[Hiring] Director of Professional Services @Caseware

Role Description

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 a full-time, permanent position.

Location: This is a remote position and is available to all applicants residing and eligible to work in the US.

Qualifications

• 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.

Requirements

• 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.

Benefits

• 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.
• 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.