Expert360 sells for $16m, founder and early investors get nothing
Sydney talent marketplace Expert360 is selling to AI job-matching platform SwipeJobs for $16 million. Founder Bridget Loudon and early-stage investors will receive no payout from the transaction.
The deal, first reported by Capital Brief and confirmed by the AFR, values the company well below the roughly $30 million it raised since launching in 2013. Expert360 had positioned itself as Australia and New Zealand's leading platform for contractors, consultants, and fractional executives, with offices across Sydney, Melbourne, Auckland, Wellington, and San Francisco.
Documents underpinning the sale show the transaction heavily favours investors holding Series C and C1 preference shares, primarily AirTree Ventures and Rampersand. Seed and earlier-round backers get wiped out. This is not a down round. This is a structured exit where liquidation preferences mean late money gets paid first, and everyone else gets nothing.
What happened here
Expert360 raised at least three rounds: $4.1 million early, $12 million in 2020, and a $13 million Series B in 2024 led by AirTree. Public estimates put total funding at $26.1 million and annual revenue at roughly $23.5 million, though those are unaudited figures. Headcount sits at around 151 employees, down 6% year-on-year.
The company hired a VP Sales, multiple sales directors, and heads of operations and sales enablement in recent years, which suggests a push into enterprise. That did not translate into an exit that rewarded early believers or the founder who built it.
Why this matters for sales professionals
If you are negotiating equity at a startup, this is the risk. Preference shares mean late-stage investors get paid first in a sale. If the exit price does not cover their investment plus liquidation preference, earlier shareholders and common stock holders (founders, employees) get zero.
Questions to ask when evaluating equity offers:
- What is the liquidation preference stack? (1x is standard, anything higher means late money gets paid multiple times before you see a dollar)
- How much has been raised, and at what valuation?
- What is the preference order? (Series C gets paid before Series B, Series B before Series A, everyone before common stock)
- What happens to unvested options in an acquisition? (They typically get cancelled unless the buyer agrees to honour them)
Expert360's story is a reminder: equity in a private company is worth nothing until it is worth something. If you are joining a startup for the equity upside, make sure you understand the cap table and liquidation preferences. If the company has raised multiple rounds at increasing valuations, your common stock sits at the back of the line.
For sales roles, this also underscores the importance of cash comp. OTE you can spend. Equity is a lottery ticket that often expires worthless, especially if the company raises heavily structured later rounds to stay alive.
Expert360 was a well-known name in the ANZ startup ecosystem. The fact that its founder walks away with nothing after 13 years should recalibrate how you think about equity as part of your comp package.