Plaza Ventures is rolling its stake in Stack Adapt into a single-asset continuation vehicle, buying more time with one of Canada's highest-returning venture bets. Kline Hill Partners led the transaction, with additional capital sourced through syndication, according to three people familiar with the deal structure.

The move comes as AI adoption accelerates across digital advertising, threatening the programmatic platform's competitive moat. Plaza's original investment has delivered outsized returns, ranking among the country's most successful venture outcomes, but the firm isn't ready to exit amid shifting market dynamics that could compress valuations for ad-tech assets.

GP-led secondaries continue to reshape how venture firms manage vintage funds, allowing GPs to hold winners longer while returning capital to limited partners. This transaction underscores how AI disruption is forcing early exits or restructurings even for top-performing portfolio companies facing technological obsolescence in their core markets.

The deal signals that continuation vehicles have become a standard tool for navigating technological paradigm shifts in venture portfolios, particularly when disruptive innovation threatens established business models.