Doubling Down: Promoting Jessy to Principal

Our Doubling Down investment notes deep dive into our follow-on decisions. We reflect on what we got right, what exceeded our expectations, and why we're excited to continue our partnership.

Last May, Jessy joined our team as our first hire - as an Investment Manager and Head of Community. Jessy first joined our motley crew as a community member; after six months of working with us ‘after work’, she built the conviction to go all in - just a few weeks after our public launch. You can read our initial Investment Notes on Jessy here.

Since then, she has played a significant role in fundraising and community building, as well as leading deals end-to-end, and architecting the infrastructure to allow portfolio companies to access operational support from AfterWork’s community of one hundred operators.

Today, we couldn't be happier to announce her promotion to Principal.

As any founder will tell you, people decisions are among the most important decisions you make. Jessy has proven beyond a shadow of a doubt that our initial investment in her is one of the best we’ve made so far, including in ways that have exceeded our expectations. As an Investment Principal, Jessy will take on more responsibility within the Investment team; she will continue to lead deals end-to-end, shape our investment theses, and act as a trusted advisor to founders.

If you’re a pre-seed / seed stage startup looking for investment, check out our pitch deck for founders, and get in touch:

Get in touch!

Jessy will remain our Head of Community; an operational role that complements her investment one - increasing her empathy and understanding of what it’s like to build, scale, and defend a core business function.

In this note, we break down what we got right in our original investment thesis, what has exceeded our expectations, and what we’re excited to see going forward.

What we got right

She brings boundless curiosity and intellectual rigour to the investment process

Jessy isn’t afraid to champion the founders who she believes in. She consistently advocates for all kinds of founders - in particular underdogs - from first meeting to final investment decision. But while she’s a fearless champion for founders, she remains thoughtful and adaptable, and challenges AfterWork’s mental models and biases in a manner that builds robustness in both our portfolio and team.

Additionally, we cannot overstate the extent to which she’s been responsible for diligently architecting the structures to allow AfterWork’s community of operators to contribute to our investment engine - helping operators evolve their understanding of how to make investments in the next generation of iconic tech startups.

She works tirelessly for portfolio companies

Jessy has led deals end-to-end, and remained the main touchpoint for those companies. Along the way, she’s earned a fan-club of founders - no matter the task, she makes a habit of going above and beyond. She’s as comfortable pushing founders’ thinking of big strategic decisions as she is rolling up her sleeves and getting into the weeds of hiring talent or planning social media campaigns.

Jessy and Adrian with the Cake Equity team!

Her generosity and acumen has helped AfterWork to secure in several competitive rounds, including OwnHome’s Series A, where she was our internal deal lead.

She’s a relentless hustler

Jessy gets more done in a day than many do in a week. She is as considered as she is speedy, and has applied her productivity to professionalising the AfterWork machine, solidifying our processes, and driving new initiatives.

She doesn’t just dream diligently -  she also brings infectious energy to everything she does - from launching our Discord community, to building our talent network and jobs board, to formalising our portfolio support function, to hosting regular events for our community, to growing our LinkedIN audience, to hiring interns.

Jessy is also AfterWork’s most relentless brand ambassador - making a point to champion AfterWork’s vision and values in all kinds of forums. You can listen to her podcast on building a new generation of VC here:

She is a font of inspired, thoughtful, and provocative content and has used her own personal platform to help extend AfterWork’s reach. She is prolific in sharing her perspectives on how to architect welcoming digital and physical spaces, bring people together over shared values, and scale intimacy. While also teaching us obscure facts about etymology and how to use emojis like a Gen Z.

All the while, Jessy embodies our values, flying her freak flag and embodying the spirit of ‘the more we give, the more there is’.  

What exceeded our expectations

She is forging her own rivers of inquiry

Blackbird Ventures’ partner Sam Wong popularised the phrase ‘river of inquiry’ - a trickle of interest in an investment area that gathers pace and becomes a powerful current.

When she first joined, Jessy brought a depth of thinking to investments that complemented the rest of the team. Hailing from NAB Ventures, she brought existing knowledge in consumer fintech, proptech, alternative lenders, and enterprise SaaS solutions. She has capably leveraged these skills to lead our thinking on OwnHome and WageTap.

But since then, Jessy has started to emerge as a thought leader - not just within AfterWork, but across the entire Australian and New Zealand startup ecosystem - on the power of community: both as a function that can supercharge the growth of companies, but also as an investment area in and of itself. You can read some of her thoughts on community building here.

Jessy moderating a session on a New Era of Investing at Emergence 2022

If you’re building a company powered by, or powering, communities get in touch!

She learns by doing

To build her knowledge of the next frontier of community, Jessy has jumped in and is learning by doing. When community builders started tapping into the power of NFTs to rally people around a shared goal and create long-term value for members, Jessy started planning our very own NFT project - Astronauts AfterWork. The first wave of AfterNauts in our Discord have been existing community members, who’ve helped to co-create governance frameworks and verification mechanisms.

If you’re keen to get involved, our ‘nauts will start minting for 2 SOL on March 15. Watch this space!

What we’re excited for

Jessy is ambitious about building a different kind of VC

As VCs, we introduce ourselves about five times a day - to founders, operators, prospective investors, and many others. Sometimes, we get tired of saying the same old thing. Sometime last year, we noticed Jessy started riffing on her introduction. She started saying:

“The AfterWork team takes building an outlier community as seriously as the best startups take building an outlier company. It sounds grandiose, but our end-goal is to become the most straightforward mechanism for the universe to manifest the collision of brilliant people with one another”.

Affirmations and manifestations aside - one thing’s for sure, Jessy is not constrained by how things have always been done. She shows up unencumbered and ready to blow up pre-existing notions of what’s possible. And we’re there for it!

Riding high after our first LP update event

Always be growing; learning; dreaming

Over the past year, Jessy has demonstrated her ability to evolve and develop, at pace. She is always pushing her limits, and takes on feedback graciously, seriously, and open-heartedly. We think this is a real superpower and the ultimate secret weapon.

In harnessing this ability, we’ve seen her refine her ability to ask shrewd questions while still making founders feel like she’s on their team, to build the Investment Committee’s conviction in the deals she leads, and to continuously strengthen our community.

All in all, we’re excited to see Jessy continue to grow as our new Principal.