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.

Senior Business Intelligence Engineer (Remote)

Company: Enova

Location: Chicago, IL

Posted May 22, 2023

None Found

UX Copywriter (Hybrid)

Company: Enova

Location: Chicago, IL

Posted May 23, 2023

Enova International is seeking a UX Writer with a Bachelor's degree and 2-3 years of experience. The role involves writing copy for Enova's financial brands, assisting in UX projects, and collaborating with various teams. Responsibilities include authoring UX copy, digital collateral, and adapting content to brand voice and tone guides. Benefits include flexible work schedule, health insurance, 401(k) matching, and a sabbatical program. Enova is a values-driven organization committed to creating accessible credit for millions.

Analytics Engineer

Company: Cameo

Location: Chicago, IL

Posted May 24, 2023

None Found

Senior Product Security Engineer (Remote)

Company: Enova

Location: Chicago, IL

Posted May 23, 2023

Enova is currently accepting candidates for remote positions in various states for security engineering roles. The role involves building, developing, and designing strategies of embedding security testing and enforcement within the SDLC across Enova Products. The candidate will be expected to have a 'can-do' attitude and work independently to drive solutions. The role requires in-depth knowledge of software security principles and experience with AWS, Containers, Microservice architectures, and DevOps/Software engineering experience.

Cybersecurity - Senior Manager (Financial)

Company: West Monroe

Location: Chicago, IL

Posted May 23, 2023

None Found

IT Procurement Director (hybrid)

Company: Argo Group

Location: Chicago, IL

Posted May 22, 2023

Argo Group is a leader in specialty insurance with a vibrant culture that values respect, equality, wellness, and opportunity. They are an innovative organization that is flexible and agile, with a focus on creating a comfortable, respectful, and equal workplace. The company encourages diversity and design thinking, promotes collaborative service delivery, and values authentic recognition of excellence. They offer a comprehensive line of high-quality products and services, competitive compensation and profit sharing, flexible workplace policies, comprehensive health and wellness options, and a generous paid time off package. Argo Group also encourages career mobility, continuing education, and community outreach.

Analytics Engineer

Company: Cameo

Location: Chicago, IL

Posted May 24, 2023

Cameo is a global platform that enables fans to receive personalized video messages and live calls from their favorite stars and creators. The company values creativity, hard work, collaboration, direct dialogue, and employee development. Cameo is seeking an experienced Analytics Engineer to join their dynamic analytics team. The ideal candidate will develop data solutions, drive insights, and contribute to the company's growth through data-driven decision-making. The role involves creating scalable data pipelines, collaborating with cross-functional teams, designing data models, and developing data visualizations. The company offers competitive salaries, equity, health insurance, 401(k), wellness perks, and unlimited PTO.

Manager of Sales Analytics and Strategy

Company: Beyond Finance

Location: Chicago, IL

Posted May 24, 2023

Beyond Finance is a company that helps people escape debt and achieve financial freedom. They are looking for a Sales Analytics Manager to join their team and help them optimize sales effectiveness and marketing performance.

Manager, Network Engineering

Company: OCC

Location: Chicago, IL

Posted May 23, 2023

The role involves managing a team to perform network design and analysis, developing systems specifications, and coordinating complex installation projects with clients and vendors. The team works on both on-premise and cloud networks, ensuring IT/Security Governance needs are met and network performance and security standards are maintained.

Public Sector Demand Generation Manager

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted May 23, 2023

Keeper is hiring a talented Public Sector Demand Generation Manager to join the Keeper Marketing team. This is a 100% remote position. Keeper is a fast-growing cybersecurity company looking for someone to expand their presence in the U.S. public sector segment. The ideal candidate will have experience in Digital Marketing and Demand Generation for B2B SaaS organizations, strong writing skills, and experience with modern demand generation metrics and KPIs.

Senior FinPro Claims Analyst

Company: Argo Group

Location: Chicago, IL

Posted May 22, 2023

Argo Group is a leader in specialty insurance with a vibrant culture that values respect, equality, wellness, and opportunity. They offer high-quality Commercial Property and Casualty (P&C) insurance products and services tailored to the needs of businesses and public entities. The company is looking for a Senior Claims Analyst to work on Directors and Officers, Financial Institutions, Securities and Employment Litigation, and Employment Practices Liability claims. The role requires solving difficult problems, reporting on claims trends and developments, investigating claims, managing claims in litigation, and applying creative solutions to achieve the best financial outcome. The ideal candidate should have good business acumen, advanced knowledge of construction defect claims, a minimum of five years of experience adjudicating management and professional liability claims, a bachelor's degree from an accredited university, and a JD. The company offers a flat organizational structure, a collaborative work environment, and a work-life balance. They also offer competitive compensation, comprehensive health benefits, and professional development opportunities.

Customer Marketing Specialist

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted May 23, 2023

Keeper is a fast-growing cybersecurity company seeking a Customer Marketing Specialist to join their global team. The role involves developing and executing cross-sell and upsell campaigns, creating sales enablement collateral, and working cross-functionally with various teams. Previous B2B experience, especially in the SaaS industry, is required.

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.

Related Pages