The posting
There are NO limits to your career: come shape the future and be part of a truly unique global culture at OutSystems!
About the OutSystems Digital Team
We are the digital backbone of OutSystems' growth — building the enterprise applications, integrations, and AI agents that accelerate the company into the AI-powered era. We work in small, high-autonomy teams of two to five people, each with full AI tooling, a clear mission, and the authority to ship. We take both craft and speed seriously, and we expect the people who join us to do the same.
About the Role
You will join an existing team and take technical ownership of a portfolio of live products and SaaS, while leading the delivery of new capabilities that solve the organisation's most important problems.
This is not a role for someone who ships things and moves on. You are responsible for the quality of what is already running and the correctness of everything new that gets built. Those two things are not in tension — the same standard of judgment that protects live systems is what makes new systems worth building.
Most of your energy — roughly seventy percent — will go into innovation: new agents, new integrations, new capabilities that did not exist before. The remaining thirty percent keeps the existing portfolio healthy, coherent, and evolving. That balance is a principle, not a ceiling: when a live system needs attention, it gets it.
What You Will Own
- The quality bar for everything the team ships — new features and live systems alike. You will safeguard and enforce the architectural principles the team works against, and you are the final call on production readiness.
- Technical direction of a small, high-autonomy team — not through process and approvals, but through a clear standard of correctness that everyone can verify their work against.
- AI agent orchestration — directing tools like Claude Code, OutSystems Mentor, and Cursor toward specific outcomes; knowing when to trust their output and when to reject it.
- Context design for your domain — ensuring AI agents have the enterprise context they need to produce correct, compliant output without repeated clarification.
- Portfolio integrity — understanding the existing applications well enough to extend them without accumulating hidden debt, and well enough to know when something needs to be rebuilt rather than patched.
- Fast validation of new approaches — when there is uncertainty about a technology, a model, or an architecture, you explore quickly and return with a clear recommendation rather than committing the team to an untested path.
The Behaviors We Are Looking For
You have reached the level of system-level judgment where you can direct AI agents toward correct output without reading every line they produce. Here is what that looks like in practice:
- You evaluate at the system level. Your first question about any piece of work is not 'does it run?' but 'is it right?' — architecturally, strategically, and in the context of everything else the team maintains.
- You distinguish correct from plausible. AI output that looks right is not the same as AI output that is right. You catch the difference before it ships, not after it compounds into something expensive to fix.
- You specify before you build. You translate a vague business problem into a specification precise enough that an AI agent — or a junior developer — can execute without follow-up. This is a thinking skill, not a writing one.
- You default to experimentation over alignment. Faced with uncertainty, you run a fast test and return with evidence. You do not schedule a workshop to agree on a path when a working prototype can answer the question in a day.
- You hold the shared mental model. In a small team, the architectural vision is the immune system of the product. You maintain it actively — in documentation, in code reviews, in the feedback you give.
- You are direct about what is wrong. You tell people when an approach is incorrect, and you explain why in three sentences. You do not soften correctness into ambiguity to avoid discomfort.
- You respect what is already running. You understand that live systems have users who depend on them. You extend them with the same care you would apply to anything new — which means you understand them before you change them.
Experience
- 5+ years of hands-on development, with at least 2 years leading technical delivery
- Demonstrated experience with AI-augmented development — Claude Code, Cursor, GitHub Copilot, or similar — used in production, not in experiments
- Track record of shipping production-grade systems and maintaining them over time
- Strong architectural instincts across integration, data, and application layers
- Fluency in context engineering: specifying problems so completely that agents can execute without repeated clarification
Bonus
- Proficiency with OutSystems ODC
- Experience with MCP (Model Context Protocol) server creation and integration
- Experience integrating LLMs via API into enterprise applications
- Background in regulated industries — finance, healthcare, insurance — where governance and correctness matter beyond preference
- Prior experience in small, high-autonomy teams where every person's judgment is tested daily
This Is Not For You If...
- Your instinct when facing ambiguity is to gather requirements rather than build something and learn from it
- You need a large team or formal approval layers to feel like you are doing real leadership
- You treat maintaining existing systems as someone else's problem
- You have never caught an AI tool producing output that looked right but wasn't — or you have, and you shipped it anyway
- You measure your contribution by volume of output rather than by correctness of what ships
Why Join
You will work at the frontier of how enterprise software is actually built with AI — not in a proof-of-concept, but in a company with real products, real users, and real stakes. The small-team model is not a future ambition; it is how this team already operates.
You will have more autonomy, more architectural leverage, and more direct impact than in any traditional engineering leadership role. The skills you will develop — context engineering, AI agent governance, agentic system design — are among the highest-leverage capabilities in the industry, and they are still being invented.
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.
