Senior System/Data Analyst (Payments)

About Dwelly

Dwelly — a UK-based, AI-enabled lettings and property management platform, that is growing through a roll-up strategy acquiring estate agencies. The company leverages two arms: i) acquiring existing letting agencies, effectively buying its highly sticky, recurring revenue-type landlords portfolios, and then ii) building a top-notch technology to automate tenant management, payments, and post-rental property maintenance. The company seamlessly integrates AI services to automate all business processes within brick-and-mortar real estate agencies, integrating them into a tech-enabled digital letting platform in two months to radically improve the user experiences and increase efficiency of the business.

We’re a fast-growing, product-focused company, backed by top-tier investors and led by a team with deep experience in real estate, technology, and operations.

Position Summary

We are seeking a highly detail-oriented and versatile Senior System/Data Analyst to join our team, focusing on the critical Payments and Financial Accounting domain. This is a cross-disciplinary role that sits at the intersection of Systems Analysis, Data Engineering, and Finance, with the core mission to fully automate and optimize our complex financial workflows. You will be responsible for ensuring the absolute accuracy of money movement and financial reporting for a portfolio of thousands of properties.

Key Responsibilities:

1. Payments & financial process automation

Own the analysis and automation of the end-to-end payment lifecycle for tenant rent collection and landlord payouts across a large portfolio of properties. This includes designing logic that correctly handles complex real-world scenarios such as self-initiated payments without references, varying payment cycles, changing payer accounts, late or missing payments, and individual repayment plans for arrears.
You will deeply analyze existing production logic, read and reverse-engineer backend code, and translate complex financial workflows into precise, cent-accurate technical specifications for engineering implementation. The goal is full automation and elimination of manual reconciliation in one of the most accuracy-critical domains of the business.

2. Financial accuracy, controls & reconciliation

Design and maintain robust control mechanisms to ensure absolute financial accuracy across all systems. This includes building reconciliation logic and dashboards that validate control sums down to the cent, ensuring every inflow and outflow is correctly accounted for.
You will define and track logic for agency commissions, repair costs, expense deductions, multi-month cost splits, payment system fees, and arrears handling. Special focus will be placed on correct separation of client money and agency money in compliance with UK regulations, avoiding double counting and ensuring audit-ready financial reporting at all times.

3. System analysis & business-to-engineering translation

Act as the key bridge between complex financial operations and the engineering team. Model and document intricate financial flows, ensuring that business rules, regulatory constraints, and edge cases are fully understood and correctly implemented in code.
Rather than relying solely on documentation, you will often validate logic directly in production systems, reading backend code and, when useful, contributing small, targeted code changes or proof-of-concept pull requests to unblock progress or clarify implementation details.

4. Continuous optimisation & scalability support

Support the company’s transition from early-stage (0→1) to scaling (1→N) by ensuring that payment and accounting systems are built to scale across thousands of properties and agencies. Continuously identify gaps, edge cases, and opportunities to improve robustness, performance, and maintainability of financial systems as the business grows and diversifies.

 Qualifications & Preferred Background:

• High level of autonomy and ownership; comfortable operating as a “full-stack analyst”.
• Deep interest in financial data, system logic, and accuracy-critical workflows.
• Experience analyzing and automating complex financial or payment-related processes.
• Extreme attention to detail and a perfectionist approach to financial reporting and reconciliation.
• Comfortable reading and understanding backend code to inform specifications and decisions.
• Preference for working hands-on with data and systems rather than people management or stakeholder-heavy roles.
• Experience handling arrears, repayment plans, commissions, and expense allocation logic.
• Familiarity with regulated environments and strong appreciation for compliance requirements.
• Experience working in international or cross-border environments (a plus).
• Experience contributing to small, high-performance teams (a plus).
• Strong communication skills and fluency in English.
• Higher degree education.
• Startup mentality: resilience, adaptability, and ability to thrive in a fast-paced environment.
• Customer-centric mindset: focus on delivering value to end-users or clients.
• Strong problem-solving skills with a structured, systems-oriented mindset.

Compensation & Benefits:

• The role is fully remote, providing flexibility and enabling seamless collaboration with our geographically distributed team.
• Competitive salary with the potential for equity options based on performance, recognising exceptional contributions to our integration success.

What is it like being a Dwell-er?

Feel free to check out Dwelly Core Principles. That’s about what we believe in, how we operate and make decisions.

What we offer is not a fancy office or a static workplace. Instead, this is solving one of worlds’ most complex problems in the largest consumer industry in the world (residential rentals), to improve the experience for >30% of households (>5M in the UK, and >100M including EU and US) that live in rental homes.

This is about disrupting the largest, most antiquated industry in the world, with one of the strongest operational and technical teams that exist in the UK and the EU. We work hard, and we shoot for extremely ambitious results. But we want people to be proud of what they’ve built and be able to look back and say one day “hell yeah, that was me that did it all”.

• Customer obsession rather than competitive focus
• Passion for invention
• Operational excellence
• Long-term thinking