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Mid Market Sales in Chicago

27 active opportunities · Updated for October 2026

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

F
Fin
📍 Chicago• $226K – $251K/yr
7 days ago

Fin , now part of Salesforce, is on a mission to help businesses provide perfect customer experiences. Our AI Agent Fin is the highest-performing AI Customer Agent on the market today, enabling businesses to deliver impeccable, always-on customer support across the customer journey, from service, to sales, to ecommerce. Powered by our own AI models, Fin resolves complex customer issues end-to-end across every channel, with minimal set-up and integration. Fin can also be combined with our natively integrated Intercom help desk, giving modern support teams one single system. Together with Salesforce, the #1 AI CRM, where humans with agents drive customer success, we're building the future of customer experience. Here, ambition meets action. Tech meets trust. And innovation isn't a buzzword, it's a way of life. The world of work as we know it is changing, and we're looking for Trailblazers who are passionate about bettering business and the world through AI. Ready to level up your career at the company leading workforce transformation in the agentic era? You're in the right place. Agentforce is the future of AI, and you are the future of Salesforce. What's the opportunity? As a Mid-Market Relationship Manager, you’ll be at the forefront of growth; turning momentum into mastery. You’ll own a portfolio of fast-growing customers and help them unlock the full power of Fin. We’re building a world-class sales organization; fast, ambitious, and unapologetically driven. At Fin, we do sales differently. We don’t just pitch; we partner. We’re asking our customers to make Fin the heartbeat of their business, and that starts with salespeople who can think bigger, move faster, and win with integrity. We invest deeply in every Relationship Manager’s growth. Development isn’t a slogan here, it’s baked into how we promote, learn, and lead. In a high-velocity environment where ownership, creativity, and ambition are rewarded, you’ll find room to stretch, influence, and make

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E
1mo ago

Everpure (NYSE: P) has evolved from storage pioneer to data platform, closing fiscal 2026 with $3.7 billion in revenue, its first billion-dollar quarter, and accelerating growth into FY27. Our strategic agenda spans the companies defining the next era of technology - hyperscalers, AI labs, the AI hardware supply chain, data platform providers, and the broader AI ecosystem. This type of work—work that changes the world—is what the tech industry was founded on. So, if you're ready to seize the endless opportunities and leave your mark, come join us. THE ROLE Everpure is looking for a Territory Account Executive. In this role, you will be selling into a territory in Everpure's Central region with a focus on mid-market accounts in Indiana and Kentucky. WHAT YOU'LL DO Directly sell through an inside, direct marketing environment to deliver sales targets and consistently achieve quota Drive account strategies and coordinate team selling efforts with partners to close business on a quarterly and annual basis Develop channel relationships that will bring the sales and technical resources to each opportunity and lead to closed deals Prospect into and penetrate new accounts, reaching decision-makers and closing business Develop and present proposals to prospective customers with information that demonstrates the ability of the Everpure solution to meet customers’ business objectives and justify the sale Manage pipeline with a keen focus on conversion success and delivering an accurate forecast We are primarily an in-office environment and therefore, you will be expected to work from the office in compliance with Everpure’s policies, unless you are on PTO, or work travel, or other approved leave. WHAT YOU BRING Consistent track record of exceeding quota and driving referenceable business in a B2B technology sales environment Experience working in or understanding sales channel selling models A desire to work the bookends of the sale, from prospecting to clos

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E
1mo ago

Everpure (NYSE: P) has evolved from storage pioneer to data platform, closing fiscal 2026 with $3.7 billion in revenue, its first billion-dollar quarter, and accelerating growth into FY27. Our strategic agenda spans the companies defining the next era of technology - hyperscalers, AI labs, the AI hardware supply chain, data platform providers, and the broader AI ecosystem. This type of work—work that changes the world—is what the tech industry was founded on. So, if you're ready to seize the endless opportunities and leave your mark, come join us. THE ROLE Everpure is looking for a Territory Account Executive. In this role, you will be selling into a territory in Everpure's Central region with a focus on mid-market accounts in Ohio and West Virginia. WHAT YOU'LL DO Directly sell through an inside, direct marketing environment to deliver sales targets and consistently achieve quota Drive account strategies and coordinate team selling efforts with partners to close business on a quarterly and annual basis Develop channel relationships that will bring the sales and technical resources to each opportunity and lead to closed deals Prospect into and penetrate new accounts, reaching decision-makers and closing business Develop and present proposals to prospective customers with information that demonstrates the ability of the Everpure solution to meet customers’ business objectives and justify the sale Manage pipeline with a keen focus on conversion success and delivering an accurate forecast We are primarily an in-office environment and therefore, you will be expected to work from the office in compliance with Everpure’s policies, unless you are on PTO, or work travel, or other approved leave. WHAT YOU BRING Consistent track record of exceeding quota and driving referenceable business in a B2B technology sales environment Experience working in or understanding sales channel selling models A desire to work the bookends of the sale, from prospecting to cl

REMOTEaisupply chain
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I
24mo 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. We are seeking passionate, driven, and highly motivated sales professionals to help us expand our enterprise partnerships and continue our rapid growth across the U.S. As an Enterprise Account Executive, you will be responsible for acquiring key enterprise accounts and establishing channel partnerships within the warehousing, logistics, supply chain, and third-party logistics (3PL) sectors. You will collaborate closely with mid-market and enterprise businesses to understand their staffing needs and provide tailored solutions to meet their workforce requirements. This role requires a strategic thinker with a commitment to building lasting business relationships and a strong ability to close deals. Who You Are: 5+ years of enterprise sales experience, leading end-to-end sales cycles—from initial discovery, executive alignment, and contract negotiation—ensuring a seamless transition to onboarding and implementation. Proven experience with light industrial enterprises, specifically those in supply chain, warehousing, distribution, or third-party logistics (3PL). Proven track record of closing complex, high-value deals ($200K+) over extended sales cycles (6–12 months). Deep experience with multi-threaded sales strategies and developing relationships across various departments and leadership levels. Strong executive presence with exceptional communication, negotiation, and presentation skills. Self-starter mentality with the ability to work autonomously and adapt quickly in a fast-paced, high-growth environmen

aisalesforcesupply chain
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D
1mo ago

At Dscout, we’re building the most flexible and powerful UX research platform on the market—trusted by the world’s top brands in finance (JP Morgan Chase, Intuit, Charles Schwab, PayPal), healthcare (Aya, Headspace), consumer goods (Keen, Verizon, Target, Northface), and tech (Google, Amazon, Facebook, Meta, Spotify, AirBnB). Our tools help teams deeply understand the humans behind their products, so they can build better ones. We are expanding our smart and driven team and would love for you to join us. Lead Research Advisor, Mid-Market (Austin or Chicago) Job Description We are looking for a Lead Research Advisor to join our growing Customer Success department. You will drive and grow important relationships by helping our customers find new ways to use our platform, ensuring they achieve maximum value from their investment. This role is a critical function that merges research expertise with a customer success motion, focusing on driving platform adoption and mitigating churn risk. You will also collaborate closely with a team of Research Advisors to design, recruit, and field research projects for our customers You will have a chance to make a real difference for Dscout’s customers and build your career at the intersection of customer success and research. You are an incredible communicator and a genuine, creative problem-solver. You are our customer’s dedicated partner in success, helping them learn a new digital tool, execute powerful research, and maximize the return on their Dscout subscription. You collaborate closely with Account Directors to help to identify Dscout methodologies that best meet customer needs, build new use cases, identify growth opportunities, and ensure strong platform adoption across their organization. Internally, you are our customers’ champion, driving larger improvements to the platform and overall user experience. The Lead Research Advisor position is among the most central to Dscout’s operations, so you’ll work with people fr

salesforcefinanceCRM
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S
2mo ago

Who we are About Stripe Stripe 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. About the team The Commercial Sales team is responsible for the acquisition, growth, retention, and expansion of mid-market customers. As a Grower Account Executive, you’ll set strategy for your territory, identify opportunities for existing customers to get the most out of Stripe, execute scaled sales strategies to grow revenue and drive end-to-end campaigns to nurture relationships and increase adoption of Stripe products. What you’ll do As an Account Executive, Commercial Grower you will play an instrumental role in fueling Stripe’s growth and expanding revenue from Stripe’s existing mid-market customers. In this role, you will also help build out a new team touching more of our install base and GTM motion at Stripe. Responsibilities Generate upsell opportunities to drive revenue growth in your territory Develop and implement sales strategies to grow revenue per user, adopt new products and ensure retention Identify and understand users’ pain points to propose Stripe solutions and own the full sales cycle, from business case development to close Own contract renewals and lead commercial negotiations to increase and retain existing customer revenue and increase Stripe share of wallet Work cross-functionally to solve user pain points and improve Stripe’s product You will be required to work from the Chicago office three (3) days per week Who you are We’re looking for someone who meets the minimum requirements to be considered for the role. If you me

Who we are About Stripe Stripe 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 net 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. About the team The Commercial team is a high-velocity sales team focused on acquiring new, under-penetrated mid-market customers. As an Account Executive on the Commercial Hunter sales team, you’ll be responsible for sourcing and closing net new business, executing outbound sales strategies, and running end-to-end sales cycles to bring new customers onto Stripe. You’ll play a critical role in expanding Stripe’s reach by identifying high-potential prospects and converting them into long-term users of our platform. What you’ll do As a Account Executive, Commercial Hunter you will play an instrumental role in fueling Stripe’s growth by acquiring net new mid-market customers. In this role, you will also help build out a new team and go-to-market (GTM) motion at Stripe. Responsibilities Identify high-potential prospective users and use effective prospecting strategies to generate leads that drive net-new revenue growth in your territory Develop and implement scaled sales strategies for acquiring new customers and driving adoption of Stripe’s products across new accounts Identify and understand users’ pain points to propose Stripe solutions and own the full sales cycle, from business case development to close Work cross-functionally to solve user pain points and improve our product to better serve new customer needs Who you are We’re looking for a high performing, well-rounded seller who can manage high velocity deal cycles, enjoys building and has demonstra

Who we are About Stripe Stripe 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. About the team The Platform Sales team works with B2B Software Platforms to help them facilitate payments for their customers using our Stripe Connect product. Software Platforms, also known as B2B Indirect, are software platform businesses who serve other businesses. Platforms already using Stripe include Shopify, Lightspeed and Mindbody. As a key member to the Stripe Platforms team, you will manage and elevate relationships with a named account list while identifying new growth opportunities and ways Stripe can exceed expectations. What you’ll do As an Account Executive (New Business), you will create partnerships between Stripe and the most innovative and fastest-growing software platforms in the world by helping them to understand how Stripe’s online commerce infrastructure can make payments a competitive advantage for their businesses. Responsibilities Directly manage and nurture a named account list and develop account plans for winning and expanding business with upper middle market and enterprise companies Build and maintain key relationships with C-level executives, while orchestrating touchpoints with Stripe executives Contribute to shaping our platform partnership strategy and building repeatable processes and scaled engagement models Develop and execute outbound strategies to create and nurture opportunities Own the full sales cycle from lead to close for Startup, SMB and mid-market platforms Coordinate and support the implementation for so

H
Harvey
📍 Chicago• Full-time• Remote• $280K – $320K/yr
1mo ago

Why Harvey At Harvey, we’re transforming how legal and professional services operate. By combining frontier agentic AI, an enterprise-grade platform, and deep domain expertise, we’re reshaping how critical knowledge work gets done for decades to come. This is a rare chance to help build a generational company at a true inflection point. We have strong product-market fit and world-class investor support. We’re scaling fast and defining a new category in real time. The work is ambitious, the bar is high, and the opportunity for growth — personal, professional, and financial — is unmatched. Our team moves fast, takes ownership, and is deeply committed to the mission — operating with intensity, staying close to our customers, and pushing each other for excellence. We live by three values: Decisiveness, Simplicity, and Job's Not Finished. We act quickly on clear judgment over perfect information, we believe simplicity is what scales, and we're never satisfied with where we are. If you want to do the best work of your career alongside people who share that drive, we'd love to build with you. At Harvey, the future of professional services is being written today — and we’re just getting started. Role Overview The SMB Sales Manager joins Harvey's Commercial Sales organization to lead a team of Account Executives selling Harvey's AI platform to small and mid-sized law firms and legal teams out of the Chicago office. Reporting to the Vice President of Commercial Sales, this role owns territory planning, pipeline development, and revenue execution across the region. The manager drives a disciplined sales process while coaching AEs through the full cycle — from discovery and qualification through close — and holds the team accountable to rigorous forecasting and performance standards. It is a high-impact opportunity to shape the sales culture and operating rhythm for a fast-growing segment at one of the most innovative companies in legal technology. What You'll Do Build, coach,

REMOTEai
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F
Fin
📍 Chicago• Full-time• From $203.5K/yr
12mo ago

Fin , now part of Salesforce, is on a mission to help businesses provide perfect customer experiences. Our AI Agent Fin is the highest-performing AI Customer Agent on the market today, enabling businesses to deliver impeccable, always-on customer support across the customer journey, from service, to sales, to ecommerce. Powered by our own AI models, Fin resolves complex customer issues end-to-end across every channel, with minimal set-up and integration. Fin can also be combined with our natively integrated Intercom help desk, giving modern support teams one single system. Together with Salesforce, the #1 AI CRM, where humans with agents drive customer success, we're building the future of customer experience. Here, ambition meets action. Tech meets trust. And innovation isn't a buzzword, it's a way of life. The world of work as we know it is changing, and we're looking for Trailblazers who are passionate about bettering business and the world through AI. Ready to level up your career at the company leading workforce transformation in the agentic era? You're in the right place. Agentforce is the future of AI, and you are the future of Salesforce. What's the opportunity? As a MidMarket Account Executive, you will be a key member of the team leading the growth of our new business. We’re building a world-class sales organization, and the road ahead is going to be very exciting. This is a seat at the centre of the biggest shift selling has seen in decades. You'll be selling AI agents to companies rethinking how their entire customer experience works, which means the conversations are strategic, technical and genuinely interesting. You'll also be using AI every day to run your own territory, from qualification to research to how you read a deal, so you're not just talking about the technology, you're operating on it. As a rapidly expanding business, there is a high degree of opportunity for progression, creativity, and ownership. What will I be doing? E

aisalesforceCRM
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S
15 days ago

Who we are About Stripe Stripe 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. About the team Stripe’s SMB Solutions Architecture (SA) team works with technical and business leaders (CTO/ CIO/ CEO/ Founders etc.), payments leaders and product engineering teams in the mid-market segment to evangelize Stripe’s solutions in the market. A solutions architect’s role is to build relationships with decision makers and think strategically about the business needs of Stripe’s customers. Solution Architects identify and propose Stripe solutions to solve complex business challenges and drive growth for our customers. SAs establish and prescribe best practices around a customer’s strategy, provide business and technical thought leadership and are viewed as a trusted advisor. They work on scaling business processes aligned to maximizing account coverage while working closely with customer and partner resources to deliver a solution that can be adopted quickly. What you’ll do As a member of the team, the Solutions Architect will build highly consultative trusted relationships with c-level executives and technical decision makers in the customer’s organization to provide business and technical thought leadership, and become a trusted advisor in solving mission-critical business challenges. She/he will architect business models with them so they can drive new monetization opportunities and growth for both the user and Stripe. Responsibilities Drive thought leadership and build executive relationships with key business and technical stake

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I
Instawork
📍 Chicago• From $133K/yr
2mo 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. At Instawork, we're a full staffing platform suite that allows businesses to connect with professionals in a modern, robust way. Our labor marketplace connects over 10M professionals to top Hospitality and Logistics companies across North America, and we're looking for top talent to help us scale. We have an immediate opening for a Sales Manager with a proven track record of success to join our rapidly growing team. Reporting to the Sales Director, this role is a critical member of the sales leadership team, responsible for coaching reps through every stage of the outbound sales process, including prospecting, qualification, and pipeline building, while using data to spot gaps and drive the fixes that close them. This is a results-driven position built for someone who can build and manage remote software sales teams, and who is as comfortable in a rep's deal review as they are in a pipeline dashboard. What You'll Do & Who You Are Coach reps through the full outbound sales cycle (prospecting, qualifying, and building pipeline), with 2+ years of experience building and managing high-performing remote software sales teams Read the data and act on it : monitor pipeline, activity, and conversion metrics to spot gaps, then design and execute the coaching, process, or enablement changes that close them Bring 5+ years of quota-exceeding experience selling mid-enterprise deals, with a track record of overachievement and hitting sales targets Support deals directly as senior air cover, managing multiple stakeh

ailogistics
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