Best Sales Companies to Work for in Chicago, IL (114)

Team Support: Colleagues are often seen as kind, respectful, and helpful, with cross‑team collaboration, accessible coaching, and a strong sense of community across offices.

Mission & Purpose: Work is framed around solving the visible travel‑plus‑spend problem and removing “shadow work,” which many describe as motivating amid the platform’s AI‑native expansion.

Market Position & Stability: The company points to strong revenue milestones, recent funding and acquisitions, and expansion across the U.S. and Europe, signaling momentum and runway.

Mission & Purpose: Work is closely tied to improving patient education and provider–patient conversations at the point of care, with a large in‑office network that brings day‑to‑day tasks near clinical decision moments. Feedback suggests this scale and clarity of purpose make contributions feel meaningful.

Work-Life Balance: Hybrid/remote options by role, summer short‑day Fridays, front‑loaded flexible time off, mental‑health resources, and “no Friday afternoon meetings” are highlighted. Job postings also show fully remote roles in areas like analytics and product, signaling flexibility across functions.

Team Support: Colleagues are often seen as kind, supportive, and collaborative, with managers described as approachable and helpful. Repeated workplace recognitions and culture signals reinforce a people‑focused, collaborative environment.

Team Support: Colleagues are often described as helpful, low‑ego, and collaborative, fostering a friendly environment where people readily support one another across teams and locations. This shows up in narratives about open communication, shared ownership, and a team‑oriented culture.

Benefits & Perks: Benefits are portrayed as comprehensive, including 100% paid parental leave for all parents, employer‑paid therapy and coaching, wellness and WFH stipends, flexible time off, and company‑wide recharge days. Public materials and external recognition reinforce a benefits‑forward posture.

Work-Life Balance: Flexible schedules and a remote‑first setup help many manage personal and professional priorities. Extended holidays and recharge days are intended to support balance in a fast‑moving environment.

Career Growth: Career development and internal mobility are emphasized through promotion-from-within, mentorship, and defined progression paths, with opportunities to take on broader responsibilities quickly. A high-growth setting and visible impact create room for ownership and rapid learning.

Benefits & Perks: Benefits are described as strong for the company’s size, including employer-paid medical options, unlimited PTO with paid holidays, parental leave, and immediate 401(k) eligibility. Dental and vision coverage, FSAs/HSAs, and Chicago office perks add to the package.

Mission & Purpose: Work centers on a clear mission to modernize bulk-hauling operations with close collaboration alongside dispatchers, drivers, and operators. Customer proximity makes the work feel meaningful and motivating.

Mission & Purpose: Work is centered on improving care operations and resident outcomes in assisted living and memory care, tying daily efforts to tangible user impact. Materials emphasize solving real customer pain points and a service‑oriented ethos from the Chicago hub.

Team Support: Colleagues are often characterized as collaborative and supportive, with approachable leaders and open communication norms. Practices like pair programming, team‑based planning, and visible recognition reinforce cross‑team cooperation.

Learning & Development: Mentoring and direct access to long‑tenured technical leadership are highlighted, with opportunities to “grow up” on the engineering team. Programs such as mentorship, conferences, and online course subscriptions signal a learning‑oriented environment.

Benefits & Perks: Benefits include company-paid health, dental, and vision, a 401(k) match, paid parental leave, generous time off with separate “Refresh Days,” wellness stipends and fitness options, weekly lunch stipends, and a hybrid/flexible work model. These tangible offerings are reinforced by regular social events and team-building activities.

Career Growth: Opportunities for advancement are emphasized, supported by mentorship programs, professional development, lunch-and-learns, and a dedicated “BigTime Academy.” A scaling environment and smaller-company visibility can translate into faster learning and expanded responsibilities.

Team Support: Colleagues are often portrayed as talented, caring, and collaborative, creating a friendly atmosphere. ERGs, mixers, and cross-functional events aim to strengthen connection and inclusion across offices.

Learning & Development: Feedback suggests structured, multi‑month training and formal mentorship equip newcomers with clear playbooks and ongoing coaching. Company resources such as leadership development, LinkedIn Learning, and day‑one L&D support reinforce skill building.

Career Growth: Early‑career runway appears well defined, with entry tracks (carrier sales, business development, client success) and visible advancement for strong performers. Internal mobility and promote‑from‑within examples are frequently highlighted as part of the employee journey.

Team Support: Colleagues are often described as collaborative, approachable, and willing to help, creating an energetic in‑office community. ERGs, team events, and recognition moments contribute to a supportive peer network.

Compensation: Earnings can spike for licensed Medicare agents during peak enrollment periods, with strong commission potential when targets are met. Feedback suggests high call volumes and available overtime in AEP can further boost take‑home pay for top performers.

Learning & Development: Structured training, paid licensing, and modern sales/enablement tools are emphasized for Medicare-focused roles. Feedback suggests some employees gain useful experience and equipment that help them ramp quickly.

Mission & Purpose: Work is framed around helping seniors navigate complex Medicare choices, which can feel tangibly impactful. Company materials highlight consumer-first platforms and guidance that aim to simplify plan selection.

Team Support: Colleagues are often described as supportive with a family-like, team-oriented environment, and many cite strong relationships with managers and coworkers. Feedback suggests this camaraderie and day-to-day help are pronounced in sales, merchandising, warehouse, and driving teams.

Career Growth: Opportunities for advancement and professional development are highlighted, including training, leadership programs, and recognition that helps motivated people move from entry roles into sales or other positions. Feedback suggests it can be a strong place to launch a sales career and build industry experience.

Benefits & Perks: Benefits are considered strong, with health coverage, paid time off, incentives, and trips contributing to a rewarding experience in some roles. Feedback suggests brand-related perks and recognition programs add to the fun, energetic environment.