Team
Jonathan Spiva
Director & Architect
Jonathan Spiva is a senior technology leader with more than 15 years of experience building and scaling IT organizations for high-growth companies and diverse consulting clients. He has led IT departments through major expansions, system migrations, workplace buildouts, and security and identity modernization initiatives.
Jonathan has served as Director of IT at multiple startups, including Headway, Convoy, and OfferUp, where he built teams, modernized infrastructure, improved security, managed compliance programs, and implemented enterprise-wide systems across HR, Finance, Sales, and Marketing. He also led a full-service IT consultancy, giving him deep experience supporting organizations of all sizes with identity, automation, lifecycle management, and operational strategy.
His leadership spans budgeting and forecasting, vendor management, policy development, compliance alignment, cross-functional collaboration, and executive communication around risk and technology planning. Jonathan focuses on creating IT environments that are efficient, secure, and aligned with organizational goals, enabling teams to do their best work through thoughtful, scalable technology.
Our network
Director, Architect, Engineer & Support
Anticipate draws on a network of experienced IT professionals at every level: Director, Architect, Engineer, and Support. This extended bench allows us to scale quickly, match the right expertise to each engagement, and deliver consistent, high-quality service.
We're always looking for talented people to join our network. If you're interested, visit our Work With Us page to see current openings.