Product Manager optimizing display, video, programmatic, newsletter, and app advertising products for Canadian news media company Postmedia. Managing roadmaps, launches, analytics, and ad - tech performance.
About the role
- Senior Product Manager at Upland Software leading AI strategies in Professional Services Automation. Collaborating with teams to enhance product offerings and drive business outcomes.
Responsibilities
- Drive AI product strategy for Upland PSA and define and prioritize the roadmap from predictive intelligence to autonomous workflow orchestration.
- Identify and develop the platform's data moat across usage patterns, customer behavior, transaction history, workflow context, and decision trajectories.
- Tackle the challenge of deploying privacy-first AI capabilities across a highly configurable enterprise platform, building intelligent workflows that scale across highly varied customer configurations while maintaining strict data governance.
- Engage directly with PSA practitioners — project managers, resource managers, financial controllers and executives — to validate where AI creates measurable operational value.
- Partner with engineering, and design to ship models that drive measurable business outcomes and reduce manual effort, while carefully managing the user experience and change management required for practitioners to confidently hand over control to AI.
- Collaborate with Marketing on GTM enablement to translate AI capabilities into crisp, credible positioning.
Requirements
- 5+ years of product management experience in PSA, PPM, ERP, or adjacent professional services software.
- Deep fluency in professional services operations, including time capture, resource forecasting, project financials, billing workflows, and utilization economics.
- Mastery of core financial drivers like utilization and realization rates, paired with an understanding of modern, outcome-based KPIs such as client sentiment and project success rates.
- A fast-moving student of the AI landscape who is actively experimenting with LLMs and agents, with a clear vision of how to apply them to disrupt traditional PSA friction.
- Ability to treat data as "fuel" by identifying the instrumentation needed to fill data gaps and logically defining how feedback loops turn a system of record into an intelligent system of action.
- Ability to distinguish durable competitive advantages from commodity AI features, including building business cases for "build vs. buy vs. partner" decisions and consumption-based monetization.
- Lead through a dual-track delivery reality by advancing an AI-first roadmap while maintaining the stability and trust of a mission-critical system of record that customers depend on daily.
- Proven experience managing and mentoring a small team of Product Managers and Product Owners, with a focus on elevating their strategic thinking and execution.
- Experience navigating highly distributed, remote-first teams across multiple time zones, prioritizing high-fidelity written communication and structured asynchronous decision-making.
- Exceptional verbal and written English proficiency, with a proven ability to drive both internal and external alignment. Seamlessly translate the technical language of data science and engineering for internal stakeholders, while articulating outcome-focused value and AI strategy to external customers and the broader market.
Benefits
- Remote work options
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