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Remote Head of Professional Services (Markham)

CaseWare

Full‑time, permanent position.

Location: Available to applicants residing and eligible to work in Canada, USA, UK, Europe, or Australia.

What you will be doing

  • Lead the development and execution of Caseware’s global Professional Services strategy, including onboarding, implementation, training, and migration services.
  • 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.
  • Guide firms through seamless transitions from on‑premise to Caseware’s cloud platform and drive execution of complex migrations.
  • Act as an executive sponsor for strategic clients, providing white‑glove guidance throughout their implementation journey.
  • Collaborate cross‑functionally to solve challenges and exceed client expectations.
  • Lead global service delivery teams, manage resourcing, forecasting, and service efficiency.
  • Identify opportunities for automation, tooling, and process improvements to continuously improve time‑to‑value and project performance metrics.
  • Own services revenue and team growth, driving a high‑performance culture.

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 and 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, working with cutting‑edge technology to create impactful software solutions.
  • A collaborative culture values ideas and encourages knowledge sharing within a supportive, inclusive team.
  • Work‑life balance is important; we offer flexible work options, remote opportunities, and generous time‑off policies.
  • Competitive compensation, including salary and comprehensive benefits such as health insurance and retirement plans.
  • Impactful work that directly affects how clients manage financial processes and achieve success.
  • Recognition and rewards through performance bonuses, growth opportunities, and celebration programs.
  • Global opportunities to work on international projects with a diverse team.

We welcome and encourage candidates of all backgrounds to apply. If you require accommodations, please contact People Operations at View email address on ca.talent.com.

Caseware is a leading provider of audit and accounting software, serving over 500,000 users across 130 countries.

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Vacancy posted 4 hours ago
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