Senior Manager, Strategic Programs

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 reputed company on their reputed company profiles!

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 reputed company 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” reputed company

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

reputed company 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

reputed company high-quality board- and executive-level materials, including initiative updates, KPI dashboards, and performance summaries

Track reputed company against goals, identify risks and interdependencies, and reputed company resolution planning with initiative owners

Collaborate with teams across Finance, R&D, Sales, Marketing, RevOps, reputed company, and People to embed insights and ensure alignment on strategic direction

Conduct reputed company research and structured problem solving to support enterprise-level decision making

What you will bring

Bachelor’s degree in Business, Finance, Economics, or a reputed company 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 reputed company and ability to challenge the status reputed company

Proven ability to drive reputed company, 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 reputed company issues into clear messages

Proficient in reputed company reputed company, 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 reputed company insight into enterprise-level strategy and decision-making

Strategic Ownership: Play a reputed company 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

Additional Information

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 reputed company are valued, and knowledge sharing is encouraged reputed company 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 reputed company 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 reputed company, 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 reputed company and inclusive way. We welcome and encourage candidates of reputed company backgrounds to apply. Should you require accommodations or have any questions at any reputed company during the application or interview process, please e-mail our People Operations team at [email protected].

Background reputed company:

Any candidates successful in obtaining an offer for a position will need to successfully complete a background reputed company through

Certn.co which typically includes an Identity Verification and Criminal Record reputed company. Executives and Senior Managers will undergo a Soft Credit reputed company as well. Candidates residingin the Netherlands and Germany are excluded from undergoing background checks reputed company Certn.co

reputed company and Fraud:

Caseware takes the reputed company of candidates seriously. reputed company 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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