Dan Brockwell

Building the fastest, fairest pathway to begin a career in tech sales
Co-Founder & Head of School

What was your journey to joining your current company?

My first year of university had two watershed moments that led me to where I am today:

  1. I joined the student ambassador group at social payments startup called Tilt, backed by a16z (who I had no idea about at the time), which led to me joining the team as a Growth Intern. Within 2 months, they were acquired by Airbnb… and I had lost my job. But t was amazed by how quickly we could spread a piece of technology that made the common headache of sending, requesting and splitting payments so much easier.

  2. I stumbled into a student society called ‘BusinessOne Consulting’ which did pro-bono consulting for small businesses. I loved working with an early-stage startup on their biggest challenges, and found it way more practical than my uni classes.

Despite leaning towards the humanities growing up, I became fascinated by tech because of its human impact at scale. I started thinking: how do I put myself in a position where I can build something myself one day. I knew I needed to learn how to:

1) Build products that could scale their impact (engineering).

2) Understand what problems people had and how to put solutions into their hands (sales & marketing).

This triggered a pivot in my original degree and major choices from Finance & Biology to Computer Science & Marketing.

I didn’t know exactly what pathway in tech was the right one for me. So I decided to test out as many different roles, company sizes and problem spaces as possible to figure out what I liked, and my university classes took a bit of a backseat.

After growth at Tilt, I went into marketing at an early-stage restaurant ordering startup called Tayble, marketing at IBM’s consulting arm, UX design at Deloitte Digital, web design at a social enterprise called the Social Impact Hub, sales at Uber Eats, project management at Amazon and operations at an early-stage logistics startup called Ofload, which at the time, was 10 people.

When I was about to graduate, I had formed the hypothesis that my best career move would be joining a growth-stage startup or scale-up in the US in a product, operations or growth role. 

But that was also when COVID hit.

I was working at Ofload while finishing off my degree, and ended up taking a graduate product management offer at Atlassian, figuring it would be more fun and more relevant learning to my goal of starting my own startup than the corporate track.

Throughout this time, I had a bunch of friends & peers coming to me asking me about all these different tech roles and companies, and where to find them.

I got lucky and stumbled into the world of startups early, but it’s a really fragmented experience for university students. I began to realise the broader career literacy of uni students around Australian startups was super low.

I saw a ton of smart, ambitious people go into more traditional paths – like Consulting, Banking and Law – but ultimately hating it. Not many people were considering startups, but there were all these cool opportunities!!

I was often sharing around job listings of cool entry-level startup roles simply because I loved seeing my friends get into jobs they actually liked.

But as I began to send these to more and more friends, I realised it was pretty inefficient to message all of them one by one. So instead, I started a newsletter called ‘Earlywork’ to do this all in one place. It was basically a list of early career roles, along with job search & career advice, and interviews of young startup founders & operators. 

It started with 10 subscribers who were mostly friends, but then I started sharing this with my wider network through hundreds of 1:1 messages and posts on social media, including university discussion groups. Within 2 days, it went from 200 to 600 subscribers which was when I realised, on shit, there was some real appetite for this.

I knew if I went into a full-time role, it would be really hard to take Earlywork to the next level alone. So, over the next few months, I brought on two co-founders: Jono, who was running a recruiting service to help startups hire students, and Mazz, who was working on a newsletter to share her learnings in product management.

From our initial newsletter audience, we saw that a lot of young people didn’t know others in this space but wanted to learn and connect.

So one of the first things we did together was launch a free online community to help young people find tech startup jobs better. In doing so, we sensed that there would be something powerful in aggregating top early-career tech talent across Australia, even though we didn’t know the exact business model yet.

So that was the birth of the Earlywork Village on Slack (as you know it today) in April 2021!

The first two months we really struggled for engagement, but with the help of some early believers, we began to grow the community to a place that’s now over 5000+ members across Australia, New Zealand and Singapore.

Startups started reaching out to us to hire the awesome talent in our community, and so we tested out a bunch of offerings to connect great early-career talent with great tech companies, from a jobs board to a talent search engine to recruiting. Alongside this, we continued to coach and mentor dozens of early-career folks looking to break into their first startup role.

We started to dive deeper into the early-career hiring needs of startups, and realised something strange. In user interviews, talent leaders told us the two hardest roles to hire were engineering and… sales? Yep, sales was one of the top 3 most requested roles by companies reaching out to us, but there was a wider gap between that demand and the number of community members actively looking for tech sales roles than ANY other role. 

Despite that, we were still meeting a ton of ambitious non-technical talent struggling to break into tech, and we  realised that career literacy around tech sales roles was super low. 

There were zero tech sales degrees or bootcamps in Australia, so we decided to start Australia’s first tech sales bootcamp, Earlywork Academy

Importantly, we built our program with a job guarantee, meaning students only pay if they land a tech job within 6 months of graduating. After spending tens of thousands on tertiary education with almost no support in actually getting a job after, we wanted to design our system in a way that aligned incentives to the outcomes that mattered.

Today, I’m the Head of School for Earlywork Academy, leading the development and delivery of our tech sales & job search curriculum, alongside coaching our fellows to land roles, and helping out across admissions, marketing and company partnerships.

What about it makes it your dream company?

The gap between education and careers is mindblowing, and I wake up every day excited to build a model that bridges the two.

When you think about what we spend our time on in a given day, work is one of the largest blocks of time in our lives. In turn, it has a huge impact on your sense of self and mental health.

So it’s crazy how many people I’ve met that hate their jobs, when there are great jobs out there that would be a strong fit for their skillset & values.

It’s a problem that really pisses me off, because access to the right information and training can solve it a lot easier than most people think.

That’s why I want to do as much as I can within reason to help every ambitious person find a job that fulfils them, and we’re still so early on in this journey.

What stands out the most about the culture? 

  1. Extremely high ownership culture: People get to own a lot across a lot of different areas, and have freedom to experiment as they please. We’re not hiring super specialists; we want people that are all-rounders deeply motivated by the problem, who shapeshift to keep leveling up what we do. As a founder, I’ve gone through several iterations of focusing on different slices of the business, and I’m sure it’ll keep changing.
  2. Embrace your quirky turkey: We’re still a company of 4 people but we’ve been really intentional about values since day one. This was one we set from the beginning. We bring a playful, authentic and genuine energy to our work and we try to carry this in our branding: more casual in style, and not bullshit stale career advice.
  3. Community-minded approach to creating: When we build things, we work quite collaboratively with other folks in the industry to get to the best solution. For example, we reverse-engineered our curriculum for Earlywork Academy by sparring with industry sales leaders, and demoed our landing page to our core community ambassadors for a feedback session before launching.
  4. Open Mind, Stay Kind: We have a pretty high feedback culture, but we do that from a place of trust, respect and kindness in working towards a goal we all care deeply about. We have a retro every single week brainstorming ‘roses, thorns and buds’ in our work, we have 1:1s with all team members every week that begin with a vibe check & feedback, and as founders, each of us has 3 personal development goals per quarter that we keep each other accountable on.

How would you describe your company to a 5 year old?

When you go to the shop with your parents, like Target or Kmart, you usually meet a friendly person who is there to help you find something you’d like to buy, like a bicycle or a pair of shoes. 

We can call these different objects “products” and we can call this person a salesperson.

Now when you go back home and log onto your computer, you might see apps like Spotify, Netflix, and Minecraft.

These are quite different to bicycles and shoes, because you can only find them on the computer screen, not in a store. But they’re also products!

They are a special type of product we call “software”, and they’re created by teams of fun, smart people.

On that team, there might be someone who is a salesperson, similar to the person you see at Kmart or Target. 

Except, instead of helping people find shoes or bicycles, they help more people find out about these great software products and buy them.

So what does Earlywork do? 

Earlywork is a special type of school, different to primary school or even university. Instead of English and Maths, our school teaches adults how to be a good salesperson for software. 

They learn how to find people who might buy a software product.

They also learn how to talk to those people and show them how the software product can help them.

Once we teach students those skills, we help them find a job with a team of fun, smart people who create software.

This is also very helpful for the team that creates software, because it’s hard to find good salespeople.

Once they start their job, our students then help their new team find more customers for their software product.

Now in a lot of schools, students or their parents pay school fees.

But for Earlywork’s classes, people only pay if they get a job at the end!

We think that’s the fairest way to help our students :)

What does your day-to-day look like?

As a co-founder in a small team, you get to do a shit-ton of different stuff. It’s very fast paced, requires a high sense of ownership, has lots of ambiguity and diversity work. 

You get to bounce from one thing to another, zoom in and out – every part of the business teaches you something that will be useful for another part. I love it all.

As an example – yesterday I had:

  • 3 career coaching sessions with fellows in the program
  • 3 internal one-on-ones
  • A few onboarding calls to welcome incoming fellows into the program to make sure they’re all set up
  • A team meeting to align on ownership for strategic projects going forward
  • An evening class teaching an Intro to Tech Sales
  • A partnership call to help an Aussie scale-up build pipeline for sales
  • Some quiet time revamping educational materials for one of our sessions
  • Some ad-hoc promotion for a sales role we’re helping one of our partner companies hire for

What advice would you have for someone thinking about starting their own business?

If you want to start your own business one day, here are 3 options you should strongly consider today to put yourself in the best learning position:

  1. Work at an extremely early stage startup working directly with a founder to learn the ropes.
  2. Spend time in different roles getting functional experience across a lot of different areas, so you can see how the pieces of the puzzle come together.
  3. Start something now. You’ll learn a shit tonne along the way. If you don’t know where to start, find something that pisses you off – because if it pisses you off enough, then it’s probably a really painful need. You’ll have an uphill battle if you start a business to solve a problem that doesn’t piss you off. 

Once you start, here are some other lessons that have helped me along the journey so far:

1. If you haven’t nailed the exact problem yet, start by building an audience and figuring out their needs. Building and engaging with an audience is often what leads you to understand the problem best.

2. You don’t need a product or company from day one. Focus on identifying the narrowest, simplest, low cost solution to the very specific granular problem you’ve identified. This isn’t always a tech product. To start, this could be a call to help someone, or writing a piece of content. 

3. Put out something you’re embarrassed by (shoutout Reid Hoffman fr fr). No one cares about your imposter syndrome because they’re worrying about their own. If what you’re putting out is still a solution to an unsolved problem, don’t fret if it’s a bit raw and ugly. The precise aesthetics can be solved later. I made the original Earlywork website on Google Sites (yikes!).

4. …But that doesn’t mean shipping random product ideas as quickly as possible. Start with identifying a novel insight, and have a really clear and opinionated hypothesis on these 6 dimensions in how you build a business around that insight. Understand which ones are the riskiest assumptions that you’ll need to validate, and disproportionately spend time on those. Credit to Sachin Rehki for this ‘Product-Market Fit Narrative’:

  • Who is the target customer?
  • What is your value proposition for them?
  • How will you differentiate from competitors (direct and indirect)?
  • What are your growth channels (both for your first 100 customers and long-term scalable channels)
  • What is your core business model

5. Build the right business, not just a big business. Startups evolve quickly, but it’s useful to be intentional pretty early on about what your values are: they guide your biggest decisions of what to do and equally, what not to do. In the past, we’ve identified business models in the education & careers space that could generate a ton of revenue, but have made a call not to pursue them in the belief that those models may create net negative downstream impacts on broader society. As a team, we aligned pretty early on what the ‘right’ business looks like to us, and we hold ourselves accountable to that.

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