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Dewayne DeRozzo

Executive Strategy & Operations Leader specializing in SaaS, AI, and GTM transformation

New York, NYChief Operating Officer (began as VP of Strategy, GTM & Product Ops)13 years experienceExecutiveSaaSArtificial IntelligenceHealthcare
ScreenedReferences VerifiedIdentity VerifiedStrongly Recommended

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About

Ops/tech program leader who supported the national rollout of the 988 Suicide & Crisis Lifeline by building an enterprise OKR system and implementing Asana + real-time dashboards across technology, operations, clinical support, and communications. Has led a 15-person team and repeatedly improves executive productivity through pragmatic tool rollouts (HubSpot, SharePoint/Confluence, Slack/Zoom) and lightweight integrations.

Experience

Chief Operating Officer (began as VP of Strategy, GTM & Product Ops)WideXP
VP of Strategy & Operational ExcellenceVibrant Emotional Health
Senior Director of Tech & Innovation (expanded to VP of Digital Transformation)Marymount Manhattan College
Strategic Operations & Delivery Consultant – (fractional COO, GTM advisor for start-ups)WideXP
Director of Strategy & Operational Excellence (expanded to VP of Strategy & Operations)Vibrant Emotional Health

Education

Capella Universitymaster, Marketing & Technology
Dillard Universitybachelor, Mass Communication & Computer Science

Key Strengths

  • Built an enterprise OKR system aligning cross-functional work to executive objectives
  • Led cross-functional initiatives for the national rollout of the 988 Suicide & Crisis Lifeline
  • Implemented Asana and real-time dashboards to improve visibility, accountability, and decision-making
  • Managed a team of 15 while owning org-wide OKRs and day-to-day operations
  • Improved executive productivity by consolidating tools and workflows (HubSpot CRM, Asana, OneDrive integrations)
  • Uses transparency and early risk surfacing to resolve conflicting priorities and accelerate mitigation
  • Strong bridge between technology and operations; enables adoption via training and documentation

Reference Highlights

Strongly Recommended
  • Goes above and beyond
  • Clearly defines path to project success
  • Proactive about learning (pursues certifications to broaden knowledge)
  • Takes initiative with little direction
  • Strong sense of urgency and drive
  • Adaptable and fluid when direction changes
  • Direct, clear communicator
  • Comfortable communicating with leadership and all levels
  • Experienced working with diverse teams and cultures
  • Continuously learning and growing

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Contact

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Languages

English

Skills

Product StrategyGo-to-Market (GTM) StrategyPlatform LeadershipData-Driven StrategyMVP DevelopmentProduct RoadmappingRoadmap OwnershipOKRsKPIsGlobal OperationsSaaSArtificial Intelligence (AI)Generative AI (GenAI)Digital TransformationAutomation