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About the Role
As the Director, Operations & AI Delivery, you will own the service experience for our most important enterprise customers while reimagining how managed TEM is delivered. This role is for a builder with a relentless focus on retention, transforming operational workflows with AI and automation.
Responsibilities
- Protect and grow the customer base by acting as the senior operational leader for Cimpl's largest enterprise accounts.
- Own operational excellence by setting and consistently exceeding standards for SLAs, data accuracy, and service quality.
- Reinvent managed services by leading a clean-sheet rethink of how Cimpl Managed Services should operate in an AI-enabled world, partnering closely with Product.
- Apply AI and automation to identify and implement practical use cases across reconciliation, data validation, anomaly detection, dispute management, workflow automation, and customer support.
- Lead Customer Support by owning end-to-end resolution and ensuring recurring issues are addressed at the root cause.
- Drive cross-functional improvement by distinguishing product, process, and customer issues and ensuring the right teams solve them permanently.
- Build a scalable operating model by standardizing processes, improving reporting, and creating an operation that scales through technology and better ways of working.
Requirements
- Experience in TEM, MMS, telecom operations, or a closely related enterprise-services environment.
- A track record of owning SLAs, operational metrics, and customer outcomes.
- Experience managing enterprise customers or high-value customer portfolios.
- A strong understanding of what drives retention, customer health, and expansion.
- Demonstrated ability to identify inefficiency and transform how work gets done.
- Genuine enthusiasm for applying AI and automation to operational problems.
- Sufficient technical fluency to understand SaaS and TEM workflows.
- Strong executive communication skills and the ability to influence Product, Support, Customer Success, and customers.
- Highly organized, detail-oriented, and comfortable with accountability in a dynamic operational environment.
Skills
- Telecom Expense Management (TEM)
- Managed Mobility Services (MMS)
- AI and automation
- Workflow automation
- Robotic Process Automation (RPA)
- SaaS platforms
- Customer relationship management
- Service Level Agreements (SLAs)
- Operational metrics
- Executive communication
Location
- Remote-first
Work Type
- Remote
- Full-time
Experience Level
- Senior operator
- Director
Salary/Compensations
- $125,000-$140,000 CAD
About the Company
- Upland Software is the intelligence layer that unifies and contextualizes enterprise knowledge, content, and data, turning isolated information into actionable outcomes for every human and agent.
- More than 1,100 enterprise customers rely on Upland's deep domain expertise to unlock the full value of their AI and agent-driven operating models, driving measurable outcomes across customer experience, employee productivity, and regulatory compliance.
- Cimpl is Upland’s Telecom Expense Management (TEM) and Managed Mobility Expense platform—the system of record for how large enterprises manage communications spend, inventory, and vendors.
- Our customers stay with us for years because Cimpl is embedded in mission-critical workflows, and because our people make the data and outcomes trustworthy.