From 2 million users to 35 million: What hypergrowth taught former Linktree product director Jessica Box about leadership

Jessica Box held senior product roles at Australian unicorn tech company Linktree for more than three years. In this article, which was first published on Substack, she shares what she learnt about leadership during this time of rapid growth for the company. 

When I was the Managing Director of Girls in Tech Australia, I was fortunate to meet some of the most inspiring leaders around the world who are masters of their craft and driven to do business with purpose.

One of those people was Alex Zaccaria, co-founder and CEO of Linktree.

He sponsored the Girls in Tech Australia conference the year after Linktree first launched and I remember being impressed by how early the company was investing in supporting women to find a better path into tech. So when the opportunity to explore working with him arose, I leapt.

This connection to purpose and having an impact on the world through my personal values of curiosity, growth and courage has been the north star for how I do work and life. So when Alex said to me ,”I want to leave the internet better than I found it”, I knew I’d found something special.

I joined Linktree as the first leadership hire outside of the founding team, focused on building the growth engine. There were 16 people at the time — engineers, designers and three founders with a fountain of ideas to change the way the 2 million creators use the internet.

Over the next three years the company scaled globally to 200+ team members, 35 million customers and $1 billion in value. I tackled meaty problems across product, growth and analytics with some of the sharpest minds across the tech industry.

Three words to describe the journey: wild, hard, rewarding.

A couple of weeks ago I left Linktree to embark on my own startup journey as I look to create equal opportunities by making knowledge accessible to all. But before jumping in head first, I thought it was critical to stop, reflect and memorialise the life-changing experience I’ve just had.

Navigating hypergrowth is not easy, in fact, it will take everything you’re willing to give, but you do gather invaluable learnings having travelled a road not many have been down.

So, what are the top lessons I learnt from leading Linktree during hypergrowth?

Let’s dive in.

Design your culture and be the custodian of greatness

What is culture? It’s the makeup of our behaviours and operating practices that ensure we’re living our values every day.

When a startup is 14 people it’s easy to ‘feel’ the culture in how the company operates. It’s often unspoken, intangible and almost more exciting that way as the early team is intrinsically built around the founder’s core values.

Quickly, as you add more people, it’s critical for a company and ultimately its leaders to be deliberate in codifying the values and how they’re lived through behaviours and practices that drive greatness. ‘I want to leave the internet better than I found it’ is the kind of purpose-driven ambition that sets the tone for big thinking. It is imperative to leading a company through hyper-growth, going from bootstrapped to venture-backed and weathering brutal market changes.

Over time as different leaders came into Linktree I saw how important it was to set a high bar for both behaviours and operating practices across the company. Linktree’s current CPO and former CPO of Headspace, Sam Rogoway, shared an exceptional book with me that crystalised why this is important: Multipliers. I also saw how making the intangible, tangible allowed people to opt-in and out of Linktree based on alignment with who they are. Values help ensure you have the right people, all rowing in the same direction to achieve outsized impact.

Here’s how you bring your values to life through behaviours and operating practices:

Leaders are the drivers

As part of the early leadership, I worked closely with Alex, Nicky and Anth to codify their values into the fabric of the organisation, with each function responsible for bringing the vision to life. From hiring, to accountability and giving feedback, I was very deliberate in ensuring behaviours from my teams aligned with the company’s expectations. Jane Martino taught me to embody feedback as a gift and ‘to be clear is to be kind’, as Brene Brown said. I found on every occasion it was best to be direct with team members when delivering challenging news, addressing underperformance or sharing company changes. Don’t shy away from it, embrace it and you’ll see people raise the bar elsewhere as they learn.

Use rituals to create psychological safety

Stick by this and never budge. What’s even more important in leading for leaders is helping your team avoid hiring the wrong person for the sake of speed. Maintaining the bar by introducing a ‘bar raiser’ interview with someone not directly involved in the hiring pipeline can be hugely valuable here. I’d introduce this as early as possible in the org’s development — I learnt this the hard way!

What was hardest about this leadership lesson?    

Culture is ever-evolving. The hardest lesson of all is recognising when your values and the companies have evolved differently. What gets a company from zero to one, isn’t always what’s needed for what comes after and that is entirely okay. More than that, it’s normal.

Key learning: be deliberate in how you build culture by living your values in behaviours and operating principles.

Treat your organisation like a system

Hypergrowth makes for a lot of growing pains. Ouch.

By moving through the different stages at light speed (or building the plane while you’re flying it), you quickly realise to level up as a leader you need to be working ON the business and not IN it. This means treating the organisation like a system that needs the right fuel for success.

I built product growth, growth marketing, analytics, product marketing, product partnerships, creator partnerships and region growth teams during my time at Linktree. From this experience I saw how important it was to break down and iterate structures that will set the company, teams and ultimately individuals up for success. I also saw how important it was as a leader to be relentlessly focused on ‘playing for Linktree’, particularly during the challenging times we saw during both Covid and post-Covid as the bull market became bear.

Some characteristics that make up a successful system:

Create strong cross-functional partnerships

This sounds simple but is the most challenging and requires constant iteration based on the company stage. Linktree used OKRs to be deliberate about the outcomes expected from company altitude, down to team level. One objective and three key results work well, as does a traffic light session mid-quarter to review pacing and course correct if required. Setting the right metrics in the form of OKRs helps the system do fewer, bigger things.

There’s no perfect org design

Coatue’s Chairman Dan Rose said this to me early on and it stuck with me. It’s critical to optimise for productivity and remove barriers to achieving that in how the org works. Think ahead on the structure you need, but also be comfortable changing to meet the outcomes of the business, like removing layers to move at pace or sunsetting projects if they’re no longer a priority. Be transparent with the team that things will continue to change in the future.

What was hardest about this leadership lesson?

If there’s one constant in hypergrowth, it’s change. The hardest part about building for the system and not the individual is the impact change can have on people. When Linktree went through redundancies last year I made the best decisions for the business and ultimately what the system needed at the time, but that doesn’t mean it’s easy. The lesson I took away from that stage is to remain true to who you are by setting clear intentions for how you want to show up and people will understand.

Leadership learning: you’re responsible for the effective operation of a system that delivers focus for teams to achieve outcomes.

Know the value of an unfair advantage

Typically if you’ve reached hypergrowth you have an unfair advantage within the makeup of the business that has been created by the first two lessons. A large problem is being solved and customers are the fuel for continued success. This is often called a moat and is what protects a business from competition.

I remember vividly the day Linktree became the category noun for ‘link in bio’. Searches for Linktree had more than eclipsed ‘link in bio’ to the point where customers understood Linktree to = link in bio. A brand moat had been created that gave the business an intrinsic durable early advantage.

I’d not seen something so large and powerful in action before. Customers quite literally became the voice for the brand in times of crisis, like when Elon Musk accidentally blocked Linktree for 12 hours.

What knowing the value of a moat looks like:

Deepen existing unfair advantages

Monetisation is a critical lever to make the most of a company’s market position and capture value. An interesting example I saw work well for Linktree was revamping pricing. The initial SaaS pricing had been set early, before the category exploded, with only one plan tier available. Over 12 months we reviewed the value being generated in the market, customers’ propensity to pay for specific features and ultimately launched new prices as well as the introduction of two new plans. Michael Stocks and I were partners in crime in capturing more value from the existing unfair advantage that helped customers better opt in to the right product for them, which also drove outsized impact on business outcomes.

Expand to additional unfair advantages

Switching costs and network effects are two moats that are often the hardest to build but the most durable. A gap Linktree had in the product for some time was the ability for creators to be able to monetise directly which introduces higher switching costs in a relatively low switching cost product. Due to the brand moat, I drove bringing on partners like PayPal, Square and Spring who were open to partnering exclusively thanks to the trust built in the market (launch example here). More importantly, this added significant value to customers and saw exponential growth organically following its launch.

Keep an eye on the market, but don’t get distracted

It’s easy to focus energy on what your competitors are doing, but what’s harder is determining the difference between signal and noise in how they’re going to market. Linktree’s market is unique where competitors came in thick and fast to replicate the product but were unable to make a dent due to the brand moat. Putting this into context, we maintained an 85% market share of the category during my time. The team looks to leadership for their reactions to competitor releases so it’s critical to stay the course and remain focused on the long term, but alert to repeat signals as the market changes.

What was hardest about this leadership lesson?

If you don’t continue to invest in widening or deepening your moats, you’ll find yourself in a tough position. Often this can be caused by too much opportunity. It’s the leadership’s responsibility to provide a compass for the company to know what the unfair advantages look like to capture as much value as possible.

Leadership learning: be strategic in looking to the future by not resting on your current market position.

Summary

The three major lessons I’m taking with me into what’s next from leading Linktree during hypergrowth are:

1. Be deliberate in how you build culture by living your values in behaviours and operating principles.
2. You’re responsible for the effective operation of a system that delivers focus for teams to achieve outcomes.
3. Be strategic in looking to the future by not resting on your current market position.