Senior Manager, TEM Operations & AI Delivery

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 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 — a concentrated portfolio where the top relationships drive the majority of revenue. 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, with clear visibility into performance trends and account health.

Own then reinvent managed services delivery.  Lead a clean‑sheet rethink of the Cimpl managed services model: if we designed it today, with today’s AI, what would we automate, what would we elevate to human judgment, and what new value would we deliver that customers don’t yet expect? Work directly with Product Management to deliver on this vision.

Put AI to work operationally.  Identify and implement practical AI use cases across the day‑to‑day — automated invoice and inventory reconciliation, anomaly and dispute detection, faster data validation, and agent‑assisted account handling — so the team spends its time on judgment and relationships, not manual processing.

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, and drive it to the right owner — closing the loop with Support, Product, and Customer Success on recurring…