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Customer Success Director in Chicago

15 active opportunities · Updated for September 2026

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Explore current customer success director jobs in Chicago. Use filters to narrow by work mode, employment type, experience and date posted.

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Stripe
📍 ChicagoFull-time$113.7K – $144.8K/yr
3 days ago

Who we are About Stripe Stripe, LLC. is a financial infrastructure platform for businesses. Millions of companies - from the world’s largest enterprises to the most ambitious startups - use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career. What you’ll do Responsibilities Support post-sales engagements focused on the optimization, retention, and growth of Stripe’s enterprise customers. Manage a book of customers to drive overall account health, including performance, product adoption, usage velocity, account renewals and growth, referrals, and customer satisfaction. Serve as a trusted payments and product advisor to manage customers by delivering payment performance and industry insights. Perform business reviews to align on user priorities, review payments performance metrics, share company product roadmap and provide guidance on how to optimize the value from the company. Advocate for the customer to internal stakeholders. Share customer feedback and insights to Product Management, Engineering, Support, Marketing, and Sales on the innovation and improvement needed to optimize the company user experience. In coordination with an account team, support book expansion, identify and surface opportunities to ensure customers are successful. Who you are Minimum requirements Must have a Bachelor's degree or foreign equivalent in Engineering, Computer Science, Business Administration, Management, or a related field, plus four (4) years of experience in enterprise customer success or strategic account management. Must also have four (4) years of experience in each of the following: Supporting expansion of complex accounts, including identifying opportunities, driving business outcomes

airustmarketing
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Datadog
📍 ChicagoFull-timeFrom $90K/yr
1mo ago

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

aigorust
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EC
3 days ago

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? 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 → $115,000 to $200,000. The expected salary range above may vary based on qualifications and experience. Title: Senior Product Manager, Customer Platform About this Job We're looking for a Senior Product Manager to own our customer-facing energy purchasing and tracking platform during a critical high-growth phase. You'll define and drive the vision for turning that platform into an interactive, data-rich experience — think Bloomberg Terminal or Robinhood — that gives clients real-time visibility and control over their energy purchasing decisions. This is a flagship customer-facing bet, and you'll be the senior product voice shaping it end to end. What You'll Do Own the product roadmap and vision for the customer-facing platform, translating energy purchasing and tracking into an interactive, real-time interface Partner with Engineering, Design, and Quantitative Strategy to define data visualizations, live pricing displays, and interactive tools that make complex energy market data intuitive for clients Gather requirements directly from clients, Sales, and Customer Success to identify what drives engagement and decision-making on the platform Write detailed product requirements and specs, and work closely with engineering to ship features that measurably improve client engagement and retention Define and track success metrics (engagement, retention, feature a

C
1mo ago

At ClickUp, we're building the future of work: the first truly converged AI workspace unifying tasks, docs, chat, calendar, and enterprise search, all supercharged by context-driven AI. We are an AI-native company. Every team member is expected to leverage AI daily, and we evaluate AI fluency as part of our hiring process. Join us and help redefine what's possible. 🚀 We’re looking for an ambitious, high-energy Enterprise Account Executive based in Chicago who’s passionate about helping organizations transform the way they work. In this role, you’ll be at the forefront of driving growth by connecting with leading enterprises, understanding their unique challenges, and delivering tailored solutions that empower teams to do their best work. If you thrive in a fast-paced, collaborative environment and are excited to champion a platform that’s redefining productivity, we’d love to meet you. The Role: Drive net new business by proactively identifying, engaging, and converting high-value Enterprise and Strategic prospects into customers. Develop and execute strategies to penetrate new accounts, build strong relationships with key decision makers, and create tailored solutions that address complex business needs. Consistently exceed pipeline and sales targets by generating new opportunities through outbound prospecting, networking, and leveraging marketing-qualified leads. Lead expansion efforts within existing Enterprise accounts by uncovering additional use cases, identifying upsell and cross-sell opportunities, and driving adoption across multiple business units. Deliver compelling presentations and product demonstrations to both new prospects and current customers, effectively communicating value and ROI. Collaborate closely with Growth, Marketing, and Customer Success teams to optimize lead generation, accelerate sales cycles, and maximize expansion revenue. Analyze customer segments and market trends to identify new business opportunities and continuously improve the

awsmachine learningai
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D
Datadog
📍 ChicagoFull-timeFrom $154K/yr
1mo ago

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

aigorust
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EC
Energy CX
📍 ChicagoFull-time
3 days ago

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

S
19 days ago

At Snowflake, we are powering the era of the agentic enterprise. To usher in this new era, we seek AI-native thinkers across every function who are energized by the opportunity to reinvent how they work. You don’t just use tools; you possess an innate curiosity, treating AI as a high-trust collaborator that is core to how you solve problems and accelerate your impact. We look for low-ego individuals who thrive in dynamic and fast-moving environments and move with an experimental mindset — who rapidly test emerging capabilities to discover simpler, more powerful ways to deliver results. At Snowflake, your role isn't just to execute a function, but to help redefine the future of how work gets done. Our GSI partners play a key role in bringing our customers' data-backed ambitions to life by implementing and harnessing the power of the Snowflake AI Data Cloud for cutting edge workloads and use cases. Through our partnerships, we enable companies to empower their employees with the data they need when and how they need it to better engage their customers, optimize their operations, and transform their products. The Partner Development Manager, Deloitte role involves driving and building relationships with one of our top Global System Integrator (GSI) partners. Your primary objective is to strengthen and expand the collaboration between Snowflake and Deloitte to drive growth. Acting as the single point of accountability for the health and velocity of this leading partnership. The success of our partnership is demonstrated by driving growth with our joint customers, delivering key Go-To-Market (GTM) programs, establishing critical executive relationships, enabling partners to grow their Snowflake competency, and delivering customer success. We are looking for a builder and a finisher—someone who doesn't just draft the plan, but drives it to completion, mobilizes the field, and uses data to "unstick" challenges before they become blockers. KEY RESPONSIBILITIES: Strategic Go

gitrestai
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S
1mo ago

For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it’s what we show up for every day. Smartsheet is seeking change agents to join our Central/East Commercial Sales Team as an Account Executive . You will be responsible for increasing software sales and driving expansion across a territory of accounts. You will be motivated, passionate, and opportunistic. You will be a proactive and curious member of the commercial sales team, identifying growth opportunities for clients before they identify a need or gap for themselves. This remote role is part of the Commercial Sales team based in the US and reports a Manager, Commercial Sales. You Will: Build and manage a sales pipeline to meet or exceed software and services sales quotas within your book of business Execute a solution-based sales process encompassing multiple groups within our commercial mature accounts equivalent to (500-4,999 employee size) Develop new business opportunities within existing customers by analyzing and proactively targeting high-value needs across multiple departments and lines of business Leverage existing relationships to expand Smartsheet's footprint and drive revenue or growth during renewals Expand Smartsheet brand awareness at the c-suite, operational and team level Facilitate and manage partnerships with Sales Engineers, Solutions Consultants and Customer Success teams to support full sales cycle and close business Create and maintain Joint Engagement Plans for strategic solution deals Maintain accurate and up-to-date records in Salesforce leveraging MEDDICC qualification guidelines to accurately forecast Utilize existing

C
28 days ago

We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time. Job Purpose and Summary: At CVS Health, we are focused on transforming health care for our customers and making our company a great place to work. We help people navigate the health care system – and their personal health care – by improving access, lowering costs and being a trusted partner for every meaningful moment of health. Within our Retail locations, we bring this promise to life with heart every day. Our Pharmacy Managers play a critical role in cultivating a culture of excellence in their respective pharmacy by acting as a role model for all, demonstrating genuine care, and setting the bar for their pharmacy team. As a Pharmacy Manager, you will lead and develop a pharmacy team that provides exceptional patient care by promoting best practices and leading through change while identifying and addressing performance opportunities. Pharmacy Managers support novel program awareness, onboard newly hired pharmacy team members, and recognize colleagues for their success. The Pharmacy Manager consistently exhibits best practices when working the bench, including quarterbacking the team, providing patients with meaningful counseling, and abiding by all legal and regulatory guidelines, amongst other required activities. The Pharmacy Manager is responsible for direct and effective management of their pharmacy team, including but not limited to: Living our pur

customer service
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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

O
27 days ago

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 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 The Business Analyst (BA) is an essential member of the Okta Professional Services team. This role offers a unique opportunity to learn Identity and Access Management (IAM) fundamentals from the ground up. You will serve as a bridge between customer business objectives and technical implementation, developing the skills to own the requirements lifecycle and ensuring final deliveries are secure, scalable, and aligned with strategic needs. Key Responsibilities Discovery & Requirements Facilitation: Facilitate stakeholder workshops to uncover requirements, map current-state IAM processes, and identify dependencies and pain points across IT, security, and application teams. Documentation & Solution Design: Translate business needs into detailed functional and non-functional requirements. Produce clear business process flows and solution design diagrams to visualize the "how" and "why" behind the technical configuration. Traceability & Solution Integrity: Support senior team members in maintaining

machine learningartificial intelligenceai
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At Snowflake, we are powering the era of the agentic enterprise. To usher in this new era, we seek AI-native thinkers across every function who are energized by the opportunity to reinvent how they work. You don’t just use tools; you possess an innate curiosity, treating AI as a high-trust collaborator that is core to how you solve problems and accelerate your impact. We look for low-ego individuals who thrive in dynamic and fast-moving environments and move with an experimental mindset — who rapidly test emerging capabilities to discover simpler, more powerful ways to deliver results. At Snowflake, your role isn't just to execute a function, but to help redefine the future of how work gets done. Our Solution Engineering organization is seeking an AI Specialist who can provide hands-on expertise and support while working with technical decision makers and data scientists to design and architect AI solutions built on the Snowflake AI Data Cloud. This is a strategic role that works closely with cross-functional teams, including product, engineering, and the broader field organization to ensure successful execution and customer adoption of Snowflake’s AI & ML solutions. IN THIS ROLE YOU WILL GET TO: Be the technical expert in the room that positions Snowflake’s AI and ML features and value to technical stakeholders at Snowflake’s customers across the Americas. Partner with Snowflake account team teams and customer champions to scope and drive POCs to success and technical wins that prove the value of Snowflake’s capabilities, including executive readouts and business value cases. Collaborate with Snowflake’s product and engineering teams to influence Snowflake’s AI and ML roadmaps based on customer feedback. Publish content that helps the team and company scale beyond your individual efforts, like blog posts, presentations at conferences, or technical collateral like notebooks and demos. Influence, tailor and maintain Sales Engineering AI and ML selling assets, inc

pythonawsazure
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Pinterest
📍 ChicagoFull-timeFrom $79.2K/yr
1mo ago

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 . Role Summary As a Sr Client Partner at Pinterest, you will serve as a strategic visionary, cultivating trusted relationships with top-tier clients in the grocery industry through your deep expertise in full-funnel sales. By leveraging your nuanced understanding of client businesses, you will independently engage assigned customer accounts to promote Pinterest products effectively. Your primary responsibilities include meeting performance targets, developing new business, maintaining and expanding customer relationships, and resolving specific customer issues. By guiding clients’ efforts, you'll drive value for millions of Pinners seeking inspiration and action, forming strategic alliances both internally and externally. Success in this role depends on your ability to drive substantial revenue growth and spearhead a vision for long-term client su

awsgitrest
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