Director, Professional Services

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 LinkedIn profiles!

The Director of Professional Services leads a high-performing implementation organization responsible for the successful delivery of software solutions across North America. This role owns delivery excellence, customer outcomes, and services revenue, ensuring engagements are executed efficiently, at high quality, and at scale. The Director provides strategic and people leadership to a diverse team of project managers, consultants, trainers, and technical services professionals supporting multiple concurrent customer engagements. They are accountable for operational performance, talent development, and the continuous evolution of service offerings that drive measurable customer value and exceptional client experiences. Working cross-functionally with Sales, Product, Product Education, and Customer Support, the Director ensures a seamless end-to-end customer journey from sale through adoption while aligning services strategy with broader business objectives. You may be required to travel to client locations and for cross functional leadership meetings when needed (up to 25%). ❗This is an existing vacancy. ❗This is a full-time, permanent position. 📍This is role is open to remote (anywhere in Canada) or hybrid (if located in Toronto, GTA), requiring the successful candidate to work three days a week at our Toronto office  (351 King St E, Toronto, ON).

Ensure the successful delivery of all services engagements with a high degree of quality and customer satisfaction

Manage and grow revenue and increase value contribution through effective utilization of resources

Develop and motivate a skilled services delivery team, including conducting performance evaluations, identifying development opportunities and mentoring the team

Define and measure team performance against set objectives

Drive innovation, continuous improvement and guide the strategic direction of the team

Collaborate and work closely with the VP Professional Services and the regional professional services and education leaders to drive consistency in global processes and services for implementation and training

Actively participate in team and management meetings and strategy sessions

Foster strong customer and partner relationships to drive delivery excellence, managing feedback and escalations, as needed

Collaborate with internal stakeholders to identify and execute business growth strategies, develop hiring plans and develop supporting practices to drive product adoption

Partner with the sales and pre-sales team to complete statements of work, showcasing the value of our services team and sharing measurable outcomes

Maintain working knowledge of the Caseware solutions, industry trends and delivery methodologies

Ensure resources availability to support forecasted/planned organizational delivery expectations

Analyze existing workflows to surface bottlenecks where AI tools can meaningfully reduce manual effort and increase scalability.

10+ years’ experience in customer facing role (e.g., customer success, account management, implementation, product or project management) in a SAAS company serving the Accounting Profession OR

At least 10 years’ experience working in an Audit/Accounting/Professional Services Firm performing External Audit or Assurance engagements.

5+ years demonstrated management experience

Experience managing a diverse and remote team, including recruiting, training, staffing, and performance management

Knowledge of Caseware’s solutions is an asset

Strong operational management, project management, consulting, and process improvement skills

Experience with change management principles and resilience to adapt with pivots in strategies and goals

Demonstrated expertise supporting the sales of professional services, including developing statements of work, pricing, and large-scale proposal development including but not limited to RFI, RFQ and RFPs

Demonstrated ability to manage ambiguity and apply problem-solving skills to unique situations

Demonstrated experience succeeding in a fast-paced environment and managing multiple projects simultaneously

Excellent presentation skills, customer service, team building skills

Operate with an AI-first mindset, leveraging tools to enhance productivity, decision-making, and day-to-day work.

Salary Range

The annual base salary for this position is between $185,000 CAD and $200,000 CAD per year. This role is also eligible for discretionary bonus and/or commission, as well as other benefits. Actual pay within the listed range will be determined based on factors such as transferable skills, relevant experience, market conditions, and primary work location. The posted range is subject to change and may be updated periodically.

What's in it for you

▪️Innovation is at our core. We work with cutting-edge technology in accounting and financial reporting, constantly pushing the boundaries to create impactful software solutions. ▪️We are committed to a collaborative culture, where your ideas are valued, and knowledge sharing is encouraged within a supportive, inclusive team. ▪️Work-life balance is important to us. We offer flexible work options, remote opportunities, and generous time-off policies to ensure a healthy work-life balance. ▪️We offer competitive compensation, including a competitive salary and comprehensive benefits such as health insurance and retirement plans. ▪️We are driven by impactful work. Your contributions directly affect how our clients manage financial processes and drive their success. ▪️Recognition and rewards matter to us. We celebrate hard work through recognition programs, performance bonuses, and opportunities for career growth. ▪️We embrace global opportunities. Work on international projects and collaborate with a diverse, global team.

About Caseware

Caseware's cutting-edge software products are meticulously designed for accounting firms, corporations, and governments. Our teams are continually collaborating, innovating, and building upon our existing suite of products. With a customer-focused mindset, we are building technology that is shaping what the future of audits, financial reporting, and financial data analytics will look like.

With a recent strategic investment from Hg Capital in 2020, Caseware is now in its next major growth phase as we double down on the people and products that have made Caseware so successful to date.

One of Caseware's core values is Many Voices, One Team and with that in mind, we're dedicated to building teams as diverse as our customers in an equitable and inclusive way. We welcome and encourage candidates of all backgrounds to apply. Should you require accommodations or have any questions at any point during the application or interview process, please e-mail our People Operations team at talent@caseware.com.

AI Usage

The recruitment process may use AI assisted tools but not for candidate screening or assessment. All final hiring decisions are made by humans to ensure fairness, transparency, and oversight.

Background Check

Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through Certn.co which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well. Candidates residing in the Netherlands and Germany are excluded from undergoing background checks via Certn.co

Security and Fraud

Caseware takes the security of candidates seriously. All legitimate communication from us will come from email addresses ending in @caseware.com and our open positions are always listed on reputable job boards and on our website https://jobs.lever.co/caseware. We will NEVER ask for payment or financial information from you. If you receive an unsolicited job offer, proceed with extreme caution.