Alaena VanderMost

• Lead strategic operations initiatives for founders of high-growth companies, driving organizational transformation and operational scalability
• Rebuilt financial operations for a 40-person agency, eliminating 20+ hours of weekly manual work and reducing operational risk through process redesign and tech stack consolidation
• Designed and implemented centralized operating system for 32-person creative agency, increasing company valuation pre-sale and reducing founder dependency through improved workflows and performance visibility
• Designed and executed strategic plans aimed at enhancing organizational effectiveness and reducing operational costs.
• Partner with leadership to prioritize initiatives, manage organizational change, and drive execution across cross-functional teams
• Managed stakeholder communications, ensuring alignment on project goals and timely updates throughout implementation phases.

Project Manager → Product Manager → Head of Product → COO → President → CEO

• Joined one year into Company's existence as a late-stage cofounder, and led operations and business transformation initiatives that scaled the company from pre-revenue to hundreds of thousands of students, managing cross-functional programs across product, marketing, fulfillment, operations, and customer support
• Owned end-to-end operational infrastructure including workflow design, tech stack implementation, process automation, and systems integration
• Architected Teaching Assistant program that removed primary growth bottleneck, increasing cohort capacity from approximately 50 to thousands while maintaining quality and student experience
• Built executive reporting systems including KPI frameworks, analytics dashboards, forecasting models, and performance tracking that leadership relied on for strategic decision-making
• Led all operational systems evaluation and implementation including requirements gathering, vendor management, data migration, integration planning, and organizational rollout
• Managed cross-functional stakeholder alignment across product, engineering, marketing, and operations to drive program success and operational improvements

• Joined as one of first 50 employees during hyper-growth, building operational systems and processes from scratch in ambiguous, fast-scaling environment
• Recruited and managed national print-vendor network to solve supply chain constraints, improve delivery reliability, and scale fulfillment operations - collaborated closely with external manufacturing partners where quality, precision, and coordination were critical
• Led operations for Teespring Direct B2B vertical, managing enterprise client workflows, vendor coordination, and operational delivery end-to-end
• Collaborated with engineering to design and implement internal tools supporting new product lines and fulfillment processes
• Identified operational bottlenecks and risks early, drove cross-functional solutions to improve quality, speed, and scalability before issues impacted the business