Oliver Whittlef

Lead Architect @Xvoucher

Minneapolis, MN, US

Ensured development activities—from minor bug fixes to large feature builds—were grounded in our business model and product vision. This required constant translation between product, business, and engineering: keeping developers aligned with roadmap goals, and guiding the business to prioritize features that solve real customer problems within technical realities. I also drove compliance (PCIDSS, GDPR, SOC2), faster sales cycles, and GTM readiness.Freemium + Subscription Tiers: I led the design and implementation of a monetization model atop our Voucher Management system. I collaborated with stakeholders to group features by org size and use case into service tiers, then extended our feature flag system to enforce these tiers. I also built the Stripe integration for simple customer setup.Xvoucher Marketplace: I worked cross-functionally to define a lean MVP using our existing e-commerce stack. This fast GTM move succeeded, and our internal enhancements later became client offerings—an intentional monetization strategy.Learning Credits (LC): Architected and later led this complex project enabling orgs to define custom ‘currencies’ and delegate purchasing power via credit allocations. I owned the technical design, guided the team through financial/tax nuance, and wrote core finance-related code through MVP delivery.Internal Initiatives: • Identity Management: Led migration from ASP.NET Membership to a centralized Cognito IdP supporting MFA, SSO, and federation. Architected the system, staffed new talent, and contributed across the stack. • Dev Innovation Program: Co-created a developer idea pipeline. MCed the inaugural event, facilitated stakeholder alignment, and mentored devs monthly on articulating business value. • Voucher Stocking Improvements: Proposed, designed, and implemented a fulfillment module overhaul—introducing deferred actions, context-aware alerts, and automatic recovery—to eliminate manual restocking delays and improve customer outcomes.

University of Minnesota

Master of Science - MS

University of Minnesota-Twin Cities

Bachelor of Science - BS

University of Minnesota

Minor

Minneapolis Community and Technical College

Associate of Science - AS