SherwebSH

Head of Enterprise Applications & AI Enablement

Sherweb is a leading cloud solutions provider based in Sherbrooke, Quebec, offering innovative services to over 60,000 businesses globally.

Sherweb

Employee count: 1001-5000

Canada only

Location: Montreal or Sherbrooke; remote considered

Here's what we do and why we do it.
We work to simplify the cloud for IT professionals so they can focus on what really matters, making their customers' lives better. Find out how we do that here: www.sherweb.com/about/

Here's how you will contribute to the company’s success

  • Lead and evolve the enterprise systems strategy.Partner with key stakeholders to architect and execute the roadmap for core business applications (ERP, CRM, HRIS, Finance, etc.), balancing productivity, scalability, cost-efficiency, security, and compliance across a growing global operation.
  • Establish standards and guidelines for technology adoption.Drive growth through scalable platforms. Evaluate and recommend system improvements or new technologies aligned with the company’s strategic goals while optimizing the overall SaaS footprint.
  • Champion cross-functional collaboration and governance. Partner with IT, Finance, People & Culture (HR), and Operations to align processes, support change management, and establish disciplined governance in system usage.
  • Drive AI and automation enablement.Identify opportunities to integrate AI tools (e.g., Microsoft Copilot, Power Automate) and intelligent automation into business workflows to reduce friction, enhance the employee experience, and increase data intelligence.
  • Promote transparency through dashboards and KPIs. Define and implement performance metrics to evaluate the health and business value of systems, including AI maturity and automation impact.
  • Lead systems integration and optimization during M&A. Oversee application rationalization and post-merger integration efforts to ensure the seamless consolidation of tools, licenses, data, and processes.
  • Support vendor relationships and licensing strategies. Influence and assist in managing vendor contracts, renewals, and procurement strategy as needed.
  • Act as a technology change agent. Advocate for the adoption of enterprise systems and AI across both technical and non-technical audiences, fostering a culture of innovation and agility.

Here's what you need to have and master to get the job

You are a strategic, execution-focused leader who balances short- and long-term priorities. You bring a strong mix of business and financial acumen, paired with deep technical expertise. You have experience modernizing enterprise systems and understand how to leverage automation, AI, and analytics to scale operations and improve outcomes. You have:

  • 10+ years of experience in enterprise applications, business systems, or technology leadership roles
  • Proven track record leading ERP/CRM/HRIS strategy, implementation, and integration
  • Deep knowledge of Microsoft Dynamics 365 (F&O, CRM), Azure, and data & analytics
  • Familiarity with UKG (or any other HRIS/HCM platform), autotask, and Great Plains is a plus
  • Demonstrated experience enabling automation and AI across business workflows
  • Experience with post-merger system integration and managing complex cross-functional projects
  • Strong skills in process optimization, stakeholder engagement, and change management
  • Analytical mindset with the ability to translate complex business needs into scalable system architecture.

Why this role matters

We are entering a pivotal phase in our digital transformation where enterprise technology and intelligent automation will be critical to unlocking operational scale, increasing efficiency, and enhancing both customer and employee experiences across our growing organization. This role is essential to shaping our future technology backbone and positioning the compagny for long-term success.

Benefits of working at Sherweb

Sherweb is, above all, an environment where the needs of our customers are at the heart of our actions. We are committed to living our values of passion, teamwork and integrity every day.

A fast-paced work environment that adapts to you

  • A friendly and diverse work culture with inclusion and equality at the heart of our actions
  • State-of-the art technology and tools
  • A results-oriented culture where talent, action, and thinking outside the box are given due recognition
  • Annual salary review based on performance
  • Generous and caring colleagues of various professional and cultural backgrounds

A flexible total compensation offer

  • Vacation time that considers your previous experience
  • Advanced paid hours to recharge your batteries (holidays and mobile days)
  • Flexible benefits plan that adapts to your needs
  • Flexible savings fund options
  • A monthly home internet allowance

Considerable growth opportunities

  • A career path with opportunities to learn and grow
  • Proximity to your direct manager and open, honest communication to support your development
  • Multiple initial and on-the-job training opportunities and tools to track your progress and help you scale up in your career

Last but not least: “Sherweblife” - a rich calendar of activities that allow us to gather virtually and face-to-face throughout the year

At Sherweb, we believe in pay transparency and fairness. The salary range provided is intended to give an indication of what you might expect for this role. However, we recognize that each candidate brings a unique set of skills and experiences. As such, the final compensation package will be tailored to reflect the specific qualifications and expertise of the chosen candidate, ensuring that we remain competitive and equitable in our offerings.

Reasons for the requirement of English: Sherweb has international customers and fluency in English is the only way to ensure proper service delivery to them. The main tasks related to this position require written and oral communication with an English-speaking clientele at all times.

#AG1

About the job

Apply before

Posted on

Job type

Full Time

Experience level

Director
Executive

Location requirements

Hiring timezones

Canada +/- 0 hours

About Sherweb

Learn more about Sherweb and their company culture.

View company profile

What started as a small initiative has transformed into a dominant presence in the cloud solutions market. Sherweb, founded in 1998 in Sherbrooke, Quebec, began in a basement, driven by the vision of the Cassar brothers, Peter and Matthew. Recognizing early on the profound impact the Internet would have on business operations, they developed a strategy that prioritized partner relationships and innovative service offerings. Over two decades, Sherweb has evolved into a leader in providing cloud solutions, boasting a vast portfolio that includes email, collaboration, security, and backup services.

The heart of Sherweb’s success lies in its partner-first approach. The company has established a robust marketplace that empowers Managed Service Providers (MSPs) to deliver top-tier cloud solutions to their clients effortlessly. With a focus on value-added services, Sherweb not only provides cloud products but also equips its partners with the tools necessary for sustainable growth, including dedicated support, customizable solutions, and continuous training and resources.

Claim this profileSherweb logoSH

Sherweb

Company size

1001-5000 employees

Founded in

1998

Chief executive officer

Peter Cassar, Matthew Cassar

Employees live in

View company profile

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Sherweb hiring Head of Enterprise Applications & AI Enablement • Remote (Work from Home) | Himalayas