Q&A with Anna Osipov Heymann from OIF

Bronson Fernandez
Bronson Fernandez
January 25, 2023
Q&A with Anna Osipov Heymann from OIF

OIF Ventures is a leading venture capital firm that invests in high-growth and disruptive Australian technology start-ups. Having raised three funds to date, OIF manages over $500 million of investor funds.

In March 2022, Mastt raised $9.5 million in a Series A funding round led by OIF Ventures. We chatted with Anna Osipov Heymann from OIF who worked closely with us during the fundraising process.

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Can you tell me about your journey before joining OIF Ventures?

I hope it’s not too complicated. I was born in Ukraine and raised in Israel. My first job at uni was in a family office where we did angel investments. We were making very small investments into start-up companies with nothing more than an idea but the job taught me everything I need to know about investing in tech companies and early-stage investments. I stayed there for six years, then an established Venture Capital office in a full-service corporate law firm.

I spent five years in New York when my husband relocated with his company, joined a retail tech start-up, and raised their series A in the US. I did that for three years in between having two baby girls before our second relocation to Australia.

I'd never been here before, but I heard these amazing stories about Australia as a great country for work-life balance. Compared to Israel or New York where you have very little time for yourself outside work, Australia was a better choice for us.

We moved here with no family and only a few friends. At that time I was considering between going back to my start-up life and the career I’m always passionate about with early-stage investments. That was when I met one of the partners here at OIF.


Do your kids also like living in Australia?

If you ask my kids if they're American or Australian, they'll say Australian for sure.


What would you say about Australia's start-up space?

The Australian community in New York was large, but the big companies were only Atlasian, Canva, and Afterpay. I didn’t know how the ecosystem looked in Australia. I thought it was super small and they were more focused on green tech, water tech and fin tech than anything.

When I got here and started to be more involved, I was quite surprised at how big and pumping the space is and how many great companies are coming out of Australia. Of course, it's still quite new, so you don't have a lot of third-timers or fourth-timers. But I can tell you we’re getting about 20 decks per week, all inbound, which is crazy. I'm meeting an average of 5 to 8 new companies a week. The biggest verticals are: FinTech, Prop-tech, Ed-tech and Software.

It doesn’t mean that we look at verticals to decide which start-up companies to invest in. We invest in founders. You know you can work with a team when you can connect to their founders, see that the co-founders have great dynamics, and their teams and traction look good. We see it as a long-term relationship. We know we're getting into it for at least 6 to 10 years and we're here to support our portfolio companies.

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Anna (middle) and the OIF team.

What did you see in Mastt that made you decide to invest?

We saw great dynamics between the co-founders, Jamie, Doug, and Raman. As part of the legal due diligence and commercial due diligence, we called your existing customers and asked them “What is it like working with Mastt? Would you like Mastt to develop any new features in the future?” or “Would you invest personally in Mastt if you had the chance?”

Those 30-minute calls were to understand exactly how your customers are using the platform and their use cases. We also called your potential customers, someone that doesn't use Mastt, to ask if Mastt is of interest to them, and if they see the big value this platform can bring them.

With Mastt, we also did a technology due diligence process with Jamie and Doug. They had to be able to show us the product roadmap, the features you'll be developing in the next five years, and the self-service version.

Those conversations came before we invest. We looked at your competitors, how big the market is, and your potential of going global. We need to feel very comfortable around the product to make the decision.

Three project management professionals smiling in front of a media wall
Anna (left) at Mastt's 3rd birthday party.

Describe your daily job as an investor

It's very hard to give a specific answer to that because yesterday didn't look like today at all. But in general, I’ll start my investment with deal flow work, which is the first meeting with new companies that we’re considering potential investments.

Sometimes I will take a step back when it is too early for us or it's not a tech business. But once I find a company that meets our criteria and offers interesting products, I will take it to the rest of the team.

Let’s say the traction looks good, the founders are great, the market is big enough. Then we start a process of due diligence, then the deal goes to the IC (Investment Committee). Next is deal negotiation, basically working with the lawyers, negotiating the terms of the deals before we close and finalise the deal.

No two days are the same because it depends on the industry and the size of the company. Today I'm speaking to a female-led bra company, then straight after that I’ll be talking to a cybersecurity tech. Then an hour later, I'll be talking to someone in solar tech. Every day you get to meet so many different people, founders, ideas and companies.

A woman speaking among a group with other women about project management
Anna at the Brisbane Startup Bootcamp.

What's been your biggest career mistake?

If you asked different investors they would have the same answer to this question.

We chose to not invest, or not invest on time into a specific company that now became a crazy unicorn. Not to mention the names, but I could invest in a very, very successful company today with a very small kind of check back then. The founders were great, and everything else was great. It was just way too early, and the risk was high.

Then the space became so attractive that the next round was too expensive for me. I kind of live with it every day, but it is what it is. And that’s not the only one.


Are you a different person at work and at home?

My short answer is no, I'm not that type of person.

When I’m at home, I’m the same person as you see here. I think it's important particularly in our space to stay the same, be ourselves, and be very human.

I see our companies as customers but also as people I would love to grab a beer with after work. I want them to see that I’m here for them and to help them grow.

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