Work Management & AI Operations Specialist

Radwell International•Chicago, IL

29d•$80,000 - $120,000•Hybrid

About The Position

Radwell is seeking a Work Management & AI Operations Specialist —a new and pivotal internal role dedicated to optimizing the planning, execution, and visibility of our digital initiatives in part by leveraging AI. You'll help digital teams scale impact by configuring and managing project intake, prioritization, and workflow execution using work platforms like Monday.com. You'll also embed AI across planning and reporting processes to reduce manual effort and elevate decision-quality across marketing, sales, operations, customer service, and beyond.

Requirements

3+ years in internal project/program/operations management, ideally in digital, transformation, or SaaS environments.
Hands-on experience as an administrator or power user for work platforms such as Monday.com, Asana, Workfront, or Smartsheet.
Proven ability to bring clarity and efficiency to digital delivery.
Skilled in using data and AI tools to drive reporting, insights, and execution.
Strong communicator at all levels; confident facilitating cross-functional alignment and adoption.

Nice To Haves

Familiar with digital delivery contexts—marketing campaigns, ecommerce flows, customer experience operations, sales processes.
Practical experience implementing AI automations that reduce manual workload (e.g., status auto-drafts, risk triage, resource forecasting).
Experience using low-code/no-code orchestration and automation tools that operationalize AI and ML workflows to deliver tangible business value.

Responsibilities

Administer and evolve our work management platform (Monday.com), creating standardized intake forms, prioritization templates, dashboards, and facilitating portfolio views across the organization.
Collaborate with the enterprise PMO to define and manage workflows that ensure clarity on delivery pipeline, ownership, and status across digital teams and projects and at an enterprise portfolio level.
Bring consistency to how work is captured, sequenced, and executed by aligning stakeholders on prioritization criteria and workflow stages.
Deliver real-time project visibility through dashboards and visualizations that surface progress, risk, dependencies, and outcomes.
Leverage AI to automate status summaries, identify execution bottlenecks, synthesize project risks, and predict throughput—so stakeholders get timely, intelligent updates.
Partner with teams to co-create reporting that aligns with strategic goals and drives accountability.
Collaborate with marketing, creative, product, marketplace, eprocurement, and engineering teams to integrate work management discipline in their execution models.
Lead recurring cadences—e.g., planning reviews, dependency syncs, status check-ins—to maximize speed and quality of project deliverables.
Facilitate adoption of work management and AI workflows through training, playbooks, and ongoing support.
Use project performance data—cycle times, completion rates, status accuracy, work backlog—to continuously refine workflows and platform models.
Automate routine manual work (status chasing, intake consolidation, executive report compilation), enabling digital teams to focus on delivering value with minimal overhead and administration.
Stay current on work management and AI automation trends to continuously elevate Radwell's operational maturity.