Ai Senior Systems Engineer in Chicago

As an Enterprise Customer Success Manager, you will proactively drive new product attachment and effective strong relationships across our largest and most strategic customers. You’ll advocate for the customer internally and focus on a positive customer experience. Interactions are rooted in relationship-management, first and foremost, while also advocating for growth opportunities. Enterprise Customer Success Managers follow a well-defined methodology that helps them identify the customer's unique needs and clearly convey the value of the Datadog product. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Act as a strategic partner to customers, orchestrating cross-functional internal teams and engaging executive, technical, and business stakeholders to understand customer goals and translate them into a clear, deliverable Datadog value narrative. Proactively build and maintain executive relationships to deliver clear, outcome-driven value stories that connect Datadog technical use cases to measurable business results. Lead QBRs and strategic reviews as a forum to demonstrate impact, align on priorities, and define next-step initiatives. Analyze adoption and usage trends to quantify value delivered, extract insights from large datasets, identify gaps, and drive financially grounded commercial recommendations and strategic opportunities. Position Datadog as a critical observability platform that enables reliability, efficiency, and informed decision-making. Own and project manage the on-boarding process for new customers Collaborate cross-functionally with AEs, SEs, TAM, Product, Support, Enablemen and other technical teams to ensure consistent value delivery and messaging. Who You Are: Customer-centric with 3+ years in a Customer Success

We are Datadog’s in-house technical leaders. The Technical Account Management team drives Datadog’s continued global growth by ensuring our customers realize long-term value from our platform through successful adoption, expansion, and partnership. As a Manager 1 in Technical Account Management, you will lead and develop high-performing technical teams while influencing strategy, execution, and outcomes across customers, internal partners, and the broader organization. Manager 1 leaders at Datadog are people-first managers, trusted collaborators, and operational owners. You will coach and mentor individual contributors, drive execution against team and organizational goals, and serve as a strong voice for customer needs and technical excellence. At Datadog, we place value in our office culture; the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Lead and coach a team of up to 6 Technical Account Managers, providing regular 1:1s, team meetings, and bi-annual performance feedback Own and track team KPIs , including scheduling, utilization, productivity, and delivery outcomes Partner closely with Sales, Customer Success, Presales, Product Management, Support, and Marketing to align post-sales strategy and execution Lead and participate in customer-facing engagements when appropriate, including escalations, strategic reviews, and key account discussions Drive account strategy discussions focused on product adoption, expansion, and services delivery Actively participate in recruiting , hiring, and onboarding efforts across your team and the broader organization Gather and synthesize customer feedback to influence product direction, process improvements, and internal initiatives Lead multiple OKR initiatives annually , coordinating and delegating efforts across your team Demonstrate thought leadership by identifyi

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. Build the operational and technical skill set that runs global trade At Flexport, we believe global trade can move the human race forward. We're shaping the future of a $10T industry with technology and people who understand it end to end. The Rotational Development Program (RDP) exists because that combination — real supply chain fluency plus the ability to build and automate — doesn't exist at scale in the market today. So we're building it ourselves. This is an 18-month program, not a rotation for rotation's sake. Every assignment is live, revenue-generating work. Every participant leaves with a certification in AI and low-code tooling running alongside their operational and commercial training. And every graduate places into a role with real scope: primarily Account Management, with paths into Automation Engineering, Forward Deployed Engineering/Consulting, Sales Engineering, or a traditional Ops/Sales/Customs track. What you'll do You'll rotate through three functions, six months each, with AI/low-code curriculum running continuously across all three: Gateway Ops (Air or Ocean). Own the shipment lifecycle. Execute bookings, manage exceptions, and hold data int

Secure Every Identity, from AI to Human Identity is the key to unlocking the potential of AI. Okta secures AI by building the trusted, neutral infrastructure that enables organizations to safely embrace this new era. This work requires a relentless drive to solve complex challenges with real-world stakes. We are looking for builders and owners who operate with speed and urgency and execute with excellence. This is an opportunity to do career-defining work. We're all in on this mission. If you are too, let's talk. Get to know Okta Okta is The World’s Identity Company. We free everyone to safely use any technology, anywhere, on any device or app. Our flexible and neutral products, Okta Platform and Auth0 Platform, provide secure access, authentication, and automation, placing identity at the core of business security and growth. At Okta, we celebrate a variety of perspectives and experiences. We are not looking for someone who checks every single box - we’re looking for lifelong learners and people who can make us better with their unique experiences. The Customer First Team We are a team of Identity and Access Management experts. We help customers, businesses, and organisations maximise their Okta IAM platform investment, providing rapid time-to-value in adoption and usage and promoting scalability and agility. Our team sits within the Customer First area - focused on ensuring the long term success of our customers. Join our team! We’re building a world where Identity belongs to you. Role Summary Reporting to the Sr. Manager, Strategic Programs and Delivery Governance, the Program Manager, Services Solutions & Delivery Acceleration is a key operational and technical enablement leader within our Global Professional Services and Delivery Success organization. This role treats "services as a product"—transforming custom, highly complex implementation workflows into standardized, packaged service solutions and reusable delivery acceleration toolkits. Work

About Energy CX: Energy CX is redefining the energy brokerage industry as the fastest-growing player in the US. By bringing cutting-edge technology, advanced analytics, and innovative solutions, we are disrupting a space that has operated in the dark for too long. Why Energy CX? Recession proof industry Uncapped commission with competitive salary Entrepreneurial and ambitious culture with a great team oriented environment Fastest growing energy broker in the country One of the fastest growing companies in Chicago Recognized by Fortune and Great Places to work US Named on Inc 5000’s list of America’s fastest growing companies Compensation Year 1 Expected Earnings → $130,000 - $170,000 Title: Revenue Operations Manager About this Job Energy CX is hiring a Revenue Operations Manager to build and own the revenue operating system that powers how the company makes decisions, turning fragmented data into a trusted, self-sustaining system for pipeline, forecasting, and capacity planning. This person will own HubSpot and the broader revenue tech stack, build the metrics and forecasting infrastructure the business runs on, and connect marketing, sales, customer success, and finance around a single source of truth, ensuring the right answers surface before anyone has to ask. Objectives of this Role Own and evolve ECX's revenue operating system, including pipeline intelligence, forecasting, and capacity planning, as the foundation for how the company makes revenue decisions. Own HubSpot and the broader revenue tech stack as the system of record, enforcing data quality standards across the full lead-to-cash lifecycle Diagnose and anticipate structural gaps in data, process, and cross-team handoffs Build a metrics layer that runs on its own: pipeline, forecast, and revenue reporting that requires no manual reconciliation Support GTM enablement infrastructure: comp plans, quota tracking, territory design, and capacity/headcount planning Daily and Month

Fanatics Commerce is the global leader in licensed sports merchandise, operating a vertically integrated platform that designs, manufactures, and delivers officially licensed apparel, jerseys, headwear, and collectibles for major leagues, teams, and events worldwide. With more than 900 e-commerce sites and a global omnichannel presence across digital, in-venue, and retail, Fanatics Commerce reaches fans in over 180 countries and powers official fan experiences for many of the world's most iconic sports properties. At Fanatics, we bring our BOLD Leadership Principles to life every day - building championship teams, obsessing over fans, acting with entrepreneurial speed, and delivering with a determined and relentless mindset. ROLE OVERVIEW The Retail Associate delivers business and fan impact through BOLD leadership and execution excellence, leveraging data, automation, and AI-enabled insights. Home game shifts are considered a core responsibility of the position and may include pre-game, in-game, and post-game operational support. HOW WILL YOU DRIVE IMPACT Success is measured by the ability to deliver results through BOLD capabilities and measurable outcomes. Fan & Customer Impact (Obsessed with Fans) Greet fans and ask questions to help make their shopping experience an enjoyable one Make recommendations based on observations and conversations with fans Help execute a brand connection by ensuring fans enjoy a top-notch shopping experience Maintain sales floor and/or stockroom standards with an eye to detail Ownership & Execution (Determined & Relentless Mindset) Process sales transactions via the Fanatics Point of Sale System (POS) Maintain the highest standards of professionalism and customer service to ensure the Fanatics Brand and Team/League are always positively represented Perform additional responsibilities as directed by the management team Innovation & Problem Solving (Entrepreneurial Spirit) Identify opportunities to improve processes, pro

Fanatics Commerce is the global leader in licensed sports merchandise, operating a vertically integrated platform that designs, manufactures, and delivers officially licensed apparel, jerseys, headwear, and collectibles for major leagues, teams, and events worldwide. With more than 900 e-commerce sites and a global omnichannel presence across digital, in-venue, and retail, Fanatics Commerce reaches fans in over 180 countries and powers official fan experiences for many of the world's most iconic sports properties. At Fanatics, we bring our BOLD Leadership Principles to life every day - building championship teams, obsessing over fans, acting with entrepreneurial speed, and delivering with a determined and relentless mindset. ROLE OVERVIEW The Retail Associate delivers business and fan impact through BOLD leadership and execution excellence, leveraging data, automation, and AI-enabled insights. Home game shifts are considered a core responsibility of the position and may include pre-game, in-game, and post-game operational support. HOW WILL YOU DRIVE IMPACT Success is measured by the ability to deliver results through BOLD capabilities and measurable outcomes. Fan & Customer Impact (Obsessed with Fans) Greet fans and ask questions to help make their shopping experience an enjoyable one Make recommendations based on observations and conversations with fans Help execute a brand connection by ensuring fans enjoy a top-notch shopping experience Maintain sales floor and/or stockroom standards with an eye to detail Ownership & Execution (Determined & Relentless Mindset) Process sales transactions via the Fanatics Point of Sale System (POS) Maintain the highest standards of professionalism and customer service to ensure the Fanatics Brand and Team/League are always positively represented Perform additional responsibilities as directed by the management team Innovation & Problem Solving (Entrepreneurial Spirit) Identify opportunities to improve processes, pro

Fanatics Commerce is the global leader in licensed sports merchandise, operating a vertically integrated platform that designs, manufactures, and delivers officially licensed apparel, jerseys, headwear, and collectibles for major leagues, teams, and events worldwide. With more than 900 e-commerce sites and a global omnichannel presence across digital, in-venue, and retail, Fanatics Commerce reaches fans in over 180 countries and powers official fan experiences for many of the world's most iconic sports properties. At Fanatics, we bring our BOLD Leadership Principles to life every day - building championship teams, obsessing over fans, acting with entrepreneurial speed, and delivering with a determined and relentless mindset. ROLE OVERVIEW The Retail Lead delivers business and fan impact through BOLD leadership and execution excellence, leveraging data, automation, and AI-enabled insights. Home game shifts are considered a core responsibility of the position and may include pre-game, in-game, and post-game operational support. HOW WILL YOU DRIVE IMPACT Success is measured by the ability to deliver results through BOLD capabilities and measurable outcomes. Fan & Customer Impact (Obsessed with Fans) Drive sales results by consistent execution of daily operations Support back of house operations; maintain stockroom organization Knowledge of retail operation systems including but not limited to OpSuite5.0 (online inventory manager), POS (point of sales) and CAYAN (credit card machines) Partner with Leadership team when making decisions including but not limited to; revenue targets, per cap and UPT (unit per time) Work with Retail Associates to ensure an exemplary fan experience Ownership & Execution (Determined & Relentless Mindset) Communicate expectations for assignments and projects to Retail Associates Provide training and assistance to Retail Assoc

ROLE: CREATIVE DIRECTOR, PORTFOLIO TEAM: THE KITCHEN NORTH AMERICA LOCATION: TORONTO / CHICAGO (HYBRID) 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 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 As the Creative Director, Portfolio you will lead multidisciplinary creative teams across a portfolio of iconic Kraft Heinz brands, partnering with Sr. Creatives, Designers, Accounts and Strategists to develop breakthrough ideas that extend seamlessly across every consumer touchpoint-from national campaign and social content to retail experiences and the moment of purchase. Unlike a traditional Creative Director role, this position requires someone who is equally comfortable developing breakthrough brand platforms as they are tra

POSITION: TOUR DRIVER LOCATION: REMOTE, U.S DATES: NOV 2nd - DEC 20th COMPANY OVERVIEW Salt is a North American marketing agency that creates connected experiences through creative, digital & media innovation. Our mission is to “Earn The World’s Attention” and Salt is built to find, develop, execute, and amplify the ideas that are worthy of our clients’ audiences. We’ve structured our agency to do what’s right for our clients – to connect different perspectives, to work across mediums, and to focus on delivering meaningful, effective results. We’re committed to living up to the values in our name. “Salt of The Earth” means we value collaborative, humble, hard-working people here. We’re looking for people who are as smart as they are kind because we believe the right talent and the right culture help us do what’s right for our clients. We are hiring experiential Holiday Tour Managers for the 2026 Coca-Cola Holiday Caravan, spreading joy and sharing acts of kindness with people across America. The contract runs from November 2 through December 20, 2026, with two truck teams scheduled to conclude on December 13 based on their assigned routes. Tour Managers will be on the road for the majority of their contracts, traveling with a team of four crew members. Accountabilities include working with venues, retailers, and vendors, and acting as a liaison between the Salt back-office team and field staff. *Please note that this is a freelance/contracted 1099 role and is open to applicants across the United States. RESPONSIBILITIES: Crew/team management (2 crew members will be licensed drivers) Setup and teardown support at all tour stops Preparing logistics for all tour stops with venue contacts Facilitating licensing and permitting where necessary Working as hybrid of manager and brand ambassador at every tour stop, engaging with consumers EXPERIENCE & SKILLS: Proven In-field / Tour

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

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

Instawork is on a mission to create meaningful economic opportunities for skilled hourly professionals in communities around the globe. Our AI-powered labor marketplace helps local businesses scale, and enables global technology companies to push the frontiers of robotics and AI. Backed by world-class investors like Benchmark, Spark Capital, Craft Ventures, Greylock, Y Combinator, and others, we’re looking for exceptional talent to reimagine the way the world works. Role Type: Contract (3–6 months, with potential to extend) Location: San Francisco or Chicago We are looking for a GTM Recruiting Consultant (3- 6 months contract with potential for full time), you are at the absolute center of our growth engine. The Sales and Account Management teams you build are the ones bringing new businesses onto our platform and ensuring their success. By finding and hiring top-tier commercial talent, you directly accelerate our market expansion and fuel our revenue growth. it is a direct lever on Instawork’s top-line business success. Key Responsibilities Full-Cycle Recruiting: Manage the end-to-end recruitment process for a variety of GTM roles (e.g., Account Executives, Enterprise Account Managers, and Business Development Representatives). Strategic Alignment: Partner closely with GTM hiring managers to deeply understand their business objectives, team dynamics, and specific hiring needs. Creative Sourcing: Actively source passive talent (LI recruiter, Juicebox etc.), specialized networks, and creative outbound strategies to build robust, diverse pipelines. Candidate Experience Champion: Deliver a high-touch, transparent, and inclusive candidate experience from initial outreach through to the offer stage. ATS Hygiene: Maintain impeccable data hygiene in our Applicant Tracking System (Greenhouse) to ensure accurate reporting and seamless collaboration. What We’re Looking For Growth mindset with hands on AI powered recruiting expertises. Experience: 5+ years of full-cycle

Instawork is on a mission to create meaningful economic opportunities for skilled hourly professionals in communities around the globe. Our AI-powered labor marketplace helps local businesses scale, and enables global technology companies to push the frontiers of robotics and AI. Backed by world-class investors like Benchmark, Spark Capital, Craft Ventures, Greylock, Y Combinator, and others, we’re looking for exceptional talent to reimagine the way the world works. Instawork is the #1 marketplace connecting businesses with skilled hourly workers, with 10M+ workers across 40+ markets in North America. Our downtown Chicago office is looking for a reliable and organized part-time Office Coordinator to help keep our downtown Chicago office running smoothly. This is a hands-on, part-time position focused on office organization, coordination, and general administrative support. We're looking for someone available to work 10–20 hours per week , with some flexibility around academic commitments. What You’ll Do Keep office supplies, shared spaces, and conference rooms organized. Order supplies and coordinate with vendors and building management. Receive mail, packages, deliveries, and occasional visitors. Prepare the office for meetings, team lunches, and small events. Organize documents, receipts, and office records. Assist with scheduling and other basic administrative tasks. Help identify and resolve routine office needs. Support occasional errands and special projects. Who You Are Organized, dependable, and attentive to detail. Comfortable taking initiative and working independently. Friendly and professional when communicating with others. Able to manage multiple small tasks and follow through. Familiar with Google Workspace. Able to work approximately 10 - 20 hours per week at our office in the Loop. Previous office or administrative experience is helpful but not required. For IL-based applicants The hourly compensation for this position is $25/hour #LI-Onsite O

Secure Every Identity, from AI to Human Identity is the key to unlocking the potential of AI. Okta secures AI by building the trusted, neutral infrastructure that enables organizations to safely embrace this new era. This work requires a relentless drive to solve complex challenges with real-world stakes. We are looking for builders and owners who operate with speed and urgency and execute with excellence. This is an opportunity to do career-defining work. We're all in on this mission. If you are too, let's talk. Business Analyst Chicago, Illinois Secure Every Identity, from AI to Human Identity is the key to unlocking the potential of AI. Okta secures AI by building the trusted, neutral infrastructure that enables organizations to safely embrace this new era. This work requires a relentless drive to solve complex challenges with real-world stakes. We are looking for builders and owners who operate with speed and urgency and execute with excellence. This is an opportunity to do career-defining work. We're all in on this mission. If you are too, let's talk. The Customer First Team We are a team of Identity and Access Management experts. We help customers, businesses, and organizations maximize their Okta IAM platform investment, providing rapid time-to-value in adoption and usage and promoting scalability and agility. Our team sits within the Customer First area - focused on ensuring the long term success of our customers. Join our team! We’re building a world where Identity belongs to you. Role Summary The Business Analyst (BA) is a central figure on the Okta Professional Services team. Your mission is to serve as the bridge between customer business objectives and technical implementation, driving high-impact outcomes for Okta Identity and Access Management (IAM) deployments. You will own the requirements lifecycle—from initial discovery and stakeholder alignment to functional design and solution integrity—ensuring that the final delivery is secure, scalable,