Best Sales Companies to Work for in Chicago, IL (117)

Mission & Purpose: Work connects directly to improving operations and resident outcomes in assisted living and memory care, with materials and spotlights emphasizing solving real customer pain points from the Chicago hub. Ongoing product releases and integrations in this domain reinforce a tangible sense of end‑user impact.

Team Support: Colleagues and leaders are often described as approachable, kind, and supportive within a people‑first culture. Collaborative practices like pair programming, team‑based planning, and open‑door norms reinforce cross‑team cooperation.

Work-Life Balance: Flexible arrangements (in‑office, hybrid, and remote depending on role) and manager‑set cadences are cited, alongside generous PTO and parental leave. These practices point to reasonable expectations and support for daily balance.

Learning & Development: Structured onboarding, mentorship, and leadership programs are emphasized, with resources like LinkedIn Learning and extended ramp periods for sales. Feedback suggests early‑career employees gain skills quickly through a clear playbook and in‑person coaching.

Team Support: The day‑to‑day environment is described as energetic and collaborative, with teammates sharing knowledge and celebrating wins through programs like President’s Club and ERGs. Office‑centered hubs in Austin, Chicago, San Antonio, and Tampa reinforce hands‑on support and camaraderie.

Benefits & Perks: Medical, dental, vision, a 401(k) with match, an ESPP, parental leave, and mental‑health resources are highlighted, alongside PTO and various office perks. These offerings indicate a broad, competitive benefits baseline across roles and locations.

Work-Life Balance: Flexible options across hybrid, remote and field roles—plus front‑loaded five weeks of flexible PTO, summer hours, and “no Friday meetings after 3 p.m.”—support balance. Mental‑health support and paid volunteer time further reinforce time and wellbeing priorities.

Mission & Purpose: Products aim to engage patients and providers “in the moments care decisions are made,” which makes work feel directly tied to patient–provider conversations. Company profiles consistently emphasize this patient‑focused mission.

Benefits & Perks: Health and family benefits include Cigna medical plans, Delta Dental, EyeMed vision, mental‑health platform access, paid parental leave, and fertility reimbursement up to a $10,000 lifetime max. Financial perks such as a 401(k) with a 3% safe‑harbor contribution and HSA contributions add meaningful support.

Benefits & Perks: Wellness stipends, mental‑health resources, flexible time off with “Refresh Days,” paid parental leave, and a 401(k) match are offered alongside hybrid/remote options. Additional perks such as gym access in Chicago, catered lunches, and company‑paid health/vision/dental are highlighted on company and Built In pages.

Career Growth: Promotion‑from‑within messaging, mentorship programs, “Camp BigTime” onboarding, and customized development tracks point to structured advancement. A scale‑up setting backed by a major PE investment and acquisitions expands scope for cross‑functional work and learning.

Team Support: Colleagues are often characterized as friendly, collaborative, and supportive, with ERGs and regular mixers/all‑hands strengthening cross‑team ties. Leaders are described as accessible via open‑door policies and skip‑level check‑ins in several culture descriptions.

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.

Career Growth: Internal mobility is emphasized through promotion-from-within, mentorship, and defined progression paths, enabling rapid responsibility expansion and, in some cases, multiple promotions within short periods. Early-career hires are given ownership and coaching that accelerates learning.

Benefits & Perks: Benefits include employer-paid medical options, unlimited PTO with paid holidays, immediate 401(k) eligibility, and parental leave, alongside extras like a free Chicago gym membership and stocked office amenities. Compensation is framed as competitive with performance bonuses and pay transparency.

Team Support: A low-ego, collaborative environment is reinforced by cross-functional work, weekly all-hands, shared KPIs, and clear ownership structures to keep projects moving. Engineering practices such as pair programming and public shout-outs strengthen peer support and recognition.

Work-Life Balance: A remote-first setup with flexible schedules, company-wide recharge days, and home-office support is emphasized to help employees manage work and life across time zones. Autonomy around location and time is positioned as a core element of day-to-day operations.

Team Support: Employee testimonials describe a respectful, highly collaborative, low-ego environment where colleagues readily help across functions and geographies. This collaborative tone is highlighted as especially important for distributed teams.

Benefits & Perks: Comprehensive offerings include day-one healthcare, employer-paid therapy and coaching, generous parental leave, wellness and WFH stipends, and flexible time off. Recurring “Best Places to Work” recognition is cited as reinforcing investment in total rewards.

Work-Life Balance: Reasonable hours and flexibility are common in many teams, with hybrid or remote options varying by role and manager. Balance appears to be a relative strength across functions.

Team Support: Colleagues are often seen as helpful and collaborative, creating a generally supportive environment. Partner-style collaboration and collegial relationships show up across multiple groups.

Innovation & Products: Active investment in cloud ERP and embedded AI creates engaging, hands-on work across product, services, and data roles. Roadmaps and ongoing releases indicate forward momentum and practical modernization projects.

Market Position & Stability: The Amazon Prime partnership and national brand campaigns under Wonder’s ownership are described as driving usage and visibility, signaling durable demand-side momentum. Fresh investment and integrations since late 2024 point to renewed focus on go-to-market and product execution.

Benefits & Perks: Company materials highlight comprehensive benefits, well-being programs, ERGs, weekly Grubhub credits, and a free Grubhub+ subscription, fostering a social, events-driven culture. Hybrid or flexible arrangements are noted for some corporate roles, adding lifestyle appeal.

Learning & Development: Career pages and leadership content emphasize cross-functional collaboration, visibility, and formal development programs, including returnships and ongoing training. Many roles are framed around high-velocity, problem-solving work with scope across product, engineering, and business.