Best E-commerce Companies to Work for in Chicago, IL (422)

Benefits & Perks: Total rewards are highlighted as comprehensive, with day-one medical coverage, generous PTO, tuition support, wellbeing programs, and an automatic 6% 401(k) company contribution. Additional perks such as paid parental leave, ESPP, charitable matching, and mental health resources are frequently noted.

Market Position & Stability: The company is portrayed as a large, profitable MRO leader serving millions of customers, often seen as providing job stability and resources for growth. Recent performance disclosures and ongoing expansion reinforce a perception of durability.

Career Growth: Structured development, rotational programs, internships, and internal mobility are emphasized across functions like sales, supply chain, technology, and corporate roles. Mentorship, robust training, and paid certifications are commonly available to support advancement.

Community Impact: Work modernizes lottery operations (notably in Illinois) with proceeds directed to education, health, and other causes, and pride in contributing to communities is strongly emphasized. Responsible‑gaming and ethical practices are highlighted as part of the mission.

Work-Life Balance: Hybrid flexibility, encouragement to take time off, and well‑being supports such as wellness stipends, weekly in‑office yoga, and volunteer days are widely described. Flexible on‑site expectations and people‑first rituals reinforce sustainable pacing when possible.

Benefits & Perks: The package includes 12 weeks fully paid parental leave, immediate‑vesting 401(k) match up to 6%, tuition reimbursement, student‑loan repayment, 529 matching, healthcare, and quarterly wellness stipends. These offerings signal an employee‑centric approach for a small Chicago‑based team.

Work-Life Balance: A remote-first model with role-based flexibility and generous PTO is emphasized, allowing people to choose remote, hybrid, or office setups. Feedback suggests this flexibility is a standout draw and supports balance across distributed teams.

Compensation: Pay and equity are viewed as competitive for many roles, with programs like an ESPP and 401(k) match highlighted alongside global family benefits. Feedback suggests total rewards stack up well versus peers, though ranges vary by level and location.

Mission & Purpose: The stated goal of economic empowerment across brands like Square and Cash App makes the work feel meaningful and tied to real-world impact. The breadth of ecosystems offers varied, purpose-linked problems to solve.

Compensation: Pay is considered above market across multiple tracks and is often paired with profit sharing or bonuses. Total rewards are frequently cited as a primary reason to join and remain.

Benefits & Perks: Health coverage, tuition reimbursement, paid parental leave, and company‑funded retirement are consistently highlighted. Additional programs such as adoption/surrogacy assistance and wellness resources are also emphasized.

Market Position & Stability: Operations are often described as well‑run and profitable with clear processes supporting a vast catalog. Predictable schedules in several roles and long‑term viability add to the sense of stability.

Mission & Purpose: Connecting fans to live events is described as motivating, with monthly ticket credits reinforcing a direct link to the product. Hybrid collaboration and visible impact on a large consumer marketplace add day-to-day energy.

Benefits & Perks: Monthly ticket credits/discounts, wellness programs, and comprehensive health coverage are consistently highlighted as distinctive. In‑office amenities and catered lunches at the renovated Chicago HQ enhance the workplace experience.

Team Support: Colleagues are often seen as friendly, collaborative, and passionate about sports and music, creating strong camaraderie. Recognition programs, town halls, and company‑sponsored events contribute to a supportive atmosphere.

Benefits & Perks: Company materials highlight comprehensive wellness and travel programs, charitable donation matching, and stipends across multiple countries. Travel discounts and lifestyle reimbursements are positioned as tangible perks that many teams leverage.

Mission & Purpose: Work centers on building travel technology at global scale across brands like Expedia, Hotels.com, and Vrbo, within a culture that celebrates travel. Travel-centric programs and perks reinforce the connection to the company’s purpose.

Work-Life Balance: A structured hybrid policy expects most full-time employees in the office at least three days per week with flexibility on remaining days. This clarity enables predictable routines that support balance for many roles.

Work-Life Balance: A hybrid model with two in-office days and remote Fridays at a transit-accessible Chicago HQ supports a practical balance between collaboration and personal time. This setup is repeatedly highlighted as a convenience for commuting and team coordination.

Benefits & Perks: Day-one medical, dental, and vision coverage, paid parental leave, and an automatic 401(k) contribution stand out, complemented by PTO, bonuses, and office amenities. These offerings provide a strong baseline of financial, family, and everyday support.

Market Position & Stability: Backing from W.W. Grainger and participation in the “Endless Assortment” segment provide resources and operating stability. A large online catalog and scaled operations signal durable business footing.

Team Support: Colleagues are often seen as collaborative and quick to help across product, engineering, and customer-facing teams, with a stated value of “collaboration over egos.” Leadership is described as accessible with open communication and an emphasis on cross-functional partnership.

Learning & Development: An “AI-first/learning mentality,” mentorship, formal training, certifications, and quarterly career check-ins are emphasized, with clear development pathways and internal mobility highlighted. Opportunities to build skills and progress into new roles are called out across company and workplace profiles.

Benefits & Perks: Hybrid and remote options, flexible schedules, and unlimited PTO are paired with day-one health coverage, parental leave, mental health support, 401(k) matching, and home-office support. Recognition programs such as awards and President’s Club reinforce an appreciation culture.

Team Support: Teams are often described as cross-functional, open, and supportive, partnering across brands with clear ownership and accountability. Associate-led communities and approachable leaders help foster belonging and collaborative problem‑solving.

Career Growth: Career paths and internal mobility across brands are emphasized through structured programs, mentoring, and accessible learning platforms. Leaders are frequently noted for investing in development and encouraging transparency around progression.

Work-Life Balance: Flexible, hybrid norms and well-being resources are highlighted, including encouragement to use paid time off and support for caregiving. When priorities are clear and leadership support is present, workloads are portrayed as manageable.

Mission & Purpose: Work is often framed around empowering sellers, with Square’s tools reaching millions of merchants so incremental efforts can impact real businesses quickly. Feedback suggests this scale and purpose are motivating day to day.

Benefits & Perks: Total rewards highlight competitive pay, equity for all employees, strong health coverage, flexible time off, parental leave, and wellness/mental‑health resources. Feedback suggests these programs are a major draw for candidates and employees.

Work-Life Balance: Block describes a distributed model with no designated HQ and encourages working wherever you’re most creative, and many teams support remote/WFH flexibility. Feedback suggests this flexibility is a consistent plus, though local team norms can vary.

Work-Life Balance: Hybrid flexibility and a light in‑office cadence support balance, with practices like one day per week on site, flexible/unlimited PTO, and wellness/remote-work stipends highlighted. These arrangements are presented as “work however you work best,” reinforcing quality‑of‑life benefits.

Team Support: Collaboration, respect, transparency, and approachable leadership are emphasized, and the small, close‑knit environment is portrayed as supportive. Day‑to‑day work often includes cross‑functional partnership and accessible leaders.

Learning & Development: A lean, fast‑moving setting offers broad ownership and rapid skill growth, with opportunities to learn quickly in high‑demand roles. Formal supports like mentorship programs and online course subscriptions are also noted.

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.

Work-Life Balance: Hybrid schedules with about three in-office days, Summer Fridays, and generous PTO are highlighted as supporting manageable day-to-day rhythms. Feedback suggests flexibility is available in many roles and locations.

Team Support: Colleagues are often seen as talented, kind, and helpful, with cross-brand collaboration a common part of the work. Feedback suggests teams partner closely across editorial, studio, product, data, and revenue functions.

Mission & Purpose: A people-first publishing mission and work on 40+ recognizable brands provide a sense of impact and pride. Feedback suggests new platforms, branded studio work, and events add momentum and meaningful projects.

Mission & Purpose: Work sits at the intersection of retail and customer data science and often turns into real shopper and revenue outcomes. A clear “customer first” orientation across loyalty, pricing, assortment, and retail media reinforces purpose.

Work-Life Balance: Hybrid “blended working,” formal flexible options, and supportive teams are highlighted as part of day-to-day norms. These practices point to sustainable pacing relative to many tech or consulting environments.

Belonging & Inclusion: Inclusion programs, DE&I reporting, and active employee networks are presented as standard across the company. These signals indicate attention to belonging alongside flexibility in how work gets done.

Mission & Purpose: An operator-first mission focused on helping restaurants run more profitably is emphasized. This gives day-to-day work tangible customer impact in hospitality.

Innovation & Products: Frequent release notes, update digests, and new integrations signal active product velocity. This creates ongoing opportunities to build, iterate, and learn in restaurant tech.

Benefits & Perks: A comprehensive package—medical/dental/vision, 401(k) match, equity grants, flexible time off, parental leave, ERGs, mental health resources, and a tech stipend—is highlighted. These offerings align with mid-stage tech standards and support employee wellbeing.