Digital Transformation Lead

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

We’re not just improving business processes — we’re reimagining them through the practical application of AI.

Reporting to the Director of Digital Transformation, the Team Lead, Digital Transformation & AI will lead a multidisciplinary team responsible for delivering AI-enabled digital products and transformation initiatives that improve customer and employee experiences.

In this role, you will apply an AI-first mindset, using Generative AI, agentic AI, automation, and data to redesign workflows, improve decision-making, and create measurable business value.

You will operate at the intersection of technology, product delivery, and business execution. You will translate strategic priorities into clear plans, guide the team through discovery and delivery, remove blockers, and ensure solutions are scalable, maintainable, and aligned with user needs.

This is a hands-on role for someone who believes AI is not simply a feature, but a new way of designing digital products, processes, and experiences.

What You Will Lead/Do or Key Responsibilities

Digital Strategy Execution: Drive the execution of selected digital transformation priorities, translating the strategy defined by Digital Transformation leadership into clear initiatives, roadmaps, and measurable outcomes aligned with business goals and global objectives.

Project Leadership:

• Lead a portfolio of digital transformation initiatives within the Customer Adoption and Expansion domain, providing direction, guidance, and formal team leadership. Set clear goals and deliverables.

• Oversee the delivery of high-impact digital solutions that drive customer success. Ensure consistency across projects by establishing a structured discovery and planning phase (often referred to as "Sprint 0") that focuses on clear problem definition, feasibility assessment, and stakeholder alignment before development begins.

• Balance speed and quality, ensuring solutions are scalable and maintainable.

• Remove blockers, manage risks, and escalate challenges proactively.

• Work closely with engineering, UX, customer success, and product teams to ensure effective execution.

Optimize Customer Journey: Contribute to the evolution of the OutSystems customer journey by leading the design and delivery of selected AI-enabled digital experiences. Recognizing the complexity of B2B experiences, apply Generative AI and agentic AI to personalize, automate, and streamline customer-facing platforms and supporting internal systems. Understand that exceptional customer experiences depend on effective employee experiences, and identify opportunities to embed AI-driven efficiency and intelligence across selected customer and employee touchpoints.

Data-Driven Decision-Making: Leverage data analytics and business intelligence to make informed decisions, identify opportunities for optimization, and enhance business processes and digital experiences. Foster data-informed decision-making within the team and across the stakeholder groups supporting assigned initiatives.

Ensure solutions are delivered to enhance the user experience and deliver measurable business value. Work with cross-functional teams to translate business goals into technical execution. Track and report on key operational and business impact metrics.

Operational Execution & Prioritization:

• Drive operational execution, ensuring digital initiatives are delivered on time, within scope, and with measurable impact.

• Apply clear prioritization frameworks across the assigned portfolio, ensuring the team addresses the most critical and highest-impact work first.

• Promote a culture of focus, where teams concentrate on delivering a few high-impact outcomes rather than spreading efforts too thin.

• Define and improve team and delivery processes to optimize efficiency and reduce unnecessary complexity.

• Foster a high-performance environment that values clarity, discipline, and meaningful results.

• Continuously evaluate and refine delivery strategies to improve speed, alignment, and business value.

• Apply critical thinking to connect strategy with execution, solve complex problems, and anticipate downstream implications of decisions.

Stakeholder Engagement: Collaborate with stakeholders across business and technology, including senior management, to build alignment and support for assigned digital transformation initiatives. Effectively communicate progress and outcomes. Serve as a bridge between technical teams and business stakeholders. Ensure decisions are made transparently and with stakeholder input from day 0. Proactively manage cross-team dependencies and facilitate alignment on priorities, escalating unresolved trade-offs when required. Communicate fluently in English to ensure alignment across global teams and stakeholders.

Change Management: Develop and implement change and adoption plans for assigned digital solutions. Identify adoption barriers, address resistance, and support stakeholders as they adopt new tools, processes, and ways of working. Act as an AI advocate, helping teams build literacy, confidence, and responsible practices in the use of Generative AI and agentic AI.

Team Management: Lead and develop a multidisciplinary delivery team, working closely with cross-functional contributors across the organization. Set clear expectations, provide regular feedback, support performance management, and coach team members to increase their maturity and autonomy.

Risk Management: Identify and manage delivery, technology, adoption, and operational risks within assigned initiatives. Partner with the appropriate legal, security, privacy, and compliance teams, escalating material risks when required. Financial Oversight: Track project budgets, delivery costs, and resource requirements. Recommend capacity and investment trade-offs and escalate material budget variances when required.

Quality Assurance: Ensure the quality of digital deliverables by defining and monitoring project quality standards and conducting regular reviews.

Vendor and Partner Management: Support the evaluation of technology vendors and service providers, providing input on business needs, technical fit, delivery capability, cost, and risk. Manage day-to-day relationships and delivery performance for vendors supporting assigned initiatives.

Innovation and Technology Evaluation: Evaluate emerging technologies and trends, assess their relevance to the assigned portfolio, and recommend opportunities for experimentation, adoption, or scaling. Evaluate emerging technologies and trends, assess their relevance to the assigned portfolio, and recommend opportunities for experimentation, adoption, or scaling.

Qualifications / What You Need To Succeed

• AI-Driven Transformation: Hands-on experience applying Generative AI and agentic AI to improve business processes, decision-making, digital products, or user experiences, with evidence of measurable outcomes.

• Automation Strategy: Proven ability to design and implement AI-powered automation, such as workflow orchestration and intelligent agents, to reduce manual effort and unlock operational efficiency.

• Data & Customer Insight: Strong competency in using advanced analytics to extract actionable insights, personalize experiences, and improve customer and employee outcomes.

• AI Integration: Experience leading cross-functional teams in embedding AI into digital products, platforms, business workflows, or internal systems—ideally within a composable architecture or low-code environment.

• Emerging Tech Fluency: Comfortable navigating fast-evolving AI technologies, with sound judgment in selecting and applying the right tools to deliver measurable business value.

• Evangelism & Enablement: Experience building AI literacy and maturity within teams and stakeholder groups. Able to demystify AI, influence adoption, and ensure safe and effective usage.

• Critical Thinking: Ability to analyze complex problems, challenge assumptions, and make evidence-based decisions. Navigates ambiguity and connects strategy to execution.

• Customer-Facing & Product Orientation: Previous experience in customer-facing or product-oriented roles, with strong empathy for user needs and a passion for delivering elegant solutions.

• Fluent Communication: Fluency in English (spoken and written), with stong communication and stakeholder management skills to align global, cross-functional teams.

• Agile & Collaborative Leadership: Proven experience leading development teams in an agile environment and working collaboratively with UX, engineering, QA, and business teams.

• Transformation & Execution: Strong grasp of digital transformation principles, customer experience design, SaaS platforms, and translating business needs into technical action.

• Mentorship & Team Development: A coaching mindset and commitment to developing talent, fostering high performance, and building resilient, empowered teams.

• Bachelor's degree in a relevant field (e.g., Computer Science, Business, Engineering, or related discipline); a master's degree or certifications in product management, digital transformation, or AI are preferred.

• Typically 7 or more years of relevant experience in digital transformation, digital product management, technology delivery, consulting, or customer experience, including experience leading complex cross-functional initiatives. At least 2 years of experience formally leading, coaching, or developing team members is preferred.

• Proven experience applying AI-driven automation, including Generative AI and agentic AI, to reimagine and streamline business processes.

• Strong analytical and critical thinking skills—able to interpret complex information, challenge assumptions, and make sound, data-informed decisions.

• Strong understanding of digital technologies, SaaS platforms, automation, and emerging trends, with the ability to translate them into practical opportunities.

• Demonstrated formal people leadership experience, including setting expectations, providing feedback, coaching team members, and contributing to the development of a high-performing team.

• Excellent product management capabilities—able to define and prioritize solutions, oversee implementation, and drive measurable value.

• Stong communication, stakeholder engagement, and negotiation skills across technical and non-technical audiences.

• Proficiency in change management principles and methodologies, with the ability to lead adoption within stakeholder groups.

• Experience managing vendor relationships, external delivery partners, or technology service providers is preferred.

• Relevant certifications in product management, agile delivery, or digital transformation (e.g., PMP, Prince2, CDTMP, SAFe, or AI-related certifications) are a plus.

More about OutSystems

OutSystems is a leading AI Development Platform built for the enterprise. Global organizations trust OutSystems to rapidly build mission-critical apps and agents, modernize legacy processes with agentic systems, and govern their entire AI portfolio across complex regulatory environments, all on one unified platform.

As the future becomes agentic, our customers need us now more than ever. While AI has opened the door to extraordinary possibilities, most large organizations find themselves stuck on one side of the "enterprise gap" because AI by itself doesn't solve their complex use cases and business challenges. OutSystems bridges the "enterprise gap" by combining the speed of generative AI with a deterministic, enterprise-grade framework. We provide the tools for teams of any size to deliver high-quality, reliable AI solutions that drive real business impact.

We are looking for passionate, talented, and motivated people to join us as we empower organizations to build, deploy, and scale the next generation of enterprise software. While we are leading the charge into the agentic era, our mission is broader: we are the platform enterprise leaders trust to evolve their entire business, accelerating innovation through secure, governed human-AI collaboration.

OutSystems is a global company, with more than 900k developer community members, 1,700 employees, more than 600 partners, and thousands of active customers in over 75 countries and across 21 industries. Founded in 2001, OutSystems now has offices in the United States, United Kingdom, the Netherlands, Portugal, Germany, the UAE, Japan, Hong Kong, Malaysia, Australia, India, and Singapore, and includes a thriving, worldwide community of remote employees.

Our customers are some of the world's most recognizable brands across diverse industries— such as Toyota, Heineken, Bosch, KeyBank, and UCLA—who trust OutSystems to deliver ROI and transformational impact.

Consistently recognized as a leader by top analyst firms Gartner, IDC and Forrester, OutSystems continues to shape the future of enterprise software development in the agentic era. We are proud to be named a leader in more than 100 categories on G2, including #1 in Customer Satisfaction in Enterprise Low Code Development, and most recently as a leader in AI Agent Building in the G2 Spring 2026 Reports.

Working at OutSystems

Our culture is built on our core values of Trust, Customer Success, Innovation, and Alignment. We operate as one global OutSystems team, taking ownership to pursue our vision of being the AI platform enterprise leaders trust to build, secure, and evolve their most critical applications and systems.

What do we have to offer you?

• A company at the vanguard of the agentic revolution, where we don’t just react to AI innovation—we architect it. Joining OutSystems means stepping onto a high-growth rocket ship that combines the fearless agility of a startup with the sophisticated, global foundation of an enterprise powerhouse.

• Real growth opportunities. We don't just talk about development; we invest in it through structured programs designed to scale your expertise. Whether you are aiming for vertical progression, exploring lateral moves into new domains, or mastering specialized AI skills through our Professional Development Fund and Internal Mobility Program, we provide the resources to get you there.

• A global collective of world-class talent, where you’ll collaborate with enterprise software legends and sought-after thought leaders. At OutSystems, our industry experts aren't just visionaries—they are accessible, approachable mentors who are deeply invested in your growth as we architect the agentic future together.

OutSystems nurtures an inclusive culture where talented individuals from all backgrounds are empowered to learn, experiment and make an impact. . We believe that driving our next phase of growth requires the radical creativity that only comes from diverse perspectives. We are committed to building a team as global and diverse as the organizations we serve, ensuring every individual can perform to their full potential. As an equal opportunity employer, all qualified applicants receive equal consideration regardless of race, origin, religion, sex, sexual orientation, gender identity, disability, veteran status, or any other protected status.