Senior Manager, Product Strategy & Operations

Caseware International; Toronto; On-site; CAD 115,000 - 130,000; Full time

Benefits offered by this job

Flexible work options

Remote opportunities

Generous time-off policies

Health insurance

Retirement plans

Competitive compensation

Global project exposure

Job summary

Caseware is seeking a Senior Manager, Product Strategy & Operations in Toronto to own the product strategy and drive where we play and how we win. You’ll shape an AI-native transformation, major portfolio decisions, pricing and packaging, and market strategies across the globe.

This is a full-time hybrid role requiring three days in the Toronto office at 351 King St E, Suite 1100. You will partner with the CPO and leadership to turn ambiguity into executable strategy and prepare executive

Qualifications

• 3–5 years leading strategic workstreams with senior executives.
• Proven ability to craft analyses and stories that executives defend.
• Structured problem solving and hypothesis-driven storytelling.
• Excellent written materials for board and C-suite audiences.
• Comfort presenting to C-level stakeholders and driving decisions.
• Hands-on fluency with AI tools and modern product strategy.
• Experience in B2B SaaS, fintech, or regulated software.

Responsibilities

• Own the Product Board narrative end-to-end and prepare exec-ready materials.
• Lead priority strategy initiatives from ambiguity to executive decision.
• Design annual planning frameworks and synthesize global inputs.
• Turn multi-stakeholder questions into crisp decision documents.
• Act as a trusted thought partner to senior product leadership.

Skills

Strategic leadership

Executive communication

AI tools (Claude)

Pricing & packaging

Board/C-suite materials

Stakeholder management

B2B SaaS

Regulated 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!

As Senior Manager, ProductStrategy &Operations, you willownhowdrivetheproductstrategy work that decides where we play and how we win. Our strategy agenda is bigger than ever:an AI-native product transformation, major portfolio decisions, pricing and packaging, and market strategies across the globe.

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.

This is a Full-time permanent position

This is a new position

Location: This is a hybrid role requiring the successful candidate to work 3 days a week in our Toronto office, locatedat 351 King St E, Suite 1100, Toronto, ON.

What you will be doing:

• Own the Product Board narrative end-to-end: build the storyline, synthesize theinsight, sharpen the message, and prepare the CPO and Product leadership to deliver it.

• Lead priority strategy initiatives end-to-end: Productmaintainsa standing pipelineof ourhighest-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 fromour teamsworldwide, and producethe corestrategyartifacts leadership decides on.

• Turn ambiguity into decisions: structure multi-stakeholder questions into crispnarratives,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 youdroveand 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).

• ExperiencewithB2B 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 residingin 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.