[Hiring] Head of TEM Operations & AI Delivery @Upland Software

Role Description

As Head of TEM Operations & AI Delivery — Cimpl, you own the operational and delivery engine behind Cimpl’s most important accounts. You are the person our largest enterprise customers trust to keep their program running flawlessly and to bring them ideas they didn’t ask for. You will hold the line on SLAs and data accuracy, and you will push the organization to move up the value curve — from a reliable back office to a proactive, insight-driven partner customers cannot imagine operating without.

This is a builder’s role with a retention-first mandate. You do not need to be an engineer, but you should understand how Cimpl and TEM workflows actually work — well enough to see where mechanical labor is hiding inside professional work, and where AI and automation can eliminate it. You will be given room to challenge how managed services has always been done and the accountability to prove a better way.

What You’ll Own

• Retain and deepen the base.
• Serve as the senior operational partner for Cimpl’s largest enterprise accounts, partnering with the Customer Success Organization.
• Protect these relationships, resolve escalations before they threaten renewals, and turn operational excellence into expansion.
• Own the service standard.
• Hold internal and customer-facing SLAs to a consistently-met-or-exceeded bar across TEM operations.
• Own then reinvent managed services delivery.
• Lead a clean-sheet rethink of the Cimpl managed services model.
• Put AI to work operationally.
• Identify and implement practical AI use cases across the day-to-day.
• Diagnose and route root cause.
• Recognize whether an operational issue originates in the product, an internal process gap, or a customer’s own configuration or workflow.
• Own Customer Support.
• Own the resolution of customer support issues end to end and lead the Customer Support organization.
• Make performance visible.
• Build and maintain the operational reporting and dashboards that track SLA performance, process efficiency, automation impact, and account health.
• Standardize and scale.
• Document and codify managed services procedures.

Qualifications

• Experience in Telecom Expense Management (TEM), Managed Mobility Services (MMS), or a closely related operational/telecom domain is strongly preferred.
• A track record of owning SLAs and operational metrics in a customer-facing or customer-adjacent role.
• Experience supporting or managing relationships with enterprise-level accounts.
• Demonstrated ability to identify inefficiency and drive process change.
• Genuine enthusiasm for applying AI and automation operationally.
• Enough technical fluency to understand how a SaaS/operational platform like Cimpl functions.
• Strong communication skills.
• Highly organized, detail-oriented, and comfortable owning outcomes in a fast-paced operational environment.

Nice to Have

• Prior hands-on experience with TEM/telecom management platform.
• Experience managing or mentoring a small operations or managed-services team.
• Familiarity with workflow automation, RPA, or AI-assisted operations tooling.
• Exposure to enterprise renewal and expansion motions alongside operations.

What Success Looks Like — First 12 Months

• Internal and customer SLAs are consistently met, with trusted, transparent visibility into performance and account health.
• Cimpl’s largest accounts regard this person as a strategic operational partner.
• At least one managed-services workflow is measurably transformed by AI or automation.
• The team spends demonstrably less time on manual processing and more on judgment, insight, and customer relationships.
• A credible, sponsored point of view exists for what Cimpl’s managed service should become.

Compensation

$105,000-$115,000