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.

Surety Underwriter, Portfolio Management

Company: Argo Group

Location: Chicago, IL

Posted May 18, 2023

Argo Group is a specialty insurance leader with a vibrant culture emphasizing respect, equality, wellness, and opportunity. They offer flexible workplace policies and a comprehensive benefits package, including competitive compensation, merit-driven profit sharing, and extensive health, wellness, and financial planning options. The company is currently seeking a Surety Underwriter for its Portfolio Management Team in Chicago, IL, with potential for remote work. The role involves underwriting, administering, and servicing existing contract accounts and new business, as well as collaborating on data-driven surety operations projects.

FP&A Analyst

Company: Beyond Finance

Location: Chicago, IL

Posted May 17, 2023

Beyond Finance is a mission-driven organization helping Americans escape debt and achieve a debt-free life. They are seeking a FP&A Analyst to perform analysis, source data, and report KPI metrics. The ideal candidate should have a strategic mindset and strong analytical skills. The role involves performance reporting, conducting insightful analyses, and resolving issues.

Human Resources Manager

Company: Curaleaf

Location: Chicago, IL

Posted May 17, 2023

Curaleaf Holdings, Inc. is a leading international provider of consumer products in cannabis with a mission to enhance lives by cultivating, sharing, and celebrating the power of the plant. The company operates in 19 states with 150 dispensaries and employs nearly 5,500 team members. Curaleaf International is the largest vertically integrated cannabis company in Europe with a unique supply and distribution network throughout the European market. The company is committed to taking corporate and social responsibility very seriously and has initiatives focused on giving back to the communities where they operate.

Analyst I, Marketing Analytics

Company: Grubhub

Location: Chicago, IL

Posted May 18, 2023

None Found

Manager, Marketing Strategy & Operations

Company: West Monroe

Location: Chicago, IL

Posted May 17, 2023

West Monroe is currently seeking a talented Manager for their Marketing Strategy & Operations team. The Manager will lead project teams, develop customer-centric strategies, and increase customer acquisition and engagement. The role involves client delivery, people and practice development, and business development. Qualifications include 7+ years of experience in consulting or marketing leadership, strong communication skills, and industry marketing consulting abilities. West Monroe offers competitive total rewards, including medical, dental, vision, life insurance, 401k, and unlimited flexible time off.

Security Manager

Company: SpotHero

Location: Chicago, IL

Posted May 17, 2023

SpotHero is seeking a Security Manager to build out a security program for their production applications and corporate cloud-based IT. The role requires a technically senior individual with experience in Cybersecurity, application security, and managing people. The successful candidate will drive SecOps and DevSecOps methodologies, build an education program, and manage risks and issues. The company offers competitive benefits, flexible PTO, and an award-winning culture.

Vice President, Product Management

Company: FOURKITES

Location: Chicago, IL

Posted May 16, 2023

FourKites is a leading predictive supply chain visibility platform that offers real-time visibility and predictive analytics for a broad network of global 1000 companies and third-party logistics firms. The company uses a proprietary algorithm to calculate shipment arrival times and covers all modes, including truckload, LTL, ocean, rail, intermodal, last mile, and parcel. FourKites is known for being highly innovative and responsive to customers' needs, with a focus on creating more agile, efficient, and sustainable supply chains.

FP&A Associate

Company: Beyond Finance

Location: Chicago, IL

Posted May 17, 2023

Beyond Finance is a forward-thinking organization dedicated to helping people escape debt and achieve a debt-free life. They are seeking a skilled Financial Senior Associate to support their FP&A team with financial and business analysis, annual budgeting, forecasting, financial modeling, and strategic planning.

Head of Credit Card (Hybrid)

Company: Enova

Location: Chicago, IL

Posted May 16, 2023

The role of Head of Credit Card at Enova International involves leading and growing two credit card businesses, managing risk, and collaborating with various teams to ensure customer experience and adherence to regulatory requirements. The position requires 10+ years of industry experience, strong strategic thinking, and excellent communication skills.

Vice President, Operations- Corporate Development

Company: Halo Investing

Location: Chicago, IL

Posted May 18, 2023

Halo Investing is a leading FinTech company that has raised over $100 million in Series C funding. They are based in Chicago with offices in Zurich and Abu Dhabi and are known for their strong company culture and collaboration. The VP of Operations role involves driving operational efficiency, leading corporate development activities, and contributing to the company's revenue growth goals.

Manager, Growth

Company: Grubhub

Location: Chicago, IL

Posted May 18, 2023

Grubhub is seeking a Manager to lead their Digital Marketing Channel Analytics team. The role involves leveraging large data sets, designing experiments, and collaborating with internal and external teams to drive Search channel strategy. The successful candidate will have a Bachelor's degree, 6+ years of strategic/analytical experience, and people management skills.

Director of Outbound Sales

Company: Paro

Location: Chicago, IL

Posted May 18, 2023

Paro is a company that empowers business professionals to pursue meaningful work on their own terms, democratizing access to business solutions. They provide flexible finance and accounting solutions via a network of freelance experts, using AI-powered platforms to match clients with the best-fit experts. The company is expanding and looking for an outbound sales director to build a high-performance sales team and drive growth.

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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