{"id":1911235,"url":"https://alion.io/job/caseware-technical-program-manager-ai-programs","title":"Technical Program Manager, AI Programs","company":{"id":4176,"name":"Caseware","domain":"caseware.com","url":"https://alion.io/company/caseware","size_band":"501-1000","is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Lever","truth_index":{"grade":"A","score":88,"open_postings":4,"ghost_share":0,"stale_share":0.5,"repost_share":0,"time_to_fill_p50_days":42,"computed_at":"2026-10-10T05:45:15Z"}},"role":"Product","role_family":"Product","seniority":"middle","employment_type":"full_time","work_mode":"hybrid","remote_scope":null,"remote_scope_basis":null,"remote_working_hours":null,"hiring_geo_confidence":"explicit","locations":["Toronto, Canada"],"countries":["CA"],"hiring_countries":[],"hiring_countries_total":0,"salary":null,"salary_estimate":{"min_usd":60000,"max_usd":129000,"period":"year","method":"role_seniority_country_remote_cell","sample_n":31},"experience_years_min":3,"visa_sponsorship":false,"relocation_package":false,"has_equity":false,"technologies":[],"status":"live","first_seen_at":"2026-10-02T18:57:02Z","employer_posted_date":"2026-10-02","last_verified_at":"2026-10-10T22:01:25Z","board_verified":true,"closed_at":null,"days_open":8,"trust":{"level":"ok","repost_count":null,"flags":[],"days_open":8},"description":"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.\nYou 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.\nThis 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.\nThis is a New Role\nThis is a full-time, permanent position.\nLocation:\nThis 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.\nWhat you will be doing:\nOwn the AI Roadmap and its Single Source of Truth\nMaintain 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.\n\nEstablish and run the operating cadence (planning reviews, status reporting, roadmap updates) that keeps stakeholders aligned by default.\n\nWork with the team to translate AI strategy into sequenced programs with clear milestones, owners, dependencies, and measurable success criteria.\n\nDrive AI Launch Programs\nManage AI feature and capability launches end to end, coordinating product, engineering, design, marketing, enablement, and support.\n\nBuild and maintain launch plans, readiness checklists, and go/no-go criteria, and track execution against them.\n\nOwn cross-functional sequencing and dependency management so launches ship on time and at quality.\n\nBe the Consistent Unblocker\nProactively identify dependencies, risks, and blockers across AI programs and drive them to resolution before they slow delivery.\n\nAct as the point of connection between AI initiatives and the teams they depend on, escalating with clear context and options when decisions are needed.\n\nReduce friction in decision-making by keeping trade-offs, owners, and open questions explicit and visible.\n\nOperational Excellence and Reporting\nMaintain program documentation, dashboards, and reporting that give real-time visibility into AI roadmap health.\n\nDefine and track program metrics such as delivery predictability, launch readiness, and adoption.\n\nContinuously improve the AI program management operating model, templates, and tooling.\n\nWhat you will bring:\n3+ years in technical program management, product operations, or a related discipline in SaaS or platform environments, including cross-functional program delivery.\n\nA track record of orchestrating complex, cross-functional programs from strategy through launch, on time and at quality.\n\nStrong technical fluency: able to engage credibly with engineering on AI/ML, APIs, data, and cloud architecture, and to translate between technical and business audiences.\n\nDemonstrated ability to create clarity and a single source of truth in ambiguous, fast-moving environments.\n\nExcellent stakeholder management, communication, and risk and dependency management skills.\n\nProven ability to drive outcomes across multiple teams without direct authority.\n\nPreferred Qualifications:\nExperience managing AI/ML product or platform programs.\n\nFamiliarity with feature flagging, experimentation, or launch tooling (for example, LaunchDarkly).\n\nProgram management certification such as PMP, SAFe, or equivalent.\n\nDegree in Computer Science, Engineering, or equivalent technical field.\n\nExperience in fintech, audit, or regulated 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