Senior Manager, Product Strategy & Operations

Caseware; Toronto; Hybrid; CAD 115,000 - 130,000; Full time

Benefits offered by this job

Health insurance

Retirement plans

Flexible work options

Job summary

Caseware is seeking a strategic leader to own and elevate our product strategy narrative. You will drive high-stakes initiatives, build executive-ready stories, and shape annual planning frameworks across global teams.

Ideal candidates bring 3–5 years in management consulting or corporate strategy with a strong track record of influencing C‑suite decisions. This hybrid Toronto role partners with the Director of Global Product Operations and the CPO's leadership team to steer product direction,

Qualifications

• 3–5 years of experience spanning top-tier management consulting and/or in-house corporate strategy of comparable rigor.
• Demonstrated leadership of strategic workstreams: analyses and storylines you drove and defended to senior executives yourself.
• Structured problem-solving fluency: hypothesis-driven storylines, top-down communication, synthesis of ambiguous inputs.
• Excellent written communication: decision documents and executive materials that stand on their own.
• Executive presence: comfortable presenting to, and pushing back on, C-level stakeholders.
• Hands-on fluency with modern AI tools (such as Claude).
• Experience with B2B SaaS, fintech, audit/accounting, or another regulated software environment.
• Experience contributing to Board-level or C-suite materials.
• Familiarity with pricing & packaging or product lifecycle decisions.

Responsibilities

• Own the Product Board narrative end-to-end: craft the storyline and prep leadership.
• Lead priority strategy initiatives from ambiguity to executive decision.
• Drive the strategy layer of annual planning and produce core artifacts.
• Turn ambiguity into decisions with crisp narrative and decision documents.
• Partner with the Director of Global Product Operations and the CPO's leadership team.

Skills

Strategic leadership

Structured problem-solving

Executive communication

AI tools (Claude)

B2B SaaS experience

Fintech/regulatory software

Job description

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!

Full‑time permanent position

New 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 St E, Suite 1100, Toronto, ON.

What the seat offers: Board‑level narrative ownership, direct C‑suite proximity, on a team that works AI‑natively, with Claude in the workflow every day.

What you will be doing:

• Own the Product Board narrative end-to‑end: build the storyline, synthesize the insight, sharpen the message, and prepare the CPO and Product leadership to deliver it.
• Lead priority strategy initiatives end-to‑end: Product maintains a standing pipeline of our highest‑stakes strategy questions, and this role owns taking each from ambiguous problem to executive decision.
• Drive the strategy layer of annual planning: design the frameworks, synthesize inputs from our teams worldwide, and produce the core strategy artifacts leadership decides on.
• Turn ambiguity into decisions: structure multi‑stakeholder questions into crisp narratives, and decision documents that executives act on.
• Operate as a trusted thought partner to the Director of Global Product Operations and the CPO's leadership team, in conversations that set Product's direction.

What you will bring:

• 3–5 years of experience spanning top‑tier management consulting and/or in‑house corporate strategy of comparable rigor.
• Demonstrated leadership of strategic workstreams: analyses and storylines you drove and defended to senior executives yourself.
• Structured problem‑solving fluency: hypothesis‑driven storylines, top‑down communication, synthesis of ambiguous inputs.
• Excellent written communication: decision documents and executive materials that stand on their own.
• Executive presence: comfortable presenting to, and pushing back on, C‑level stakeholders.
• Hands‑on fluency with modern AI tools (such as Claude).
• Experience with B2B SaaS, fintech, audit/accounting, or another regulated software environment.
• Experience contributing to Board‑level or C‑suite materials.
• Familiarity with pricing & packaging or product lifecycle decisions.

Salary range:

The salary range for this position would be between CAD$115,000 and CAD$130,000, depending on experience level. 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 [e-mail].

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.