Head of TEM Operations & AI Delivery (Senior Manager level) / Responsable des opérations TEM et de la livraison de l'IA

Company: Upland Software

Location: Ottawa, ON K2K 2E4 (Remote)

Type: Full-time

Remote: Yes

Posted: 2026-08-29

About this role

At Upland Software, you’ll find smart, creative teams who love working together to deliver value for our customers, and a global culture of growth and possibility. Our operating model has always supported remote work—and as we keep growing and evolving our workplace, that won’t change. We’re passionate. We’re proactive. We take pride in our work, and we love a good challenge. Sound like you?

Cimpl is Upland’s Telecom and Managed Mobility Expense platform — the system of record for how large, complex organizations govern their communications spend, inventory, and vendors. Our customers stay with us for years because Cimpl sits inside mission-critical workflows and because our people, not just our software, make the numbers trustworthy. That relationship is our moat.

It is also the moment to expand what that relationship delivers. The traditional TEM promise — collect the invoices, reconcile the charges, report the spend — is being commoditized. The next generation of buyers expect their TEM to predict, decide, and act, not just record. This role exists to lead that shift on the Managed Services side of the house: to turn a concentrated, high-value account base into an even stickier one, and to reimagine, with AI at the center, what a managed TEM should do for a customer.

About the Role

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 t...

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