Stephen Cherico

Consulting firm specializing in travel payments, reservation‑lifecycle workflows, and multi‑system data integrations. I lead product operations, workflow design, and technical delivery for enterprise clients, helping them build scalable systems that improve accuracy, throughput, and customer experience across SaaS and AI‑native environments. My work centers on bringing structure and clarity to complex, multi‑team programs. I established program governance frameworks that improved delivery predictability by 25% and reduced cross‑team blockers by 30%. I also built operating rhythms (QBR/MBR/WBR) that strengthened alignment, surfaced risks earlier, and increased decision velocity by 35%. I implemented KPI dashboards and SLA reporting that improved visibility, accountability, and stakeholder confidence across global delivery teams. To reduce onboarding friction, I standardized workflows, improved sequencing, and strengthened cross‑team coordination, cutting onboarding effort by 40–42%. I designed governance artifacts including dependency tracking, risk logs, change‑request workflows, and milestone reporting for high‑visibility, multi‑team programs. I also managed multi‑system data workflows and integrations with GDS, PMS/CRS, and back‑office systems, achieving 99%+ accuracy across 10+ partner platforms. A major part of my role involves translating ambiguous requirements into structured program plans, configuration guides, and acceptance criteria—reducing customization needs by 25% and improving roadmap clarity. I serve as the program‑level context owner, ensuring risks, dependencies, and decisions are captured, communicated, and resolved across global stakeholder groups. I also facilitate executive steering sessions and cross‑functional alignment reviews that clarify priorities, accelerate decision pathways, and strengthen program‑level accountability.

CTS Systems is a global financial operations provider supporting high‑volume settlement, reconciliation, and commission processing for TMCs, OTAs, and hospitality partners. In my role as Director of Operations & Program Delivery, I led high‑volume financial workflows, automation initiatives, and cross‑functional delivery programs that improved accuracy, throughput, and operational predictability across global client portfolios. I built financial workflow governance models that improved program predictability by 22% across multi‑currency settlement and reconciliation operations. I also implemented intake, prioritization, and routing systems that strengthened decision‑making across Product, Engineering, and Operations, reducing cycle time and improving cross‑team alignment. To increase visibility and accountability, I developed KPI dashboards and SLA governance models used across global delivery teams. I redesigned workflows and operational playbooks that improved processing accuracy by 30% and increased onboarding speed by 25%. Through automation and workflow orchestration, I tripled throughput and reduced manual effort by 35%. I designed escalation pathways and issue‑resolution workflows that reduced backlog aging and improved response times across support, engineering, and operations. I also led multi‑system reconciliation and settlement workflows across TMCs, OTAs, and hotel partners, improving financial accuracy and reducing disputes by 50%. A major part of my role involved building SLA monitoring and exception‑handling workflows that reduced service interruptions and strengthened operational reliability across high‑volume financial processes. I also created SOPs, reconciliation templates, and financial processing guides that standardized execution across distributed teams and improved audit readiness.

Dell Technologies is a global enterprise SaaS and infrastructure provider serving more than 40,000 hospitality customers worldwide. As Director of Product Management & Global Onboarding, I led large‑scale onboarding, implementation, and customer success alignment programs that improved time‑to‑value, platform stability, and delivery consistency across global client portfolios. I directed global onboarding programs that improved time‑to‑value by 30% through standardized deployment workflows, clearer sequencing, and stronger coordination between Product, Engineering, and Customer Success. I built operating rhythms that reduced execution gaps, improved cross‑team alignment, and created predictable delivery patterns for complex, multi‑system implementations. A major part of my role involved reducing customization needs by 30% by translating customer requirements into scalable, program‑aligned features and standardized configuration patterns. I also improved issue‑resolution times by 20% by designing structured escalation pathways and governance models that clarified ownership and accelerated cross‑team response. I led multi‑system integrations across PMS/CRS platforms, payment gateways, and back‑office systems, ensuring high‑accuracy data exchange and consistent reservation‑lifecycle processing. I implemented governance models including milestone tracking, risk logs, and change‑control workflows that strengthened executive visibility and improved delivery predictability. To support global readiness, I developed SOPs, configuration guides, and training materials used across worldwide delivery teams, reducing onboarding escalations by 35% and improving customer adoption. I also delivered onboarding readiness reporting and client‑facing status updates that improved transparency, strengthened stakeholder confidence, and accelerated decision‑making during complex implementations

Perot Systems was an enterprise technology & services firm delivering large‑scale hospitality, travel, & financial system implementations. As Director of Product & Solutions Delivery, I led multi‑property rollouts, enterprise integrations, & complex implementation programs for global hospitality & travel clients, ensuring predictable delivery & high‑availability service levels. I directed implementation programs that improved deployment predictability & reduced delivery variance across multi‑region environments. I led cross‑functional teams across Product, Engineering, QA, & Client Services to deliver integrations spanning PMS/CRS platforms, GDS connections, payment gateways, & back‑office systems, centering on data accuracy, platform stability, & seamless reservation‑lifecycle processing. I built standardized onboarding frameworks & configuration playbooks that reduced implementation time by 20% & improved execution consistency across distributed teams, and designed workflow architectures & data‑exchange models that strengthened reservation‑lifecycle accuracy & reduced reconciliation issues by 30%. I managed client migrations, platform upgrades, & multi‑property rollouts, ensuring minimal disruption & maintaining high‑availability service levels. I established governance structures including milestone tracking, risk logs, dependency management, & change‑control workflows that improved executive visibility & strengthened program accountability. I partnered with engineering leadership to translate customer requirements into scalable product enhancements, reducing custom development requests & improving roadmap clarity. I developed training materials, SOPs, & operational guides used across global delivery teams, improving onboarding readiness & reducing escalations. As the primary escalation point for enterprise clients, I resolved complex technical & operational issues under tight timelines, restored service continuity, & strengthened long‑term client relationships.

Citibank is a global financial institution supporting high‑volume, multi‑currency transaction processing and treasury operations. In my role, I supported daily financial workflows across multi‑currency accounts, ensuring accurate processing, reconciliation, and exception handling for large transaction volumes. I managed end‑to‑end payment and settlement workflows, including ACH, wire, and international transactions, ensuring data accuracy and timely processing across distributed teams. I researched and resolved discrepancies, partnering with Risk, Compliance, and Technology to maintain audit‑ready documentation and strengthen operational controls. I developed reconciliation templates, reporting checklists, and standardized procedures that improved processing consistency and reduced error rates. I also supported system enhancements and workflow improvements that increased accuracy and reduced manual effort across high‑volume financial operations. This role built the foundation for my later work in payments, settlement, and multi‑system financial workflows across the travel and SaaS ecosystem.

Softbank operated large‑scale global support and technology services during major enterprise software rollouts. In this role, I supported Microsoft’s worldwide deployment of Windows 95 and Microsoft Server products, providing technical assistance across Microsoft applications and a wide range of third‑party enterprise software. I managed the client and customer support desk and staffed a global overnight call center, ensuring 24×7 coverage, consistent service quality, and smooth handoffs across regions. I handled escalations, resolved complex technical issues, and maintained service continuity during high‑volume rollout periods. I also contributed to support documentation, troubleshooting guides, and knowledge‑base articles that improved team readiness and reduced repeat incidents. This role established the foundation for my later work in global operations, multi‑system troubleshooting, and enterprise‑scale delivery.