Director, Operations & AI Delivery

Canada·OttawaRemotesenior

OperationsOtherManagerOperations Manager

2 views0 saves0 applied

Apply Now

Quick Summary

Key Responsibilities

Be the senior operational leader for Cimpl's largest enterprise accounts. Build trust, prevent escalations, support renewals, and create opportunities for expansion.

Technical Tools

OperationsOtherManagerOperations Manager

Reinvent managed TEM. Build what comes next.

At Upland Software, smart, creative teams work together to solve meaningful customer problems and build what’s next. We’re remote-first, global, and driven by a culture of ownership, growth, and possibility.

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.

Now we have an opportunity to take that relationship further.

The traditional TEM model is being commoditized. The next generation of enterprise customers will expect their managed-services partner to do more than collect, reconcile, and report. They will expect it to predict, recommend, and act.

The Role

We’re looking for an experienced TEM, Managed Mobility Services (MMS), telecom operations, or enterprise-services leader to become the operational and transformation leader for Cimpl Managed Services.

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.

What You'll Own

Protect and grow the customer base: Be the senior operational leader for Cimpl's largest enterprise accounts. Build trust, prevent escalations, support renewals, and create opportunities for expansion.
Own operational excellence: Set and consistently exceed standards for SLAs, data accuracy, service quality, and account health.
Reinvent managed services: Lead a clean-sheet rethink of how Cimpl Managed Services should operate in an AI-enabled world, partnering closely with Product.
Apply AI and automation: Identify and implement practical use cases across reconciliation, data validation, anomaly detection, dispute management, workflow automation, and customer support.
Lead Customer Support: Own end-to-end resolution, coach the team, and ensure recurring issues are addressed at the root cause.
Drive cross-functional improvement: Distinguish product, process, and customer issues and ensure the right teams solve them permanently.
Build a scalable operating model: Standardize processes, improve reporting, and create an operation that scales through technology and better ways of working—not simply more people.

What We're Looking For

You are likely a senior operator who brings:

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.
A demonstrated ability to identify inefficiency and transform how work gets done.
Genuine enthusiasm for applying AI and automation to operational problems.
Enough technical fluency to understand SaaS and TEM workflows without being an engineer.
Strong executive communication skills and the ability to influence Product, Support, Customer Success, and customers.

Experience leading a managed-services or operations team, and familiarity with workflow automation, RPA, or AI-assisted operations, are strong pluses.

What Success Looks Like

In your first 12 months:

Cimpl's largest customers see you as a strategic partner and reason to renew and expand.
SLAs and service standards are consistently met or exceeded, with clear visibility into performance and account health.
At least one significant managed-services workflow is measurably transformed through AI or automation.
The team spends less time on manual processing and more time on judgment, insight, and customer relationships.
A clear vision for the next generation of Cimpl Managed Services is established—and the first pieces are already being delivered.

Why This Role Matters

Cimpl already has what many companies struggle to build: deep, trusted relationships inside complex enterprise environments.

Your opportunity is to turn that foundation into the next generation of managed TEM—one that doesn't just record what happened, but helps customers understand, anticipate, and act.

If you're ready to run a great operation today while building what managed services becomes tomorrow, we want to hear from you.

Compensation: $125,000-$140,000 CAD

Chez Upland Software, vous rejoindrez des équipes intelligentes et créatives qui aiment travailler ensemble pour créer de la valeur pour nos clients, au sein d’une culture mondiale axée sur la croissance et les possibilités. Notre modèle opérationnel a toujours favorisé le travail à distance — et alors que nous continuons à faire évoluer notre environnement de travail, cela ne changera pas. Nous sommes passionnés. Nous sommes proactifs. Nous sommes fiers de notre travail et nous aimons relever de bons défis. Cela vous ressemble ?

Cimpl est la plateforme d’Upland dédiée à la gestion des dépenses liées aux télécommunications et à la mobilité (Telecom and Managed Mobility Expense). Elle constitue le système de référence permettant aux grandes organisations complexes de gérer leurs dépenses de communication, leurs inventaires et leurs fournisseurs. Nos clients restent avec nous pendant des années parce que Cimpl est intégrée à des processus essentiels à leur activité et parce que nos collaborateurs, et pas seulement notre logiciel, rendent les données fiables. Cette relation constitue notre avantage concurrentiel.

C’est également le moment d’élargir la valeur apportée par cette relation. La promesse traditionnelle du TEM — collecter les factures, rapprocher les frais et produire des rapports sur les dépenses — devient progressivement une commodité. La nouvelle génération d’acheteurs attend de sa solution TEM qu’elle prévoie, décide et agisse, et pas seulement qu’elle enregistre les données. Ce poste a pour objectif de piloter cette évolution du côté des services gérés : transformer une base de comptes concentrée et à forte valeur en une base encore plus fidèle, et repenser, avec l’IA au cœur de la démarche, ce qu’un service TEM géré devrait apporter à ses clients.