Talent & teams
Career Q&A with Jackie & Elicia
What's it *actually* like to work in VC or for a tech startup?

Australia’s startup scene is booming. So it’s no surprise that there’s a lot of interest in working in venture capital to get a front-row seat while these incredible companies are built.

But what’s it actually like to work in VC or for a tech startup? To help answer this question and many others, we got AirTree’s Partners Elicia and Jackie together for an AMA session on all things career-related.

You can watch the session here.

Or check out the Q&A below👇

Let’s start with Elicia and Jackie’s journeys to Airtree.

Elicia [E]:I started studying Commerce & Law at University, majoring in Finance. But if we go back a little further, I loved studying economics and the sciences at high school. I liked using data and analysis to draw meaning from things. In physics and economics, you’re explaining a phenomenon you see in either the economy or the world and using data analysis to draw those conclusions.

I got an internship with Credit Suisse a couple of years before I graduated in the investment banking team, working in M&A. Looking back, the reason why I chose that career path was it’s quite prestigious, hard to get into and paid well — all things that you shouldn’t make career decisions based upon. But at that stage in my career, that’s what was important to me.

When I started my job at Credit Suisse, I quickly discovered that I wasn’t passionate about investment banking. It wasn’t the life that I wanted. I didn’t look at the senior leadership there and aspire to be them in 10 to 15 years time.

I’d always been fascinated by technology, and my whole family is in the technology industry. One night I got home from work and was on Seek at 3am and found a startup that I ended up joining in a sales role. It was completely different going from investment banking and sitting behind an excel document for 18 hours a day to then being front and centre in a sales role and driving a GoGet all around Sydney selling a SaaS platform to charities to help them fundraise online.

After that, I went to a sales role at LinkedIn. I loved the energy of being around a sales-driven team and dealing with clients. What I really liked about LinkedIn was that we had a huge amount of data on the platform that we could use to communicate value to our clients. So it brought together my passion for a great product, using data and analysis to draw meaning and being very people-focused.

I had always thought if I was ever going to leave LinkedIn, it would be to start my own business, become a founder or join a Series A startup and scale with it. Then a recruiter contacted me about the role at AirTree, and I realised that sitting across a portfolio of the best startups in the country and working really closely with the founders who are building the future sounded fascinating.

VC wasn’t something that I planned to do, but it is perfect for my skill set. I always think of the Steve Jobs quote “You can’t connect the dots looking forward; you can only connect them looking backwards.” If I look back, what I did was follow my passions, move away from what I didn’t like, and move towards what I do like, which led me to a job that I really enjoy now.

Jackie [J]:I grew up in the UK and studied history at University. It’s much more common in the UK to study an academic subject that has nothing to do with what you want to do in the future. In many ways, what I did in that degree was perfect for the job I do today — consuming a vast amount of information, analysing it, and writing up an opinion at the end of the week. As a VC, we meet a founder, try and learn everything about that industry, business model and product to quickly form an opinion and write up an investment paper at the end and make a decision.

I hadn’t thought a tonne about my career while I was studying. I talked to a few friends, and one said “I think you’d be really good on the trading floor”. I applied for 10 jobs, got one interview and ended up in Citi’s grad program. I was the only arts grad out of 40 people and I didn’t know what a bond was — so it was a baptism of fire. As I rotated through different functions, I picked equity derivatives because I thought it was the hardest and would be the most interesting. I spent the next 18 months learning economics in real life and I really enjoyed it. But after that, I started to get bored.

I had a few of my own projects on the side, but I was too afraid to jump out and take the risk. I was being paid very welland questioned how on earth could I be so arrogant or ungrateful to think that there’s more than this.

After three and a half years at Citi, I really wanted to leave and got given the opportunity to set up a business at Merrill. I worked with US Hedge funds and institutions trading European equity derivatives for a couple of years which was fun initially, but again, once I stopped learning, it got boring.

This was an extremely emotional time for me. Eventually, I summoned up the courage with a little bit of help from Tony Robbins to jump out and do the startup thing. My job description was doing anything and everything, and eventually, that role became Chief of Staff. I worked on everything from go-to-market to special projects with the founder.

At the time, my partner and I were getting bored of London, so we decided to move to Australia because we both loved it. I thought VC would be a great way to enter a market and meet loads of people to figure out what company I wanted to start or join. I began in NAB’s venture capital fund and found corporate VC wasn’t for me. It was very jarring going back to corporate after working in a startup. I knew I liked the VC part, so I got to know John, James and a few other people at AirTree, and when the role came up, I put my hat in the ring.

When did you know you wanted to work in VC?

E: I was pretty sceptical at the start. However, working in the Talent Solutions division at LinkedIn meant my role was focused on a product that is all about how the best talent should be open to new opportunities all the time. So I thought I should walk the walk and have a conversation with the team. When I realised how my passions and values were aligned with what AirTree was building, I was inspired.

Like Jackie’s story, in previous roles, I found I’d spend the first 6 months learning everything and the next 6 months putting it into practice. But then I’d be looking for my next challenge. I’m 5 years into AirTree and VC, and there’s just no way you can possibly get bored of this job. You’re constantly learning about new areas of technology, meeting founders and working with some for many years as they grow and scale.

J: I knew I wanted to work in VC 2 years after I started in VC!

I think it’s unsurprising that quite a few of us were sceptical on our way in, as many people don’t think they would want to work in VC because they want to run a business. But if you can’t focus on one particular thing for an extended period, you’re not well-suited to running a startup.

I worked with an exec coach about a year into joining AirTree to grapple with whether I wanted to be a founder or an investor. Through working through things with a coach, I realised it was my perfect job, and I needed to unwrap my ego from the idea of being a founder.

As non-founders, do you think that puts you at an advantage or disadvantage?

J: I think people can be great at VC for a bunch of different reasons:

  • They’re well-connected and can link up founders to global experts easily.
  • People want to work with them because they’re smart, kind, have conviction and move fast.
  • They have operational experience, scaling a business to hundreds of employees and have hard-won lessons that make their advice valuable.

E: It’s not as black and white as saying if you’re a founder, you’ll be an amazing VC, and if you’re not you won’t be.

In an episode of the Acquired podcast, they go into Andreessen Horowitz and how the narrative of being an operator in VC just wasn’t that prevalent until they came along. They pushed that narrative out there because it played to their advantage.

What I do think is absolutely necessary is founder empathy. Behind the scenes, founders go through blood, sweat and tears along the way, and all we see from the outside is just the headlines announcing a massive capital raise.

No investor is going to be able to tick every single box for a founder. So long as you have one area that you’re confident you can add a huge amount of value to that founder, it will help you find the best investment opportunities and convince that team that you’re the right partner for them.

Do you need to have a finance background to be in VC?

J: At school, I found numbers difficult. There’s nothing natural about my relationship with numbers, I just brute-forced my way through. I didn’t know how to do financial modelling before I joined AirTree. I taught myself and was coached by people in the team as I was upskilling. Now I’m a big believer that you can teach yourself anything that you want to learn.

While you don’t need a finance background, you do need an interest. What the numbers meant interested me. I think they’re a way of understanding competitive advantage and measuring success.

E: Rather than focusing on what you did or didn’t study, or what’s on your CV, it’s about demonstrating a hunger and willingness to learn that you can plug into any gaps you have.

How quickly could you pivot out of the VC world if you wanted?

E: I think one of the most natural pivots out of VC would be becoming a founder. You’re in a role where you’re building your brand in the startup ecosystem, meeting heaps of founders and seeing different business models and what happens behind the curtains as they create successful companies. I’ve learnt a lot of valuable skills if I wanted to go down that path.

The other path is joining a portfolio company. AirTree’s portfolio has many different industries and companies at different stages. It would be a natural transition to join one of them and make that my full-time focus.

J: What I’d add to that is, one of the mistakes I made when I was younger was how I thought a career was all about your end goal, and as you climb the ladder the whole point is to get to the top of the ladder.

I wish I’d taken more risks. I wish I’d tried things, and if they weren’t right, I could just move on to the next thing.

Over time, you’re narrowing down on the thing that you actually enjoy. It’s tempting to try and keep your options open the whole time and do the thing that will give you the most opportunities. But unless you actually commit to something and try it, you’re never going to find out either way. Nobody cares these days if you only stayed in a role for a year or two. I would bite the bullet and try more things.

What are some of the uncomfortable and hard things you went through in your career that you’re glad you did?

J: The hardest thing was leaving banking. It had an obvious path, and I made a lot of money. Making the decision to leave was challenging psychologically and mentally. But I feel ever since I left that job and took a risk on myself, everything worked out.

E: When I was in banking, I wasn’t very exposed as a junior in a large team. I didn’t have a huge amount of responsibility weighing on my shoulders. When I moved into a sales role, I had a quota against my head. It didn’t matter how you performed at school or how many books you read; what mattered is whether you hit your quota. I’d never done a sales role before, so it was a lot of pressure. But the skills I learnt there have helped me in my role, as there’s a lot of sales elements in VC.

Have you worked somewhere that didn’t align with your values?

E: I got frustrated with so many things in banking. I felt there were things beyond my control that wouldn’t change the bigger beast no matter what I was doing. My solution to that was to exit the machine and find a different way. I really struggled with that, though, because up until that point, I’d followed a very traditional path. I didn’t want to say I’d failed at anything. I struggled with the idea that I’d be stepping away from something and admitting that it wasn’t for me. But a big part of that was I just didn’t have that values alignment with what I was doing.

J: On the trading floor, the people around me only cared about money and sports. That’s fine for a couple of years because it’s an experience, but I grew increasingly frustrated that they weren’t interested in learning new things or about the world. I didn’t feel connected to those people or their values.

What’s been interesting about moving to another country and starting from scratch has been that I’ve been able to interlink my work and life. I love the people I’ve met through startups and VC; we have so many shared interests, and I’ve been able to learn from them. Being inspired by the people you work with is a real privilege.

Is there an opportunity for value-aligned work in VC?

J: I value learning, building relationships, working with people who are doing hard things, and supporting them. I find that every aspect of the work aligns with my values.

More broadly, we don’t invest in gambling, weapons or porn. We talk about investing in things that are great and that we’d be proud to tell our grandkids about. If you can find the right team, you should be able to do work that aligns with your values.

E: As investors, we can do deep dives and build areas of specialty around things we’re most passionate about. So long as you can build an investment case that stacks up, you can go very deep into areas you care about, like ClimateTech.

How do you get into VC if you don’t have a top tier consulting or finance background?

E: There is no set path into VC. We try and screen this out in our hiring process to ensure we aren’t biased towards top-tier institutions, a particular degree people have done, or a company they’ve worked for.

The first step in our hiring process is asking questions about what kind of investments you would make and what startups you are interested in to demonstrate the kinds of things that actually matter in this role: a genuine passion for technology and a genuine interest in products and people.

J: You might know of Turner Novak from the US; he was in his early 20s, no contacts, not the “right” uni or “right” degree. He created a portfolio of startups he would have invested in and built his Twitter following talking about this portfolio and reaching out to VCs. Over a two year period of putting stuff out into the world, those companies started doing really well. And over time, he’s been able to raise his own fund, purely off the back of hustling and showing his passionate interest.

We frequently turn down people who have beautiful CVs full of wonderful institutions if we don’t think they’ll be able to go out and convince someone who doesn’t want to talk to them to take a meeting with us.

E: On that point, don’t hesitate to reach out to people doing the job and start building your network. That’s a key part of the actual role.

What’s an underrated soft skill in VC?

J: Many people think VC is a finance job, but it’s actually a sales job. Your job is to be able to find great founders and build relationships with them. You will know if you’re that kind of person or not from a young age.

E: You also need to be able to sell internally. You need to convince the founder to take your money and persuade the fund’s partners that this is a great investment. Part of that is done through the written word and analysis, but you also need to build a strong case and show you have conviction in something.

There’s that saying that every role eventually becomes a sales role, but in VC, right from the get-go as an associate, when you enter the investment team it’s primarily as a salesperson.

Do you need a personal brand to get noticed?

E: We’ve never cut anyone out of the recruitment process because they didn’t have enough LinkedIn connections. It helps if you’ve invested in building your personal brand, whether that’s through social media or blogging. That’s something you’re going to use as an origination tool to find great founders, attract them to your fund, and help them build conviction that you’re the right partner for them.

J: People do this job in very different ways. Some VCs are completely under the radar and are extremely well respected by the founders they work with. As a result, they get the right to invest in amazing companies and their personal brand is their reputation of doing outstanding work over a long period of time.

I personally think that getting your voice out there is a great way at the beginning to earn the right to have conversations with the best founders. I find writing to be a helpful way of letting people know what I’m interested in and feel that they know me because they’ve read things I’ve written. Everything about it is terrifying. Hitting publish on a Tweet for the first time is terrifying. The same goes for your first Medium post. My first seven Medium posts have less than 30 views. I was just writing into the ether for years before anybody cared. But you have to get over that fear, and you do that through repetition. You can feel safe in the knowledge of knowing that even if you say something stupid at the beginning, nobody’s listening.

What’s a typical day like in the life of a VC partner?

E: Every day looks pretty different. I try and bucket into 3 broad categories:

  • Origination and finding the next best investment: We obsess over making sure we’re there to back the best founders coming out of Australia and New Zealand every year. We’re always meeting with new founders and hearing about how their work is going. We think about new investment theses, what the world will look like in 10 years time, and who the great founders are making that come to life.
  • Diligence: if we find a great company and founder that we’re excited about, we write an investment paper to build a case to invest in that company. It involves a range of different things from high-level market analysis to speaking with their customer, using their prodigy and going through financial data — it changes depending on the stage.
  • Portfolio support: we might have a board set in our investments, and if we don’t, we have regular catch-ups with the founder to support them through their journey.

I try and block out one day a week to get deep work done, thinking about new areas to invest in and writing investment areas.

J: This is leading me towards a question that nobody has asked, but I feel like someone should: Who is VC not for? It’s not for people who like to work on one thing for a long, sustained period. You won’t have that opportunity to do that as you’re always context-switching. It’s not for people who like to get deep into the weeds of projects.

We’re looking at so many different things all the time; our job is to be high-level, broad and shallow rather than narrow and deep. For some people, that’s not as fulfilling as feeling like the project owner, e.g. releasing a product feature over a three to six month period.

You’re working for yourself, by yourself a lot of the time. We do collaborate, but you do research by yourself and often have one-on-one conversations externally. You need to be comfortable being self-directed and working alone.

Favourite resources for staying on top of everything happening in the VC and startup world:

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