--- title: 'Technical Program Manager, AI Programs at Caseware' canonical: 'https://feeny.ai/job/technical-program-manager-ai-programs-caseware-toronto-tpvy5yz902ad' type: 'job' last_seen: '2026-10-17' --- # Technical Program Manager, AI Programs at Caseware - **Company:** Caseware - **Location:** Toronto, Canada - **Employment:** full-time - **Work type:** hybrid - **Posted:** 2026-10-02 - **Last confirmed live:** 2026-10-17 - **Apply:** https://jobs.lever.co/caseware/c8a2572d-e3bb-402b-b7ba-593e12483a7b ## 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! We are seeking a Technical Program Manager (TPgM), AI Programs to drive the planning, coordination, and delivery of Caseware's AI roadmap across our Firm and Solution portfolios. This role sits at the center of our AI initiatives, turning a fragmented, hard-to-track view of AI work into a single trusted source of truth, and acting as the consistent unblocker that keeps AI programs moving from strategy through launch. You will partner across product, engineering, design, and go-to-market teams to manage AI launch programs end to end, surface and resolve dependencies before they become blockers, and give leadership clear, current visibility into where every AI initiative stands. If you are energized by bringing order to complex, cross-functional programs and by being the person who makes AI delivery predictable, this role is for you. This is an ideal opportunity for a program manager with strong technical fluency who wants to own high-visibility AI programs at scale and shape how a category leader builds and ships AI for assurance professionals. ❗This is a New Role ❗This is a full-time, permanent position. 📍 Location: This position is available to all applicants eligible to work in Canada and residing in Toronto, Ontario. This is a hybrid role, working from office 3 days a week from our Downtown, Toronto office. What you will be doing: Own the AI Roadmap and its Single Source of Truth - Maintain one authoritative, always-current view of the AI roadmap across Firms and Solution products, so leadership and teams know status, priorities, sequencing, and risk at any time without chasing updates. - Establish and run the operating cadence (planning reviews, status reporting, roadmap updates) that keeps stakeholders aligned by default. - Work with the team to translate AI strategy into sequenced programs with clear milestones, owners, dependencies, and measurable success criteria. Drive AI Launch Programs - Manage AI feature and capability launches end to end, coordinating product, engineering, design, marketing, enablement, and support. - Build and maintain launch plans, readiness checklists, and go/no-go criteria, and track execution against them. - Own cross-functional sequencing and dependency management so launches ship on time and at quality. Be the Consistent Unblocker - Proactively identify dependencies, risks, and blockers across AI programs and drive them to resolution before they slow delivery. - Act as the point of connection between AI initiatives and the teams they depend on, escalating with clear context and options when decisions are needed. - Reduce friction in decision-making by keeping trade-offs, owners, and open questions explicit and visible. Operational Excellence and Reporting - Maintain program documentation, dashboards, and reporting that give real-time visibility into AI roadmap health. - Define and track program metrics such as delivery predictability, launch readiness, and adoption. - Continuously improve the AI program management operating model, templates, and tooling. What you will bring: - 3+ years in technical program management, product operations, or a related discipline in SaaS or platform environments, including cross-functional program delivery. - A track record of orchestrating complex, cross-functional programs from strategy through launch, on time and at quality. - Strong technical fluency: able to engage credibly with engineering on AI/ML, APIs, data, and cloud architecture, and to translate between technical and business audiences. - Demonstrated ability to create clarity and a single source of truth in ambiguous, fast-moving environments. - Excellent stakeholder management, communication, and risk and dependency management skills. - Proven ability to drive outcomes across multiple teams without direct authority. Preferred Qualifications: - Experience managing AI/ML product or platform programs. - Familiarity with feature flagging, experimentation, or launch tooling (for example, LaunchDarkly). - Program management certification such as PMP, SAFe, or equivalent. - Degree in Computer Science, Engineering, or equivalent technical field. - Experience in fintech, audit, or regulated industries. Salary Range: The annual base salary for this position is between $110,000 and $130,00 CAD per year. 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 talent@caseware.com. 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. ## About Caseware ## Company Overview - **One-liner**: Caseware provides a cloud-enabled, AI-powered platform purpose-built for audit and financial reporting, helping accounting firms and organizations deliver high-quality, defensible engagements. - **Entity Type**: Private (backed by a leading private equity technology investor; funding stage not publicly disclosed) - **Headquarters**: Toronto, Ontario, Canada - **Founded**: 1988 - **Founders**: Not publicly disclosed ## Core Business - **Primary industry/industries**: Audit & Accounting Software, Financial Reporting, Data Analytics - **Target customers**: Accounting firms (from small to large), corporations, and government regulators (B2B) - **Mission or purpose statement**: To deliver trusted outcomes through workflow-embedded intelligence, helping customers answer the key question: “Why?” ## Products & Services - **[Caseware Platform]**: An end-to-end cloud-enabled platform that serves as the system of record for modern engagements. It integrates AI agents and intelligence directly into workflows. - **[Caseware Verity]**: An AI-powered tool operating within engagements and across the full assurance workflow. It understands context, applies a firm’s methodology, and helps navigate complexity. - **[Caseware Agents]**: Purpose-built AI agents that perform real work across every phase of an engagement—from preparation to reporting—automating tasks, generating outputs, and accelerating delivery. - **[Data Analytics Solutions]**: Tools for digging deeper into financial data to transform insights into impact. ## Market Standing - **Valuation/Market Cap**: Not publicly disclosed - **Key Metric**: Annual Revenue of $55M (estimated); serves 23k+ organizations and 475k+ users across 130 countries. - **Notable Investors/Partners**: Backed by “one of the world’s leading private equity technology investors” (specific name not disclosed in source materials). - **Growth Signals**: Headcount of 460 employees (+6.8% YoY, +40 people); expanding quickly in multiple markets globally; LinkedIn followers growing at +21.8% yearly. ## Competitive Advantages - **Deep Domain Expertise**: 35+ years focused exclusively on assurance and financial reporting, giving them unmatched domain depth. - **Governed AI**: Every AI-assisted decision is reviewable, explainable, and defensible, with context preserved and authority explicit—critical for regulated industries. - **Measurable ROI**: Reports 107-167 hours of AI time savings per engagement, and 35-50% reduction in evidence collection time. - **Embedded Intelligence**: AI operates directly inside existing, trusted workflows rather than as a separate tool, reducing friction and adoption barriers. ## Strategic Focus - **AI-First Platform**: Continuing to embed frontier intelligence and purpose-built AI agents into every phase of the audit and accounting lifecycle. - **Global Expansion**: Scaling presence across multiple markets worldwide, backed by private equity resources. - **Talent Growth**: Actively hiring across technology, product, customer experience, sales, marketing, finance, and people operations to support growth. ## Why Work Here - **Work Flexibility**: Offers flexibility to work remotely, from one of their global offices, or a combination of both. - **Global Collaboration**: A truly global company with team members and partners across 130+ countries, offering a diverse and connected work environment. - **Learning & Development**: Invested in employee development at every career stage through training programs, conferences, educational opportunities, and meaningful projects. - **Comprehensive Benefits**: Provides healthcare and wellbeing benefits tailored to local standards, plus retirement savings and long-term financial planning benefits. - **Engineering Culture**: Technology teams design, build, secure, and scale the platforms customers depend on daily, working with cloud, ML, and AI technologies. - **Growth Trajectory**: Backed by a leading private equity investor and expanding quickly, offering opportunities for career advancement in a growing company. ## Sources 1. [caseware.com](https://www.caseware.com/) 2. [caseware.com/about](https://www.caseware.com/about) 3. [caseware.com/careers](https://www.caseware.com/careers) 4. 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