Senior Director, Sales Strategy, Planning & Operations
Senior Director, Sales Strategy, Planning & Operations
Posted on :
12-07-2025
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1 Vacancy
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Monthly Salary
Not Disclosed
Salary Not Disclosed
Vacancy
1 Vacancy
Posted on :
12-07-2025
Job Description
Caseware is one of Canadas original Fintech companies having led the global audit and accounting software industry for over 30 years with more than 500000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles!
The Sr. Director of Sales Strategy Planning & Operations will lead the charter for driving GTM planning revenue governance sales coverage and operational execution. This leader will be instrumental in building scalable sales strategies and implementing repeatable processes to drive predictable growth across regions and segments.
This is a Full time position
Location: This is a hybrid role requiring the successful candidate to work 3 days a week in our Toronto office located at 351 King Street East Suite 1100 Toronto ON M5A 4T9.
Open to candidates residing in the US for a remote opportunity
What you will be doing:
- Lead annual sales planning process including quota setting territory design and capacity planning
- Design and implement revenue management cadences such as weekly forecast monthly and quarterly performance reviews.
- Partner with Sales Marketing Finance and Product teams to align GTM execution with strategic priorities.
- Drive sales performance analysis funnel diagnostics and rep productivity insights.
- Support executive revenue governance forums with insights and reporting.
What you will bring:
- 10 years of experience in Sales Strategy RevOps or GTM leadership roles within B2B SaaS.
- Demonstrated experience in leading quota and territory planning incentive design and forecasting.
- Strong cross-functional collaboration skills especially with Sales Finance and Product leaders.
- Ability to lead and mentor a high-performing ops team and scale operations globally.
Whats 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:
Casewares cutting-edge software products are meticulously designed for accounting firms corporations and 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 Casewares core values is Many Voices One Team and with that in mind were 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
Background Check:
Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well. Candidates residingin the Netherlands and Germany are excluded from undergoing background checks via
Security and Fraud:
Caseware takes the security of candidates seriously. All legitimate communication from us will come from email addresses ending in @ and our open positions are always listed on reputable job boards and on our website We will NEVER ask for payment or financial information from you. If you receive an unsolicited job offer proceed with extreme caution.
Required Experience:
Exec
Employment Type
Full-Time
Key Skills
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