Enterprise Sales Executive Jobs in Chicago, IL
Enterprise Sales Executive jobs in Chicago are concentrated in the Loop, River North, and Fulton Market, with strong demand from employers in enterprise software, financial services, logistics technology, and healthcare IT. Top companies hiring right now include Uber, Rippling, and SentiLink. See the openings below and apply to the ones that match your experience.
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INTRODUCTION
At Anaplan, we are a team of innovators focused on optimizing business decision-making through our leading AI-infused scenario planning and analysis platform so our customers can outpace their competition and the market.
What unites Anaplanners across teams and geographies is our collective commitment to our customers' success and to our Winning Culture.
Our customers rank among the who's who in the Fortune 50. Coca-Cola, LinkedIn, Adobe, LVMH and Bayer are just a few of the 2,400+ global companies who rely on our best-in-class platform.
Our Winning Culture is the engine that drives our teams of innovators. We champion diversity of thought and ideas, we behave like leaders regardless of title, we are committed to achieving ambitious goals, and we love celebrating our wins – big and small.
Supported by operating principles of being strategy-led, values-based and disciplined in execution, you'll be inspired, connected, developed and rewarded here. Everything that makes you unique is welcome; join us and let's build what's next – together!
ROLE AND RESPONSIBILITIES
Anaplan is seeking a results-driven Enterprise Account Executive - Financial Services to join our dynamic sales team. In this role, you will leverage your proven track record of selling sophisticated SaaS solutions to represent an incredibly versatile and powerful platform. We're looking for a competitor with a hunter mindset who loves to win. You will be a catalyst for our continued growth by leading digital transformation and helping industry leaders end siloed decision-making.
This role reports directly to the Regional Vice President (RVP) and manages a territory consisting of both greenfield opportunities and existing Anaplan customers. This requires a unique individual who can hunt for and secure new logos while also identifying and growing opportunities within our current customer base. You will embody our core values (Innovative, Accountable, Collaborative, Transparent, Resilient, Empathetic, Authentic, Learner) as you help customers achieve their immediate goals and prepare their business for the future.
Your Impact
- Engaging with targeted financial services enterprise prospects to identify broken business processes and position Anaplan's unique ability to solve the problem
- Build and communicate Anaplan's business value throughout the selling engagement, navigating complex prospect environments to align stakeholders around the Anaplan solution.
- Conduct highly effective, consultative presentations to key C-suite level decision-makers, including CFOs, CROs, and senior leaders across Supply Chain, Finance, and HR.
- Develop and own opportunity management from start to finish across multiple customer targets and functions.
- Apply Anaplan's value-based selling methodology to manage a robust sales process and accurately forecast your business.
- Employ outstanding account leadership skills to identify expansion opportunities by cross-selling and up-selling within your targeted accounts.
- Collaborate effectively with a matrixed team of Sales Development Reps, Marketing professionals, Solution Consultants, and Customer Success partners to ensure customer success.
BASIC QUALIFICATIONS
- Ideally 5+ years of direct, consultative sales experience, with a consistent track record of overachieving quota in a competitive market.
- Has experience selling into Financial Services prospects and accounts or selling a FinTech Solution.
- Extensive experience selling complex SaaS solutions (enterprise resource planning, supply chain management and/or human capital management) into Fortune 2000 companies.
- Proven success selling into multiple Lines of Business (LOBs) and navigating complex, multi-threaded buying centers.
- A demonstrated history of career stability.
- Mastery of outcome-based sales methodologies such as Challenger selling, TAS, MEDDPICC or Miller Heiman.
PREFERRED QUALIFICATIONS
The Ideal Candidate
- You are a humble, hungry and collaborative team player with a strong hunter mindset bringing grit and competitiveness while thriving in a team environment.
- Strong business acumen and a naturally curious, consultative approach to understanding and solving customer challenges.
- You embody our I ACT REAL values: you are an Innovative, Accountable, Collaborative, Transparent, Resilient, Empathetic, Authentic Learner.
OUR COMMITMENT TO DIVERSITY, EQUITY, INCLUSION AND BELONGING (DEIB)
We believe attracting and retaining the best talent and fostering an inclusive culture strengthens our business. DEIB improves our workforce, enhances trust with our partners and customers, and drives business success. Build your career in a place where diversity, equity, inclusion and belonging aren't just words on paper – this is what drives our innovation, it's how we connect, and it contributes to what makes us a market leader. We believe in a hiring and working environment where all people are respected and valued, regardless of gender identity or expression, sexual orientation, religion, ethnicity, age, neurodiversity, disability status, citizenship, or any other aspect which makes people unique. We hire you for who you are, and we want you to bring your authentic self to work every day!
We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, perform essential job functions, and receive equitable benefits and all privileges of employment. Please contact us to request accommodation.
FRAUD RECRUITMENT DISCLAIMER
It has come to our attention that fraudulent and fictitious job opportunities are being circulated on the Internet. Prospective candidates are being contacted by certain individuals, mainly through telephone calls, emails and correspondence, claiming they are representatives of Anaplan. The main purpose of these correspondences and announcements is to obtain privileged information from individuals.
Anaplan does not:
- Extend offers to candidates without an extensive interview process with a member of our recruitment team and a hiring manager via video or in person.
- Send job offers via email. All offers are first extended verbally by a member of our internal recruitment team whenever possible and then followed up via written communication.
All emails from Anaplan would come from an @anaplan.com email address. Should you have any doubts about the authenticity of an email, letter or telephone communication purportedly from, for, or on behalf of Anaplan, please send an email to people@anaplan.com before taking any further action in relation to the correspondence.
See All 268+ Enterprise Sales Executive Jobs in Chicago
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Find JobsEnterprise Sales Executive Job Market in Chicago
Who's Hiring
- Uber11

- Rippling9

- SentiLink9

- Braze8

- Gartner5

Top Industries Hiring
- Technology & Software119
- Consulting & Professional Services17
- Marketing & Advertising13
- Insurance11
- Media & Entertainment10
Enterprise Sales Executive Jobs in Chicago: Frequently Asked Questions
How do I get a enterprise sales executive job in Chicago?
Focus your search on the Loop and River North, where the highest concentration of enterprise technology, fintech, and professional services employers operate. Chicago's market rewards candidates who can demonstrate experience closing complex, multi-stakeholder deals, particularly in SaaS, logistics tech, or financial services. Building relationships through local sales communities and targeting mid-market to enterprise-stage companies headquartered or regionally based in Chicago gives you a real edge.
Which companies hire enterprise sales executives in Chicago?
Chicago enterprise sales executive roles are posted by Uber, Rippling, and SentiLink and others right now, based on current listings on Migrate Mate as of June 2026. Chicago draws a mix of globally headquartered technology firms, regional financial services companies, and fast-growing logistics and healthtech players, all of which maintain active enterprise sales teams here.
Are there remote enterprise sales executive jobs in Chicago?
Yes, though enterprise sales executive roles are moderately remote-friendly since relationship-building and client meetings often require in-person presence. About 57% of enterprise sales executive openings tied to Chicago are remote or hybrid as of June 2026, with hybrid arrangements most common among software and cloud-services companies based in the Loop and River North.
How can I get a enterprise sales executive job in Chicago with little or no experience?
The most realistic entry path in Chicago is moving up from a sales development representative or account executive role at one of the city's many mid-stage SaaS or fintech companies, where internal promotion into enterprise sales is common. Chicago employers in logistics technology and professional services also hire associate enterprise sales roles that reward strong discovery and consultative skills over tenure, making them accessible with two to three years of B2B experience.
Which industries hire the most enterprise sales executives in Chicago?
Most enterprise sales executive openings in Chicago sit in Technology & Software, Consulting & Professional Services, and Marketing & Advertising, per current listings on Migrate Mate as of June 2026. Chicago's role as a national hub for financial technology, supply chain software, and healthcare administration creates concentrated, sustained demand for enterprise sellers who can navigate long sales cycles and complex buying committees.
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