Unlimited Pto Jobs in Chicago, IL

16,263 open positions · Updated daily

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.

Customer Service Representative (Customer Hero)

Company: SpotHero

Location: Chicago, IL

Posted Aug 06, 2024

SpotHero is a fast-growing startup that empowers people to get everywhere easier through technology. The company is looking for a Customer Hero to assist customers in resolving daily parking issues and provide exceptional customer experience.

Strategic Customer Success Manager

Company: Tegus

Location: Chicago, IL

Posted Aug 05, 2024

Tegus is a leading market intelligence platform that provides products and services to institutional investors, corporations, and consultancies. The company is looking for a Strategic Customer Success Manager to ensure the success and satisfaction of its most strategic customers.

Actuarial Analyst - Mortgage Reinsurance (Peoria, IL; Chicago, IL or Remote)

Company: RLI Insurance Company

Location: Peoria, IL

Posted Aug 03, 2024

RLI is a company that values its employees, offering a range of benefits and opportunities for growth. The company has a strong financial track record and is committed to diversity and inclusion.

API Customer Success Director

Company: NinjaTrader

Location: Chicago, IL

Posted Aug 06, 2024

NinjaTrader is a fintech company seeking a customer success director to grow their team. The company is committed to equal employment opportunity and offers a range of benefits.

Major Account Executive- Hospitality

Company: Hireology

Location: Chicago, IL

Posted Jul 31, 2024

Hireology is looking for a driven sales-minded Account Executive to join their Hospitality team. The role involves qualifying, developing, and closing new opportunities within high-growth sales verticals. The company offers a unique culture, unlimited paid time off, and amazing growth opportunities.

Junior Linguist - Remote

Company: Datapeople

Location: Chicago, IL

Posted Aug 04, 2024

The job posting is looking for a Junior Linguist to join their team to improve the quality and accuracy of their language platform. The role involves auditing content, troubleshooting linguistic issues, and creating new guidance. The company offers comprehensive benefits, unlimited PTO, and a remote-first work environment.

Sales Support Specialist

Company: ABATIX

Location: Chicago, IL

Posted Jul 31, 2024

Abatix is hiring a Sales Support Specialist to assist customers, provide product information, and resolve issues. The ideal candidate has excellent communication skills, is friendly, and willing to go above and beyond. The company offers competitive pay, benefits, and a positive work environment.

Panel Manager, Online Communities

Company: Ipsos

Location: Chicago, IL

Posted Aug 04, 2024

The job description is for a key player in managing the panel build process, working closely with the account team, researchers, web designers, and clients. The job requires strategic thinking, collaboration, and strong communication skills. The company offers opportunities for career development, an exceptional benefits package, and a strong collaborative culture.

Senior Software Engineer, Orchestration Team

Company: Prove

Location: Chicago, IL

Posted Aug 06, 2024

Prove is a company that provides digital identity solutions, and they are looking for a Senior Software Engineer to join their Orchestration Team. The job involves designing and implementing software components, systems, and features to improve the capability, availability, scalability, latency, security, compliance, and efficiency of their solutions.

Senior iOS Engineer

Company: Reverb

Location: Chicago, IL

Posted Aug 01, 2024

Reverb is a company that connects buyers and sellers of musical instruments, with a focus on inspiring content, price transparency, and a music-savvy customer service team. The company has a vibrant community of users and offers a range of benefits, including a generous PTO policy, professional development opportunities, and a charitable contribution match.

Engineer III, Backend (Integrations Squad)

Company: SpotHero

Location: Chicago, IL

Posted Jul 30, 2024

SpotHero is seeking a Backend Engineer to join the Operator League for the Integrations Squad. The company is rapidly growing and is looking for a candidate with strong coding skills and experience in building and maintaining scalable backend services. The role involves contributing to the codebase, designing sophisticated systems, and collaborating with other engineers. The company offers excellent benefits, flexible PTO policy, and opportunities for professional growth.

Insurance Advisor, Startups (Chicago)

Company: Vouch Insurance

Location: Chicago, IL

Posted Jul 31, 2024

Vouch is a new technology-first insurance company that is creating a new business insurance for high-growth companies. They are looking for a sales team member to ensure clients have a great experience through the sales and onboarding process.

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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