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Commercial Sales Engineer in Chicago

5 active opportunities · Updated for September 2026

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

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

F
17 days ago

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

sqlawsai
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B
Box
📍 ChicagoFull-timeFrom $109.5K/yr
4 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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I
Instawork
📍 ChicagoFull-time
4 days ago

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

restaigo
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D
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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