Head of 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!
We’re looking for a visionary Head of Professional Services to lead the global delivery of client onboarding, implementation, training, and migration services. If you’re passionate about delivering exceptional client outcomes, scaling professional services at a global SaaS company, and making a strategic impact—this role is for you. 
❗This is a full-time, permanent position.  📍 Location: This position is available to all applicants residing and eligible to work in Canada or USA.

What you will be doing:

• Lead Our Global Services Strategy:
• Own and evolve Caseware’s Professional Services strategy across onboarding, implementation, training, and migrations. 
• Build scalable, high-impact service models that support firms of all sizes—across North America, EMEA, and APAC. 
• Set standards, frameworks, and KPIs to deliver consistency, quality, and efficiency worldwide. 


• Oversee Cloud Migrations:
• Guide firms through seamless transitions from on-premise to Caseware’s cloud platform. 
• Drive execution of complex migration projects using tools like Caseware CloudBridge and bulk import templates. 
• Ensure data integrity, accurate setup, and minimal disruption for clients. 


• Deliver Exceptional Client Experiences:
• Act as an executive sponsor for strategic clients, providing white-glove guidance throughout their implementation journey. 
• Tailor services to client workflows across audit, review, and AUP engagements. 
• Collaborate cross-functionally to solve challenges and exceed client expectations. 


• Drive Operational Excellence:
• Lead global service delivery teams, and manage overall resourcing, forecasting, and service efficiency. 
• Identify opportunities for automation, tooling, and process improvements. 
• Continuously improve time-to-value and project performance metrics. 


• Own Services Revenue and Team Growth:
• Lead global service delivery teams,and manage overall resourcing, forecasting, and service efficiency. 
• Identify opportunities for automation, tooling, and process improvements. 
• Continuously improve time-to-value and project performance metrics

What you will bring:

• 10+ years of leadership experience in Professional Services, Customer Success, or SaaS delivery roles. 
• Proven ability to scale global services teams and deliver complex client implementations or data migrations. 
• Deep knowledge of accounting/audit workflows and engagement file structures. 
• Experience with Caseware tools is a strong asset. 
• Strong communication and stakeholder management skills—including executive presence. 
• Experience with mid- to large-sized accounting firms and familiarity with hybrid cloud environments. 

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