Sales Enablement Leader

Posted:
8/4/2026, 2:45:26 PM

Location(s):
Toronto, Ontario, Canada ⋅ Ontario, Canada

Experience Level(s):
Junior ⋅ Mid Level ⋅ Senior

Field(s):
Sales & Account Management

Workplace Type:
Hybrid

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!

Caseware is hiring its first Sales Enablement Leader to build the enablement function from the ground up. This is a highly hands-on role for someone who can create structure in an evolving environment, partner across the business, and deliver practical tools and training that help our sales teams perform at a higher level.

In the near term, you will be responsible for building the core content, resources, and programs that Sales and Solutions Consulting rely on every day. You will work closely with Product Marketing, Sales Operations, Training, and other cross-functional partners to close gaps across the pre-sales, sales, and onboarding journey.

As the function grows, this role may expand to include 1–2 direct reports later this year. Over time, you will also help shape the broader strategy, operating model, and priorities for sales enablement at Caseware.

This is a rare opportunity to build a critical function from the ground up at a global company with strong market credibility. You will help shape how Caseware equips its sales teams, improves consistency in the field, and scales enablement globally over time.

This is an Existing vacancy
 
This is a full-time, permanent position.
 
This role is hybrid (working from Toronto office) or remote depending on candidate location and open to candidates who reside in and are eligible to work in Canada  

Salary Range:  

The annual base salary for this position is between $100,000 CAD and $115,000 CAD per year. 

This role is also eligible for discretionary bonus and/or commission, as well as other benefits. Actual pay within the listed range will be determined based on factors such as transferable skills, relevant experience, market conditions, and primary work location. The posted range is subject to change and may be updated periodically. 


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 [email protected].

AI Usage:
The recruitment process may use AI assisted tools but not for candidate screening or assessment. All final hiring decisions are made by humans to ensure fairness, transparency, and oversight. 

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.