Unlimited Pto Jobs in Chicago, IL

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Looking for Unlimited Pto jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Unlimited Pto position in the Chicago, IL area.

Client Retention Specialist

Company: Beyond Finance

Location: Chicago, IL

Posted Apr 25, 2024

Beyond Finance is a company dedicated to helping Americans overcome debt and achieve financial stability. They are seeking a Retention Specialist to join their Customer Success Team. The role involves educating clients about their financial hardship programs, empathizing with their financial difficulties, and helping them navigate the program. Key responsibilities include educating clients, empathizing and deescalating, navigating the CRM system, analyzing financial situations, retaining clients, achieving retention goals, and providing excellent customer service. The ideal candidate should have experience in retention, sales, or collections, be tech-savvy, and have strong communication and problem-solving skills. Beyond Finance offers a collaborative work environment, competitive benefits, and opportunities for career development.

Senior Associate, S&O - Collections & Recovery (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Apr 25, 2024

Enova is seeking a Strategy & Operations Senior Associate with 6-8 years of experience in process improvement, management consulting, or data analytics, preferably in credit risk or collections. The role involves supporting a core P&L, managing projects for business efficiency, and collaborating with cross-functional teams. The company offers a hybrid work model, comprehensive benefits, and a values-driven culture. Enova is committed to equal employment opportunities and fostering an inclusive environment.

Principal, Data Architecture

Company: OCC

Location: Chicago, IL

Posted Apr 25, 2024

The role involves designing data architecture and solutions for OCC, ensuring strategic goals are met, and overseeing evaluations of technology and processes. Key responsibilities include creating data models, setting up data modeling standards, and driving short and long-term architecture strategy. The ideal candidate should have extensive experience in data lake/warehouse solutions, schema design, and data science/analytics solutions. They must be able to prioritize tasks, communicate effectively, and work collaboratively in a fast-paced environment.

Mid/Sr UI/UX Designer (Remote!)

Company: BenchPrep

Location: Chicago, IL

Posted Apr 25, 2024

BenchPrep, a leading provider of advanced and flexible learning experiences, is seeking a Mid/Sr UI/UX Designer. The role involves collaborating with cross-functional teams, translating complex concepts into intuitive user interfaces, and creating wireframes, prototypes, and user flows. The ideal candidate should have 5+ years of UX/UI experience, knowledge of Modern JavaScript, CSS, and HTML, and exceptional visual design skills. BenchPrep offers a competitive total rewards package, including a professional development stipend and flexible paid time off.

Licensed Sales Representative

Company: Kin Insurance

Location: Chicago, IL

Posted Apr 24, 2024

<div> <p>Kin is on a mission to change home insurance from what it is to what it should be Whether were leveraging data to create customizable coverage or providing claims service that goes above and beyond expectations our members are at the heart of everything we do In the face of evergrowing climate risk they deserve an insurance company that cares about them We aim to stick with our members through thick and thin<p> <p>Use efficient technology that lets homeowners buy directly from us to keep costs down This is the essence of Kin Our approach has fostered amazing growth attracted marquee investors and earned us accolades including being named to<p> <ul><li>Built In Chicagos Best Places to Work Midsize Companies 20212024<li> <li>Forbes Americas Best Startup Employers 2021 2023<li> <li>Inc 5000 FastestGrowing Private Companies<li> <li>Forbes Fintech 50<li> <ul><p>Simply put our people are what make us great we need forwardthinking inspired gamechangers like you to join us in our mission<p> <div> <p><b><strong>So whats the role<strong><b> <p><p>Kin Insurance is seeking <strong>L<strong><strong>icensed Sales Representatives<strong> to join our growing Operations Team As a Sales Agent you will play a crucial role in driving the growth of our business by connecting with homeowners and promoting our insurance products <p> <p>In this role you have the opportunity to connect with individuals to provide important consultation for not only their home insurance needs but also other products such as auto and flood insurance Best of all this role requires no cold calling you will receive qualified leads that are brought in from our Marketing team You will help to develop the best policies to protect the insureds home alongside building customized quotes to ensure they receive the best service possible<p> <p><b><strong>A day in the life could include <strong><b> <p><ul><li>Connecting with customers via calling email and text actively engaging with potential customers to understand their insurance needs and present suitable solutions<li> <li>Effectively communicating the unique features and benefits of Kin products to potential customers addressing any inquiries or concerns they may have<li> <li>Working primarily with leads provided by the company to maximize your sales potential and conversion rate<li> <li>Consistently following up with your prospects utilizing phone text and email to stay in contact and drive toward the sale<li> <li>Meeting and exceeding sales targets on a regular basis by employing persuasive sales techniques and actively seeking new business opportunities<li> <li>Collaborating with crossfunctional teams including underwriters and customer service representatives to ensure a seamless customer experience<li> <li>Maintaining accurate and uptodate records of customer interactions and sales activities using our CRM system<li> <li>Building custom policies for each customer using internal tools and systems<li> <li>Educating customers on the finer points of home insurance to ensure their best understanding<li> <li>Staying updated on industry trends product knowledge and competitor offerings to effectively position Kin<li> <ul><p><b><strong>Ive got the skills but do I have the necessary ones<strong><b> <p><ul><li>An active Property amp Casualty license<li> <li>Excellent communication and interpersonal skills with the ability to build rapport and effectively engage with diverse audiences<li> <li>Strong negotiation and persuasion skills with a natural ability to close deals<li> <li>Selfmotivated and resultsoriented with a demonstrated commitment to achieving and exceeding sales targets<li> <li>Ability to meet and exceed sales targets on a regular basis by employing persuasive sales techniques and actively seeking new business opportunities<li> <li>Exceptional time management and organizational skills with the ability to prioritize tasks and deadlines<li> <li>Proficiency in using CRM software and other toolssoftware<li> <ul><p><b><strong>Shift Requirements<strong><b> <p><p>Your flexibility allows you to work one Saturday shift every 46 weeks and to work either of the following shifts 8am5pm CST or 9am6pm CST<p> <p><em>Shift times will be assigned based on need 9am 6pm CST is highly preferred<em><p> <p><b>Oh and dont worry weve got you covered <b> <p><ul><li>Medical dental and vision insurance<li> <li>16 days of PTO plus federal holidays and two floating holidays<li> <li>Remote work<li> <li>Generous equity package<li> <li>401K with company match<li> <li>Parental leave<li> <li>Continuing education and professional development<li> <li>The excitement of joining a highgrowth Insurtech company and seeing your work make an impact<li> <ul><div><b><strong>About Kin<strong><b> <p>Kin is the only pureplay directtoconsumer digital insurer focused on the growing home insurance market We make policies convenient and affordable through a technology platform that delivers a seamless user experience customized options for coverage and fast highquality claims service Kin is a fully licensed carrier that offers coverage through its reciprocal exchanges which are owned by its policyholders To learn more visit wwwkincom<p> <p><b><strong>EEOC Statement<strong><b> <p><p>Kin is proud to be an Equal Employment Opportunity and Affirmative Action Employer We dont just accept difference we honor it nurture it and celebrate it We dont discriminate based on race religion color national origin gender including pregnancy childbirth or related medical conditions sexual orientation gender identity gender expression age status as a protected veteran status as an individual with a disability or other applicable legally protected characteristics<p> <p><span>LI<span>Remote<span><span><p> <div>

Account Executive, Inside Sales

Company: Cars Commerce

Location: Chicago, IL

Posted Apr 24, 2024

Cars Commerce is a leading company in the automotive industry, offering a range of services including Cars.com, Dealer Inspire, AccuTrade, and the Cars Commerce Media Network. The company values collaboration, diversity, and integrity, and has been recognized as a U.S. News & World Report Best Company to Work For in 2024. The role involves acting as a point of contact for existing customers, focusing on customer success, retention, and growth. The ideal candidate should have excellent planning and solutions selling experience, strong communication skills, and a proven track record in sales. The total target compensation range for this role is $70,900—$86,800 USD.

Human Resources Generalist

Company: CancerIQ

Location: Chicago, IL

Posted Apr 25, 2024

CancerIQ is a company that is working to end cancer as we know it. They are looking for an HR Generalist to join their team and are offering a competitive salary and benefits package. The company is committed to building a diverse and inclusive work environment.

Bilingual Insurance Agent

Company: Kin Insurance

Location: Chicago, IL

Posted Apr 24, 2024

<div> <p>Kin is on a mission to change home insurance from what it is to what it should be Whether were leveraging data to create customizable coverage or providing claims service that goes above and beyond expectations our members are at the heart of everything we do In the face of evergrowing climate risk they deserve an insurance company that cares about them We aim to stick with our members through thick and thin<p> <p>Use efficient technology that lets homeowners buy directly from us to keep costs down This is the essence of Kin Our approach has fostered amazing growth attracted marquee investors and earned us accolades including being named to<p> <ul><li>Built In Chicagos Best Places to Work Midsize Companies 20212024<li> <li>Forbes Americas Best Startup Employers 2021 2023<li> <li>Inc 5000 FastestGrowing Private Companies<li> <li>Forbes Fintech 50<li> <ul><p>Simply put our people are what make us great we need forwardthinking inspired gamechangers like you to join us in our mission<p> <div> <p><b><strong>So whats the role<strong><b> <p><p>Kin Insurance is seeking <strong>Bilingual Licensed Sales Agents<strong> to join our growing Operations Team As a Sales Agent you will play a crucial role in driving the growth of our business by connecting with homeowners and promoting our insurance products <p> <p>In this role you have the opportunity to connect with individuals to provide important consultation for not only their home insurance needs but also other products such as auto and flood insurance Best of all this role requires no cold calling you will receive qualified leads that are brought in from our Marketing team You will help to develop the best policies to protect the insureds home alongside building customized quotes to ensure they receive the best service possible<p> <p><b><strong>A day in the life could include <strong><b> <p><ul><li>Connecting with customers via calling email and text actively engaging with potential customers to understand their insurance needs and present suitable solutions<li> <li>Effectively communicating the unique features and benefits of Kin products to potential customers addressing any inquiries or concerns they may have<li> <li>Working primarily with leads provided by the company to maximize your sales potential and conversion rate<li> <li>Consistently following up with your prospects utilizing phone text and email to stay in contact and drive toward the sale<li> <li>Meeting and exceeding sales targets on a regular basis by employing persuasive sales techniques and actively seeking new business opportunities<li> <li>Collaborating with crossfunctional teams including underwriters and customer service representatives to ensure a seamless customer experience<li> <li>Maintaining accurate and uptodate records of customer interactions and sales activities using our CRM system<li> <li>Building custom policies for each customer using internal tools and systems<li> <li>Educating customers on the finer points of home insurance to ensure their best understanding<li> <li>Staying updated on industry trends product knowledge and competitor offerings to effectively position Kin<li> <ul><p><b><strong>Ive got the skills but do I have the necessary ones<strong><b> <p><ul><li>An active Property amp Casualty license<li> <li>Ability to communicate fluently in Spanish<li> <li>Excellent communication and interpersonal skills with the ability to build rapport and effectively engage with diverse audiences<li> <li>Strong negotiation and persuasion skills with a natural ability to close deals<li> <li>Selfmotivated and resultsoriented with a demonstrated commitment to achieving and exceeding sales targets<li> <li>Ability to meet and exceed sales targets on a regular basis by employing persuasive sales techniques and actively seeking new business opportunities<li> <li>Exceptional time management and organizational skills with the ability to prioritize tasks and deadlines<li> <li>Proficiency in using CRM software and other toolssoftwares<li> <ul><p><b><strong>Shift Requirements<strong><b> <p><p>Your flexibility allows you to work one weekend shift every 46 weeks and to work either of the following shifts 8am5pm or 9am6pm CST<p> <p><em>Shift times will be assigned based on need 9am 6pm CST is highly preferred<em><p> <p><b>Oh and dont worry weve got you covered <b> <p><ul><li>Medical dental and vision insurance<li> <li>16 days of PTO plus federal holidays and two floating holidays<li> <li>Remote work<li> <li>Generous equity package<li> <li>401K with company match<li> <li>Parental leave<li> <li>Continuing education and professional development<li> <li>The excitement of joining a highgrowth Insurtech company and seeing your work make an impact<li> <ul><p><br ><br ><p><div><b><strong>About Kin<strong><b> <p>Kin is the only pureplay directtoconsumer digital insurer focused on the growing home insurance market We make policies convenient and affordable through a technology platform that delivers a seamless user experience customized options for coverage and fast highquality claims service Kin is a fully licensed carrier that offers coverage through its reciprocal exchanges which are owned by its policyholders To learn more visit wwwkincom<p> <p><b><strong>EEOC Statement<strong><b> <p><p>Kin is proud to be an Equal Employment Opportunity and Affirmative Action Employer We dont just accept difference we honor it nurture it and celebrate it We dont discriminate based on race religion color national origin gender including pregnancy childbirth or related medical conditions sexual orientation gender identity gender expression age status as a protected veteran status as an individual with a disability or other applicable legally protected characteristics<p> <p><span>LI<span>Remote<span><span><p> <div>

Supervisor, Member Care Center - Hybrid

Company: Alliant Credit Union

Location: Chicago, IL

Posted Apr 25, 2024

The Supervisor role involves leading and coaching employees in a contact center, managing team performance, and ensuring member satisfaction. Responsibilities include hiring, training, and retaining team members, monitoring phone calls, and resolving member escalations. The role requires a high school diploma or equivalent, with a bachelor's degree in finance or business preferred. At least 5 years of sales, customer service, or related experience is required, with 1 year of people management experience preferred. Benefits include competitive medical, dental, and vision benefits, paid parental leave, and a generous PTO policy.

Employee Relations Specialist

Company: ALIS by Medtelligent

Location: Chicago, IL

Posted Apr 25, 2024

Medtelligent, a senior living software company founded in 2005, is seeking an Employee Relations Specialist. The role involves managing employee relations issues, ensuring policy compliance, and promoting a positive work environment. The ideal candidate should have 2+ years of experience with Rippling HR Software, change management, and HR policies. The company offers a competitive salary, generous PTO, comprehensive benefits, and a collaborative work environment. Medtelligent values diversity and promotes an equal opportunity employment policy.

Sr. Product Manager, Net Credit - Credit Card Ops (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Apr 25, 2024

Enova International is seeking a Senior Product Manager with 4+ years of experience in product management, ideally with API management. The role involves driving product roadmaps, collaborating with various departments, and defining requirements. The candidate will also construct business cases, work with Engineering, and communicate key milestones to stakeholders. Enova offers a competitive benefits package including hybrid roles, health insurance, 401(k) matching, PTO, and more. Enova is a values-driven organization committed to making it an awesome place to work, with a focus on inclusion and culture.

Inside Sales Account Manager - Remote

Company: Neuron team at CDK Global

Location: Chicago, IL

Posted Apr 25, 2024

The Inside Account Manager role involves developing customer relationships, selling layered applications, and growing revenue. Key responsibilities include generating interest, qualifying prospects, presenting solutions, closing sales, and ensuring monthly goals are met. The role requires excellent communication skills, time management, and product knowledge. The ideal candidate should be customer-focused, results-driven, and have 3+ years of sales experience, preferably in technology. The position offers a competitive hourly rate, commissions, benefits, and opportunities for advancement. CDK Global is an Equal Opportunity Employer committed to diversity and inclusion.

Frequently Asked Questions

What are typical salary ranges by seniority for Unlimited PTO tech roles?
Junior engineers earn $70k–$95k, mid‑level $95k–$140k, senior $140k–$190k, and lead/principal roles $190k–$250k. Product managers follow a similar tier: $80k–$110k, $110k–$160k, $160k–$210k, and $210k–$280k for senior PMs.
What skills and certifications are required for Unlimited PTO positions?
Core tech roles demand proficiency in AWS, GCP, or Azure, Terraform, Docker, and CI/CD pipelines. Product managers often hold Certified ScrumMaster (CSM) or Product Owner certifications, while data scientists are expected to know SQL, Python, TensorFlow, and experience with BigQuery or Redshift.
Is remote work common for Unlimited PTO jobs?
Yes, over 90% of Unlimited PTO listings are fully remote or hybrid, with 80% of companies offering flexible scheduling and no fixed office hours. Remote teams use Slack, Zoom, and distributed version control to maintain collaboration.
What career progression paths exist within Unlimited PTO companies?
Candidates can advance from Junior → Mid → Senior → Lead Engineer, or from Associate PM to Senior PM, then to Director or VP of Product. Many firms also offer lateral moves into technical leadership, data science squads, or design leadership, enabling cross‑functional growth.
What industry trends affect Unlimited PTO roles?
The tech sector is moving toward AI‑driven product development, cloud‑native architectures, and continuous delivery. Companies emphasize equity, health benefits, and unlimited PTO to retain top talent in a competitive remote work landscape.

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