Sr Project Billing Analyst

About Wynford

At Wynford, we create live and digital experiences for Fortune 100 and emerging clients, from incentive travel and large-scale events to workshops and product launches.

Our Finance team supports the financial administration and analysis behind multiple client programs, budgets, suppliers, and timelines at once. This role helps ensure project billing is accurate, complete, and supported by reliable financial information.

About the Role

The Senior Project Billing Analyst owns the reconciliation and analysis of billing across Wynford’s event projects.

Working closely with Sales Directors, project teams, Accounts Payable, Accounts Receivable, the Project Billing Manager, and the Director of Finance, you will gather information from across the organization to understand how projects were scoped, sold, staffed, and delivered. Success in this role depends on building strong cross-functional relationships, asking thoughtful questions, and proactively seeking context rather than waiting for information to come to you.

Following training, you will independently lead project billing reviews and close-outs, maintain accurate reconciliation files, and provide clear financial insights that support timely decisions. This is not a siloed analysis role. You will need to identify gaps in your own knowledge, connect information from multiple sources, and actively seek the answers required to create an accurate financial picture of each project.

Salary range: $75,000–$85,000

What You’ll Own

• Preparing accurate project billing reconciliations aligned with project milestones, contracts, and client agreements.
• Tracking project costs, labour, expenses, credits, and revenue to ensure billing is complete and accurate.
• Analyzing project billing against budgets and contracts, investigating variances, and providing clear findings and recommendations.
• Reviewing project financials throughout the event lifecycle and identifying concerns early so stakeholders can take action.
• Reviewing labour hours and costs charged to projects, confirming time is allocated correctly, and analyzing labour recovery.
• Maintaining accurate reconciliation files and supporting documentation in Excel and Smartsheet.
• Leading final project billing close-out and confirming all costs, credits, and revenue have been captured and billed.
• Preparing clear variance commentary and ensuring project financial records are complete and audit-ready.
• Supporting month-end activities related to project billing, including accruals, deferred revenue, revenue recognition, and cost tracking.
• Ensuring billing aligns with Wynford standards, client specifications, and applicable GST/HST requirements.
• Identifying opportunities to simplify billing workflows, reduce manual work, and strengthen financial reporting, templates, and documentation.

What You’ll Partner On

• Gathering project context from Sales, Event Solutions, Operations, Finance, and project teams to understand the activity behind financial results.
• Resolving billing discrepancies and aligning financial information with Accounts Payable, Accounts Receivable, project teams, and Sales Directors.
• Identifying gaps in information, documentation, or understanding and working with stakeholders to close them before they affect billing or reporting.
• Allocating supplier payments and following up on missing costs, approvals, invoice details, contract information, and supporting records.
• Helping project teams understand supplier accounting summaries, contract terms, billing formats, and financial documentation requirements.
• Improving Smartsheet integrations and project billing processes in partnership with Finance and operational teams.
• Developing a strong understanding of how Wynford programs are sold, planned, and delivered in order to provide informed financial analysis and recommendations.

What Success Looks Like

In the first 6 to 12 months, success would look like:

• Project billing reconciliations are accurate, complete, and delivered on time.
• Costs, labour, credits, and revenue are consistently captured and assigned to the correct projects.
• Billing and budget variances are identified early, investigated, and clearly communicated.
• Project close-outs include complete financial records and useful variance commentary.
• Missing information is followed up on before it delays billing or month-end activities.
• Reconciliation files, trackers, and supporting records are current and audit-ready.
• Project teams have clearer guidance on billing requirements, financial documentation, and contract terms.
• Strong working relationships have been built across departments, and the Senior Project Billing Analyst is viewed as a trusted and resourceful partner.
• Financial results can be confidently connected to operational decisions and project activity.
• Stakeholders trust this person to independently investigate issues, gather the right information, and arrive at sound conclusions.
• Billing workflows are more consistent, and opportunities to reduce manual work have been identified or implemented.

Must-Have Skills

• Experience analyzing and reconciling project financial performance, including billing, budgets, profitability, labour costs, and variances.
• Proficient in Microsoft Excel with the ability to efficiently manage, analyze, and organize data
• Ability and preference to work independently and navigate ambiguity.
• Ability to gather information, connect the dots, and make sound decisions with incomplete information.
• Strong organization, attention to detail, and follow-through.
• Strong relationship-building skills and the ability to work effectively with stakeholders across multiple functions and levels.
• Clear written and verbal communication.

Trainable Skills (Nice to Have)

• Smartsheet or similar workflow tools.
• Tax and compliance requirements related to project billing.
• Supplier accounting and reconciliation processes.
• Incentive Travel/Events industry-specific terminology and workflows.

Experience That May Be Helpful

• Experience in incentive travel, meetings and events, destination management, experiential marketing, hospitality, or another complex project-based service environment is strongly preferred.
• Knowledge of project budgeting, reconciliation, supplier management, and the operational realities of delivering complex client programs.
• Familiarity with event planning cycles and how project milestones affect billing timelines.
• Experience working with multiple internal teams, external suppliers, and client-specific billing requirements.

This Role Is a Strong Fit If...

• You enjoy solving problems by bringing together information from multiple sources and stakeholders.
• You are naturally curious and take the initiative to understand the story behind the numbers, not just the final result.
• You are comfortable working across departments and building relationships that help you gather context, resolve issues, and move work forward.
• You work independently, recognize when information is missing, and seek clarification or answers without waiting for direction.
• You are comfortable navigating complexity as projects evolve and new information becomes available.
• You take pride in accuracy and want to understand the root cause of discrepancies rather than simply correcting them.
• You enjoy improving processes, reducing manual effort, and creating more reliable ways of working.

This Role May Not Be a Fit If...

• You prefer work that is highly structured, predictable, and follows the same process each day.
• You prefer roles where all required information is provided upfront and limited stakeholder engagement is needed.
• You are most comfortable working independently with minimal collaboration across teams or departments.
• You find it difficult to navigate ambiguity, investigate missing information, or piece together context from multiple sources.
• You are looking for a traditional accounting role focused primarily on transactions rather than project-based financial analysis.
• You prefer to escalate issues rather than independently researching, investigating, and problem-solving first.
• You are uncomfortable asking questions, challenging assumptions, or following up when information is incomplete.

Education

Post-secondary education in accounting, finance, business, or a related field is an asset. Equivalent relevant experience will also be considered.

What We Offer

Total Compensation: Competitive salary with a comprehensive benefits package.

Hybrid Work Environment: Flexibility with a hybrid working structure to support work/life balance.

Dog-Friendly Office: Bring your furry friend to work for good vibes.

Time Off: Enjoy paid time off, including a winter holiday closure, birthday off, and additional personal time.

Professional Development: Access monthly training, industry memberships, and learning opportunities.

Wellness: Benefit from health & dental plans, fitness discounts, and an annual stipend for your wellness needs.

Bonuses & Incentives: Participate in a company-wide bonus structure and recognition programs like the WynList Awards.

Extra Perks: Enjoy discounts on activities, retail stores, team lunches, and fun off-site gatherings to keep the team spirit high.

Interested?

Apply on LinkedIn or send your resume and cover letter to [email protected].

In your cover letter, tell us what interests you about the opportunity and what kind of operating environment helps you do your best work.

At Wynford, we’re committed to creating an inclusive workplace where every voice is valued. We welcome applications from all qualified candidates and will provide accommodation throughout the recruitment process in accordance with the Accessibility for Ontarians with Disabilities Act (AODA).