion conversation. Keep an ideas bank for observations and content you want to share. And keep it somewhere personal, not locked inside a work system you will lose access to if your role ever changes.

Her final call to action was to feel the cringe and do it anyway. You cannot be known for your thinking if nobody ever sees it. Sharing your perspective, whether that is on LinkedIn or in the room, is what makes your expertise visible beyond the people you already work with. Value does not automatically create visibility. You need both.

About Ashton Tuckerman

Ashton Tuckerman is Managing Director at TwentyTwo Digital, a Brisbane-based female-led digital marketing agency. Over more than 14 years, she has built brands and led marketing strategy across organisations including Flight Centre, Youfoodz and Havas, moving between specialist and generalist roles and working her way from Account Director to Chief Marketing Officer along the way. She is a recent MBA graduate of the University of Queensland, completed leadership and management training at Harvard Business School, and is an active mentor through the Assisterhood program.

This masterclass was hosted as part of the Women in Digital members’ webinar series. Want access to sessions like this? Learn more about WID membership.