Rosey Bailey
Senior Project Manager, Implementations , Professional Services SaaS ☁️ AWS
- Role
- Senior Project Manager at Skedulo
- Location
- Houston, TX, US
- LinkedIn followers
- 500 followers
About Rosey Bailey
I lead complex, enterprise-scale SaaS and cloud transformation programs where delivery risk is high, stakeholders are senior, and outcomes matter.Over the last 6 years, I’ve owned multi-million-dollar portfolios across Fortune 500 and high-growth organizations—driving measurable gains in delivery velocity, system performance, and operational scalability.My edge is sitting at the intersection of strategy, execution, and executive alignment: • Translating business goals into executable delivery roadmaps • Leading globally distributed engineering and services teams • Managing $2M+ budgets, risk, and scope with zero-surprise delivery • Partnering with C-suite and VPs on modernization, automation, and scaleDomains: Enterprise SaaS, AWS & cloud migration, workforce optimization, SDLC, Agile deliveryI’m most effective in environments where ambiguity is high, stakes are real, and leadership expects ownership, not just coordination.
Experience
Senior Project Manager
May 2023 — Present
Lead enterprise SaaS implementations for Fortune 500 and high-growth companies, ensuring seamless adoption and measurable business impact.• Innovation: Spearheaded initiatives that positioned Skedulo as a leader in scalable, cloud-native workforce optimization technology.• Global Collaboration: Directed distributed teams across time zones, building culture and alignment around measurable outcomes.• Oversee $2 million+ in project budgets, managing scope, risk, and cross-functional collaboration to deliver high-value solutions.• Partner with C-suite and senior stakeholders to optimize workforce management, driving efficiency through process automation and workflow transformation.• Implement Agile and SDLC best practices, reducing project delivery timelines by 10% and improving stakeholder satisfaction.• Spearhead strategic initiatives that enhance operational scalability, positioning Skedulo as a leader in workforce optimization technology.
Education
Houston City College
Associate of Arts and Sciences
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