AI Operations Specialist (Hybrid)

Rewards Network•Chicago, IL

1d•Hybrid

About The Position

Rewards Network is investing in AI to expand what our Sales and Operations teams can accomplish — improving output quality, increasing throughput, and enabling the organization to grow its impact without proportional resource growth. The AI Operations Specialist is responsible for agent training, maintaining, refining, and supporting the adoption of AI solutions that enable Sales and Operations teams to perform at their best. This role works at the intersection of technology and people, partnering closely with Sales, Operations, and Product teams to support and coach users, maximize adoption, and continuously improve AI tools based on user feedback. Once solutions are live, this role stays engaged: gathering user feedback, suggesting improvements, and building the AI literacy across the organization that makes adoption stick. This is a hybrid position with in office presence 3 days a week (Tuesday-Thursday) at our downtown Chicago office.

Requirements

Bachelor’s degree in Business, Information Systems, or other related field
2–4 years of experience in operations role with responsibility in AI workflow augmentation and automation
Experience with using AI automation platforms in a business setting (Agentforce, Copilot Studio, Claude, or equivalent)
Demonstrated ability to translate business requirements into solutions, manage operational change, and communicate clearly in both directions
Genuine passion for AI — actively experiments with tools, follows the space closely, and forms informed opinions from direct experience
Strong analytical and problem-solving skills; able to diagnose operational friction and design effective AI-enabled solutions
Logical, semi-technical mindset — comfortable structuring agent instructions, defining guardrails, and testing behavior
Excellent communication and interpersonal skills — able to translate between technical and non-technical audiences with clarity, coach and support peers, and build strong collaborative relationships
Collaborative working style with a demonstrated ability to influence without authority across Sales, Operations, and Product teams
Commitment to continuous improvement — finds satisfaction in iterating on solutions based on real user feedback
Strong project coordination skills; keeps stakeholders informed and work moving forward
Comfortable operating in ambiguity; able to define a path forward when the playbook doesn’t exist yet

Nice To Haves

Background in fintech, B2B SaaS, or revenue operations environments
Prior experience in a change management, L&D, or internal enablement capacity

Responsibilities

Configure and train AI agents. Define how agents think, respond, and act — setting instructions, topics, guardrails, and behaviors that make them effective in real operational contexts. Initially focused on refining existing agents, with future responsibility for creating new solutions as adoption matures.
Configure AI workflows and agent behavior across a variety of platforms including Salesforce Agentforce, Microsoft Copilot Studio, Claude, and Power Automate — translating business requirements into instructions, guardrails, and responses that drive operational performance.
Maintain deployed solutions and monitor ongoing performance — tracking output quality, identifying gaps, and keeping solutions functioning reliably across user groups.
Suggest and implement enhancements based on user feedback and operational performance data, maintaining a continuous improvement cycle between end users and deployed tools.
Drive AI literacy across Sales and Operations. Develop best-practice guidance and deliver hands-on enablement that helps teams get more out of the tools they use, improving both adoption depth and output quality.
Gather and close the feedback loop. Actively collect input from end users, translate their experience into prioritized improvements, and serve as the primary conduit between the people using the tools and the people building them.
Coordinate with Product and Operations teams on efficiency initiatives — ensuring agent training and configuration aligns with platform implementation and RTB process requirements.
Evaluate emerging AI tools and platforms. Stay current on the AI landscape and bring forward-looking recommendations on new capabilities, tools, and enhancement opportunities to leadership.
Support change management and adoption by developing communications, training materials, and rollout plans that drive sustainable adoption of new AI workflows and tools across the organization.

Benefits

Competitive Paid Time Off and company holidays
Generous dining reimbursement when you dine with our restaurant clients
401(k) plan with a company match
Two medical plan options- Standard PPO or High Deductible Health Plan (HSA with company match for HDHP participants)
Partnership with Rx n Go, offering certain prescriptions for free
Dental plan options and a vision plan
Flexible Spending Accounts and a pre-tax commuter benefit program
Accident, Critical Illness, and Hospital Indemnity Insurance Plans
Short Term and Long Term disability
Company-paid life insurance and AD&D insurance, supplemental employee, spouse, and child life insurance
Employee Life Assistance Program