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AI Operations Specialist (Hybrid)

Chicago, IL

About Rewards Network

Celebrating 41 years in business, Rewards Network has helped restaurants increase their revenue, traffic, and customer engagement through our innovative financial, marketing services, and premier dining rewards programs. We connect diners to fantastic restaurant experiences by offering unique card-linked offers.  Our offers leverage advanced technology and powerful data analytics, providing value to our restaurants, diners, and strategic partners' loyalty programs.

Our Culture 

At Rewards Network, you will find a passionate and diverse group of professionals that enjoy working collaboratively, solving problems, and taking ownership of not only their own careers and success, but the success and continued growth of the organization. We take pride in partnering with the world's most powerful loyalty programs to bring full price paying customers and better ways to access working capital options to local restaurants. We offer a challenging and rewarding environment where you can maximize your potential.

Job Overview

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. 

What you’ll bring to the table: (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.

Do you have the right mix of ingredients: (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

Education, Certifications and Experience: (Preferred)

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

What you’ll love about us: 

  • This is a full time, exempt position, and the base compensation for this opening is expected to be $85,000-$100,000, depending on level, candidate experience, skills and other factors. This position is eligible for a 7.5% bonus with a total compensation of $91,375-$107,500
  • 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
  • Hybrid working space in our state of the art office downtown located by the Metra and Ogilvie train stations

Rewards Network is an Equal Opportunity Employer (EOE). We encourage and strongly support workplace diversity.

 

Expected Pay Range

$85,000 - $100,000 USD

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