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.

Manager, Engineering

Company: Grubhub

Location: Chicago, IL

Posted Mar 06, 2024

Grubhub is a company that values innovation, teamwork, and fun. They are looking for a team lead to manage the engineering team responsible for their dispatch system. The ideal candidate will have experience with Agile methodologies, algorithmic solutions, and cloud-based offerings. The company offers a range of benefits, including flexible PTO, health and wellness programs, and a generous compensation package.

Engineer III, Backend (Operator Panel Squad)

Company: SpotHero

Location: Chicago, IL

Posted Mar 05, 2024

SpotHero is seeking a Backend Engineer III to join the Operator Panel Squad. The successful candidate will be responsible for developing tools and services to help parking facility operators maximize their facilities' capacity and provide drivers with a good parking experience. Key responsibilities include identifying, designing, developing, testing, and releasing high-quality functionality, collaborating with the team to deliver quality products, and ensuring data security and integrity. Relevant experience includes strong coding skills, 3+ years of engineering experience, and production experience with Python, Django, Flask, Java, Kotlin, GoLang, PostgreSQL, Airflow, and Spark. SpotHero offers excellent benefits, flexible PTO, an annual parking stipend, and a collaborative work environment.

Data Operations Analyst

Company: HirexHire

Location: Chicago, IL

Posted Mar 06, 2024

HirexHire, a Chicago-based recruiting firm, is seeking a Data Operations Analyst for a remote role in the Healthcare Technology sector. The analyst will optimize customer experience with the product, network, and services by integrating customer data into the SaaS platform. Key responsibilities include collaborating with clients, developing data integration solutions, ensuring data accuracy, and maintaining documentation. The ideal candidate has 0-2 years of experience in integration, quality assurance, and data analytics, proficiency in SQL and Excel, and the ability to handle multiple projects.

Actuary

Company: RLI Insurance Company

Location: Chicago, IL

Posted Mar 06, 2024

RLI is a Glassdoor Best Places to Work company with a strong financial track record. They offer a variety of roles, including an Actuarial Analyst position, which involves conducting analysis, pricing, and risk assessment. The role requires a bachelor's degree in a related field and 3+ years of experience with 3 actuarial exams completed. RLI encourages professional growth through educational opportunities and offers a comprehensive Total Rewards program, including an ESOP, 401(k), bonuses, and various benefits like health insurance, flexible work arrangements, and fitness discounts.

Associate Sales Exec, Corp

Company: Grubhub

Location: Chicago, IL

Posted Mar 06, 2024

Grubhub is a leading online food ordering platform with over 300,000 restaurant partners. The company offers an innovative technology, user-friendly platforms, and streamlined delivery capabilities. They are seeking a sales professional with 2+ years of B2B sales experience, preferably in SAAS, to accelerate corporate sales growth. The role involves prospecting, cold calls, outreach emails, and strategic sales planning. The successful candidate will build relationships with key decision-makers, tailor value propositions, manage sales pipeline, and forecast accurately. Grubhub values a fun, diverse, and inclusive culture, offering flexible PTO, health benefits, competitive pay, learning opportunities, meal perks, and social impact initiatives.

Account Manager I (Remote)

Company: Denim

Location: Chicago, IL

Posted Mar 06, 2024

Denim is a tech-forward freight factoring partner that offers flexible factoring solutions to freight brokers and fleets. The company is committed to increasing diversity and ensuring a positive work environment. The Account Manager I role involves providing customer service, managing client relationships, and collaborating with other teams.

Marketplace Manager

Company: CookUnity

Location: Chicago, IL

Posted Mar 05, 2024

CookUnity, a chef-to-you marketplace, is seeking a Marketplace Manager to oversee day-to-day operations in kitchens. The role involves managing inventory, ensuring food safety, and training staff. The ideal candidate should have 2-3 years of experience in a similar role, extensive food knowledge, and understanding of food safety standards. Benefits include health insurance, PTO, and CookUnity credits.

Sr. Global Sales Methodology Manager

Company: G2

Location: Chicago, IL

Posted Mar 06, 2024

G2 is a company that values its employees, offering a diverse and inclusive work environment with generous benefits. The company recently secured Series D funding of $157 million for growth. The Sr. Global Sales Methodology Manager role involves managing and scaling the sales methodology, leading skill training, and improving productivity. The ideal candidate should have 7+ years of sales and sales enablement experience, strong communication skills, and the ability to drive change management efforts.

Business Development Representative

Company: Upwork

Location: Chicago, IL

Posted Mar 06, 2024

Upwork, a global work marketplace, is seeking a Business Development Representative to prospect for new business and book sales meetings. The role involves making outbound calls, identifying enterprise opportunities, and achieving weekly and monthly commitment targets. Upwork offers a remote-first culture, competitive benefits, and a commitment to diversity and inclusion. The company's mission is to create economic opportunities for better lives.

Product Designer

Company: Double Good

Location: Chicago, IL

Posted Mar 06, 2024

<p>Double Goods mission is to create joy We create joy with our delectable and awardwinning popcorn We create joy with our easytouse fundraising platform that raises a meaningful amount of money for youth sports and activities empowering kids to pursue their dreams We create joy through our Kids Foundation which hosts Double Good Days events across the country to bring allability fun to children with special needs and their families <p> <p>As featured on the Today Show Double Good is not just about the product we have a strong social mission<p> <p>In recent years Double Good has seen 40 year over year growth and were excited about our future Were excited about the possibility of you joining our mission The Product teams focus is to create a bestinclass user experience from both the web and our native app for all stakeholders in our B2B2C model The Product Designer will work closely with our team of researchers product managers and engineers to understand and fulfill business goals adapt our product to new personas and markets as we continue to rapidly scale and implement and improve our design systems <p> <p>This role is based in Chicago and we are open to candidates in other US locations<p> <p><strong>About the role<strong><p> <ul><li>Champion and cultivate a designdriven culture through every touchpoint in the customer journey utilizing GenchiGenbutsu principals<li> <li>Own and lead all phases of the product design life cycle ranging from strategy ideation prototyping design review implementation and iteration<li> <li>Partner with Engineering to evolve the design system that provides an accessible consistent user experience across our platform and faster product designiteration<li> <li>Promote a designdriven culture through research knowledge sharing and implementing industry best practices and tools<li> <li>Regularly interact with the end users in a culture responsive to their ideas and desires<li> <ul><p><strong>Experience amp Skills we value<strong><p> <ul><li>At least five years of nativeapp product design experience ideally building a product from strategy to iteration<li> <li>Strong understanding of Figma and other design tools Adobe Suite<li> <li>Experience with building and implementing Design Systems<li> <li>Please include a link to your design portfolio with your application<li> <ul><p><strong>About Double Good<strong><p> <p><strong>Were on a mission to create more joy in peoples lives and that includes our internal employees We create a place people love to be a part of where people can discover and practice their unique skill sets a place where they can contribute and do their best work We do this by offering our employees <strong><p> <p><strong>Benefits and Perks<strong><p> <ul><li>Medical Dental Vision insurance<li> <li>Flexible Spending Account Health Savings Account<li> <li>401k with 4 Company Match<li> <li>Generous PTO<li> <li>11 Holidays in the year<li> <li>Paid Parental Leave<li> <li>Comprehensive Employee Assistance Program EAP available to all employees 247<li> <li>Company sponsored disability and life insurance <li> <li>Monthly Popcorn Allowance yup free popcorn<li> <li>Volunteer opportunities with charity partners and the Double Good Kids Foundation<li> <li>Company events Happy Hours Ice Cream Trucks Summer Shindig Holiday Party<li> <ul><p><br >We are an equal opportunity employer and value diversity at our company We want our employees to reflect the diverse communities we serve We embrace the uniqueness in everyone and we encourage each person to be their true selves Your age skin color beliefs sexual orientation nationality disability parental status vet status gender identity are valued here We do not stand for discrimination or harassment of any kind Come as you are<p>

Account Executive (Remote)

Company: Denim

Location: Chicago, IL

Posted Mar 06, 2024

Denim is a remote-first tech-forward freight factoring company that offers fast access to working capital for freight brokers and fleets. They are committed to diversity and providing a comprehensive benefits package, including unlimited PTO, generous parental leave, and professional development opportunities. The Account Executive role involves managing complex sales processes, working in a fast-paced environment, and presenting innovative solutions. Denim values candidates with 2+ years of new business closing experience, a track record of exceeding targets, and a data-driven sales approach.

Business Development Representative - Promotion Path Sales Role

Company: CancerIQ

Location: Chicago, IL

Posted Mar 05, 2024

CancerIQ, a digital health start-up focused on cancer prevention, is hiring a Business Development Representative. The ideal candidate will be passionate about healthcare innovation and committed to CancerIQ's mission. The role involves outbound prospecting, lead generation, and nurturing, with opportunities for growth into senior sales positions. The company offers competitive pay, benefits, and a dynamic work environment.

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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