Team – Anticipate

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, strengthened security posture, managed IT compliance programs, and implemented enterprise-wide systems supporting functions such as HR, Finance, Sales, Marketing, as well as many companywide operations. His background also includes leading 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 has access to a broad network of highly experienced IT professionals at the Director, Architect, Engineer, or Support tier level. Many of these individuals do not appear on the website due to ongoing commitments or confidentiality considerations, but they are available to contribute their expertise as needed. This extended bench allows us to scale quickly, match the right skill sets to each engagement, and ensure consistent, high-quality service delivery.