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Top Chicago, IL Sales Companies With Best Leadership & Management (95)

Artera
Healthtech • Other • Sales • Software • Analytics • Conversational AI
10 Offices
250 Employees
66 Benefits
Artera delivers a platform-level patient communications solution that integrates across a health system’s tech stack.

Artera, a SaaS leader in digital health, transforms patient experience with AI-powered virtual agents (voice and text) for every step of the patient journey. Trusted by 1,000+ provider organizations — including specialty groups, FQHCs, large IDNs and federal agencies — engaging 100 million patients annually. Artera’s virtual agents support front desk staff to improve patient access including self-scheduling, intake, forms,...

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Artera

Artera's Top Leadership & Management Strengths

Strategic Vision & Planning: Strategic Vision & Planning: Leadership consistently centers the company on “agentic AI” to automate and orchestrate the end‑to‑end patient journey, with a coherent mission carried from the WELL→Artera rebrand. This through‑line spans product architecture (Co‑Pilots, Flows Agents, AI Agents) and public education like the “Decoding AI Agents” series.

Resource Support: Resource Support: Capital and partnerships are explicitly aligned to the plan, including a growth raise to accelerate agentic AI and deep EHR/federal integrations (e.g., Oracle Health, MEDITECH; FedRAMP High in process). Leadership links moats in domain expertise, data, and distribution to this investment and go‑to‑market.

Strong Execution: Strong Execution: External recognition (Best in KLAS 2026 for Patient Communications) and published usage outcomes on virtual agents are tied directly to the AI‑driven roadmap. Leadership also points to named milestones like contracted ARR thresholds and large‑scale deployments to evidence progress.

Perk
Artificial Intelligence • Fintech • Greentech • Sales • Software • Travel • Hospitality
12 Offices
1,800 Employees
41 Benefits Hiring Now
Perk: the intelligent platform powering real work.

Perk (formerly TravelPerk) is the intelligent platform for travel and spend management. Built to tackle the time-consuming, manual work that gets in the way of real work, our tools automate everything from travel bookings to expenses, invoice processing, and more. By eliminating this shadow work that wastes hours, erodes morale, and saps innovation, we’re on a mission to power real...

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Perk

Perk's Top Leadership & Management Strengths

Strategic Vision & Planning: Public materials consistently frame the mission as removing “shadow work” via an AI‑native, unified platform for travel, spend, invoices, and payments across site, press, and investor channels. Leadership maintains a coherent narrative that ties purpose directly to product scope.

Accountability & Follow-Through: Announced priorities like U.S. expansion and platform broadening are matched by concrete moves such as the AmTrav acquisition and a steady cadence of releases under the unified Perk brand. Help center and release notes show ongoing delivery that reinforces the integrated travel‑and‑spend direction.

Open & Transparent Communication: Messaging is repeated across the company site, press materials, investor summaries, and support content, presenting a consistent direction at multiple touchpoints. The executive team and global leaders are clearly presented, reinforcing visibility into who is driving the strategy.

Arrive Logistics
Logistics • Sales • Software • 3PL: Third Party Logistics
Arrive Logistics is one of the fastest-growing freight brokerages in the nation.

At Arrive Logistics, our relentless pursuit of perfection fuels our ability to optimize operations, identify efficiencies, build technology, and deliver innovation that pushes businesses like yours forward. But it’s not just what we do that sets us apart from everyone else — it’s what we’re made of grit, determination, and a 24/7 commitment to our partners. The details matter. We don’t...

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Arrive Logistics

Arrive Logistics's Top Leadership & Management Strengths

Strategic Vision & Planning: Leadership positions the CEO as owner of the strategic vision and consistently reiterates a people‑plus‑technology, service‑led brokerage thesis. Public materials align on priorities like building the best team and technology, operational productivity, and profitable growth through cycles.

Purposeful Goal Setting: Leaders publish concrete operating aims such as defined productivity lifts, specialized‑mode mix targets, and multi‑year load‑volume ambitions. These goals link technology investment and training to improved cost‑to‑serve and share capture.

Open & Transparent Communication: Regular market outlooks and a detailed freight forecast explain how the company expects to navigate demand, capacity, and pricing. Ongoing public insights and appearances provide stakeholders a view into operating posture and market stance.

BigTime Software, Inc.
Productivity • Professional Services • Sales • Software • Consulting
4 Offices
175 Employees
62 Benefits Hiring Now
The AI-powered Professional Services platform enabling intelligent decisions and delivering profitable growth.

Leading a successful professional service firm is an art. Running a profitable firm is a business. We understand this because our founder ran an IT Consulting firm for over 15 years. He grappled with the same challenges that professional service firm owners face today. How do I know what my employees are working on? How can I connect time and...

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BigTime Software, Inc.

BigTime Software, Inc.'s Top Leadership & Management Strengths

Strategic Vision & Planning: Leadership communications consistently articulate an AI‑centric PSA strategy with clear segmentation for mid‑market versus complex enterprises. Announcements and product materials align on expanding resource planning and quote‑to‑cash capabilities as core priorities.

Resource Support: Executive hires across product, engineering, and finance are positioned to accelerate AI growth and scale the PSA roadmap. Organizational design and capital backing are framed as enablers of the stated direction.

Strong Execution: Tangible delivery such as the Foresight resource management launch demonstrates progress beyond rhetoric. New modules and rebranded offerings map to the services‑lifecycle focus on utilization, forecasting, and profitability.

OpenX Technologies
AdTech • Enterprise Web • Information Technology • Machine Learning • Marketing Tech • Sales
4 Offices
420 Employees
55 Benefits Hiring Now
OpenX is an ad tech company that drives optimal value for advertisers through high-scale marketplaces across all screens

OpenX is The Intelligent SSP™ (supply-side platform), simplifying advertising for marketers, advertisers, and publishers worldwide. As one of the largest SSPs globally, OpenX combines the industry’s only fully cloud-based infrastructure with leading AI capabilities to make digital advertising easier and more effective across every format, including CTV. Built to responsibly deliver quality, performance, and adaptability, OpenX makes digital advertising safer,...

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OpenX Technologies

OpenX Technologies's Top Leadership & Management Strengths

Strategic Vision & Planning: Recent communications explicitly rebrand OpenX as “The Intelligent SSP” with three pillars (Quality, Performance, Adaptability) and a streamlined suite (OpenXSelect, OpenXBuild, OpenXControl, OpenXExchange). Consistent strategic through-lines emphasize prioritizing quality over scale, AI-driven curation, and cloud-native infrastructure.

Open & Transparent Communication: Leadership messaging is unusually explicit about direction, with the CEO directly articulating the simplicity/quality thesis and repeating the storyline across updates. Product architecture and positioning are laid out in plain language to make comparisons and workflows clearer for buyers and partners.

Collaborative & Aligned Leadership: New and expanded leadership roles across Product, Partnerships, and Curation were announced explicitly to deliver on the rebrand’s pillars. Feedback suggests organizational moves and product simplification aim to reduce complexity and align teams around shared objectives.

Toro TMS
Cloud • Enterprise Web • Sales • Software • Transportation
Chicago
80 Employees
37 Benefits
Easy-to-use TMS built for Bulk Haulers

At Toro TMS, we are on a mission to deliver technology that drives lasting improvements for the trucking industry. Our dedicated team has built an easy-to-use, modern end-to-end TMS specifically designed for bulk haulers. From load management and dispatch, to accounting and driver payroll, we provide a single software solution to help our customers move more loads.

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Toro TMS

Toro TMS's Top Leadership & Management Strengths

Open & Transparent Communication: Public materials describe weekly all-hands, regular 1:1s, and visible recognition that clarify expectations and day-to-day alignment.

Strategic Vision & Planning: Company messaging consistently positions Toro as a focused provider for bulk haulers with a partnership-centric ethos repeated across channels, signaling a coherent strategy.

Strong Execution: Operational practices emphasize rapid, in-person implementations and hands-on enablement, indicating a bias toward delivery and outcomes.

PatientPoint
AdTech • Digital Media • Healthtech • Marketing Tech • Sales • Analytics • Pharmaceutical
5 Offices
660 Employees
82 Benefits
The Point of Change Company

At PatientPoint, we're transforming every doctor-patient interaction with cutting-edge, technology-driven solutions designed to improve health outcomes and quality of life. By delivering impactful, digital, in-office patient education at no cost to physicians across the country, we empower healthcare professionals to connect more meaningfully with their patients. Through partnerships with trusted healthcare brands like Pfizer, P&G, Sanofi, Merck, NatureMade, and Bristol...

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PatientPoint

PatientPoint's Top Leadership & Management Strengths

Strategic Vision & Planning: Public materials consistently frame the mission as improving outcomes via behavior change at the point of care and repeatedly emphasize leadership of a large in‑office digital network. Recent launches extend into programmatic and consumer health, reinforcing a coherent plan to broaden monetization and targeting within clinical settings.

Strong Execution: Concrete roadmap moves in March 2026 (Consumer Health Network and Health Audiences) operationalize stated strategy with time‑stamped product rollouts. Expansion of MRC accreditation further supports a direction grounded in measurable, at‑scale digital engagement in physicians’ offices.

Open & Transparent Communication: A structured operating rhythm—monthly steering committee cascading to weekly standups—aims to make priorities, success measures, and decision rights explicit across the organization. This mechanism is described as connecting day‑to‑day work to company‑level outcomes.

ALIS
Healthtech • Sales • Software
Chicago
79 Employees
30 Benefits Hiring Now
ALIS is the industry leading provider of assisted living specific software.

We are a purpose driven healthcare technology company passionate about innovation and using technology to help people by solving real world problems. The ALIS team designs, builds, delivers, and supports our flagship product ALIS (pronounced “Alice” and stands for Assisted Living Integrated Solution).

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ALIS

ALIS's Top Leadership & Management Strengths

Strategic Vision & Planning: Public materials consistently describe a coherent direction to build a unified operating system for senior living, with embedded AI and benchmarking as core pillars. Examples include the Ask ALIS initiative and the ALIS 500 benchmarking program tied to operator outcomes.

Collaborative & Aligned Leadership: Leadership bios and site narrative align roles to the stated strategy, describing an evolution from a clinical EHR into an integrated platform that unifies CRM, clinical, billing, AI, and business intelligence. This alignment indicates shared priorities and a coordinated path across the executive team.

Strong Execution: Specific, dated initiatives (e.g., Ask ALIS with a stated GA window and the launch of ALIS 500) show movement from vision to shipped milestones. The integration strategy and App Store positioning further signal delivery against a platform roadmap.

Legacy Consulting Agencies
Agency • Insurance • Sales • Consulting • Financial Services
Oak Brook
5 Employees
21 Benefits
Culture focused people helpers for brokers and businesses.

We are a culture focused start-up helping many people in many ways. For the health brokers, P&C brokers and Financial Advisors, we provide a service to strategize and enroll their Voluntary Benefits as a new revenue stream and as a way to bring more value to their clients. We can typically add 25% to their bottom line without having to open...

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Legacy Consulting Agencies
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CPS, inc.
Agency • Other • Professional Services • Sales
Chicago
100 Employees

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CPS, inc.
Growth Panda
Agency • Cloud • Marketing Tech • Sales
Chicago
6 Employees
6 Benefits

We’re a team of entrepreneurs, sales execs, designers, developers, marketers, and doers who are addicted to hard problems. We work with companies across industries to help them leverage modern sales, marketing, service, and operational technologies to take their business to the next level.

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Growth Panda
Autotask
Sales • Software
Schaumburg
500 Employees
9 Benefits

Founded in 2001, Autotask Corporation provides the world’s leading web-based IT Business Management software built specifically to automate, streamline and optimize business processes for technology solution providers. The software integrates a broad range of critical business systems, including customer relationship management (CRM), service desk,

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Autotask
Onyx Company
Food • Other • Sales • Transportation
Chicago
20 Employees
12 Benefits

At Onyx, we’re more than a supply company. We’re the forward-thinking partner that unpacks more for our customer's business. Through our global and local manufacturing partners, a broad range of products, flexible distribution models, and custom solutions, we keep businesses of all sizes moving forward.

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Onyx Company
Edge Logistics
Logistics • Sales • Transportation
Chicago
120 Employees
26 Benefits
We deliver superior transportation management solutions to our customers through efficiency, technology and innovation.

Our Mission is Simple! Edge delivers superior transportation management solutions to our customers through efficiency, technology, and innovation. Edge has an unmatched history of data and analytics through its CAPACITY platform that utilizes proprietary algorithms to improve data research. Our employees understand the value and importance of leveraging these strengths in a competitive transportation market and promote a strong working...

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Edge Logistics
Waltz Health
Healthtech • Sales • Software • Pharmaceutical
Chicago
30 Employees
16 Benefits Hiring Now
Waltz is a Chicago-based technology startup, leading a new way forward for prescription care.

Waltz Health is a Chicago-based technology startup that is leading a new way forward for prescription care. We're rethinking the pharmaceutical supply chain, introducing AI-driven marketplaces that drive down costs, and new consumer tools that guide decisions on care. Led by a team of industry experts, Waltz is fixing the high costs and broken experiences that define our pharmaceutical supply...

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Waltz Health
Fresh Tech Maid
Artificial Intelligence • Other • Sales • Analytics
Chicago
16 Employees
Fresh Tech Maid is taking on the housekeeping industry with fair wages, great management, and chemical free cleaning.

Fresh Tech Maid is taking on the $61 billion dollar housekeeping industry with fair wages, great management, and chemical free cleaning. With locations in Chicago and Arlington Heights, we service much of Chicagoland and its suburbs. We are looking to grow and expand our business, which is where you come in. If you want to be part of the change...

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Fresh Tech Maid
Shoe Drop
Sales
Chicago

Shoe Drop is a tech-enabled company that is revitalizing the cobbler industry. We've partnered with dry cleaners, office buildings, and high-rise residential buildings to make shoe care and repair efficient and accessible.

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Shoe Drop
Workforce.com
HR Tech • Information Technology • Mobile • Sales • Software
Chicago
140 Employees
24 Benefits
Workforce.com is the World's #1 Workforce Platform.

Workforce.com is the market leading workforce management platform. We empower businesses that employ hourly workers to run more profitably so they can create more jobs - an essential service in today's world. Founded in Brisbane, Australia in 2012, we moved our headquarters to Chicago in 2019.

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Workforce.com
The Bradford Exchange
Retail • Sales
Niles
262 Employees

We are a world leader in direct marketing and provider of limited-edition gifts, collectibles, home décor, and jewelry. Founded in 1973, we have an unyielding commitment to product quality and exceptional customer service which has helped us become one of the premier direct marketing companies in today’s international economy. Our company’s vision is to bring joy and happiness to customers...

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The Bradford Exchange
The CARA Group, Inc.
Oakbrook Terrace
129 Employees

The CARA Group is focused on change management, learning, and communications solutions to enable your talent to embrace the future of work. Whether it’s a change management strategy for a major digital transformation, a blended learning program to upskill a sales team, or even a curated collection of microlearning topics, CARA will manage your project from inception to implementation while...

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The CARA Group, Inc.

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