There are NO limits to your career: come shape the future and be part of a truly unique global culture at OutSystems!
About This Role
As a Principal Program Manager, you will be a strategic partner to the CIO and the Digital Leadership Team, acting as the operational and strategic hub for our entire digital transformation portfolio. You will not just manage programs. As a Principal Program Manager, you will orchestrate the complex planning and execution of our digital transformation efforts, especially in environments embracing AI, Agentic AI Solutions, and automation as strategic enablers. Your primary focus will be to act as the execution engine that translates strategic goals into successfully delivered initiatives, driving the change required to help OutSystems scale.
What You Will Lead/Do Or Key Responsibilities
- Strategic Program & Portfolio Management:
- Partner with the CIO, Digital Leadership Team (DLT), other cross functional company program managers, and other business stakeholders to manage the digital portfolio. The goal of this cross-functional partnership is to ensure cohesive roadmaps.
- Co-create and manage the multi-year digital transformation roadmap, guiding investment decisions and the sequencing of key initiatives.
- Program Roadmap Execution & AI Opportunity Translation: define, plan, and execute program roadmaps that align with strategic priorities, translating high-level objectives into actionable plans with clear phases and deliverables. Collaborate cross-functionally, including with technical and data teams, to turn AI opportunities into impactful, business-relevant initiatives.
- Support program budgets, resource allocation, and timelines, ensuring optimal utilization and efficient delivery across the portfolio.
AI Innovation & Enterprise Change Leadership
- Serve as a thought leader on the application of AI to solve business challenges, you will proactively identify high-value AI opportunities and champion them when approved, ensuring the right teams are enabled to build the corresponding business cases for inclusion in the strategic roadmap.
- Drive the enterprise-wide change management and communication strategy for the digital portfolio, with a special focus on managing the cultural and workflow shifts associated with implementing AI solutions.
Cross-Functional Mobilization & Collaboration
- Mobilize and inspire high-performing, cross-functional teams from various departments (e.g., engineering, product, marketing, sales, operations, legal), fostering a culture of strong execution, ownership, and high performance.
- Drive seamless collaboration and communication across all stakeholders, ensuring everyone is aligned on program objectives, progress, and challenges.
- Proactively identify and resolve inter-team dependencies, conflicts, and roadblocks, ensuring smooth program execution and progression.
- Champion agile methodologies and best practices to optimize team efficiency and adaptability across initiatives.
Execution Governance & Oversight
- Orchestrate the continuous improvement of the operating model for the Digital organization, you will facilitate alignment across teams on ways of working, reporting cadences, QBRs and governance frameworks, ensuring progress is tracked against established plans.
- Implement robust program governance frameworks, including clear reporting structures, decision-making processes, and escalation paths.
- Establish and enforce rigorous program management processes, tools, and standards (e.g., risk management, quality assurance, change control).
- Monitor program progress meticulously, tracking key performance indicators (KPIs) and identifying potential deviations from the plan.
- Conduct regular program reviews with stakeholders and senior leadership, providing transparent updates and actionable insights.
- Maintain comprehensive program documentation, ensuring clarity and traceability of decisions and changes.
Risk Management & Proactive Problem Solving
- Proactively identify, assess, and mitigate program risks, developing contingency plans to address potential issues.
- Lead root cause analysis for program challenges and implement effective solutions.
- Demonstrate exceptional problem-solving skills, navigating ambiguity and driving resolution in complex situations.
Stakeholder Communication & Expectation Management
- Act as the primary point of contact for program-related inquiries and updates, translating complex data into clear, actionable insights for the DLT and other executives.
- Develop and execute a comprehensive communication plan to keep all stakeholders informed and engaged.
- Manage stakeholder expectations effectively, building strong relationships and fostering trust across all levels of the organization.
Continuous Improvement & Operational Excellence
- Evaluate program performance post-completion, capturing lessons learned and identifying areas for process improvement.
- Champion a culture of continuous learning and operational excellence within the program management function, consistently seeking ways to optimize processes and delivery.
Qualifications / What You Need To Succeed
- Bachelor’s degree in Business Administration, Engineering, Computer Science, or a related field; Master’s degree preferred.
- 12+ years of progressive experience in program management, with a proven track record of successfully delivering large-scale, complex, cross-functional programs in global technology environments.
- PMP, PgMP, or equivalent certification is highly desirable.
- Proven experience in budgeting, financial management, and resource allocation for high-impact digital initiatives.
- Deep expertise in portfolio management, strategic planning frameworks (e.g., OKRs), business case development, and benefits realization.
- Strong command of program management methodologies (Agile, Waterfall, Hybrid) and tools (e.g., Jira, Asana, Microsoft Project, Smartsheet).
- Demonstrated success delivering AI-driven initiatives, with understanding of the change management and adoption dynamics in enterprise environments.
- Proven leadership presence and influencing skills, capable of mobilizing and motivating diverse teams without direct authority.
- Exceptional organizational and structural thinking skills, with the ability to bring clarity and order to ambiguous or complex situations.
- Excellent communication, interpersonal, and presentation skills, with the ability to articulate complex information clearly and concisely to technical and non-technical audiences.
- Demonstrated ability to anticipate risks, solve problems creatively, and make sound decisions under pressure.
- Passion for innovation and a strong interest in leveraging emerging technologies, particularly AI and automation, to drive operational and strategic advantage.
- Experience in the SaaS industry is a significant plus.
The Longer Story
OutSystems enables enterprise teams to build AI-powered applications and agents that reduce manual work, streamline internal operations, and accelerate impact. A proven low-code foundation combined with agentic AI and AI app generation capabilities empowers teams to move up to 10x faster with the assurance of security, scalability, and governance built in.
As the future becomes agentic, our customers need us now more than ever. AI has opened the door to extraordinary possibilities—but inside the enterprise, things are moving fast and feeling chaotic. Some early adopters are making progress in production, but for many, AI tools are sprawling without governance, data isn’t ready, and talent isn’t there yet. Enterprises are still drowning in application backlogs and struggling with legacy systems. But with the right platform, AI doesn’t have to add to the chaos. It can become the breakthrough that brings clarity—and drives real, enterprise-wide impact. At OutSystems, we’ve built that platform, providing the tools necessary for enterprises to overcome these hurdles.
We are looking for passionate, talented, and motivated people to join us in helping our customers build, deploy, and scale apps and agents—fast, helping them accelerate innovation while enabling secure, governed human-AI collaboration.
OutSystems is a truly global company, with more than 850,000 developer community members, 1,700 employees, more than 500 partners, and thousands of active customers in over 75 countries and across 21 industries. Founded in 2001, OutSystems has offices in the United States, United Kingdom, the Netherlands, Portugal, Germany, the UAE, Japan, Hong Kong, Malaysia, Australia, India, and Singapore, and of course has a thriving, worldwide community of remote employees.
Amongst our 2,400 customers are some of the world's most recognizable brands across diverse industries—brands like Toyota, Heineken, Bosch, KeyBank, and UCLA. These customers are the reason we have a 4.6 star rating on G2. Their success is ours, and their stories demonstrate tangible ROI and transformational impact. We are a 9x Gartner Magic Quadrant Leader for Low-Code Application Platforms and a multi-year leader in the Forrester Wave. We’re recognized not just as leaders but as visionaries with a strong ability to execute, now extending our leadership into the AI and agentic application development arena.
Working at OutSystems
Our goal is to ensure that OutSystems is a place for bright, happy, and motivated people who share a common purpose and take pride in doing excellent work to pursue our vision of providing the AI-powered low-code development platform enterprise leaders trust to build, secure, and evolve their business applications, agents, and core systems. Our culture is focused on our core values of trust, customer success, innovation, and alignment. Our team members operate with transparency, integrity, and accountability, define success through the lens of the outcomes we deliver for our customers, push the boundaries with excellence, and work together toward our shared vision to deliver on what matters most.
What do we have to offer you?
- A company that is always growing, changing, and innovating. We challenge each other to innovate in our products, in our team, and how we use our own technology. And we give our teams space to be proactive and creative.
- Real career opportunities. We care about growth and development. Yes, vertical career progression is a possibility, but it's not the only one. From lateral moves and joining different teams to mastering specialized skills, we support your growth no matter what your goals are.
- Work colleagues that are as smart, hard-working, and driven as you. We act as one global OutSystems team, taking ownership and working together toward a shared vision.
- Disrupting the status quo is in our DNA. In fact, it’s why our company exists.
- We ask “why” a lot. It helps us connect our individual work to the bigger picture and sometimes even uncover a better way.
Are you ready for the next step in your career? Then we’d love to hear from you!
OutSystems nurtures an inclusive culture of diversity, where everyone feels empowered to be their authentic self and perform at their best. A company that embraces the creativity and innovation that comes through diverse perspectives. We are committed to creating a team that reflects society through inclusive programs and initiatives and are proud to be an equal opportunity employer. All qualified applicants receive equal consideration regardless of race, place of origin, color, age, marital status, religion, sex, sexual orientation, gender expression or identity, protected veteran status, disability status or any other status protected by law.
