We’re hiring a Senior Manager, Strategic Programs to join our Office of the CEO, reporting directly to the Chief of Staff and working closely with the Executive Leadership Team (ELT). This is a high-impact, high-visibility role that will take ownership of some of Caseware’s most critical strategic priorities—including our flagship "Win in the US" initiative. You’ll combine strategic thinking, analytical rigor, and cross-functional execution to accelerate enterprise priorities, establish PMO discipline, and drive performance against company objectives.
This role is ideal for someone who thrives in ambiguity, enjoys solving complex problems, and wants to operate at the center of strategic decision-making in a global SaaS business.
❗This is a full-time, permanent 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, Toronto, Ontario
What you will be doing:
- Own and drive cross-functional strategic initiatives, including program management of Caseware’s “Win in the US” priority
- Act as a thought partner to the Chief of Staff and ELT in designing, tracking, and course-correcting high-impact projects across regions and functions
- Lead business case development, financial analysis, and market research to support prioritization and investment decisions.
- Stand up and manage a lightweight PMO function—bringing rigor, transparency, and accountability to strategic execution
- Develop high-quality board- and executive-level materials, including initiative updates, KPI dashboards, and performance summaries
- Track progress against goals, identify risks and interdependencies, and lead resolution planning with initiative owners
- Collaborate with teams across Finance, R&D, Sales, Marketing, RevOps, Customer Success, and People to embed insights and ensure alignment on strategic direction
- Conduct ad hoc research and structured problem solving to support enterprise-level decision making
What you will bring:
- Bachelor’s degree in Business, Finance, Economics, or a related field
- 5+ years of experience in Management Consulting, Corporate Strategy, or a similar strategic or analytical role
- Strong critical thinking and problem-solving skills, with a strategic mindset and ability to challenge the status quo
- Proven ability to drive complex, cross-functional programs with senior executive stakeholders
- Highly resourceful, adaptable, and capable of navigating ambiguity with minimal guidance
- Experience in financial analysis, investment decision-making, and data-informed strategy work
- Excellent written and verbal communication skills, with the ability to distill complex issues into clear messages
- Proficient in Microsoft Excel, PowerPoint, and Word; able to produce polished executive-ready deliverables
- Experience with primary and secondary research, including data synthesis, is a plus
- Demonstrated discretion, trustworthiness, and professionalism in handling confidential matters
Why join the Office of CEO:
- Executive Exposure: Partner closely with the CEO and Chief of Staff and gain insight into enterprise-level strategy and decision-making
- Strategic Ownership: Play a lead role in Caseware’s most mission-critical initiatives, from GTM acceleration to operational transformation
- Learning & Growth: Work alongside high-performing leaders from consulting, finance, and tech—sharpening your skills in strategy, operations, and execution
- Cross-Functional Impact: Operate at the intersection of Strategy, Finance, R&D, and GTM in a fast-paced, global SaaS environment
- Meaningful Mission: Help transform how auditors and financial professionals work—through modern, data-driven software that makes a difference
▪️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].
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.
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