digital-chief-of-staff
(2)
Way2B1
Way2B1 is a San Francisco-based SaaS company that builds a secure, cloud-based collaboration platform for family offices, wealth managers, and the ultra-high-net-worth families they serve. Positioned as a 'digital chief of staff,' the platform centralizes secure messaging, document management, asset tracking, approvals, signatures, and decision history into one command center, with an integrated AI assistant to automate routine tasks. Founded in 2015 by family-office veteran Wayne Osborne and former Palantir engineer Casey Ketterling, the company raised a $5.5M Series A in 2017 and helps offices coordinate complex lives with greater clarity, security, and auditability.
WorkBoard
WorkBoard is a Redwood City-based enterprise SaaS company that builds an AI-native strategy execution and OKR platform. It helps large organizations set objectives and key results, align teams around them, automate business reviews, and track progress in real time so strategy turns into a repeatable 'operating rhythm.' Co-founded in 2014 by CEO Deidre Paknad and Daryoush Paknad, the company serves major enterprises including Boeing, 3M, Cisco, Capital One and Workday, and in 2025 acquired rival Quantive to consolidate the enterprise OKR market.