VP of Operations
Location: Cardiff - You'll help build our Cardiff hub, shaping the culture, operations, and centre of excellence from the ground up.
Reporting to: CEO
About Sidekick
We’re Sidekick - a digital wealth platform reimagining how ambitious individuals build financial security and long-term wealth.
Our mission is simple: make wealth-building tools once reserved for the ultra-rich available to everyone. Whether it’s high-yield savings, professionally managed investment portfolios, or the ability to borrow against your investments without selling, Sidekick is putting powerful financial tools in the hands of professionals, founders, freelancers, and tech-savvy doers.
Since launching in 2022, we’ve grown our user base to 4,500 and it’s accelerating fast, and we’re now looking to scale our product and expand internationally
We’re at a pivotal stage in our growth and we’re looking for a VP of Operations to join our team, lead from the front, and help shape the company’s direction from the inside out.
Why This Role Matters
As VP of Operations, you’ll be the person who takes our vision and makes it real. You’ll build the processes, systems, and frameworks to support thousands (and soon tens of thousands) of users, working closely with the Founding team to ensure Sidekick scales without friction.
You’ll be our first dedicated operations leader, with the opportunity to build your own team as we grow. This is not a role for someone looking to “maintain.” You’ll be creating from scratch, building structure where none yet exists, and playing a central role in the next chapter of our journey — with a clear path to step into a Chief Operating Officer role as we scale.
What You’ll Do
👊 Day-to-Day, You'll:
* Build and run Sidekick’s operational engine - from customer success flows to back-office automation.
* You’ll collaborate closely with our Head of Compliance to support the operational delivery of regulated processes,
* Identify inefficiencies, automate what you can, and build scalable processes that support our growing user base and expanding product suite.
* Be a strategic voice in how we shape the company, influencing product, customer, and commercial strategy.
* You’ll drive regulatory excellence, helping ensure operational processes are built to be audit-ready and scalable in a FCA-regulated
* Recruit, grow, and inspire a lean, high-impact operations team.
Who You Are
We're looking for a builder, a thinker, and a problem-solver. Someone who lights up when they’re given a blank page and asked to create something that matters.
✅ Must-Haves:
* 6+ years’ experience in operational leadership roles, ideally in fintech, wealth management, or digital financial services.
* Proven track record of building or scaling operations from scratch.
* Startup experience - you’ve thrived in environments with ambiguity, fast growth, and rapid decision-making.
* Data-driven and analytical - you love using data to solve problems, not just diagnose them.
* People leadership - you’ve hired and developed top talent, and know how to inspire them to execute at pace.
What We’re Really Looking For
💡 Problem-solving DNA - This is the #1 trait we value. You’re a person who sees challenges as puzzles to solve. Whether it’s rethinking a customer flow, building a process from scratch, or fixing a cross-functional breakdown, you lead with initiative, not instruction.
🛠️ Builder’s mindset - You're not afraid of rolling up your sleeves. You’ll thrive if you like starting things, tweaking them, and scaling them fast.
🎯 Commercially sharp - You think in terms of users, margins, and scale, not just process. You understand how operations contribute to revenue, retention, and ROI.
🤝 Collaborative leader - You can rally teams around you and know how to influence without ego.
Why Join Sidekick?
💥 Game-changing mission - We’re bringing wealth-building power to the masses, not just the 1%.
🌍 Real momentum - With 4,500 users and fast growth, you’ll be part of a rocketship in motion.
🎙️ Seat at the table - As part of the exec team, you’ll shape the entire future of the business.
📈 Career-defining opportunity - You’ll be in line to step into the Chief Operating Officer seat as we scale.
📊 Backed to win - We’re well-capitalised and focused on smart growth.
🎯 People who get it - You’ll work with a driven, supportive founding team with real fintech pedigree and vision.
What We Offer:
* A unique startup experience, contributing to a private wealth startup from its earliest stages.
* The opportunity to be part of a product that can help build wealth for hundreds of thousands of people.
* Work with a passionate and driven team from diverse backgrounds.
* Competitive startup compensation package, plus an options package.
* An extra day off for your birthday.
* Benefits via SimplyHealth
Our Commitment to Diversity and Inclusion: At Sidekick, we are committed to fostering diversity and inclusion. Our hiring process is designed to be fair, promoting diversity, and unlocking access to wealth-building products for a new generation.