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.

Systems Engineer I-II (On-Site: Orland Park, IL)

Company: Entara

Location: Chicago, IL

Posted Aug 20, 2024

Entara is seeking an Onsite Reactive Services Systems Engineer to provide temporary and unique boots on the ground presence for one of their key client accounts. The ideal candidate is a talented relationship builder with strong communication and collaboration skills, and a knack for wrangling client environments into tiptop shape.

Franchise BD for Enterprise Brands

Company: Groupon

Location: Chicago, IL

Posted Aug 20, 2024

Groupon is seeking enthusiastic Sales Representatives to join their team. The role involves driving sales efforts, building customer relationships, and negotiating deals. The company offers a competitive compensation package and a mission to build strong communities through thriving small businesses.

Director, Controller

Company: Beyond Finance

Location: Chicago, IL

Posted Aug 21, 2024

Beyond Finance is a company that helps people escape debt and achieve financial freedom. They are seeking a Director/Controller in Chicago to lead their accounting team and provide financial guidance. The company offers a collaborative work environment, benefits, and opportunities for career development.

General Counsel

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Aug 20, 2024

Keeper Security is hiring a General Counsel to oversee legal aspects of the company's operations. The role involves providing legal advice, negotiating contracts, and managing the company's legal files. The company offers a range of benefits, including medical, dental, and vision insurance, and a generous PTO plan.

Senior React Native Developer

Company: Beyond Finance

Location: Chicago, IL

Posted Aug 21, 2024

Beyond Finance is a company that helps people escape debt and achieve financial freedom. They are looking for collaborators to help them grow and are offering a range of benefits and opportunities for development.

Account Development Representative

Company: Billtrust

Location: Chicago, IL

Posted Aug 20, 2024

The job posting is for a Sales Development Representative at Billtrust, a company that provides B2B order-to-cash software and digital payments. The role involves prospecting and program strategies to support the sales team in achieving booking targets. The company offers a competitive salary, flexible working hours, and a range of benefits.

Logistics Manager (Strategy & Operations / Analytics)

Company: Grubhub

Location: Chicago, IL

Posted Aug 20, 2024

Grubhub is a company that values innovation, teamwork, and fun. They are looking for a Logistics Manager to join their team, who is data-driven, analytical, and passionate about excellence. The role involves managing the delivery network, optimizing cost, speed, and quality, and working on projects to improve metrics.

Account Manager - Merchant Accounts (Mandarin Speaking)

Company: Grubhub

Location: Chicago, IL

Posted Aug 20, 2024

Grubhub is a company that values innovation, teamwork, and fun. They offer a range of benefits, including a generous PTO policy, health and wellness programs, and a compensation package with incentives. The company is looking for an Account Manager to oversee a restaurant portfolio and drive growth.

Account Manager

Company: Snapsheet

Location: Chicago, IL

Posted Aug 21, 2024

Snapsheet is a company that simplifies claims by leveraging virtual estimating and innovative claims management technology. The job posting is for an Account Manager who will manage relationships with target clients, develop account plans, and collaborate with internal teams to introduce new products.

IT Support and Database Specialist

Company: Brilliant PR & Marketing

Location: Chicago, IL

Posted Aug 20, 2024

Brilliant PR amp Marketing is a remote company seeking a Fulltime IT Support and Database Specialist. The job requires excellent time management, problem-solving skills, and experience with database management. The company offers unlimited PTO, paid time off, and other benefits.

Senior Salesforce Administrator

Company: Beyond Finance

Location: Chicago, IL

Posted Aug 21, 2024

Beyond Finance is a company that helps people escape debt and achieve financial freedom. They are looking for a Senior Salesforce Administrator to join their team and help improve their Salesforce platform.

Enterprise Strategist (Perm - Hybrid at our Chicago HQ by O'Hare Airport)

Company: Alliant Credit Union

Location: Chicago, IL

Posted Aug 21, 2024

The job description is for an Enterprise Strategist who will guide the company's strategic direction and vision, develop and implement strategic initiatives, and ensure the company remains competitive. The role requires collaboration with senior leaders, market research, and analysis of business performance.

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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