
Two HR platforms promised to make work less painful. One became infrastructure inside TriNet; the other is still betting that advice and software belong together.

Justworks, TriNet and Insperity sell similar relief from HR complexity, but their operating models reveal three different ideas about how a small business should scale.
Barrett Boston is the former Chief Executive Officer of Ottimate (formerly Plate IQ), a San Francisco-based AI-powered accounts payable automation platform. Appointed CEO in October 2021 following FTV Capital's majority investment, Boston transformed the company from a restaurant-focused invoice tool into a multi-industry AP automation leader serving hospitality, healthcare, grocery, retail, construction, and manufacturing sectors. Under his leadership, Ottimate rebranded from Plate IQ, raised $160 million in Series B funding, launched an industry-first AI engine for AP, and introduced Conversational AP - an AI assistant for finance teams. Boston stepped down in March 2026, passing the CEO role to Shawn Lane. His career spans IBM, TravelClick, TriNet, and Merrill Lynch, with an MBA from Harvard Business School and a BA in Economics from Duke University.