Remote Principal Project Manager: Strategic Delivery Leader

Ensono; Annapolis (MD); Remote; USD 155,000 - 210,000; Full time

Benefits offered by this job

Unlimited Paid Days Off

401k match

Education Reimbursement

Sabbatical leave

Flexible schedule

Job summary

Ensono is seeking a Principal Project Manager (Remote) to lead complex programs across the full software development lifecycle, delivering sustainable business value for clients. You will act as a trusted adviser to senior stakeholders, shape program vision, and drive governance, risk, and financial management within Ensono Digital.

You will guide delivery culture, mentor teams, and extend expertise in emerging technologies, while developing long-term client engagement strategies and ensuring

Qualifications

• Bachelor’s degree in Business, Information Technology, Computer Science, Engineering, or related discipline, or equivalent experience.
• 10+ years of experience leading enterprise technology delivery programs, software development initiatives, or digital transformation engagements.
• Demonstrated experience delivering cloud transformation, application modernization, microservices, and enterprise platform initiatives.
• Strong understanding of SDLC practices, DevOps, CI/CD pipelines, release management, and operational readiness.
• Expertise in Agile as well as more traditional delivery frameworks, and a good understanding of when to leverage practices from each to benefit project delivery.
• Advanced proficiency with Azure DevOps and Atlassian products for project management. Smartsheet proficiency is desired.
• Proven ability to manage project and program budgets, financial forecasting, profitability, and commercial performance.
• Experience managing Fixed Price, Time & Materials, and Managed Services engagements.
• Strong risk management, dependency management, and governance expertise.
• Exceptional communication, facilitation, negotiation, and executive presentation skills.
• Proven ability to influence stakeholders at all organizational levels, including senior executives.
• Strong analytical and problem-solving capabilities with a focus on business outcomes.
• Experience leading geographically distributed and cross-functional teams.
• Demonstrated success creating collaborative team environments and driving accountability for results.
• Ability to identify opportunities for continuous improvement and implement scalable delivery practices.
• Commitment to mentorship, team development, and delivery excellence.

Responsibilities

• Lead complex program and interconnected workstreams, establishing clear outcomes, integrated plans, critical paths, dependencies, milestones and decision points.
• Define and evolve delivery methodologies, organizational planning standards and supporting tools, promoting sustainable delivery practices and measurable business outcomes.
• Contribute to business transformation strategies and translate strategic goals into coherent delivery models, governance arrangements and executable roadmaps.
• Influence C-level stakeholders and steering committees to shape program vision, success measures, priorities and investment decisions.
• Develop long-term client engagement strategies, leveraging your extensive delivery experience, market insight and knowledge of relevant emerging technologies to benefit the client and their goals.
• Act as a trusted adviser, balancing client strategy, delivery feasibility, technical context and commercial obligations to support successful project delivery and high-quality client outcomes.
• Define reporting and governance standards, ensuring progress, risks, issues, finances and decisions are visible, actionable and aligned to strategic outcomes.
• Implement best practice RAID management, overseeing portfolio risk, and anticipating structural threats such as budget or resourcing constraints, dependencies and other challenges before they affect delivery.
• Develop contingency strategies and elevate material risks in a way that drives clarity and constructive action without unnecessary alarm.
• Effectively manage program budgets, optimizing spend to maximize profitability and maintaining transparency over program commercials.
• Maintain broad knowledge of Ensono Digital products and services, analyze service interactions at solution-architecture level and connect client needs with appropriate Ensono specialists.
• Lead and coordinate high-quality proposals and presales responses, applying client and competitor insight, challenging assumptions and strengthening mitigations where delivery or commercial risks have not been adequately addressed.
• Contribute to the Delivery Management competency strategy and steer the team towards its goals through knowledge sharing, application of best practices and championing a culture of continuous improvement.
• Encourage professional development and lead mentoring initiatives across Delivery Management.
• Curiosity and openness to innovation: actively seeking out and experimenting with new platforms, tools, and AI-driven approaches to improve delivery efficiency, team collaboration, and client outcomes.

Skills

Enterprise delivery leadership

SDLC & DevOps

Agile delivery

Executive influence

Education

Bachelor’s degree in IT or related

Tools

Azure DevOps

Atlassian tools

Smartsheet

Job description

Ensono is seeking a Principal Project Manager (Remote) to lead complex programs across the full software development lifecycle, delivering sustainable business value for clients. You will act as a trusted adviser to senior stakeholders, shape program vision, and drive governance, risk, and financial management within Ensono Digital.

You will guide delivery culture, mentor teams, and extend expertise in emerging technologies, while developing long-term client engagement strategies and ensuring