Senior Scrum Master/Engineering Execution Lead

About the CompanyfileAI builds AI-powered workflows that turn unstructured documents into structured business outcomes. We help organisations automate document-heavy processes across operations, finance, compliance, and customer workflows - reducing manual work, improving accuracy, and unlocking the value of enterprise data at scale.

About the Role

This is a high-impact role focused on improving how engineering runs day to day. You will drive sprint discipline, planning quality, backlog health, visibility of risks and dependencies, and follow-through across key initiatives.

Responsibilities

• Own and drive the operating cadence for engineering, including sprint planning, backlog refinement, daily standups, retrospectives, and delivery reviews.
• Improve the quality of sprint planning by ensuring work is clearly defined, appropriately scoped, prioritized, and assigned with clear ownership.
• Build stronger execution discipline across the team by driving follow-through on commitments, action items, blockers, and cross-functional dependencies.
• Partner closely with Product and Engineering to convert business priorities into actionable sprint plans and realistic delivery timelines.
• Surface risks, bottlenecks, misalignment, and scope creep early, and drive timely resolution and escalation where needed.
• Create visibility for leadership on sprint health, delivery confidence, team capacity, execution risks, and progress against priorities.
• Maintain strong backlog hygiene and help teams break down larger initiatives into manageable, sequenced work with clear acceptance criteria.
• Improve coordination across Engineering, Product, Design, QA, and Customer Success to ensure smooth execution of cross-functional initiatives.
• Facilitate retrospectives and continuous improvement efforts that lead to measurable improvements in team effectiveness and delivery predictability.
• Support a culture of accountability, transparency, and operational excellence across the engineering organisation.
• Help strengthen team workflows, planning habits, and communication practices as file
• AI scales.

Qualifications

• 5+ years of experience as a Scrum Master, Agile Project Manager, Technical Project Manager, Program Manager, or similar execution-focused role in a software development environment.
• Proven experience improving delivery consistency, planning quality, team accountability, and cross-functional coordination.
• Strong working knowledge of Agile and Scrum methodologies, with the judgment to apply them pragmatically in a startup or scale-up environment.
• Experience working closely with software engineers, product managers, and technical stakeholders.
• Strong facilitation, organisation, and stakeholder management skills.
• Ability to identify execution risks early and drive clarity, ownership, and momentum across teams.
• Confidence in challenging ambiguity, weak planning, or lack of follow-through in a constructive and credible way.
• Strong written and verbal communication skills.
• Comfortable operating in a fast-paced environment where processes are still being built and refined.
• Experience in SaaS, enterprise software, or AI-driven product companies is preferred.

Preferred Skills

• You are highly organised, calm under pressure, and naturally bring structure to fast-moving teams.
• You are not process-heavy, but you know when more discipline is needed and how to introduce it in a way that improves outcomes rather than slowing people down.
• You are someone who notices when priorities are unclear, when ownership is weak, or when execution is slipping - and you step in to create clarity and momentum.
• You earn trust by making teams more effective, aligned, and accountable.
• Pay range and compensation package
• Play a central role in improving how engineering operates as the company scales.
• Work closely with senior leaders and cross-functional teams on high-priority initiatives.
• Help shape the execution engine behind a fast-growing AI company.
• Join a team solving meaningful enterprise automation and workflow challenges.

Equal Opportunity StatementfileAI is committed to diversity and inclusivity in the workplace.