Systems Delivery Manager (UK, Remote)

About us

Pickle is amongst our many great services, a talent partner for fast-growing businesses. We help ambitious founders and leadership teams hire exceptional people across operations, product, technology, customer success, commercial, finance, and executive leadership.

We specialise in identifying high-quality permanent and contractor talent that can make an immediate impact, supporting businesses through key growth stages with a thoughtful, consultative approach to hiring. Whether it's a critical leadership appointment or building out an entire function, we work as an extension of our clients' teams to find people who combine the right skills, mindset, and cultural fit.

We believe great hiring goes beyond matching CVs to job descriptions. It's about understanding how businesses operate, what success looks like, and connecting them with people who will help them grow for the long term.

About the Role

Our client is a growing, UK-based organisation focused on creating better ways of working through people, process and technology.

They are looking for a Systems Delivery Manager with a strong background in digital transformation and IT to join their systems and transformation function.

Reporting to the Operating Systems Lead, you will take ownership of the successful delivery of complex, cross-functional programmes that bring the organisation's business systems roadmap to life.

You'll translate strategic priorities into coordinated delivery, ensuring initiatives are implemented effectively, adopted successfully and deliver measurable business value.

This is a role for someone comfortable working independently, bringing structure to ambiguity and connecting people, processes and technology to keep important initiatives moving.

Role Details

• Location: UK-based
• Working arrangement: Remote-first
• Salary: Approximately £60,000-66,500,00 per annum

What This Role Is Really About

This role is about turning strategy into successful delivery.

Working closely with the Operating Systems Lead, you'll translate agreed business systems priorities into structured, well-managed programmes of work. You'll coordinate delivery across teams, manage dependencies, remove blockers and maintain momentum to ensure initiatives are delivered successfully and embedded across the business.

You won't simply track plans or report progress. You'll bring the right people together, surface decisions that need to be made, manage competing priorities and ensure projects remain focused on delivering meaningful business outcomes.

About You

You'll thrive in this role if you:

• Have experience delivering complex technical or digital transformation programmes and initiatives.
• Have strong project or programme delivery experience within a technology or systems environment.
• Enjoy coordinating work across multiple business functions.
• Naturally create clarity where priorities, ownership or delivery become unclear.
• Enjoy bringing people together to solve problems and keep work moving.
• Remain calm, organised and pragmatic when priorities shift.
• Build credibility through delivery, collaboration and follow-through.
• Communicate confidently with technical and non-technical stakeholders.
• Can balance multiple projects without losing sight of outcomes.
• Enjoy planning, coordinating and driving delivery.
• Can influence and collaborate effectively without relying on formal authority.
• Proactively identify risks and work with others to resolve them.
• Care about delivering meaningful change that improves how people work.

The One Thing

Connect the dots across the business and keep change moving towards the outcome.

Your First 90 Days

First 30 Days — Understand

• Build an understanding of the systems and transformation function and how it supports the wider organisation.
• Understand the business systems roadmap, priorities and delivery approach.
• Build relationships across Commercial, People, Finance, Operations and Technology.
• Review active projects, milestones, risks, governance and delivery plans.
• Understand stakeholder responsibilities and governance structures.
• Learn the systems, tools and reporting processes that support delivery.
• Identify immediate delivery risks and opportunities.

Days 31–60 — Diagnose

• Take ownership of agreed projects and workstreams.
• Validate plans, milestones, dependencies and expected outcomes.
• Develop a clear understanding of cross-functional dependencies and stakeholder responsibilities.
• Establish effective reporting and communication rhythms.
• Identify delivery risks and opportunities to improve coordination.
• Build trusted relationships across delivery teams.
• Support decision-making by providing clear delivery insight.

Days 61–90 — Lead

• Independently coordinate delivery across agreed initiatives.
• Maintain strong stakeholder alignment throughout execution.
• Resolve blockers and manage competing priorities confidently.
• Deliver clear reporting and governance updates.
• Improve delivery predictability through proactive coordination.
• Support successful adoption and embedding of project outcomes.
• Establish yourself as a trusted delivery partner across the business.

Key Responsibilities

• Lead the delivery of technical and digital transformation initiatives from initiation through to successful implementation.
• Translate business systems priorities into clear plans, milestones and delivery activities.
• Coordinate work across teams, systems, vendors and business functions.
• Build trusted relationships with both technical and business stakeholders.
• Manage cross-functional dependencies, risks and delivery issues.
• Maintain momentum through effective planning, communication and coordination.
• Support business readiness, adoption and embedding of new systems and ways of working.
• Make pragmatic recommendations when delivery challenges arise.
• Provide clear reporting, visibility and stakeholder updates.
• Identify opportunities to improve delivery practices and collaboration across teams.

What You'll Be Doing

You'll lead initiatives involving business systems improvements, platform implementations, systems integrations, operational process changes and wider digital transformation programmes.

Working from an agreed roadmap and set of priorities, you'll partner with the Operating Systems Lead to translate strategic direction into clear delivery plans.

You'll coordinate the people, processes and activities required to ensure projects are delivered successfully, while keeping stakeholders aligned, informed and accountable.

You'll work closely with teams across areas such as Commercial, People, Finance, Operations and Technology to understand requirements, coordinate dependencies and ensure initiatives remain aligned with business priorities.

You'll establish and maintain project plans, milestones, dependencies, reporting, risks and governance, creating enough structure to provide confidence and visibility without unnecessary bureaucracy.

When delivery risks emerge, you'll quickly understand the root cause, bring together the right stakeholders and drive practical action to keep things moving.

You'll be confident communicating with both technical and non-technical stakeholders, making complex information easier to understand and helping teams navigate priorities, decisions and trade-offs.

You'll also capture lessons learned and contribute to continuously improving the way systems and transformation initiatives are planned, coordinated and delivered.

What Success Looks Like

You'll know you're succeeding when:

• Systems and transformation initiatives deliver their agreed business outcomes.
• Stakeholders remain aligned on priorities, dependencies and responsibilities.
• Decisions consider the wider impact across teams, processes, data and systems.
• Initiatives have clear outcomes, owners, milestones, governance and decision-making routes.
• Risks, dependencies and delivery issues are identified early and actively managed.
• Stakeholders trust your judgement and have clear visibility of project status.
• Projects maintain pace despite changing priorities or emerging challenges.
• New systems and ways of working are successfully adopted and embedded.
• Delivery practices become clearer, more effective and scalable over time.

Why Join?

This is an opportunity to join a collaborative and ambitious team where you can make an immediate impact. You’ll work on meaningful projects, help drive operational excellence, and play a key role in ensuring successful delivery across the business.

What You Get

Our client offers a competitive benefits package designed to support employees in doing their best work.

• Competitive salary: £60,000–£66,500 per annum.
• Remote-first and flexible working: Work remotely while benefiting from regular opportunities for in-person collaboration and team connection.
• Private medical insurance: Access to private healthcare benefits, subject to location.
• Employee Assistance Programme: Confidential wellbeing and mental health support.
• Enhanced annual leave: Generous leave entitlement, with benefits varying by location.
• Additional company-wide time off: The business also provides additional paid time off around the end-of-year holiday period.
• Travel support: Opportunities for face-to-face collaboration with colleagues and clients, with travel support where required.

Recruitment Process

• Chat with Pickle
• Initial introductory interview with their team
• Final competency interview.

Diversity & Inclusion

Pickle People recognises the benefits of a diverse workforce and strives to be an inclusive organisation. We are committed to treating everyone with dignity and respect regardless of race, culture, gender, disability, age, sexual orientation, religion or belief and we promote diversity of thought. We would appreciate your help to enable us to measure the diversity within our recruitment process. Completing this form is voluntary and the information provided will remain anonymous. Please submit your information here.