44 Best Chicago Employee Benefits Startups & Businesses – Revolutionising The Employee Benefits industry

September 1, 2022

This article showcases our top picks for the best Chicago based Employee Benefits companies. These startups and companies are taking a variety of approaches to innovating the Employee Benefits industry, but are all exceptional companies well worth a follow.

We tried to pick companies across the size spectrum from cutting edge startups to established brands.

We selected these startups and companies for exceptional performance in one of these categories:

  • Innovation
    • Innovative ideas
    • Innovative route to market
    • Innovative product
  • Growth
    • Exceptional growth
    • Exceptional growth strategy
  • Management
  • Societal impact
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Top Chicago Employee Benefits Startups

Data sourced from Crunchbase and SemRush.

Five to Nine

Five to Nine

Crunchbase Website Twitter Facebook Linkedin

Five to Nine manages & evaluates virtual event programming so you can focus on building the employee experience.

Maestro Health

Maestro Health

Crunchbase Website Twitter Facebook Linkedin

Maestro Health offers a technology-meets-service platform that is reimagining employee benefits.

Maestro Health

ThreeFlow

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ThreeFlow is a provider of enterprise software for employee benefits brokers and carriers.

Maestro Health

Peanut Butter

Crunchbase Website Twitter Facebook Linkedin

Student loan assistance as an employee benefit

Maestro Health

Spring

Crunchbase Website Twitter Facebook Linkedin

Spring provides a holistic, unbiased financial wellness benefit to companies to increase employee recruitment, productivity, and retention.

Maestro Health

hiitide

Crunchbase Website Twitter Facebook Linkedin

An immersive experience for learners that turns long-form & fragmented content into guided micro-learning.

Maestro Health

Working Credit NFP

Crunchbase Website Twitter Facebook Linkedin

Working Credit NFP is a non-profit organization that provides credit building education, counseling, and employee benefits services.

Maestro Health

Code SixFour

Crunchbase Website Twitter Facebook Linkedin

The Code SixFour Benefits Consulting Cloud empowers insurance agents and benefits brokers to deliver better benefits outcomes to employers.

Maestro Health

Know Your Team

Crunchbase Website Twitter Facebook Linkedin

Know Your Team is software that helps managers become a better leader.

Maestro Health

SpringFour

Crunchbase Website Twitter Facebook Linkedin

SpringFour’s technology platform connects consumers to local financial health resources, tools and products. SpringFour is a B2B solution.

Maestro Health

Global Recruiters Network

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Global Recruiters Network is an expanding network that offers management, technical, professional and executive search services.

Maestro Health

RELO Direct, Inc.

Crunchbase Website Twitter Facebook Linkedin

RELO Direct, Inc. is an employee mobility & relocation management company offering mobility management services to employees.

Maestro Health

Engagement Multiplier

Crunchbase Website Twitter Facebook Linkedin

Engagement Multiplier is an online program that gives companies the power to measure and improve employee engagement.

Maestro Health

Policemen’s Annuity and Benefit Fund of Chicago

Crunchbase Website Twitter Facebook Linkedin

Policemen’s Annuity and Benefit Fund of Chicago offers retirement, survivors and disability benefits.

Maestro Health

Cs Insurance Strategies

Crunchbase Website Twitter Facebook Linkedin

CS Insurance Strategies offers risk management, commercial insurance, and group employee benefit solutions.

Maestro Health

Laurus Strategies

Crunchbase Website Twitter Facebook Linkedin

Laurus Strategies is provides business consulting services.

Maestro Health

Health Strategy

Crunchbase Website Twitter Facebook Linkedin

Health Strategy focuses on pharmacy benefits, self-funded employers and consulting services for health care decisions and solutions.

Maestro Health

MarketStaff

Crunchbase Website Twitter Facebook Linkedin

MarketStaff provides total payroll management solutions, recruiting, training, human resource management & benefits administration services.

Maestro Health

Shore Tompkins Actuarial Resources

Crunchbase Website Twitter Facebook Linkedin

Shore Tompkins Actuarial Resources design and administration all types of retirement and pension plans with financial advisory services.

Maestro Health

The Illinois State Board of Investment

Crunchbase Website Twitter Facebook Linkedin

The Illinois State Board of Investment manages benefit assets of the state employees, judges, and the general assembly retirement system.

Maestro Health

TeamCare Health Plan

Crunchbase Website Twitter Facebook Linkedin

TeamCare Health Plan focuses on providing medical, prescription, dental, vision, disability, and retirement benefits plans.

Maestro Health

Launchways

Crunchbase Website Twitter Facebook Linkedin

Launchways specializes in providing human resources, employee benefits, business insurance and managed payroll solutions.

Maestro Health

Benefit Educators

Crunchbase Website Twitter Facebook Linkedin

Benefit Educators is an employee benefits enrollment and communication firm.

Maestro Health

IXSolutions

Crunchbase Website Twitter Facebook Linkedin

IXSolutions is an insurance company that provides a range of health insurance, dental insurance and employee benefits services.

Maestro Health

Rightway Insurance Agency

Crunchbase Website Twitter Facebook Linkedin

Rightway Insurance Agency provides auto, bonds, general liability, business owners, homeowners, motorcycle, and trucking insurance.

Maestro Health

Odoni Partners

Crunchbase Website Twitter Facebook Linkedin

Odoni Partners is an accounting firm that offers audit, employee benefits, financial advisory, payroll, tax preparation & planning services.

Maestro Health

360 Benefits

Crunchbase Website Twitter Facebook Linkedin

360 Benefits provides employee benefits consulting solutions.

Maestro Health

PHILLIPS BROS. INSURANCE AGENCY

Crunchbase Website Twitter Facebook Linkedin

PHILLIPS BROS. INSURANCE AGENCY provides insurance and risk management programs.

Maestro Health

Cacciatore Insurance

Crunchbase Website Twitter Facebook Linkedin

Cacciatore Insurance offers a wide range of insurance services including auto, life, health, real estate, home, and commercial property.

Maestro Health

FinHealthCheck

Crunchbase Website Twitter Facebook Linkedin

An insights platform that enables organizations to optimize for financial health

Maestro Health

Chessboard Consulting

Crunchbase Website Twitter Facebook Linkedin

Chessboard Consulting Inc is an HR consulting firm that helps clients improve employee engagement and organizational performance.

Maestro Health

Byrne, Byrne and Company

Crunchbase Website Twitter Facebook Linkedin

Byrne, Byrne and Company specializes in risk management, employee benefits, wellness, property, casualty and personal insurance services.

Maestro Health

Ganan & Shapiro

Crunchbase Website Twitter Facebook Linkedin

Ganan & Shapiro is a legal firm that specializes in workers’ compensation defense and related subrogation matters.

Maestro Health

Aegis Administrative Services

Crunchbase Website Twitter Facebook Linkedin

Aegis Administrative Services provides plan reinsurance, claims administration, enrollment, and billing.

Maestro Health

Leal Associates

Crunchbase Website Twitter Facebook Linkedin

Leal Associates is an employee benefits consulting firm.

Maestro Health

Corcoran, Ender & Associates

Crunchbase Website Twitter Facebook Linkedin

Corcoran, Ender & Associates offers bookkeeping, accounting, audits, consulting, employee benefits, taxation & retirement planning services.

Maestro Health

National Institute of Pension Administrators

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National Institute of Pension Administrators is a national association representing the retirement plan and employee benefit plan.

Maestro Health

VESTHQ

Crunchbase Website Twitter Facebook Linkedin

VESTHQ is a financial services firm, focuses on maximize retirement outcomes.

Maestro Health

Charles D Spencer and Associates

Crunchbase Website Twitter Facebook Linkedin

Charles D Spencer & Associates provides employee benefits information services.

Maestro Health

EmployeeTech

Crunchbase Website Twitter Facebook Linkedin

EmployeeTech is an integrated HR consulting, benefits administration, ACA reporting and technology services provider.

Maestro Health

Executive Risk Management

Crunchbase Website Twitter Facebook Linkedin

Executive Risk Management is provides employee risk management and benefits insurance solutions planning services.

Maestro Health

Center For Companies That Care

Crunchbase Website Twitter Facebook Linkedin

Center for Companies That Care is dedicated to enhancing the well-being of employees and communities by educating and inspiring employers.

Maestro Health

Power Voluntary Benefits

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Power Voluntary Benefits specializes in offering a comprehensive range of financial tools and resources for employees.

Maestro Health

VG Insurance Solutions

Crunchbase Website Twitter Facebook Linkedin

VG Insurance Solutions offers a wide range of insurance services including life, disability, final expense, auto, home, and business owners.

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