Head of Professional Services
Boston / Toronto, ON
Customer Experience – Professional Services & Training /
Full Time - Permanent /
Remote
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, USA, UK, Europe or Australia.
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 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.
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.
