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Remote Chicago Jobs in Madison, WI (NOW HIRING)

Chicago, Naperville, or Rock Island, IL; Des Moines, IA; Farmington Hills, MI; or Madison, WI ... Hybrid and/or remote work schedule available Sponsorship: Not available What You'll Do * Assist in ...

This is a Remote (work from home) position. Company Overview Monroe Infrared is a Guidant Power subsidiary. Guidant Power is a Chicago-based company specializing in electrical safety, reliability ...

Infrared Thermographer

Madison, WI ยท On-site +1

$50K - $70K/yr

This is a Remote (work from home) position. Company Overview Monroe Infrared is a Guidant Power subsidiary. Guidant Power is a Chicago-based company specializing in electrical safety, reliability ...

Senior Specialist, Payroll

Madison, WI ยท On-site +1

$29.75 - $40.50/hr

... Chicago and Boston. Baker Tilly Advisory Group, LP and Baker Tilly US, LLP (Baker Tilly) provide ... While this position is mostly remote, team members must be within 50 miles of a Baker Tilly office ...

Senior Software Engineer

Madison, WI ยท Remote

$125K - $165K/yr

This is remote position requiring occasional in-person office meetings for candidates residing in one of the following metro areas Maison, WI, Chicago, IL, San Francisco CA, Phoenix AZ, Denver CO, or ...

Senior Specialist, Payroll

Janesville, WI ยท On-site +1

$29 - $39.50/hr

... Chicago and Boston. Baker Tilly Advisory Group, LP and Baker Tilly US, LLP (Baker Tilly) provide ... While this position is mostly remote, team members must be within 50 miles of a Baker Tilly office ...

... Chicago and Boston. Baker Tilly Advisory Group, LP and Baker Tilly US, LLP (Baker Tilly) provide ... While this position is mostly remote, team members must be within 50 miles of a Baker Tilly office ...

Senior Specialist, Payroll

Madison, WI ยท On-site +1

$29.75 - $40.50/hr

... Chicago and Boston. Baker Tilly Advisory Group, LP and Baker Tilly US, LLP (Baker Tilly) provide ... While this position is mostly remote, team members must be within 50 miles of a Baker Tilly office ...

Senior Specialist, Payroll

Janesville, WI ยท On-site +1

$29 - $39.50/hr

... Chicago and Boston. Baker Tilly Advisory Group, LP and Baker Tilly US, LLP (Baker Tilly) provide ... While this position is mostly remote, team members must be within 50 miles of a Baker Tilly office ...

Senior Research Engineer

Madison, WI ยท On-site +1

$90K - $115K/yr

While we're mostly remote, Slipstream can only hire in select states (outlined in the application ... We have offices in Madison, WI and Chicago, IL. What You'll Do * Lead technical analysis and ...

Senior Research Engineer

Madison, WI ยท On-site +1

$105K - $144K/yr

While we're mostly remote, Slipstream can only hire in select states (outlined in the application ... We have offices in Madison, WI and Chicago, IL. What You'll Do * Lead technical analysis and ...

Senior Software Engineer

Chicago, IL ยท On-site +1

$126K - $166K/yr

This is remote position requiring occasional in-person office meetings for candidates residing in one of the following metro areas Maison, WI, Chicago, IL, San Francisco CA, Phoenix AZ, Denver CO, or ...

Remote Chicago information

See Madison, WI salary details

$24.8K

$92.1K

$206.3K

How much do remote chicago jobs pay per year?

As of Aug 9, 2026, the average yearly pay for remote chicago in Madison, WI is $92,117.00, according to ZipRecruiter salary data. Most workers in this role earn between $56,314.00 and $121,368.00 per year, depending on experience, location, and employer.

How do remote employees based in Chicago typically stay connected and collaborate with their teams?

Remote employees in Chicago often use a combination of digital communication tools such as Slack, Zoom, and project management platforms to stay connected with their teams. Regular virtual meetings, collaborative documents, and scheduled check-ins are common practices to ensure alignment and effective teamwork. Many companies also encourage participation in virtual team-building activities and provide resources for setting up productive home offices. This approach helps maintain a sense of community and keeps remote workers engaged, even when working from different locations.

What are the key skills and qualifications needed to thrive as a remote worker based in Chicago, and why are they important?

To thrive as a Remote Worker based in Chicago, you need strong self-management skills, time management, and proficiency in your field's core competencies, often supported by relevant degrees or experience. Familiarity with collaboration tools like Slack, Zoom, Microsoft Teams, and cloud-based project management systems is typically required. Excellent communication, adaptability, and proactive problem-solving are crucial soft skills for remote success. These abilities ensure productivity, effective teamwork, and the ability to meet goals independently in a remote work environment.

What is a Remote Chicago job?

'Remote Chicago' jobs refer to employment opportunities that are based in Chicago or offered by Chicago-based companies, but allow employees to work from a remote location instead of commuting to a physical office. These positions can span various industries, including technology, finance, education, healthcare, and more. While the job may require candidates to reside in the Chicago area for tax, legal, or occasional onsite meeting purposes, the primary work is performed remotely. This arrangement offers flexibility and can enhance work-life balance for employees. Many companies have adopted remote work policies to attract a wider pool of talent and adapt to changing workforce trends.
What are the most commonly searched types of Chicago jobs in Madison, WI? The most popular types of Chicago jobs in Madison, WI are:
What are popular job titles related to Remote Chicago jobs in Madison, WI? For Remote Chicago jobs in Madison, WI, the most frequently searched job titles are:
What cities near Madison, WI are hiring for Remote Chicago jobs? Cities near Madison, WI with the most Remote Chicago job openings:
Infographic showing various Remote Chicago job openings in Madison, WI as of August 2026, with employment types broken down into 1% As Needed, 83% Full Time, 12% Part Time, and 4% Contract. Highlights an 90% Physical, 4% Hybrid, and 6% Remote job distribution, with an average salary of $92,117 per year, or $44.3 per hour.

Medical Device Account Executive - Midwest (WI & IL)

EnsoData

Madison, WI โ€ข Remote

$220K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 15 days ago


Job description

Hi, I'm Courtney, the Regional Sales Director (RSD) for the midwest US at EnsoData! We're excited to announce that we're looking for an Account Executive based in Chicago, IL, Milwaukee, WI or Madison, WI. We are looking for a self-starter who is eager to contribute to the growth of our business dedicated to improving healthcare. This remote position offers the following compensation:

  • Base salary: $90,000
  • At plan: $220,000
  • New hire guarantees for the first six months
  • Bonus potential after annual target is reached
  • Uncapped commissions
  • Stock options
  • Additional benefits such as paid time off, healthcare insurance, and parental leave.

The company is based in Madison Wisconsin but the territories are field based. This territory will cover Wisconsin and northern Illinois.

We are searching for proven account executives in the medical device industry so highlight your achievements on your resume!

The person in this role will be focused on growing the EnsoHST solution to all sleep, and referring physicians. This person needs to be professional and knowledgable in the business of sleep and medical devices.

Primary responsibilities:

  • Strive to exceed the monthly revenue quota
  • Identify prospective customers, generate and convert leads to sales; collaborate with new and existing customers to identify needs and sell solutions
  • Coordinate the sales process with marketing and the Sales Solutions Engineer (demonstrations)
  • Negotiate contracts and pricing with the RSD and/or CCO
  • Maintain their customer details in our CRM, HubSpot
  • Partner with Marketing and others to develop and refine sales and marketing strategies
  • Represent EnsoData at shows and, as needed, travel for onsite demonstrations

EnsoData

EnsoData strives to make healthcare more accurate, efficient, and affordable through waveform artificial intelligence (AI) technology. Using AI and machine learning, our software analyzes billions of data points collected from sensors placed throughout the human body. Our first solution, EnsoSleep, reduces the time clinicians spend analyzing, scoring and managing sleep studies. This results in a simplified and accelerated patient testing, diagnosis, and treatment workflow. Our AI-powered technology has the capability of informing health decisions beyond sleep medicine, from monitoring patient health in the ICU or through wearables, to detecting and capturing seizure data, to providing earlier detection of heart disease, diabetes, stroke, and Alzheimer’s.

Requirements

This is what we need in our new team member:

  • Previous experience in sleep medicine, specifically home sleep testing sales (PPG is preferred)
  • Healthcare Software as Medical Device, SaaS or healthcare software sales knowledge preferred
  • Clinical aptitude, business acumen & strong work ethic
  • Hunter mindset w/ creative thinking
  • Preferred 5+ years account executive experience
  • Experience closing business in a health system required
  • Enterprise health system sales experience preferred
  • Experience working with CRM, preferred but not required
  • Bachelor's degree is preferred
  • Excellent people skills and positive attitude, ability to partner with a dynamic team
  • Experience working with remote and hybrid office/remote teams
  • Previous experience at a startup, tech, software engineering, or similar company is a bonus
  • Desire to contribute to building groundbreaking technologies to make healthcare more efficient, affordable, and effective
  • Personal qualities of integrity, perseverance, and commitment to the mission
  • Ability to travel up to 50% of the time - the position will focus on remote selling as compared to being on the road each day/week.

Candidates who apply but do not live in the territory area will not be considered.


Company Culture - Embrace the Pineapple!

How do we do this? https://www.ensodata.com/blog/why-the-pineapple/

  • Make Healthcare Better - is passionate about moving healthcare to a better place for everyone everywhere
  • Put Customers First - delights customers by working closely with them to support their initiatives
  • Be a Great Teammate - spreads the good vibes and is a joy to work with; also understands the value of helping one's teammates
  • Gets $#!t Done - bias toward action and intrinsically motivated to go above and beyond; demonstrates the ability to work autonomously as well as across teams
  • We also practice a Focus on Quality and look for teammates who don't cut corners and demonstrate integrity and attention to detail

Benefits

The benefits package includes, but is not limited to, the following:

Remote and flexible schedule - we are a remote company with hybrid options and support for flexible schedules! That being said, we have an amazing office headquarters in downtown Madison, WI with views of the capitol that you are welcome to work at anytime. In case you didn't know, Madison has consistently been ranked as one of the top places to live in the US (businessinsider.com, money.com, livability.com)!

Health, dental, and vision insurance with options to choose a plan that fits you and your dependents needs.

Paid time off options - we want our employees to rest, recharge, and feel better.

Stock options - we want team members to feel ownership in the organization. When EnsoData does well, you do well.

401k to help people invest in the future.

Team Summits! We look forward to opportunities to gather in person and enjoy a few days together. We participate in team events and gain some great in-person time. (Hint: check out our blog for info from former team gatherings!)

Interview Process

  1. Submit a resume online and our hiring team will choose those that seem like the best candidates.
  2. We look forward to meeting you face-to-face! A few candidates will be chosen for a video call to get to know each other, discuss your experience, and explain the position in more detail.
  3. Expect an opportunity to demonstrate your skills.
  4. The final candidates will have a chance to meet a few people from the team.
  5. Offer!

Let’s talk

EnsoData seeks to recruit, hire, and retain the most talented people from a diverse candidate pool. Research shows that while men apply to jobs when they meet an average of 60% of the criteria, women and other marginalized folks tend to only apply when they check every box. If you think you’re a great fit, but don't necessarily check every box on the job description, please still get in touch.

To learn more about our ongoing commitment to diversity, see our updated website here.

Note: this role is based in the continental United States and currently EnsoData is unable to support sponsorships so candidates must be legally eligible to work and reside in the United States now and in the future.

Equal Employment Opportunity

EnsoData is proud to be an Equal Employment Opportunity employer. We do not discriminate against, nor do we tolerate unlawful harassment against, team members or any other covered persons on any basis of race, color, protective hairstyles, national, social, or ethnic origin, gender, pregnancy, childbirth, gender orientation, identity or expression, sexual, relationship, or romantic orientation, marital, civil union or domestic partnership status, family or parental status, age, protected veteran status, arrest record, expunged or sealed convictions, criminal history, source of income, credit history, housing status, physical, mental, or sensory disability, medical condition, genetic information, religion, or any other status protected by the laws or regulations in the locations where we operate.

We value, celebrate, and support diversity, inclusion, and our differences. We are committed to providing a safe work environment and a company culture of mutual respect where equal employment opportunities are available to all applicants and teammates. We seek to recruit, hire, and retain the most talented people from a diverse candidate pool. We strongly encourage women, people of color, LGBTQIA+ individuals, people with disabilities, members of ethnic minorities, intersectional individuals, foreign-born residents, and veterans to apply. We have a deep conviction that diversity and inclusion among our teams, our communities, and our physical and virtual workplaces is vital to the success of EnsoData’s mission to improve healthcare access, outcomes, and affordability for patients and communities everywhere globally.

If you are a job seeker applying to EnsoData and you feel that you need to request an accommodation or alternative application, please contact Angela at angela@ensodata.com.

The applicant tracking system used to collect candidate resumes has artificial intelligence features built into it which may or may not be used during candidate recruitment and selection.