Talent.com
Caseware
Remote Head of Professional ServicesCaseware • Barrie, Ontario
Remote Head of Professional Services

Remote Head of Professional Services

Caseware • Barrie, Ontario
30+ days ago
Job type
  • Full-time
  • Permanent
  • Remote
Job description
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.
Create a job alert for this search

Remote Head of Professional Services • Barrie, Ontario

Similar jobs

Head Of Sales & Growth - Multi-Unit Leader

Canadian Door InstituteBarrie, Canada
Full-time

A leading provider of garage door solutions in Barrie, Ontario is seeking a Head of Sales & Growth to lead their sales teams and scale operations.The ideal candidate has over 8 years of B2B sal... Show more

 • Promoted

corporate sales manager

North America Electrical Energy Equipments Co., Ltd.Bolton, Ontario, Canada
Full-time

Work must be completed at the physical location.There is no option to work remotely.Plan and control budget and expenditures.Work with the marketing department to understand and communicate marketi... Show more

 • Promoted

EAP Network Provider

ComPsychSevern, ON, CA
Full-time

ComPsychⓇ is the worldwide leader in organizational mental health, well-being, and absence management, dedicated to igniting human potential in workplaces across the globe.For over 40 years, we hav... Show more

 • Promoted

Career Growth Client Benefits Representative

MediumVaughan
Full-time

Transform your career as a Client Benefits Representative with Global Elite Empire Consultants, where flexibility and growth opportunities abound.Work remotely while crafting a schedule that suits ... Show more

 • Promoted

Professional Practice and Education Leader

Mackenzie HealthVaughan
Full-time

The Professional Practice & Education Leader (PPEL) facilitates processes to support excellence in patient-centered practice based on relevant best practice, conceptual frameworks, research literat... Show more

 • Promoted

Elite Real Estate Agent — Training, Leads & Tech

RE/MAX Hallmark Chilton Realty BrokerageBarrie, ON, CA
Full-time

A leading real estate brokerage in Barrie, Ontario, is seeking motivated real estate professionals to join their team.Candidates must have a postsecondary diploma and strong sales, negotiation, and... Show more

 • Promoted

Director Technology Networking & Operations

Longo'sVaughan
Full-time +1

We are looking for a Director, Technology - Networking & Operations, who is passionate about food and enjoys working in a fast paced, customer service centric, team environment!.The Director, Techn... Show more

 • Promoted

Diamond Consultant - High-Earning, Expert-Level Training

Spence Diamonds Ltd.Vaughan
Full-time

A leading diamond retailer in Vaughan is seeking a Diamond Consultant to guide customers through a unique shopping experience.The role requires a minimum of 2 years in sales, strong communication s... Show more

 • Promoted

Platform Economy Manager

BLAZESOFTVaughan
Full-time

Join our dynamic and innovative gaming company, passionate about creating immersive and cutting‑edge gaming experiences.We pride ourselves on a culture of creativity, collaboration, and a commitmen... Show more

 • Promoted

Director Of Leadership And Learning Programming - C$80,000 - C$105,000 A Year

HollyhockBarrie, Canada
Full-time

Director of Leadership and Learning ProgrammingAbout HollyhockHollyhock is a globally recognized transformative learning and leadership center located on wild and beautiful Cortes Island, the tradi... Show more

 • Promoted

Global Benefits Lead

Husky TechnologiesBolton, Ontario, Canada
Full-time

As the Global Benefits Lead at Husky, you will be responsible for leading the design, governance, administration, and continuous improvement of the company’s global benefits programs.This role will... Show more

 • Promoted

Performance-Driven Consultant: Remote Work Opportunity

AO Garcia AgencyVaughan
Remote
Full-time

Redefine your success as a Performance-Driven Consultant with Global Elite Empire Consultants.This remote position focuses on guiding clients toward their goals without the stress of cold outreach.... Show more

 • Promoted

Inbound Sales Expert in High-Value Building Materials

WP MillworksVaughan
Full-time

Become a crucial player in sales as an Inbound Sales Representative for premium building materials.Drive success in a fast-paced, remote environment while engaging directly with trade professionals... Show more

 • Promoted

Sales Leadership Role at Neo

Neo FinancialVaughan
Full-time

Become a Sales Team Lead at Neo, guiding a team of representatives to secure new customers and foster a stronger financial future for Canadians.Drive performance and engagement.As a leader, your mi... Show more

 • Promoted

Enterprise Managed Services Leader

BDO CanadaBarrie
Full-time

Putting people first, every day.BDO is a firm built on a foundation of positive relationships with our people and our clients.Each day, our professionals provide exceptional service, helping client... Show more

 • Promoted

Salon Manager: Lead Team, Grow Profits & Service

Regis CorporateBarrie, ON, CA
Full-time

A leading salon franchise in Barrie, Ontario is seeking a Salon Manager to oversee salon operations, lead the team, and ensure exceptional customer service.The ideal candidate will have a cosmetolo... Show more

 • Promoted

Government Sales Pro | Uncapped Commissions & Travel

GSCI Advanced PhotonicsVaughan
Full-time

A leading supplier of advanced optical systems is seeking a Business Development Representative to engage government clients and drive sales.Reporting to the Sales and Marketing Manager, you will m... Show more

 • Promoted

Manager of Application Support Services

Echelon 56Vaughan
Full-time

Become the Manager of Application Support Services, specializing in Roadside and Travel applications.Lead a team, enhance system operations, and boost productivity with innovative solutions.In this... Show more

 • Promoted

Entrepreneurial B2B Sales Partner – Managed PBX as the Door to IT Services

LivelinxBarrie
Full-time

Entrepreneurial B2B Sales Partner – Managed PBX as the Door to IT Services.At Livelinx, we help Canadian small and mid‑sized businesses connect, secure, and operate smarter through managed business... Show more

 • Promoted

Vice President Institutional Sales

B. Riley FarberVaughan
Full-time

Are you a dynamic sales leader ready to scale an investment management firm? Do you excel at creating and executing innovative sales strategies? Are you passionate about driving growth, leading hig... Show more