Job Description
Description
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
Our philosophy is that we are a small, closely-knit team, and we care deeply about you:
Competitive pay rates
Fully remote work environments
Self-managed time off.
Team trips and special events
At OpenVPN, we pride ourselves on our commitment to creating innovative and secure networking solutions. If you join us, you will have the unique opportunity to shape the product that millions worldwide will interact with daily.
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