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It Automation And Ai Engineer in Chicago

48 active opportunities · Updated October 2026

Explore current it automation and ai engineer jobs in Chicago. Filter by work mode, employment type, experience, department, date posted and distance.

F
📍 Chicago, Illinois, United States
✓ Quality checkedCompany trend -85.5%

About Flexport: At Flexport, we believe global trade can move the human race forward. That’s why it’s our mission to make global commerce so easy there will be more of it. We’re shaping the future of a $10T industry with solutions powered by innovative technology and exceptional people. Today, companies of all sizes—from emerging brands to Fortune 500s—use Flexport technology to move more than $19B of merchandise across 112 countries a year. The recent global supply chain crisis has put Flexport center stage as we continue to play a pivotal role in how goods move around the world. We are proud to have the support of the best investors in the game who believe in our mission, solutions and people. Ready to tackle global challenges that impact business, society, and the environment? Come join us. The opportunity: We’re looking for a pragmatic, growth-minded Sales Leader with a proven history of driving success to guide our Mid-Market Sales Team in Chicago, IL . In this role, you’ll coach and develop Account Executive, building high-performing, inclusive teams to achieve company goals for volume growth and net revenue. You’ll play a critical part in developing talent for progression and promotion within our fast-growing organization. Reporting directly to our General Manager, you’ll collaborate closely with the Mid-Market Leadership Team to deliver key outcomes. This role features a 50/50 compensation model (Base + Uncapped bonus), designed for strong leaders to effectively maximize their earnings through a heavily incentivized sales program. You will: Build, inspire, and lead strong sales teams that consistently meet and exceed targets. Provide inclusive leadership and clear direction to a high-performance team, including hiring, training, and development. Establish and drive specific, targeted goals and quotas to expand and accelerate revenue opportunities. Create, monitor, and manage key performance metrics to drive performance and results. Identify

Supply Chain
P
📍 Chicago, IL, United States· Remote
✓ High-confidence listingCompany trend -85.6%
Quick readStrong listing-quality and freshness signals

About Pinterest: Millions of people around the world come to our platform to find creative ideas, dream about new possibilities and plan for memories that will last a lifetime. At Pinterest, we’re on a mission to bring everyone the inspiration to create a life they love, and that starts with the people behind the product. Discover a career where you ignite innovation for millions, transform passion into growth opportunities, celebrate each other’s unique experiences and embrace the flexibility to do your best work. Creating a career you love? It’s Possible. At Pinterest, AI isn't just a feature, it's a powerful partner that augments our creativity and amplifies our impact, and we’re looking for candidates who are excited to be a part of that. To get a complete picture of your experience and abilities, we’ll explore your foundational skills and how you collaborate with AI. Through our interview process, what matters most is that you can always explain your approach, showing us not just what you know, but how you think. You can read more about our AI interview philosophy and how we use AI in our recruiting process here . Sr. Manager, General & Administrative Strategic Sourcing Pinterest is seeking a strategic sourcing leader to lead General & Administrative sourcing and manage an approximately $150M annual third-party spend portfolio . You’ll partner with leaders across Finance, Legal, Trust & Safety, People, IT, Workplace and other corporate functions to create supplier strategies that balance commercial value, risk management, operational excellence and stakeholder experience. You’ll also lead and develop a team of sourcing professionals while helping evolve Pinterest’s sourcing capabilities. This role reports to the Global Head of Strategic Sourcing & Supplier Intelligence. What you’ll do: Lead category strategy and sourcing plans for General & Administrative spend, translating business priorities into multi-year roadmaps and measur

AIFinanceSupply ChainProcurement
P
📍 Chicago, United States
✓ High-confidence listingCompany trend -85.6%
Quick readStrong listing-quality and freshness signals

About Pinterest: Millions of people around the world come to our platform to find creative ideas, dream about new possibilities and plan for memories that will last a lifetime. At Pinterest, we’re on a mission to bring everyone the inspiration to create a life they love, and that starts with the people behind the product. Discover a career where you ignite innovation for millions, transform passion into growth opportunities, celebrate each other’s unique experiences and embrace the flexibility to do your best work. Creating a career you love? It’s Possible. At Pinterest, AI isn't just a feature, it's a powerful partner that augments our creativity and amplifies our impact, and we’re looking for candidates who are excited to be a part of that. To get a complete picture of your experience and abilities, we’ll explore your foundational skills and how you collaborate with AI. Through our interview process, what matters most is that you can always explain your approach, showing us not just what you know, but how you think. You can read more about our AI interview philosophy and how we use AI in our recruiting process here . Pinterest is on a mission to improve the comprehensiveness and shoppability of ads on our platform. We’re accomplishing this by expanding our advertising demand sources through partnerships with third-party ad platforms and working closely with Agencies and media companies who manage performance marketing budgets. As a member of the Programmatic Technical Operations team, you will drive the success of Pinterest’s programmatic ad products by serving as the primary client contact for deal creation, campaign setup, and launches. You’ll troubleshoot technical issues, optimize campaigns for performance, and collaborate closely with cross functional teams to elevate client outcomes and enhance internal processes. What you'll do: Act as a key point of contact for clients, supporting programmatic deal creation, campaign setup, and ensuring smooth campai

C-
📍 Chicago, IL, United States
✓ High-confidence listing

$150K – $350K/yr

Quick readStrong listing-quality and freshness signals

CLEAR is building THE secure identity company of the future. Our mission is to make experiences safer and easier—physically and digitally. With more than 43 million Members and a growing network of partners across the world, CLEAR's secure identity platform is transforming the way people live, work, and travel. Whether it’s at the airport, stadium, or throughout your everyday life, CLEAR unlocks the magic of frictionless experiences. The Enterprise Account Executive will drive C1’s growth by identifying, structuring, and closing strategic deals with large enterprise organizations. This role will expand CLEAR’s networked identity platform across industries by building high-impact relationships and delivering scalable, revenue-generating deals. What you'll do: Drive enterprise growth by sourcing, developing, and closing strategic partnerships across key industries Own the full deal lifecycle from prospecting through negotiation, contracting, and launch Build and manage a robust enterprise pipeline, leveraging outbound efforts, industry relationships, and market insights Partner cross-functionally with Product, Legal, Security, and Partner Success to align solutions with partner needs and CLEAR capabilities Represent CLEAR externally through executive meetings, industry events, and thought leadership to strengthen market presence How you'll measure success: Total contract value (TCV), annual contract value (ACV), and revenue generated from enterprise partnerships Pipeline growth, conversion rates, and deal velocity across enterprise opportunities Number of new enterprise logos and expansion within existing partners Successful launch and activation of enterprise partnerships What you're great at: 8+ years of experience in enterprise business development, partnerships, or B2B sales within SaaS, identity, fintech, or enterprise technology Proven track record of sourcing, negotiating, and closing complex, high-value enterprise deals Strong executive presence

SX
📍 Chicago, United States
✓ High-confidence listing

$100K – $120K/yr

Quick readStrong listing-quality and freshness signals

ROLE: SENIOR STRATEGIST TEAM: THE KITCHEN NORTH AMERICA LOCATION: CHICAGO COMPANY OVERVIEW: The Kitchen brings together a range of disciplines and capabilities. It’s a team of creatives, producers, data analysts and social experts working together to deliver remarkable ideas that live in a variety of mediums, from everything from social to TV. This team moves at the speed of culture. It is built to respond to trends and events as they happen, coming up with the ideas that transcend social media to capture the spirit of the moment, earn media impressions, and get the country talking. Are you ready to join an award-ambitious team that's making waves in the advertising industry? Our incredible team has been recognized internationally by industry giants like Cannes, One Show and was named Campaign's Global ‘In-House Agency of The Year’, further solidifying our position as a leader in the industry. Join us and be a part of something truly special - a team that's dedicated to creating ground-breaking work and pushing limits. At The Kitchen, we're not just looking for individuals who want to be a part of the advertising industry - we're looking for trailblazers who are ready to lead the way to the next big thing! We want individuals who are passionate about producing award-winning work and have an innate drive to their craft and are eager to generate innovative ideas both within and outside of the brief. ROLE OVERVIEW: The Senior Strategist at The Kitchen is responsible for serving as the day-to-day strategic lead across multiple brands. We seek someone who thrives in a fast-paced, creative environment. This role demands a unique blend of strategic thinking, cultural curiosity, and, above all, a passion for social media. Day-to-day responsibilities include developing strategies for brand activations an

B
📍 Chicago, Illinois, United States
✓ High-confidence listing
Quick readStrong listing-quality and freshness signals

WHAT IS BOX? Box (NYSE:BOX) is the leader in Intelligent Content Management. Our platform enables organizations to fuel collaboration, manage the entire content lifecycle, secure critical content, and transform business workflows with enterprise AI. We help companies thrive in the new AI-first era of business. Founded in 2005, Box simplifies work for leading global organizations, including JLL, Morgan Stanley, and Nationwide. Box is headquartered in Redwood City, CA, with offices across the United States, Europe, and Asia. By joining Box, you will have the unique opportunity to continue driving our platform forward. Content powers how we work. It’s the billions of files and information flowing across teams, departments, and key business processes every single day: contracts, invoices, employee records, financials, product specs, marketing assets, and more. Our mission is to bring intelligence to the world of content management and empower our customers to completely transform workflows across their organizations. With the combination of AI and enterprise content, the opportunity has never been greater to transform how the world works together and at Box you will be on the front lines of this massive shift. WHY BOX NEEDS YOU Are you excited by the opportunity to use data and analytics to drive business growth? Do you bring strong business judgment and a passion for ecommerce, digital analytics, and customer behavior? This is a challenging but rewarding role, set in an entrepreneurial environment backed by strong resources and support. We're looking for a smart, self-driven professional who thrives in a high-visibility position reporting to senior executives. As the Senior Business Analyst for Online Sales, you'll partner with leaders across Sales and Marketing, using behavioral data and digital analytics to drive insights and business action. WHAT YOU'LL DO You'll support our online sales strategy — what we sell, how we sell it, and at what price.

SQLAISalesforceTableau
B
📍 Chicago, Illinois, United States
✓ High-confidence listing
Quick readStrong listing-quality and freshness signals

WHAT IS BOX? Box (NYSE:BOX) is the leader in Intelligent Content Management. Our platform enables organizations to fuel collaboration, manage the entire content lifecycle, secure critical content, and transform business workflows with enterprise AI. We help companies thrive in the new AI-first era of business. Founded in 2005, Box simplifies work for leading global organizations, including JLL, Morgan Stanley, and Nationwide. Box is headquartered in Redwood City, CA, with offices across the United States, Europe, and Asia. By joining Box, you will have the unique opportunity to continue driving our platform forward. Content powers how we work. It’s the billions of files and information flowing across teams, departments, and key business processes every single day: contracts, invoices, employee records, financials, product specs, marketing assets, and more. Our mission is to bring intelligence to the world of content management and empower our customers to completely transform workflows across their organizations. With the combination of AI and enterprise content, the opportunity has never been greater to transform how the world works together and at Box you will be on the front lines of this massive shift. WHY BOX NEEDS YOU It's an amazing time to be working at Box and transforming the content management landscape cannot be done without providing best-in-class support for our developers, administrators, and end users. In this role, we support our users through a variety of channels on all aspects of Box products. We are intelligent, resourceful, clever, and committed. We provide innovative and creative solutions and break through walls to solve our customers' problems. We do not follow scripts. WHAT YOU'LL DO Become a technical expert on a product domain of the Box product suite and rapidly grow technical and product knowledge overtime. Engage on customer-facing activities, such as product troubleshooting and providing support to enhance the

AIProject Management
R
📍 Chicago, Illinois, United States· Full-time
✓ High-confidence listing

$22 – $28/hr

Quick readStrong listing-quality and freshness signals

Who we are: Since 2009, we've been on a mission to bring sustainable fashion to everyone. Named one of Fast Company’s Brands That Matter and winning a Best Carbon Footprint award, we have big goals like being Climate Positive by 2025 , Circular by 2030 , and pushing the whole industry forward along the way. Our work has gotten love in Drapers and Sourcing Journal , and TIME wrote about how great our CEO, Hali Borenstein, is. Basically, we're saving the Earth and looking damn good doing it. We're a global brand with 50+ stores (and counting) around the world, and our own sustainable factory in LA . We innovate across categories like accessories , swimwear , and sleepwear , and we reach millions of people with campaigns like this , this and this . None of this work is possible without the incredible people behind it. We're a mission-based company that invests in an inclusive culture, so we can innovate together and ensure everyone has the space to grow, thrive, and belong. And starting right now, we want to do all that with you. Work Location/ Schedule: Available to work a minimum of 30 hours per week, but up to 40 hours per week Daily open availability across a full 7 day work week Able to work flexible schedule (days, nights, weekends, & holidays if required to meet the needs Full Time Sales Lead At Reformation, the sales lead is an elite sales professional and a central figure in the Reformation store ecosystem. This is an elevated, commission-based role designed for a high-performing entrepreneur who views retail as a career. You are a Wardrobe Consultant, responsible for managing a private book of business, driving exceptional SPH, and acting as a trend authority. You don't just facilitate transactions; you foster long-term loyalty through expert service and sophisticated clienteling leading to transformational experiences. Reporting to the Store Manager, essential responsibilities include but are not limited to: What You’ll Do Drive Performance &

AWSGitAIGo
SX
📍 Chicago, United States· Full-time
✓ High-confidence listing

From $73K/yr

Quick readStrong listing-quality and freshness signals

ROLE: ART DIRECTOR TEAM: THE KITCHEN NORTH AMERICA LOCATION: CHICAGO (HYBRID) ABOUT THE KITCHEN NORTH AMERICA The Kitchen brings together a range of disciplines and capabilities. It’s a team of creatives, producers, data analysts and social experts working together to deliver remarkable ideas that live in a variety of mediums, from social to TV. This team moves at the speed of culture. It is built to respond to trends and events as they happen, coming up with ideas that transcend social media to capture the spirit of the moment, earn media impressions, and get the country talking. Are you ready to join an award-ambitious team that's making waves in the advertising industry? Our incredible team has been recognized internationally by industry giants like Cannes, One Show and was named Campaign's Global In-House Agency of The Year, further solidifying our position as a leader in the industry. Join us and be a part of something truly special, a team that's dedicated to creating ground-breaking work and pushing limits. At The Kitchen, we're not just looking for individuals who want to be a part of the advertising industry, we're looking for trailblazers who are ready to lead the way to the next big thing. We want individuals who are passionate about producing award-winning work and have an innate drive to their craft and are eager to generate innovative ideas both within and outside of the brief. OVERVIEW You're not just an Art Director, you’re a cultural observer, a visual storyteller, and a creative problem solver. You’re energized by the pace of modern creativity and thrive in environments where ideas need to happen now . You care deeply about craft, but you’re just as passionate about relevance and impact. You’re ambitious, not just to make great work

B
📍 Chicago, Illinois, United States· Full-time
✓ High-confidence listing

From $238K/yr

Quick readStrong listing-quality and freshness signals

WHAT IS BOX? Box (NYSE:BOX) is the leader in Intelligent Content Management. Our platform enables organizations to fuel collaboration, manage the entire content lifecycle, secure critical content, and transform business workflows with enterprise AI. We help companies thrive in the new AI-first era of business. Founded in 2005, Box simplifies work for leading global organizations, including JLL, Morgan Stanley, and Nationwide. Box is headquartered in Redwood City, CA, with offices across the United States, Europe, and Asia. By joining Box, you will have the unique opportunity to continue driving our platform forward. Content powers how we work. It’s the billions of files and information flowing across teams, departments, and key business processes every single day: contracts, invoices, employee records, financials, product specs, marketing assets, and more. Our mission is to bring intelligence to the world of content management and empower our customers to completely transform workflows across their organizations. With the combination of AI and enterprise content, the opportunity has never been greater to transform how the world works together and at Box you will be on the front lines of this massive shift. WHY BOX NEEDS YOU Box is transforming how the world works together. Our Enterprise Sales team is expanding, and we’re hiring a high-impact Enterprise Account Executive to drive net-new logo acquisition across the Insurance vertical. This is a hunter role owning a white-space territory—prospecting into large, complex enterprises, building executive relationships, and closing multi-stakeholder, enterprise-wide deals. You’ll shape repeatable Insurance industry go-to-market motions while partnering cross-functionally to help customers securely manage, govern, and collaborate on their most critical content. If you thrive on opening doors, navigating ambiguity, and creating measurable business outcomes, this role offers visibility, growth, and the chance t

GitAIGoExcel
B
📍 Chicago, Illinois, United States· Full-time
✓ High-confidence listing

From $113K/yr

Quick readStrong listing-quality and freshness signals

WHAT IS BOX? Box (NYSE:BOX) is the leader in Intelligent Content Management. Our platform enables organizations to fuel collaboration, manage the entire content lifecycle, secure critical content, and transform business workflows with enterprise AI. We help companies thrive in the new AI-first era of business. Founded in 2005, Box simplifies work for leading global organizations, including JLL, Morgan Stanley, and Nationwide. Box is headquartered in Redwood City, CA, with offices across the United States, Europe, and Asia. By joining Box, you will have the unique opportunity to continue driving our platform forward. Content powers how we work. It’s the billions of files and information flowing across teams, departments, and key business processes every single day: contracts, invoices, employee records, financials, product specs, marketing assets, and more. Our mission is to bring intelligence to the world of content management and empower our customers to completely transform workflows across their organizations. With the combination of AI and enterprise content, the opportunity has never been greater to transform how the world works together and at Box you will be on the front lines of this massive shift. WHY BOX NEEDS YOU Box is expanding into a new era of monetization, one that blends our trusted subscription model with dynamic, consumption-based pricing for AI-powered and Platform capabilities. As the Program Manager, Consumption Products, you will own the day-to-day operations of this early-stage but high-priority business, sitting at the intersection of product, finance, analytics, and our customer-facing teams. This is a rare opportunity to build something new at scale: you will help define how Box monetizes AI Units today and lay the operational foundation for expanding consumption-based models across our Platform and beyond. This role reports to the VP, Renewals and Consumption and carries direct visibility with Box's Chief Operating Officer and othe

AIGoRustMarketing
B
📍 Chicago, IL, United States· Full-time
✓ High-confidence listing

From $135K/yr

Quick readStrong listing-quality and freshness signals

WHAT IS BOX? Box (NYSE:BOX) is the leader in Intelligent Content Management. Our platform enables organizations to fuel collaboration, manage the entire content lifecycle, secure critical content, and transform business workflows with enterprise AI. We help companies thrive in the new AI-first era of business. Founded in 2005, Box simplifies work for leading global organizations, including JLL, Morgan Stanley, and Nationwide. Box is headquartered in Redwood City, CA, with offices across the United States, Europe, and Asia. By joining Box, you will have the unique opportunity to continue driving our platform forward. Content powers how we work. It’s the billions of files and information flowing across teams, departments, and key business processes every single day: contracts, invoices, employee records, financials, product specs, marketing assets, and more. Our mission is to bring intelligence to the world of content management and empower our customers to completely transform workflows across their organizations. With the combination of AI and enterprise content, the opportunity has never been greater to transform how the world works together and at Box you will be on the front lines of this massive shift. WHY BOX NEEDS YOU As an AI-first company, we are on a mission to reimagine the way work gets done. We are operating in a time of dramatic disruption and change and must anticipate the ways in which organizational structures, teams and individual jobs will need to evolve. Success will ensure our business is set up to thrive and we will be able to attract and retain the very best talent in the market. We're looking for someone who can build the structural backbone — job families, leveling criteria, career frameworks — and also assess what's happening across a large organization's data and formulate a point of view on what to change and improve. This is a consultative architect and builder's role: you'll be designing frameworks and programs that don't exist ye

AIGoMarketingHR
B
📍 Chicago, IL, United States· Full-time
✓ High-confidence listing

From $109.5K/yr

Quick readStrong listing-quality and freshness signals

WHAT IS BOX? Box (NYSE:BOX) is the leader in Intelligent Content Management. Our platform enables organizations to fuel collaboration, manage the entire content lifecycle, secure critical content, and transform business workflows with enterprise AI. We help companies thrive in the new AI-first era of business. Founded in 2005, Box simplifies work for leading global organizations, including JLL, Morgan Stanley, and Nationwide. Box is headquartered in Redwood City, CA, with offices across the United States, Europe, and Asia. By joining Box, you will have the unique opportunity to continue driving our platform forward. Content powers how we work. It’s the billions of files and information flowing across teams, departments, and key business processes every single day: contracts, invoices, employee records, financials, product specs, marketing assets, and more. Our mission is to bring intelligence to the world of content management and empower our customers to completely transform workflows across their organizations. With the combination of AI and enterprise content, the opportunity has never been greater to transform how the world works together and at Box you will be on the front lines of this massive shift. WHY BOX NEEDS YOU As part of the broader Go-To-Market (GTM) Enablement team, the Commercial Sales Enablement Manager will drive revenue growth by architecting and delivering strategic enablement programs that equip our Small and Medium Business (SMB) and Mid-Market sales teams with the strategies, skills, content, and modern tools necessary to accelerate productivity and win rates. In this role, you will operate as an autonomous subject matter expert and trusted advisor to Commercial Sales leadership. You will develop comprehensive enablement roadmaps, translate global strategic vision into clear "why" context for the field, advocate for segment priorities, and independently determine the methods and procedures to design, execute, and govern high-impact ena

AIGoRustExcel
P
📍 Chicago, IL, United States· Full-time
✓ High-confidence listingCompany trend -85.6%

From $92K/yr

Quick readStrong listing-quality and freshness signals

About Pinterest: Millions of people around the world come to our platform to find creative ideas, dream about new possibilities and plan for memories that will last a lifetime. At Pinterest, we’re on a mission to bring everyone the inspiration to create a life they love, and that starts with the people behind the product. Discover a career where you ignite innovation for millions, transform passion into growth opportunities, celebrate each other’s unique experiences and embrace the flexibility to do your best work. Creating a career you love? It’s Possible. At Pinterest, AI isn't just a feature, it's a powerful partner that augments our creativity and amplifies our impact, and we’re looking for candidates who are excited to be a part of that. To get a complete picture of your experience and abilities, we’ll explore your foundational skills and how you collaborate with AI. Through our interview process, what matters most is that you can always explain your approach, showing us not just what you know, but how you think. You can read more about our AI interview philosophy and how we use AI in our recruiting process here . As a Sr Client Account Manager, you will be in charge of driving a sophisticated book of business featuring some of the largest advertisers at Pinterest. You’ll work directly with some of our key advertisers as a trusted consultant to their business. Your strategic advice, analytical skills and sales skills are core to bringing to life the value we deliver as a platform. In this role, you will help Home Retail advertisers translate inspiration into measurable business outcomes, connecting consumers from discovery to purchase in moments of high intent. You’ll partner with brands navigating performance goals such as efficient customer acquisition, catalog sales growth, and omnichannel conversion strategies, while helping them unlock the unique value of Pinterest as a platform where planning often precedes purchase. This is an opportunity to

AWSGitRestAI
P
📍 Chicago, IL, United States· Full-time
✓ High-confidence listingCompany trend -85.6%

From $902.9K/yr

Quick readStrong listing-quality and freshness signals

About Pinterest: Millions of people around the world come to our platform to find creative ideas, dream about new possibilities and plan for memories that will last a lifetime. At Pinterest, we’re on a mission to bring everyone the inspiration to create a life they love, and that starts with the people behind the product. Discover a career where you ignite innovation for millions, transform passion into growth opportunities, celebrate each other’s unique experiences and embrace the flexibility to do your best work. Creating a career you love? It’s Possible. At Pinterest, AI isn't just a feature, it's a powerful partner that augments our creativity and amplifies our impact, and we’re looking for candidates who are excited to be a part of that. To get a complete picture of your experience and abilities, we’ll explore your foundational skills and how you collaborate with AI. Through our interview process, what matters most is that you can always explain your approach, showing us not just what you know, but how you think. You can read more about our AI interview philosophy and how we use AI in our recruiting process here . As a Client Account Manager II, you will be in charge of driving a sophisticated book of business featuring some of the largest advertisers at Pinterest. You’ll work directly with some of our key advertisers as a trusted consultant to their business. Your strategic advice, analytical skills and sales skills are core to bringing to life the value we deliver as a platform. We invite passionate candidates to join our US Enterprise Sales team, where we have open positions across several business sectors, in various locations. By applying for the Client Account Manager position, your application will be considered for all available roles that match your skills and experience. Submit your resume once, and it will be considered by multiple hiring teams. Pinterest is one of the most powerful upper-funnel platforms for CPG brands, reaching consumers at t

AWSGitRestAI
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