Senior Project Manager - Remote

Overview

OpenVPN is seeking a Senior Project Manager to lead end-to-end delivery of complex SaaS initiatives across our distributed engineering organization. Our ideal candidate has a bachelor’s degree in software engineering or computer science, 3+ years of leading software delivery in SaaS or cloud environments, and a good understanding of networking and security concepts. In this role, you will be responsible for ensuring predictable execution of roadmap initiatives, driving cross-functional alignment, managing delivery risks, and improving operational efficiency across teams.

In Short

• Lead and manage complex projects from initiation through delivery, ensuring adherence to timelines, scope, quality, and business objectives
• Partner with Product and Engineering leadership to define clear project objectives, deliverables, success criteria, and measurable KPIs
• Develop and maintain detailed project and release plans, including resource allocation, dependency mapping, risk management, and contingency planning
• Drive structured planning cadences (quarterly planning, sprint governance, release readiness) across distributed teams
• Proactively identify, quantify, and mitigate risks; escalate when necessary with clear mitigation strategies and decision options
• Establish transparent reporting mechanisms and executive-level status updates to ensure alignment and delivery predictability
• Facilitate effective communication and collaboration across cross-functional teams and time zones
• Continuously improve delivery processes, introducing automation and AI-driven workflows to enhance productivity and quality.
• Conduct post-project reviews and implement actionable improvements based on lessons learned
• Take ownership of driving the software development lifecycle (SDLC) across all phases, ensuring alignment with engineering best practices and security standards

Requirements

• Bachelor’s degree in software engineering, computer science, or equivalent practical experience
• 3+ years of experience leading software delivery initiatives within SaaS, cloud, or networking products, with demonstrated ownership of roadmap execution
• Proven experience delivering complex, multi-team initiatives in distributed engineering environments
• Strong understanding of networking and cybersecurity concepts, particularly in cloud-based architectures
• Experience working with backend, frontend, DevOps, QA, and security teams simultaneously
• PMP or PMI-ACP certification is desirable
• Strong understanding of project management methodologies, including Agile, Scrum, and hybrid models
• Experience using structured forecasting techniques (velocity tracking, Monte Carlo simulation, historical trend analysis, EVM)
• Excellent written and verbal English communication skills, including executive-level reporting
• Flexible schedule — ability to work effectively across time zones

Benefits

• Competitive pay rates
• Fully remote work environments
• Self-managed time off.
• Team trips and special events