Senior Manager, Reporting & Data (Canada)

LOCATION: Remote anywhere in Canada.

About Proof

Proof is the service-of-process marketplace modernizing how legal documents move through the real world. 10,000 law firms trust us with documents that have legal consequences: a serve has to reach the right person, at the right address, under the right rules, with a court-ready affidavit proving what happened.

That promise only looks simple from the outside. Behind every serve is a network of customers, independent process servers, and internal teams coordinating work across jurisdictions. Each request, field visit, and completed job adds to a rich picture of how legal work gets done, where it slows down, and how we can make it better.

Great data leadership here means turning that information into something people can act on. Clients need reporting they can trust, and teams across Proof need insights that help them improve the business. As we expand our use of automation and AI, the quality and accessibility of our data will shape what we can build.

The role

Our largest clients rely on our reporting to track legal work, reconcile costs, and move information into their case management and accounting systems. That means understanding both their business needs and the formats and constraints of the systems they use.

We're looking for a Senior Manager, Reporting & Data to manage Proof's data team, reporting to the Chief Product Officer. This is a player-coach role: you'll develop the team, guide technical decisions, and work directly with clients while the team does most of the implementation.
The team's immediate priority is dependable enterprise client reporting. You'll also lead our internal data and BI capabilities, shaping how Proof uses data to serve clients and guide the company's growth.

What you'll do

• Own enterprise reporting. Understand how clients use our data, turn business needs into clear requirements, and take responsibility for report content, accuracy, and delivery. Set clear service expectations and communicate openly about scope, timing, and tradeoffs.
• Own the client relationship. Our customers need crucial reports to operate efficiently. Take ownership of the relationship and ensure they succeed by providing the data they need.
• Lead and develop the data team. Set goals, coach people, give direct feedback, and grow them to the next level. Build the team's ability to take ownership and solve problems independently.
• Set priorities and guide technical delivery. Plan capacity with business and technical leaders, balancing client commitments with improvements that make future reporting faster to deliver. Review queries and data models, help resolve difficult problems, and step in for SQL or code changes when useful.
• Build dependable data systems. Own the team's approach to pipelines, shared models, and internal BI and SQL tooling, with clear standards for quality, monitoring, and access. Partner with Engineering on how data moves from the warehouse into the systems that need it.
• Turn data into business insights. Help teams across Proof use trusted data to understand performance, identify opportunities, and make decisions. Work with Product and Engineering on the data needed to improve internal tools and AI systems.
• Improve automation and tooling. Work with Business Operations to decide when to build, buy, or improve tools, including low-code automation. Base decisions on business value, reliability, and ongoing maintenance.

What you bring

• 7+ years of experience in data, analytics, or reporting, including 3+ years managing a data or analytics team, with examples of developing people, building scalable processes, and improving delivery.
• Experience leading client discovery and explaining technical tradeoffs in plain language, including difficult conversations about scope, timelines, and quality.
• Experience delivering data into client systems through recurring extracts or agreed file formats, including investigating and resolving reconciliation issues.
• Strong SQL proficiency and data-modeling knowledge to review work and investigate problems. Familiarity with Python or similar scripting is useful, along with a willingness to keep developing your technical skills.
• Experience with production data systems and automation, including data warehouses, pipelines, BI tools, and practical build-versus-buy decisions.
• Experience with complex enterprise workflows is helpful, whether in legal technology, financial operations, or environments that rely on legacy systems, electronic data interchange (EDI), and file-based exchanges. We value curiosity, agency and the ability to quickly learn the business.

What success looks like 

In your first six months, you'll build alignment on clear improvement targets and drive measurable progress in report accuracy, delivery reliability, and turnaround. Shared models and automation should reduce recurring manual work, while the team handles more decisions independently. You'll turn patterns in client and operational data into actionable insights that shape Proof's business priorities and guide where we invest our people and technology.

Benefits:

• Full-time, salary position
• Fully remote role, based in Canada
• Flexible time off and holidays 
• Equipment provided
• Comprehensive benefits package, including healthcare, dental, and disability insurance

Compensation:

• 175,000 - 200,000 CAD based on experience and location. Must be located in Canada
• Eligible to participate in company bonus plan