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Sales Performance And Enablement Director in Chicago

50 active opportunities · Updated for October 2026

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

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
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Stripe
📍 Chicago• Full-time• $113.7K – $144.8K/yr
14 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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Pinterest
📍 Chicago• Full-time• From $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 . As a Sr. Client Partner at Pinterest, you will develop and grow relationships with some of our most strategic and performance based advertisers in the Mid Market channel. 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 success. The Mid Market team is velocity based sales. What you'll do: Retain and grow partner relationships, ultimately driving Pinterest revenue. Build strong relationships with clients, agencies, C-suite, and key

awsgitrest
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Datadog
📍 Chicago• Full-time• From $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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Job Title Technical Consultant - Patient Monitoring (Field: Northern IL/WI) Job Description Launch your career as a Technical Consultant in our Hospital Patient Monitoring business, where you’ll build hands-on expertise installing and supporting advanced patient monitoring solutions, partner with diverse teams and customers, and play a direct role in delivering reliable, high-impact technology that improves patient care and outcomes. Your role: Deliver onsite and remote technical support, responding quickly to customer issues and minimizing disruption to clinical and operational workflows. Ensure reliable system performance by diagnosing and resolving system, network, and application issues using structured troubleshooting approaches. Support the full lifecycle of complex patient monitoring and IT infrastructure solutions, including installation, configuration, integration, and testing. Apply an understanding of customer environments and requirements to ensure systems are implemented effectively and optimized for long-term performance. Troubleshoot and resolve technical challenges using approved tools, test equipment, and diagnostic methodologies. Analyze root causes and implement sustainable solutions that improve system stability and reduce recurring issues. Maintain accurate and detailed documentation of system configurations, troubleshooting activities, and support procedures. Follow configuration management and version control practices to ensure consistency, knowledge sharing, and scalable support for future implementations. Collaborate with cross-functional teams including senior engineers, clinical partners, sales, and service teams to deliver high-quality outcomes. Continuously build technical expertise and contribute to knowledge sharing and improvement initiatives that enhance service delivery and customer satisfaction. <

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Reformation
📍 Chicago• Full-time• $22 – $28/hr
14 days ago

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 &

awsgitai
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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

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Pinterest
📍 Chicago• Full-time• From $62.1K/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 . As a Client Partner at Pinterest, you will manage and grow relationships with Mid-Market advertisers, helping them achieve business results through Pinterest’s advertising solutions. You will be responsible for driving revenue, identifying account growth opportunities, and delivering thoughtful, performance-focused recommendations across a velocity-based book of business. Success in this role requires strong sales execution, relationship management, and analytical problem-solving. You should be comfortable working in a fast-paced environment, using data to guide recommendations, and partnering with clients and internal stakeholders to improve outcomes. What you’ll do: Manage, retain, and grow a book of Mid-Market advertiser relationships to drive Pinterest revenue. Build strong relationships with clients, agencies, and internal partners. Underst

awsgitrest
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Pinterest
📍 Chicago• Full-time• From $92K/yr
17 days 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 . 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

awsgitrest
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Pinterest
📍 Chicago• Full-time• From $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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Pinterest
📍 Chicago• Full-time• From $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 Client Partner at Pinterest, you will serve as a strategic visionary, cultivating trusted relationships with top-tier clients 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 success in a collaborative, d

awsgitrest
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Pinterest
📍 Chicago• Full-time• From $101.6K/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 Lead Client Partner at Pinterest, you will serve as a strategic visionary, cultivating trusted relationships with top-tier clients within the CPG Food 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 c

awsgitrest
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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 . We’re looking for a Senior Ads Product Marketing Manager to shape the future of performance bidding, optimization, and measurement at Pinterest. You’ll own the go-to-market strategy for new solutions that help advertisers align campaign delivery with the business outcomes they value most. In this role, you’ll translate complex advertiser measurement needs into clear product strategy, positioning, and scalable go-to-market motions. You’ll partner closely with Product, Engineering, Data Science, Measurement, Sales, Performance Solutions, and Product Operations to bring new lower-funnel solutions from early testing through broader adoption. Your work will help advertisers optimize toward the outcomes that matter in their own measurement source of truth—and build greater confidence in Pinterest as a performance channel. What you’ll do: Own product m

airecruitment
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1mo ago

Work Flexibility: Field-based Stryker is one of the world’s leading medical technology companies and together with our customers, we are driven to make healthcare better. The Company offers a diverse array of innovative medical technologies, including reconstructive, medical and surgical, and neurotechnology and spine products to help people lead more active and more satisfying lives. Stryker products and services are available in over 100 countries. All qualified applicants will receive consideration for employment without regard to race, ethnicity, color, religion, sex, gender identity, sexual orientation, national origin, disability, or protected veteran status. Stryker is an EO employer – M/F/Veteran/Disability. Our mission Together with our customers, we are driven to make healthcare better. What you will do As a sales associate in our Sports Medicine specialty, you’ll be the face of Stryker products. You will be assisting Sales Representatives in the sales, promotion and marketing of Stryker products. You will educate and inform doctors, nurses, and appropriate staff personnel as to the proper use and maintenance of Stryker products, product functionality and updates, changes to product portfolio, and educational programs. Following extensive product training, the employee must be able to tailor Stryker’s promotional message based upon knowledge of the customer, advise on appropriate product selection, answer customer questions about product functionality and distinguish Stryker products from those of Stryker’s competitors. Every day is unique – our best sales reps have the freedom to adjust their time to focus on what will bring the most value to their customers and their market. You’ll have the privilege to not only represent one of the world’s leading medical device brands, but also impact patient care. What

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Box
📍 Chicago• Full-time• From $109.5K/yr
14 days ago

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

aigorust
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