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.

Assistant General Counsel, Regulatory (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Feb 14, 2023

The job posting is for an Assistant General Counsel, Regulatory role at Enova, a financial technology company. The role involves aiding the company's lending and financial services businesses with regulatory compliance and providing guidance to business teams. The job requires a Juris Doctorate from an accredited law school, admittance in good standing with at least one state bar, and 2+ years of law firm or corporate in-house counsel experience.

Operations Senior Program Manager

Company: Blueground

Location: Chicago, IL

Posted Feb 11, 2023

Blueground, a company founded in 2013, has raised over $258m and hosts guests in 30 cities worldwide, aiming to expand to 50 cities by 2025. They offer a culture of collaboration, inclusiveness, and opportunity, with a focus on time management, excellence, and transparency. They are seeking an Operations Senior Program Manager to drive business change, improve operational CX processes, and standardize project intake processes. The role requires 5+ years in consulting, customer success, and data-driven decision-making skills. Benefits include competitive compensation, stock options, flexible PTO, and wellness perks.

Product Manager, Prospect Pod Intern

Company: Avant

Location: Chicago, IL

Posted Feb 14, 2023

Avant is seeking a product manager intern to join their Acquisition Pod. The ideal candidate should be collaborative, comfortable leading key deliverables, and able to partner with stakeholders in Engineering, Credit, and Banking. The role involves supporting product managers in project management, pod documentation, and organization, building out reporting and analytics dashboards, and presenting on work products. Avant values authenticity, collaboration, problem-solving, customer focus, and initiative.

Associate Principal, Software Engineering - Java Development

Company: OCC

Location: Chicago, IL

Posted Feb 12, 2023

The Associate Principal role at OCC involves working with business analysts, team leads, and developers to design and develop scalable, resilient hybrid Cloud-based solutions for critical financial risk management activities. The role requires extensive experience in Java, object-oriented designs, multi-threading, and distributed message brokers. Knowledge of cloud technologies, high-speed distributed computing frameworks, and DevOps tools is desirable. The Associate Principal will also mentor developers, collaborate across teams, and contribute to transforming the enterprise into a data-driven organization.

VP of Sales

Company: Logiwa

Location: Chicago, IL

Posted Feb 11, 2023

Logiwa is a world-class partner for warehouse and inventory based businesses, offering integrated software and seamless inventory and warehouse management support. They are a growing company with a fun, inclusive, and collaborative environment, offering a fun, inclusive, and collaborative environment with endless opportunities for growth and development. They are looking for a VP of Sales to join their team and help meet sales goals, increase ROI, and design marketing materials and sales playbooks. The company offers flexibility to work remotely, 15 days of PTO, 5 personal days, and 100% employer-paid health and dental insurance.

Operations Program Manager

Company: Blueground

Location: Chicago, IL

Posted Feb 11, 2023

Blueground is a company that aims to make people feel at home wherever they choose to live. They have grown significantly since their founding in 2013, raised over $258m+ in funding, and are now hosting guests in more than 11,000 homes in 30 cities around the world. They have a culture of collaboration, inclusiveness, and opportunity, with a focus on time, excellence, and transparency. They are looking to hire an Operations Program Manager and have a recruitment process that includes several steps to assess candidates' skills and cultural fit.

Technical Sales & Solutions Engineer

Company: Evolv Technology

Location: Chicago, IL

Posted Feb 11, 2023

The Evolv Technology job posting is seeking a driven and energetic solutions engineer to develop, pilot, and launch products in various vertical markets. The role involves sales support, technical expertise, operational security, project management, and cross-functional team engagement. The team culture is based on building trust and collaboration, with a commitment to ongoing development. The role is located near Los Angeles, California, or Chicago, Illinois, and offers equity, flexible work environment, unique culture, medical and dental insurance, 401(k) plan, unlimited vacation policy, and tuition reimbursement.

Director of Sales

Company: Paro

Location: Chicago, IL

Posted Feb 13, 2023

The Role: Due to the significant growth and success of the 'White Label' team, a Director of Sales position is being introduced to scale and grow the organization. The role involves building a high-efficiency sales organization, overseeing Sales Managers, and strategizing sales & growth plans. The ideal candidate has extensive B2B sales experience, a track record of exceeding quota targets, and success in scaling and advancing sales strategies.

Help Desk Manager

Company: Baird & Warner

Location: Chicago, IL

Posted Feb 11, 2023

Baird & Warner Real Estate is a well-established company with a strong culture of support and growth. They empower their employees to succeed and make a positive impact on homebuyers and sellers. The company values strong customer service, compliance, and teamwork. They offer a variety of benefits including medical, dental, 401k, PTO, and VTO.

Financial Product Intern

Company: Avant

Location: Chicago, IL

Posted Feb 14, 2023

The job description outlines a position for a data analyst with a focus on data collection, processing, and quality checks. The role also involves converting complex data into understandable formats and communicating strategies to stakeholders. The position requires strong analytical, interpersonal, and communication skills. The company, Avant, values authenticity, collaboration, problem-solving, customer focus, and initiative. They offer competitive benefits and a flexible work environment.

SEO Analyst

Company: Everspring

Location: Chicago, IL

Posted Feb 11, 2023

The job description is for an SEO Analyst position at Everspring, a digital marketing company. The role involves performing keyword research, analyzing site structure, and creating content calendars. The ideal candidate should have a background in conversion rate optimization and experience with Google Search Console and Google Analytics.

Loan Growth Strategy Intern

Company: Avant

Location: Chicago, IL

Posted Feb 14, 2023

Avant is looking for an intern to join the Loan Growth and Strategy team. The role involves developing and optimizing new and existing product and growth strategies, refining the business case for direct debt payoff, and performing ad-hoc analysis. The ideal candidate should have experience in SQL and Python, strong analytical skills, and the ability to improve performance by analyzing and managing performance indicators.

Frequently Asked Questions

What are typical salary ranges for unlimited PTO tech roles by seniority?
Entry‑level engineers start around $90k–$120k, mid‑level $120k–$160k, senior $160k–$200k, staff $200k–$250k, and principal $250k+ annually. Product managers and designers have comparable ranges, while data scientists and DevOps engineers follow similar tiers.
What skills and certifications are required for unlimited PTO positions?
Software engineers should master Go or Rust, AWS Certified Solutions Architect, and Certified Kubernetes Administrator. Product managers need Agile Scrum or SAFe certification, proficiency in Jira, and data‑analysis skills in SQL and Python. UX designers should be fluent in Figma, have a portfolio, and understand accessibility standards. Data analysts require expertise in Snowflake, Tableau, and statistical modeling. DevOps engineers need Terraform, GitHub Actions, and CI/CD best practices.
Is remote work available in unlimited PTO roles?
Yes. Most companies offering unlimited PTO—such as GitHub, Atlassian, and Shopify—provide fully remote or hybrid options. Remote‑first culture pairs well with unlimited PTO, as employees can schedule time off around project milestones and global deadlines.
What career progression paths exist in unlimited PTO tech roles?
Typical ladders progress from Associate/Junior to Mid, Senior, Staff, and Principal levels. Unlimited PTO allows professionals to focus on skill development, certifications, and cross‑team leadership, accelerating promotion timelines. Mentorship programs and internal mobility initiatives further support upward movement.
What industry trends affect unlimited PTO positions?
The shift toward outcome‑based performance, increased emphasis on mental health, and the rise of remote‑first teams are driving the adoption of unlimited PTO. Companies use the benefit to attract high‑talent, reduce turnover, and promote a culture of trust and autonomy. Data shows that firms offering unlimited PTO often report higher productivity and employee satisfaction scores.

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