Senior Project Manager (Technical Project Manager/ Technical Manager)

OpenVPN is seeking a Senior Project Manager (Technical Project Manager/ Technical Manager) to lead end-to-end delivery of complex SaaS initiatives across our distributed engineering organization.

Our ideal candidate has a degree in computer science or a background as a Senior Software Engineer / Technical Manager, 3+ years in SaaS or cloud environments, and a strong understanding of networking and security concepts.

In this role, you will be responsible for ensuring the predictable execution of roadmap initiatives, driving cross-functional alignment, managing delivery risks, and improving operational efficiency across teams.

Important: This will be a long-term B2B contract role, not permanent employment.

Requirements

• Degree in software engineering, computer science, or equivalent practical experience, or a background as a Senior Software Engineer / Technical Manager

• Strong networking and cybersecurity concepts knowledge, particularly in cloud-based architectures

• Experience working with backend, frontend, DevOps, QA, and security teams simultaneously

• 3+ years of experience in SaaS, cloud, or networking products, with demonstrated ownership of roadmap execution

• PMP or PMI-ACP certification is desirable

• Proven experience delivering complex, multi-team initiatives in distributed engineering environments

• Strong understanding of project management methodologies, including Agile, Scrum, Kanban, Waterfall, and hybrid models

• Experience using structured forecasting techniques (velocity tracking, Monte Carlo simulation, historical trend analysis, EVM)

• Flexible schedule — ability to work effectively across time zones

• Excellent written and verbal English communication skills, including executive-level reporting

AI & Productivity Expectations

• Demonstrated experience using AI tools (e.g., ChatGPT, Claude, Copilot, Gemini, automation agents) to improve planning, documentation, reporting, and risk management

• Ability to design repeatable AI-assisted workflows that improve planning accuracy and reporting efficiency

• Experience introducing AI tools and best practices within engineering or delivery teams

• Proven ability to leverage AI to automate recurring reporting, meeting summaries, risk analysis, and delivery tracking

Duties and Responsibilities

• Lead and manage complex projects from initiation through delivery, ensuring adherence to timelines, scope, quality, and business objectives

• Take ownership of driving the software development lifecycle (SDLC) across all phases, ensuring alignment with engineering best practices and security standards

• Establish transparent reporting mechanisms and executive-level status updates to ensure alignment and delivery predictability

• Partner with Product and Engineering leadership to define clear project objectives, deliverables, success criteria, and measurable KPIs

• Facilitate effective communication and collaboration across big cross-functional teams and time zones

• 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

• 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

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