WinningWise Salary

As of April 2026, the average annual salary for employees at WinningWise in the United States is $93,012. This translates to an approximate hourly wage of $45. Salaries at WinningWise typically range from $81,748 to $105,221 annually, reflecting the diverse roles and experience levels within the company.

How Much Does WinningWise Pay for Different Roles?

Explore detailed salary information for specific jobs at WinningWise. Based on our data, the highest paying job is the Manager, Marketing & Communications, with an annual salary of $102,373. The table below outlines the annual salary ranges for most popular roles within the company.
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Current Job Openings at WinningWise

Ready for your next career move? Explore current job openings at WinningWise. Use the search tool below to find available positions by title and location and apply directly to start your career.

Is WinningWise’s Pay Competitive? Salary Benchmarking Analysis

How does WinningWise's compensation stack up against the industry and its key competitors? Our salary benchmarking analysis provides a clear comparison. The chart below visualizes this comparison alongside select peer companies.
Competitor / Benchmark Avg. Salary Variance Primary Market Influence Factor & Explanation
Meyn $88,150
-5.2%
Typical compensation structure for smaller regional agencies like Meyn.
Ellavate Inc $100,543
+8.1%
Reflects structural premiums typical of Ellavate Inc's large-cap national operations.
Signature Sports Marketing LLC $88,044
-5.3%
Reflects market rates for standard general contracting, differing from specialized roles.
4 Lakes Properties $87,812
-5.6%
4 Lakes Properties operates with a leaner overhead structure, impacting base wage offers.
Business Services Industry $120,931
+30.0%
Pay variances are driven by organizational scale, specialized skill requirements, or geographic cost-of-living factors.
Need More Granular Data? The analysis above provides a high-level market overview. To benchmark specific job codes, adjust for real-time cost-of-living changes, or access verified HR-reported datasets, upgrade to Salary.com for Business. Precision matters when building your compensation strategy.

Employee Reviews: Working at WinningWise

Considering a career at WinningWise? Explore authentic employee reviews to learn about the work environment, career growth opportunities, pay transparency and benefits. These first-hand insights can help you set realistic compensation expectations and make informed career decisions.
Career progression can take time in certain teams. There’s a clear process for knowledge transfer and a supportive attitude from everyone involved. I’ve had access to training programs and mentorship opportunities that have helped sharpen my skills. It’s a reliable place to work, but those looking for a dynamic culture may be disappointed. I’ve grown professionally while enjoying the support of a ...
It’s a decent place to gain experience, the exciting environment for ambitious professionals. Employee contributions are recognized and appreciated regularly. Employees are given real ownership of their work, with plenty of autonomy and clear expectations. Their scale meant they had specialists for every requirement. Working here has been a rewarding experience with ample opportunities for profess...
They don’t just follow trends—they help us stay ahead. The company offers work with purpose. The emphasis on employee development and diversity is commendable. Colleagues are collaborative, and diversity is celebrated across teams. The company offers a strong work-life balance.

WinningWise Overview

Website
www.winningwise.com
Founded In
2013
Employees
<25 employees
Industry
Business Services
Headquarter Address
455 N Cityfront Plaza Dr Chicago Illinois IL 60611
Revenue
<$5 Million
Phone Number
+1 3125612355
Social Media
About WinningWise
Grow Your Organization Your Culture, Your People, Yourself Our purpose at WinningWise is to help you and your organization achieve more. Quite simply, our focus is on people developmentwe help organizations transform their cultures, strengthen their leaders, align their teams and engage their talent. To grow your organization, you need to enhance the performance, engagement and leadership of your

What Benefits Does WinningWise Offer Beyond Salary?

A competitive compensation package is more than just a salary. WinningWise offers a comprehensive benefits package designed to support your health, financial future, and overall well-being. Below are the most common key benefits:
Social Security
401(K)
Disability
Healthcare
Pension
Time Off (days)
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How Much Should You Be Earning?

Get an estimated calculation of how much you should be earning and insight into your career options.

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What Is the Cost of Living Near Chicago?

Understanding the cost of living near Chicago is key to truly evaluating a salary offer or your current compensation at WinningWise.
Chicago's Cost of Living Index is approximately 106.9 (6.9% more expensive than US average; 14.0% more than IL average). Major US city, housing varies greatly by neighborhood but can be high, extensive CTA transit. When planning your budget based on a salary from WinningWise, consider these typical monthly expenses:
Expense Category Estimated Monthly Cost Key Considerations / Notes
Housing (1-BR Apt Rent) $1,700 - $2,600+ A significant portion of WinningWise salary. Location choices impact this heavily.
Utilities (Basic) $140 - $230 Electricity, Heating, Cooling, Water etc.
Public Transportation $105 (CTA 30-day pass) Essential for most commuters; car ownership is costly.
Groceries (Single Person) $430 - $640 Can be higher with more dining out or specialty stores.
Personal & Leisure $450 - $800+ Dining out, entertainment, shopping. Highly variable.
Healthcare (Individual) $400 - $750+ Varies significantly by plan & employer contribution.
Subtotal (Excluding Taxes) $3,225 - $5,025+ This subtotal does not include income taxes (federal, state, local), which can significantly impact your take-home pay.

FAQs of WinningWise

1. What is the typical salary range (low to high) for most roles at WinningWise?

The typical annual salary range for most roles at WinningWise is approximately from $81,748 to $105,221. It's important to remember that these are overall averages, actual salaries vary significantly based on specific job titles, years of experience, skills, and location.

2. How much does WinningWise pay compared to Meyn?

The average annual salary at WinningWise is $93,012, or an hourly wage of $45, in comparison to Meyn which pays $88,150 per year or $42 per hour.

3. How does experience level affect salary at WinningWise?

Experience level is a significant factor in determining salary at WinningWise, as it is with most employers. Generally, employees with more years of relevant experience and a proven track record can command higher salaries. For example, a senior-level role will typically have a higher pay band than an entry-level or mid-career position within the same job family.

4. How can I determine if a salary offer from WinningWise in Chicago is fair given the local cost of living?

To determine if a salary offer from WinningWise in Chicago is fair, first compare the gross salary to our data for similar roles at WinningWise and its competitors (see our similar company salaries section) . Then, critically, use our "Cost of Living Insights for Chicago" to understand its purchasing power.

5. What are the key factors that influence salary levels at WinningWise?

Several key factors influence salary levels at WinningWise. These primarily include: 1. Job Role & Responsibilities: More complex roles with greater impact typically command higher pay. 2. Experience & Skills: Your years of relevant experience and specific in-demand skills are critical. 3. Performance: Strong performance can lead to higher raises and bonuses. 4. Location: Office location impacts pay due to varying local market rates and cost of living. 5. Industry Benchmarks: WinningWise likely benchmarks its salaries against other companies in the Business Services sector. You can explore how these factors play out in our detailed salary data.