Head of Finance

About SkillsWave

SkillsWave is on a mission to drive people and businesses forward—building tomorrow’s most valued skills, today. By providing quality learning opportunities that align with organizational needs, we’re helping organizations transform their workforce into a competitive advantage. Our upskilling platform and strategic education partnerships not only propel career and company growth, but also deliver measurable and meaningful ROI for learning. To learn more, visit SkillsWave.com.

Catch the Wave with Us!

Dive into an exciting role as a Head of Finance. Reporting to the President you’ll ride the wave of success in a pivotal executive role that blends strategic leadership with hands-on execution. Your mission? With and emphasis on financial planning and analysis, strategic financial modelling, and insightful decision support, you will oversee accounting, invoicing, payroll and financial reporting, ensuring clarity, accuracy, and robust governance. As a key member of the leadership team, you will provide strategic financial insights, lead budgeting and forecasting activities, and communicate effectively with non-financial stakeholders and the board. This role requires curiosity, strategic thinking, strong analytical capabilities, and the ability to manage and simplify complexity as SkillsWave scales. You will also be responsible for evolving SkillsWave’s financial maturity and building a high-performing finance team as needed to support continued business growth.

Your Location, Your Workspace, Your Wave

We are looking for the right person to join our team. This position offers a remote option along with a hybrid option if you are located in the Kitchener/Waterloo area and want to enjoy our amazing space at Catalyst Commons. We can’t wait to welcome exceptional individuals that will bring their skills and passion to our team!

How Will You Make An Impact

• Strategic Financial Leadership: Drive the financial strategy, contributing significantly to organizational growth plans, capital allocation, and investment decisions.
• Financial Planning & Analysis (FP&A): Lead budgeting, forecasting, and financial modeling processes, providing clear, actionable insights for strategic decision-making.
• Business & Financial Modeling: Develop sophisticated financial and operational models to support growth, strategic initiatives, and potential future fundraising.
• Operational Finance Oversight: Oversee financial operations (AP/AR, Payroll, Taxes, GL reconciliation), ensuring processes are efficient, compliant, and aligned with strategic goals.
• Invoicing and Billing: Ensure accurate and timely invoicing of customers, tracking of receivables, and follow-up on outstanding payments.
• Financial Reporting & Compliance: Oversee preparation of monthly, quarterly, and annual financial statements and management reports, ensuring accuracy and compliance with Canadian and U.S. regulatory requirements.
• Investor Relations & Board Communication: Prepare and communicate insightful, strategic financial presentations to investors, board members, and other stakeholders.
• Process Optimization: Continuously improve finance processes, systems, and controls to support scalability, efficiency, and accuracy in a dynamic startup environment.
• Team Development & Leadership: As the business scales, build-out, mentor, and manage a high-performing finance team, emphasizing professional growth, accountability, and strategic alignment.
  
  

What You Need To Be Successful

• Minimum of 12-15 years of progressive finance leadership experience, specifically emphasizing FP&A and strategic finance, preferably in the technology sector
• Proven experience in SaaS startup environments combined with exposure to enterprise-level financial complexities.
• Bachelor's degree in Finance, Accounting, Business Administration, or related field
• CPA/CFA certification (or equivalent) in Ontario, Canada or MBA preferred.
  
  

Your Super Skills and The Wave-Riding Expertise We Need!:

• Advanced proficiency in financial software and tools (e.g., Excel, Hubspot, QuickBooks, Power BI).
• Strong knowledge of Canadian and U.S. Accounting Standards and familiarity with regulatory compliance requirements.
• Experience with payroll processing systems and familiarity with HR processes and regulations.
• Excellent organizational and time management skills, with the ability to prioritize tasks and meet deadlines effectively.
• Familiarity with AI tooling and it’s applicable use in the context of finance tasks
  
  

What You Will Bring To The Team

• An Enthusiastic Perspective: An independent self-starter, someone who is curious about what and why, is able to solution with empathy for stakeholders, and drive successful change through yourself and leveraging others
• Entrepreneurial Spirit: Demonstrating initiative, creativity, and ownership by proactively identifying opportunities, solving problems, and taking calculated risks to drive innovation and organizational growth
• Strategic Financial Acumen: Expert understanding of financial planning, modeling, strategic forecasting, and investment analysis.
• Analytical Excellence: Ability to interpret complex financial data and trends, translating insights into strategic opportunities
• Hands-on Execution: Comfortable executing and overseeing detailed financial operations, especially in early growth stages.
• Communication & Influence: Exceptional ability to clearly communicate financial strategies and results to diverse, non-financial audiences.
• Adaptability & Agility: Proven capacity to thrive in fast-paced, evolving startups with a mind to mature enterprise-level aspirations.
• Leadership & Team Development: Demonstrated skill in managing, coaching, and developing finance teams effectively
• Integrity and Ethics: Commitment to upholding ethical standards, confidentiality, and integrity in financial practices and decision-making.
  
  

Who You Are

• You Own It: You approach every challenge with the mentality of a surfer tackling a perfect wave—taking full ownership of your work and responsibilities, driving projects forward with confidence and initiative.
• You Learn It: You believe that improvement is key, constantly refining your skills. Growth and learning are always top of mind.
• You Collaborate Assertively: You engage confidently in team discussions, share your expertise, and ensure that everyone is paddling in sync toward success.
• You Work with Velocity and Quality: Whether you’re racing towards the shore or patiently navigating the break, you strike the perfect balance between speed and delivering top-notch results.
• You Care Deeply: You care deeply about your work and the lasting impact it makes—on your team, the company, and beyond.
  
  

Fuel For The Ride

Along with meaningful work, you'll enjoy a competitive compensation package and benefits that support your personal and professional success that include:

• Competitive Salary
• Vacation and Rest Days
• Health and Wellness
• Retirement Savings Plan
• Professional Development
• Participation in Future Equity Plan
  
  

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Background Check Notice

As part of our hiring process, SkillsWave may conduct a background check to ensure the safety and security of our workplace.

Disclaimer And Consent

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• to use the information you have provided for the purpose of considering and evaluating you as a candidate for employment with the SkillsWave family of companies;
• to store your information on their vendor systems;
• to share your information within the SkillsWave family of companies, their vendors, partners or other third parties for the purpose of processing your employment application; and
• to use your personal information to contact you in the future for any other suitable employment opportunities;
  
  

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To all recruitment agencies: SkillsWave does not accept agency resumes. Please do not forward resumes to our HR alias e-mail address, to any SkillsWave employee, or to other SkillsWave e-mail addresses. SkillsWave will not pay any fees related to unsolicited resumes.