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Chicago Startup Jobs (NOW HIRING)

Unframe

Regional GM - Chicago (Remote)

Chicago, IL · Remote

Chicago, Illinois (Remote) About Unframe Unframe is an AI-first startup helping the world's largest enterprises bring LLM-powered applications to life in days - not months. We combine the speed of a ...

Artera

Sales Account Executive (Chicago)

$165K - $185K/yr

About Us: Artera is an AI startup that develops medical artificial intelligence tests to ... Chicago, IL (or local area) $165,000 - $185,000 a year In addition to base salary, this role ...

Lendbuzz

Dealership Account Manager - Chicago, IL

Chicago, IL · On-site +1

$80K - $175K/yr

... in Chicago, IL to join our growing field sales team. In this role, you'll help expand our market ... Recent Achievements 2022 - Named one of America's Best Startup Employers by Forbes. 2023 - Received ...

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Chicago Startup information

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$59.5K

$129.8K

$183.5K

How much do chicago startup jobs pay per year?

As of Aug 7, 2026, the average yearly pay for chicago startup in the United States is $129,801.00, according to ZipRecruiter salary data. Most workers in this role earn between $109,000.00 and $151,000.00 per year, depending on experience, location, and employer.

What is a Chicago startup?

A Chicago startup is a newly established company based in Chicago, typically in the early stages of development and focused on innovation, technology, or unique business models. Startups in Chicago span a wide range of industries, including tech, healthcare, finance, and food services. These companies often seek rapid growth and funding from venture capital or angel investors. Chicago's vibrant ecosystem provides resources like incubators, accelerators, and networking events to help startups succeed. The city's diverse talent pool and supportive community make it an attractive location for entrepreneurs.

What are the key skills and qualifications needed to thrive as a Chicago startup founder, and why are they important?

To thrive as a Chicago Startup founder, you need a solid understanding of business development, market analysis, and entrepreneurship, often supported by experience in launching ventures or a relevant degree. Familiarity with tools like customer relationship management (CRM) systems, project management software, and basic financial platforms is common. Outstanding networking abilities, resilience, and creative problem-solving make someone stand out in this role. These skills and qualities are vital for navigating the challenges of building a business, attracting investors, and driving growth in a competitive market.

What is the difference between Chicago Startup vs Chicago Business Analyst?

AspectChicago StartupChicago Business Analyst
Required CredentialsBachelor's degree often in business, marketing, or related fieldsBachelor's degree in business, finance, or related areas; certifications like CBAP are common
Work EnvironmentFast-paced, innovative startup setting, often small teamsCorporate or consulting environments, structured workflows
Employer & Industry UsageStartups across tech, e-commerce, and servicesLarge companies, consulting firms, and corporate sectors
Common Search & ComparisonYesYes

Chicago Startup roles focus on innovation, agility, and often require a mix of business and technical skills. Chicago Business Analysts typically work in structured environments analyzing data and processes to improve business performance. While both roles require similar educational backgrounds, startups emphasize adaptability and entrepreneurial spirit, whereas business analysts prioritize analytical skills and process improvement.

What is the typical team structure and collaboration style in a Chicago startup environment?

In a Chicago startup, teams are often small and cross-functional, which means employees regularly collaborate across departments such as product, engineering, marketing, and sales. The work environment is fast-paced and dynamic, with frequent opportunities for team members to contribute ideas and take on responsibilities beyond their job title. Open communication and adaptability are valued, and it’s common to participate in brainstorming sessions, stand-up meetings, and agile workflows. This collaborative atmosphere fosters rapid learning and provides ample opportunities for professional growth and networking within Chicago’s vibrant tech ecosystem.
What cities are hiring for Chicago Startup jobs? Cities with the most Chicago Startup job openings:
What states have the most Chicago Startup jobs? States with the most job openings for Chicago Startup jobs include:
What job categories do people searching Chicago Startup jobs look for? The top searched job categories for Chicago Startup jobs are:
Chicago Startup jobs near you
Infographic showing various Chicago Startup job openings in the United States as of July 2026, with employment types broken down into 85% Full Time, 11% Part Time, 1% Temporary, and 3% Contract. Highlights an 89% Physical, 5% Hybrid, and 6% Remote job distribution, with an average salary of $129,801 per year, or $62.4 per hour.

Regional GM - Chicago (Remote)

Unframe

North Charleston, SC • Remote

Full-time

Posted 16 days ago

Job description

Regional GM at Unframe

Location: Chicago, Illinois (Remote)

About Unframe

Unframe is an AI-first startup helping the world's largest enterprises bring LLM-powered applications to life in days - not months. We combine the speed of a product company with the flexibility of a consultancy, helping customers move from idea to deployed AI systems faster than anyone else in the market.

With over $100M in TCV secured within 12 months, and a new $50M Series B led by Highland Europe, Unframe is rapidly scaling globally alongside Fortune 500 customers, backed by Bessemer, Craft, and TLV.

About the role:

We're looking for a Regional GM to join our team and help drive our go-to-market motion. You'll play a pivotal role in landing our first major customers, shaping our sales playbook, and partnering directly with the VP of Sales and founder to build a high-performance revenue engine.

What you'll do:

  • Lead complex, multi-stakeholder sales cycles into highly regulated industries (FinServ, Healthcare, Manufacturing, Retail) where our on-premises capabilities provide a competitive advantage.
  • Build pipeline from zero in an early-stage environment—identify and win strategic enterprise accounts with no hand-raisers or established playbook.
  • Translate complex AI/ML capabilities into compelling business outcomes for C-suite stakeholders, positioning Unframe for companies seeking to "buy vs. build" AI capabilities.
  • Architect multi-year expansion strategies and build deep relationships across IT, product, and innovation teams.
  • Collaborate directly with the VP of Sales and founders to refine the enterprise strategy and influence the product roadmap

What we are looking for:

  • 8+ years enterprise software sales with consistent quota over-achievement at Fortune 500 companies
  • Proven track record closing $1M+ ACV deals in early-stage environments
  • Experience selling complex technical solutions to CIO organizations
  • Background in AI/ML platforms, digital transformation, enterprise data platforms, or management consulting
  • Entrepreneurial mindset, you thrive in ambiguity, own outcomes, and build from scratch
  • Success in highly regulated industries with complex compliance requirements

Nice to have:

  • Regulated industry experience, early-stage success

Why join us?

  • Compensation is uncapped with aggressive accelerators. At $1M+ ACV deal sizes, this structure rewards over-performance on meaningful deals.
  • Our VP of Sales joined Unframe for three reasons: a founder with a proven exit, tier-one investors, and a product that's genuinely different and defensible. The GTM approach backs that up. Buyers get a free POC, tailored to their actual use case, delivered in days. No data sharing, no upfront cost, no six-month consulting engagement before anyone sees value.
  • You'll work directly with the VP of Sales and founders, shape GTM strategy, close the deals that define our market position, and hold equity in a company with real institutional backing and momentum.
  • We hire with intention. If you thrive in a performance culture with real backing behind you, you will win here.

Ready to Build the Future?

If this opportunity excites you, apply now!