Director of Business Intelligence & Strategic Finance

Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their Linked In profiles!

Caseware is seeking a Director of Business Intelligence & Strategic Finance to play a critical leadership role in shaping how the company measures, understands, and communicates its commercial performance. This is a highly visible position responsible for owning ARR and bookings reporting, building scalable reporting infrastructure, and serving as a trusted partner to the C‑suite and Sales Leadership.

The ideal candidate brings a strong blend of strategic finance, SaaS metrics expertise, and business intelligence leadership, with the ability to translate complex data into clear, actionable insights that drive decision‑making across the organization.

This role is remote and open to candidates who reside in and are eligible to work in the United States.

Note: The successful candidate will need to collaborate across North American time zones (Eastern and Pacific Time) and travel to Toronto periodically (2–4 times per year).

• ARR & Bookings Ownership
• Own the end-to-end definition, calculation, and reporting of ARR and bookings across the organization.
• Establish clear, consistent, and auditable metrics and definitions aligned with executive, finance, and sales stakeholders.
• Partner with Accounting, Rev Ops, and Sales to ensure accuracy, consistency, and alignment across systems and reporting.

• Reporting Infrastructure & Analytics
• Lead the design and build-out of scalable reporting infrastructure, dashboards, and data models to support commercial and financial insights.
• Improve data quality, automation, and reliability across core business intelligence workflows.
• Evaluate and optimize BI tools, data sources, and processes to support a growing SaaS business.

• Executive & Sales Leadership Communication
• Serve as a key advisor to the C‑suite, providing clear, concise, and insightful analysis on performance, trends, risks, and opportunities.
• Prepare and deliver executive‑level reporting and presentations for leadership meetings, board materials, and strategic planning.
• Partner closely with Sales Leadership to provide forward‑looking insights on pipeline, bookings, growth drivers, and performance against targets.

• Strategic Finance & Business Partnership
• Support strategic planning, forecasting, and long‑range growth initiatives with data‑driven insights.
• Identify opportunities to improve revenue performance, operational efficiency, and go‑to‑market effectiveness.
• Act as a thought leader in establishing best practices for SaaS metrics, reporting, and performance management.

• Leadership & Collaboration
• Lead, mentor, and develop team members within Business Intelligence and Strategic Finance.
• Collaborate cross‑functionally with Finance, Sales, Rev Ops, Product, and IT to align data and reporting with business priorities.
• Drive a culture of accountability,, and analytical rigor.

• 8–12+ years of experience in strategic finance, business intelligence, FP&A, or related roles, preferably within a SaaS or subscription‑based business.
• Deep expertise in SaaS metrics, including ARR, bookings, pipeline, churn, expansion, and revenue forecasting.
• Proven experience building and scaling reporting infrastructure and executive dashboards.
• Strong executive presence with the ability to communicate complex concepts clearly to senior leaders.
• Advanced analytical skills with experience using BI and data visualization tools (e.g., Looker, Tableau, Power BI) and working with large datasets.
• Experience supporting Sales and Go‑To‑Market organizations in a high‑growth environment.
• Background partnering with accounting on revenue recognition and metric alignment.
• Prior experience in a PE‑backed or rapidly scaling software company.
• People leadership experience with a track record of developing high‑performing teams.

• ▪️Innovation is at our…