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.Duties and Responsibilities Lead and manage complex projects from initiation through delivery, ensuring adherence to timelines, scope, quality, and business objectivesPartner with Product and Engineering leadership to define clear project objectives, deliverables, success criteria, and measurable KPIsDevelop and maintain detailed project and release plans, including resource allocation, dependency mapping, risk management, and contingency planningDrive structured planning cadences (quarterly planning, sprint governance, release readiness) across distributed teamsProactively identify, quantify, and mitigate risks; elevate when necessary with clear mitigation strategies and decision optionsEstablish transparent reporting mechanisms and executive-level status updates to ensure alignment and delivery predictabilityFacilitate effective communication and collaboration across cross-functional teams and time zonesContinuously 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 learnedTake ownership of driving the software development lifecycle (SDLC) across all phases, ensuring alignment with engineering best practices and security standardsJob requirements Bachelor's degree in software engineering, computer science, or equivalent practical experience3+ years of experience leading software delivery initiatives within SaaS, cloud, or networking products, with demonstrated ownership of roadmap executionStrong understanding of networking and cybersecurity concepts, particularly in cloud-based architecturesExperience working with backend, frontend, DevOps, QA, and security teams simultaneouslyPMP or PMI-ACP certification is desirableStrong understanding of project management methodologies, including Agile, Scrum, and hybrid modelsExperience using structured forecasting techniques (velocity tracking, Monte Carlo simulation, historical trend analysis, EVM)Excellent written and verbal English communication skills, including executive-level reportingFlexible schedule — ability to work effectively across time zonesAI & Productivity Expectations Demonstrated experience using AI tools (e.g., ChatGPT, Claude, Copilot, Gemini, automation agents) to improve planning, documentation, reporting, and risk managementAbility to design repeatable AI‐assisted workflows that improve planning accuracy and reporting efficiencyExperience introducing AI tools and best practices within engineering or delivery teamsProven ability to leverage AI to automate recurring reporting, meeting summaries, risk analysis, and delivery trackingOur philosophy is that we are a small, closely‐knit team, and we care deeply about you: Competitive pay ratesFully remote work environmentsSelf‐managed time off.Team trips and special eventsAt 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.Stay updated with the latest developments and participate in discussions about OpenVPN. Engage with OpenVPN on Github, LinkedIn, and Facebook.
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