Founder advice
Evolving yourself as CEO for the next stages of growth
Did you embrace the title of CEO from day one? Or figuring out if it fits now? Ben Thompson shares his experience.

Being a founder and being a CEO aren’t the same thing. While there’s no prescribed time or trigger for a founder to transition to CEO, you inevitably reach a point where you go from working in the business to working on the business. 

Whether you embraced the title of CEO from day one or you’re figuring out if it’s the right fit for you now, there’s a lot to be learned from founders who have been down this path before you.

With three companies of his own – Employment Innovations, KeyPay and Employment Hero – under his belt, Ben Thompson is one of those people. Ben’s ability to consistently reinforce his vision and lead from a place of authenticity is what many founders aspire to, and we’re lucky to have him share his principles and practical how-to's for evolving yourself as a CEO. 

The 4 key things a CEO can do to enable success

From writing a master plan to embracing a healthy level of paranoia, Ben boils down his experiences into 4 key things that have become force multipliers of his success:

1. Write a master plan that’s based on first principles

Ben wrote a business master plan around the time of Employment Hero’s Series A. This 2-page document based on first principles has served as an instruction manual for all employees and a blueprint for Employment Hero’s future. 

“To sell your vision succinctly, you need to write down a master plan that anyone can read and quickly understand what the business will look like in 10 years,” says Ben. 

2. Create and maintain an operating rhythm for your business

In the early days of Employment Innovations, Ben attended a Rockefeller Habits workshop with Verne Harnish focused on instilling principles of how to run a business. 

One of these principles was establishing a quarterly theme. “We run this quarterly cadence without fail, and it’s been key to our ability to scale the business, pivot quickly and stay agile,” says Ben.

3. Balance insane curiosity with a healthy level of paranoia

Every day is a race to consume as much knowledge as possible for Ben, from podcasts to YouTube – to trying to read or listen to a book a week. 

“Every week begins with paranoia and ends with a celebration,” says Ben. “I start Monday as though I’ve got a huge mountain to climb and everything’s on the line. I hope by five o’clock on Friday I feel as though I’ve done the very best I possibly could have within the week.”

4. Build a network that offers perspective and support

Throughout his career, Ben has built his network and sought out forums where he’s found confidants, friends and a support system.

“Seeking out the perspectives of people who are far smarter and more successful than I ever will be, has categorically been one of the most important things I’ve ever done,” says Ben.

Ben and the Employment Hero team at their 2021 Christmas party


Prioritise time during the early, scrappy phase

• Commit to a quarterly strategy
• Define a single success metric for the quarter
• No Milkshakes!
• Create a quarterly theme

The first couple of years of getting Employment Hero off the ground were a blur for Ben as he was still the CEO of his two other companies. Over time, he made the transition from “doer-in-chief” to “company-builder-in-chief”. The one constant throughout was that he always owned the quarterly review process.

“Every quarter, we ask ourselves the golden question of ‘What can we achieve in the next 90 days that will take us as far as possible from where we are today, towards our big, hairy, audacious goal?’” says Ben. 

The process involves the leadership team coming together for a couple of days to discuss their answers to the golden question, backed with data. The answer is usually an existential threat to the business or a massive opportunity. Then, you should find one key metric that represents success or failure.  

Before you take a step further, assess whether the one big thing for the quarter is a “milkshake”.

“A milkshake is a term we came up with, which is what happens when you blend many things into the one big thing to keep everybody happy,” explains Ben. “About 3 weeks into the quarter, you realise this isn’t one big thing, it’s 3 or 4 things, and there’s no way you can do them all. You have to be vigilant that you don’t create a milkshake and launch that at the start of the quarter.” 

If you’re confident you’re not serving up a milkshake that quarter, move on to turning that one big thing into an engaging thematic that keeps your team laser-focused on achieving it every day. 

Take Survivor Island as an example of a quarterly theme. After realising the company had become siloed and almost tribe-like, Ben and the leadership team decided to focus the quarter on breaking down those silos and encouraging collaboration. Teams wore bandanas, and by the end of the quarter, after coming together and launching and delivering new projects, they all threw their bandanas in a bucket, and started wearing the same one. 

Tactics to keep the theme top of mind throughout the quarter include:

  • Establish a theme team: Whoever owns the goal that quarter (a member of the ELT or Ben), forms a theme team across the business. As part of the onboarding process, Ben encourages new starters to join the theme team to be at the heart of the strategic project for the quarter.
  • Internal comms: From a fortnightly update at the team all-hands to a theme channel in Slack, it’s up to the theme team to use internal comms to make it pervasive throughout the business.
  • Bring it to life in the office: “Anyone who’s visited one of my businesses in the last 20 years will know there’s a quarterly theme because the whole office is branded with decorations and swag,” says Ben. 
Oktoberfest celebrations in 2019 to mark the success of the theme 'Opportunity Knocks'

Know where to go deep and where to go wide

• There are areas a CEO can't delegate – go deep on those
• You can enable success through your team in other areas – go wide on those

Having some discipline about what you spend your time on starts with knowing what you don’t know and what you’re good at, and then building a team to fill those knowledge gaps and to delegate tasks to. 

Delegation is a superpower that takes a lot of practice, and it’s not always easy for a founder to relinquish control. For Ben, it’s all about reminding himself of what he is uniquely positioned to do as the CEO and going deep on those tasks. The rest he goes wide on. Here’s what that looks like:

Ben goes deep on:
  • First principles
    “You have to go deep into the details of the first principles of the business you’re selling. I research every aspect of the business – employment, legal and financial – of every market. You need to be constantly learning.”

  • Vision, strategy, narrative and culture
    “I’ve been deliberate about creating a workplace I want to work in. When I worked in finance and insurance, I hated wearing a suit, taking a briefcase to work and going up 30 floors to my desk. As soon as the business starts to look or feel like that, I’ll break it down and make sure it’s the happy, exciting startup culture I’ve always wanted. Protecting culture is important for your own sake, if nothing else.”

  • Sales and service
    “I’m the first person to call a prospect or get involved if there’s a service issue. There’s nothing more powerful than having the CEO on the line and saying sorry if you’ve screwed up and taking it on the chin.”

  • Capital raising and investor relations
    “The advice I got early on was never to appoint an advisor for your capital raise. Your investors want to know who they’re investing in. And staying in touch with investors is important.”
Ben goes wide on:
  • Admin and systems
    “I hate admin. And if there’s a task that requires doing the same thing multiple times in a day, it’s not for me.”

  • Technical skills/Engineering
    “I don’t have great technical skills. I know just enough to know if somebody’s bulls**ting me, but no more.
  • Accounting, compliance and HR
    “These are some of my weaknesses, and I’m not good at doing them repeatedly.”

Shift strategies and behaviours in each growth phase

• Stage 1: trust yourself and commit to building something
• Stage 2: SaaS is expensive; there's no going back
• Stage 3: Obsess over your metrics
• Stage 4: Scale with experts
• Stage 5: Bringing four pillars into one platform

To achieve your company’s business goals and milestones, you need to be ready to switch gears at any time as you grow. In hindsight, Ben can see 5 distinct gear changes in his journey, each with their own lesson.

Stage 1: The Innovator’s Dilemma

After reading Clayton Christensen’s book The Innovator’s Dilemma and Marc Andreessen’s article Why Software is Eating the World, Ben was convinced he needed to create a digital platform.

Stage 1 involved taking a team out of Employment Innovations and committing all of the working capital from there and Power2Motivate, to building Employment Hero. In the first three years of the business, Ben was the CEO of all three companies, which he says is not advisable in hindsight! 

Stage 2: Burn the Boats (Series A)

Juggling multiple businesses meant Ben was burning time, energy and money. Something had to give. 

“As we started to find product-market fit, I was investing every dollar into Employment Hero, but that wasn’t enough to get the business to breakeven. We needed a lot of cash to grow as fast as possible,” says Ben.

After realising the options were either go bust or raise capital, Ben had a “burn the boats” moment before raising the Series A, which involved appointing CEOs to his other businesses and committing 110% of his time exclusively to Employment Hero. 

Stage 3: Achieve Escape Velocity (Series B, C)

As Employment Hero emerged as its own distinct business, it was all about achieving Escape Velocity, a term Ben borrows from the book of the same name on “overcoming the pull of the past and reorienting the organisation to meet the new era of competition”. 

During this stage, the priority was scaling Employment Hero as a SaaS business, which meant a hardcore focus on metrics.

“John Henderson [Partner at AirTree] was obsessed with our metrics – breaking them up, looking at them in different ways. It felt like a fair bit of hand-wringing, but it was an important lesson because once we got our core unit economics and capital efficiency right, we knew that we could grow the business and raise capital,” says Ben. 

Stage 4: Get out of your own way (Series D, E)

With their unit economics down pat, Employment Hero began scaling quickly, but the leadership team weren’t scaling themselves at the same pace. 

“Every 6 weeks, someone would come to me and say, ‘We’ve got a big problem. We can’t solve it. Everyone’s too busy,’” says Ben. “If you’re going to double or triple your growth every year, you need to be planning well ahead to get out of your own way.”

While generalists were integral to building Employment Hero, it needed experts to bring it to full scale in key roles that none of the existing team knew how to do well.  

Stage 5: Drive the strategy & narrative

8 years on, and Employment Hero is now a unicorn with its first-ever acquisition – KeyPay – locked in. Now, driving the overall company strategy and narrative is Ben's most important work.

“My role is to make sure our strategy is sound and keep everyone focused on our narrative. We’ve got 4 pillars to the business, and we’re bringing them all together in the platform. When we achieve that, which we are, we’re in a strong position,” says Ben. 

Stay genuine and accessible

• Invert your org chart
• Over-communicate
• Give recognition
• Make sure you're having fun!

There are seemingly endless demands on your time as a founder-CEO. It’s all about finding ways to maintain visibility, accessibility and accountability between you and your team, so you can stay connected and focus on your time on what matters.

Invert your org chart

One of the key pieces of advice Ben has, is to invert your org chart so that the people who service your customers are the ones that get all of your support. 

“As soon as I saw that [inverted org chart], it made complete sense. The CEO is typically furthest away from the customer, so it’s my job to serve the people at the top in sales and support roles, as they’re the most important people in the business,” says Ben. 


Ben believes the only time you’ve communicated your strategy, values and principles enough is when somebody says to you, “Can you please shut up?”. Let people know what’s coming, so they can figure out how to prepare for it.

“I spend more time talking about what we’re going to look like in 3 years from now than I do about what’s happening tomorrow,” says Ben.

Give lots of recognition

The job of the CEO is to be a cheerleader, and Ben believes you can never provide enough recognition. 

“We’re just big kids. We love the gold stars, celebrations and rewards. Just because we left primary school 30 years ago doesn’t mean that those principles aren’t relevant to us today in the workplace,” says Ben. 

Have fun!

Inspirational quotes about the startup grind splashed across stock photos aside, when you’re doing your life’s work, it’s essential to have fun at the same time. 

“There are times when I’m not having fun. I have to stop and restructure what I’m doing to make it more enjoyable,” says Ben. “When you’re having fun and having a laugh, people find you much easier to talk to and engage with than if you’re just a grumpy old bugger!”.

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