Strategic growth Explore cross-sell opportunities within Square’s ecosystem since Caviar is part of Square’s suite of tools, leveraging shared merchant networks to upsell additional Square services like payments, marketing, and analytics to existing restaurant partners.

Expansion potential Target expansion partnerships with restaurants in major metros listed (Boston, NYC, Chicago, LA, SF Bay Area, DC, etc.) and neighboring regions where delivery demand is growing, using Caviar’s platform to onboard new restaurant clients and increase order volumes.

Financial health Capitalize on mid-market revenue profile (100M–250M) and mid-sized employer base to position scalable, cost-efficient marketing, CRM, and advertising solutions that align with growth and profitability goals of partner restaurants.

Tech integration Leverage Caviar’s tech stack and data capabilities to propose enhanced analytics, customer insights, and attribution for restaurant partners, including personalized advertising via Microsoft Advertising and behavioral heatmaps via Hotjar.

Brand partnerships Build on past collaborations with social impact and women-led initiatives to offer co-branded campaigns or sponsored events with Pineapple Collaborative and similar groups, opening sponsorship and promotional revenue streams while boosting merchant loyalty.