Best AI Companies to Work for in Chicago, IL (292)

Learning & Development: Training and upskilling at scale, including formal academies and data/AI platforms, are heavily invested in. Structured coaching, clear career frameworks, and programs like the Learning Collective embed development into day‑to‑day client work.

Career Growth: Brand recognition and exposure to recognizable clients create strong career capital and exit opportunities across industry, tech, finance, and startups. Clear promotion tracks, mentorship, and mobility across a 150+ country network support advancement.

Benefits & Perks: An inclusive hybrid model with options such as reduced schedules, paid leaves, and limited international remote work is paired with two firmwide U.S. shutdown weeks. Comprehensive benefits include health and mental‑health coverage, parental leave, a 401(k) match, and financial well‑being programs like student loan assistance.

Benefits & Perks: Total rewards are described as competitive, spanning health, retirement, ESPP, paid time off, parental/adoption leave, and bonuses. Company materials also emphasize safety and well‑being programs as part of the package.

Market Position & Stability: The business is portrayed as a global leader with a long‑term footprint and 2025 sales around $67.6B, supporting perceptions of stable careers. Scale across infrastructure, mining, energy and rail contributes to durability.

Mission & Purpose: Work is closely tied to tangible infrastructure and industrial impact, which many employees cite as meaningful. The company’s stated purpose of building a more sustainable world reinforces pride in the products and industry role.

Mission & Purpose: Work is often framed as delivering measurable value to consumers and brick‑and‑mortar merchants, creating a clear sense of impact and momentum at a growth stage. Feedback suggests this visible scale and traction helps people feel their efforts matter day to day.

Leadership Communication: Leadership is described as accessible and transparent, with regular AMA sessions and open sharing of company context that keep people informed. Feedback suggests this cadence of communication strengthens connection and alignment across teams.

Benefits & Perks: Benefits include comprehensive health coverage, flexible PTO, equity participation, generous parental support, and office‑day perks alongside learning stipends. Feedback suggests these offerings support balance and well‑being while aiding attraction and retention.

Work-Life Balance: Work-life balance is considered a strength, supported by a formal global hybrid program that provides predictable flexibility. A generally collaborative, low‑ego culture in many groups helps maintain reasonable hours.

Benefits & Perks: Signature benefits such as a paid sabbatical every four years and a bonus‑to‑RSU “Shared Ownership” match stand out as distinctive long‑term perks. Wellness initiatives, flexible time off, and robust leave policies add depth to the package.

Mission & Purpose: A clear investor‑first mission and collaborative culture give the work a strong sense of purpose. Values around ethics, inclusion, and long‑term thinking are reinforced through programs and communications.

Work-Life Balance: Work-life balance is frequently highlighted, supported by hybrid 'Flexi Work' norms, extra WFH days, sabbaticals, and volunteer time off. Balance and flexibility are consistently called out as strengths across locations.

Team Support: Colleagues are often described as helpful, experienced, and collaborative, with a 'win together' mindset across global teams. Engineering groups in particular are noted for high-caliber, supportive peers.

Mission & Purpose: Work is commonly viewed as meaningful, tied to large-scale mapping, ADAS/SDV, logistics, and mobility used by major automakers and enterprises. Many reference satisfaction in doing 'constructive work' with real-world impact.

Autonomy: Work is often described as high‑agency with end‑to‑end ownership, fast iteration, and a “doer” mentality. This setup appeals to people who want to ship quickly and influence roadmaps in applied AI.

Innovation & Products: Teams build production computer vision and payments systems deployed across thousands of real‑world sites, making the work highly visible and tangible. Delivering “AI for the real world” at scale is a central part of the company’s narrative and day‑to‑day focus.

Career Growth: Internal mobility, documented progression frameworks, and rapid skill development are emphasized, especially in engineering. Many roles offer hands‑on exposure to modern CV/AI systems at scale that can accelerate development.

Work-Life Balance: A remote-friendly setup with location flexibility, core overlap hours, generous PTO, wellness days, and company-funded offsites supports balance and autonomy. Home-office support and flexible scheduling reduce commuting burdens while enabling sustainable work rhythms.

Benefits & Perks: Comprehensive offerings include health coverage, mental-health resources, a U.S. 401(k) match, region-specific parental and fertility benefits, equity, performance bonuses, learning stipends, and home-office support. These tangible benefits are positioned to enable growth, well-being, and effective remote work.

Team Support: Colleagues are often characterized as approachable, talented, and collaborative, with rituals for recognition and open idea-sharing. Managers provide real-time feedback and visible recognition across distributed teams, reinforcing a supportive culture.

Benefits & Perks: The remote-first package highlights fully covered medical/dental/vision options, a 401(k) match, paid family leave, premium hardware, and a one-time $10,000 home-office stipend. Flexible PTO, wellness resources, and periodic offsites/sprints further support a distributed workforce.

Autonomy: The culture emphasizes “everyone’s a builder,” high ownership, visible work in shared spaces, and trust to ship outcomes across disciplines. This setup gives self-directed contributors meaningful scope in a fully remote model.

Career Growth: The environment promotes rapid development through cross-functional work, experimentation, and room to take on more responsibility as the company scales. Formal supports include classes, conferences, and internal learning programs.

Work-Life Balance: Flexible remote, hybrid, or in‑office options with core hours (10 a.m.–4 p.m.) and Summer Flex Fridays are standard. Generous PTO that increases with tenure further supports time away and balance.

Benefits & Perks: Employer-covered portions of medical/dental/vision, a 401(k) with employer contributions, and quarterly profit-sharing are emphasized. Paid parental leave, remote stipends/equipment, and Chicago office amenities round out the package.

Learning & Development: Mentorship, “Guru Groups,” lunch‑and‑learns, certifications, and conference support are built in. Regular performance reviews and defined progression plans reinforce continuous growth.

Mission & Purpose: Work on experience‑management software is portrayed as mission‑driven, with leaders visibly using and advocating the product in regular company forums. This clarity of purpose, anchored by the TACOS values, cultivates a strong customer‑obsessed focus.

Benefits & Perks: Benefits are described as comprehensive, including employer‑paid healthcare, a 401(k) match with immediate vesting, wellness stipends, mental‑health support, family‑formation benefits, and short “work from anywhere” windows. Unique offerings like an annual “Experience Bonus” and hybrid amenities are emphasized in company materials.

Team Support: Colleagues are often seen as smart, collaborative, and supportive, reinforced by peer‑nominated TACOS awards and active Q Groups that build community and visibility. Early‑career sales programs also reference strong team lift and recognition rituals.

Team Support: Colleagues are often seen as collaborative and supportive, with onboarding and cross‑team help fostering a strong sense of community. Feedback suggests approachable leaders and in‑person rhythms help connection across global hubs.

Innovation & Products: The platform is commonly described as modern and AI‑native, with ongoing expansion that creates pride and energy in building a category‑leading product. Feedback suggests this momentum makes day‑to‑day work engaging and impactful across functions.

Mission & Purpose: Work is frequently tied to a clear mission of removing “shadow work” in travel and spend, which many find motivating. Feedback suggests shared belief in the product and purpose strengthens cohesion across distributed teams.

Benefits & Perks: The package includes competitive salary and equity, fully covered medical/dental/vision, 401(k), fertility benefits, paid parental leave, unlimited PTO, stipends, and paid in‑office meals; feedback suggests these remove friction so people can focus on building. Signals like relocation support, wellness programs, and daily meals further reinforce a well‑rounded offering.

Career Growth: Roles are described as high‑ownership with broad scope, cross‑team exposure, and rapid learning, enabling people to take on more responsibility quickly. Feedback suggests impact is visible and advancement flows from shipping quickly and “owning the outcome.”

Market Position & Stability: Significant funding, a large NYC headquarters expansion, and visible adoption claims indicate momentum, visibility, and resources to support ambitious roadmaps. This resourcing often translates into active hiring and opportunities to build at scale.

Mission & Purpose: Teams build real‑time, AI‑driven supply‑chain visibility tools used across food, medicine, and retail, so work often ties to outcomes customers can see. Company materials highlight “AI workers” and autonomous execution, reinforcing a sense of tangible impact at scale.

Team Support: Colleagues are often described as collaborative and “one team,” with smooth onboarding and cross‑functional cooperation across Chicago, Europe, and Chennai. Culture pages and employee spotlights emphasize inclusive groups and shared ownership when tackling complex client challenges.

Learning & Development: Employees are encouraged to experiment with AI across functions and access mentorship, customized development tracks, and programs like FourKites Academy. Cross‑functional projects and a product‑led environment expose people to data/ML, digital twins, and large partner ecosystems.

Learning & Development: Learning programs, paid industry certifications, and lunch-and-learns are highlighted, pointing to continuous skill building and broad, early exposure across functions.

Career Growth: High-ownership roles, access to leadership, and promotion pathways tied to consistent performance signal room to expand scope and advance.

Benefits & Perks: Comprehensive health coverage, retirement plans, PTO and holidays are paired with wellness and on-site perks like a company-paid fitness center, catered lunches, and regular team events.

Work-Life Balance: Flexible iMAway time off, wellness days, and hybrid/remote norms are repeatedly highlighted, enabling people to manage time without rigid caps. Trust-based scheduling is emphasized so personal needs can be balanced alongside work.

Team Support: Colleagues are often described as friendly, helpful, and collaborative, with managers leaning toward autonomy rather than micromanagement. ERGs and inclusion initiatives (e.g., iBelong, iMProud) reinforce a supportive, community feel.

Benefits & Perks: Benefits are presented as comprehensive, including enhanced parental leave (20 weeks primary, 10 weeks secondary), 401(k) matching, mental-health resources, and wellness programs. Additional perks such as flexible PTO, volunteer time, and stocked offices are also noted.

Compensation: Pay is considered competitive with meaningful equity components and performance bonuses, creating strong total rewards for many roles. Feedback suggests equity can be a significant portion of compensation with upside when the business performs.

Benefits & Perks: Materials highlight comprehensive medical coverage, generous parental leave, mental‑health support, backup care, and robust 401(k) options including a “mega backdoor” feature. Feedback suggests these programs are a notable draw alongside base pay.

Innovation & Products: Teams work on AR, AI‑enabled ads, and large‑scale consumer systems, shipping features to hundreds of millions with rapid iteration. Feedback suggests this scope makes the work feel impactful and technically engaging.

Career Growth: Opportunities to advance quickly and move up based on performance appear strong, with merit-based progression common. High performers can accelerate their careers and gain visibility.

Autonomy: People are given real ownership and decision-making room with low bureaucracy. This setup enables visible impact but expects accountability and speed.

Learning & Development: The environment promotes rapid skill-building through challenging, high-velocity work. Those who consistently hit goals gain extensive learning opportunities.

Work-Life Balance: Remote-by-default operations with core collaboration hours, async practices, and fewer standing meetings support sustainable schedules and deep work. Purposeful offsites and Studios time add connection without imposing daily commutes.

Benefits & Perks: Comprehensive health coverage, paid parental and family leave, and a flexible perks allowance—plus home-office support and travel for gatherings—are emphasized as strengths. Compensation commonly includes performance bonuses and equity alongside standard benefits.

Autonomy: The Virtual First design centers on trust and non-linear workdays, giving people meaningful control over where and when they work. Clear playbooks and transparent performance frameworks reinforce independent execution and ownership from day one.

Autonomy: Roles are portrayed as high-ownership with ideas quickly turning into shipped features and visible customer impact through “ready-to-run” deployments. Small-team dynamics and direct access to leadership enable influence beyond formal lanes.

Team Support: Colleagues are described as quick to rebalance workloads and help, with open communication about priorities to prevent overwhelm. Rituals like in-person all‑hands and an open-door approach reinforce accessibility and collaboration.

Benefits & Perks: Workplace materials outline a hybrid model, unlimited PTO, and healthcare (medical, dental, vision), with extras like training/conferences and office socials. These perks, plus occasional work-from-home flexibility, support practical work-life needs in a lean startup.

Work-Life Balance: Remote-first and hybrid options under “Work Reimagined” are prominently promoted, letting people work where they’re most effective. Flexible schedules and wellbeing programs are often linked to a healthier balance.

Team Support: Colleagues are frequently described as collaborative and approachable across functions. Employee communities and cross-team coordination reinforce a supportive, people-centered culture.

Benefits & Perks: Benefits are advertised to start on day one, including medical, dental, vision, multiple PTO types, parental leave, and wellness/mental-health support. These offerings are positioned as a core part of the employee experience.