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.

Software Engineering Manager

Company: Avant

Location: Chicago, IL

Posted Feb 20, 2023

The text describes a position at AvantWork where the product and engineering teams will develop the Ops Tech roadmap, contribute to quarterly and yearly planning, and work with contractor firms to fill immediate people needs. The role emphasizes building a reliable and scalable product, continuous improvement, and high-quality APIs and systems. The company values authenticity, collaboration, problem-solving, customer focus, and initiative. They offer terrific perks, flexible work environment, and professional development opportunities.

Support Product Specialist - Switching (IOS)

Company: Cisco Meraki

Location: Chicago, IL

Posted Feb 20, 2023

Cisco Meraki is a leading company in simple, secure, and intelligent networking and IoT platforms. They empower organizations to focus on their mission and have technology that works. The company has been named the #1 Best Company to Work For in the US by Fortune in 2021 and 2022. The Support Product Specialist role involves being an expert in Meraki's Switching (IOS) product line, helping identify and prioritize product issues, and working with PM and Engineering to build better support experiences.

Senior Customer Success Manager

Company: HealthJoy

Location: Chicago, IL

Posted Feb 21, 2023

HealthJoy is a remote-first employer seeking a Sr. Customer Success Manager to drive success for their largest and most strategic customers. The role involves post-sale customer management, product adoption and utilization, retention, and customer health. The ideal candidate should have 5+ years of account management or customer success experience in the benefits/health insurance, wellness, or healthcare sector. Strategic thinking, excellent project management skills, and a passion for problem-solving are required.

Managing Director, Product Engineering

Company: West Monroe

Location: Chicago, IL

Posted Feb 21, 2023

West Monroe is seeking a Managing Director/Partner for their Product Experience and Engineering Lab. The role involves scaling the Engineering practice, leading innovation activities, mentoring the next generation of leaders, facilitating openness and knowledge sharing, and actively participating in recruiting and retaining top talent. The individual will also be responsible for client delivery, business development, and practice operations. Qualifications include a minimum of 15+ years of leadership experience in a team-based, client-facing business, proven experience in leading custom software engineering solutions, and an active professional network. The salary range for this role is $290K - $370K.

People Resources Business Partner, Contact Center (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Feb 22, 2023

The text describes a job opening for a People Resources Business Partner (PRBP) position at Enova, a financial technology company. The role involves supporting client groups, working with management and employees, and driving People policies. The company offers benefits such as flexible work schedule, health insurance, and paid time off. Enova is committed to diversity and inclusion and provides equal employment opportunities.

Business Analyst (IT)

Company: SpotOn

Location: Chicago, IL

Posted Feb 21, 2023

SpotOn is a technology company helping small businesses and restaurants compete and win with marketing software, website development, e-commerce, reservations, online ordering, digital loyalty, review management, and POS solutions. They have recently raised $300M in Series F funding, earned awards, and are looking for a Program Management team member to ensure projects have the right documentation and systems.

Director of Sales

Company: Betterview

Location: Chicago, IL

Posted Feb 19, 2023

Betterview is seeking a passionate and experienced Director of Sales to grow into an ever-evolving marketplace. The role involves seeking a solution to disrupt the $600+ billion P&C insurance industry, which is struggling with harnessing risk and peril data to profitably underwrite business. The Director of Sales will guide new prospective customers through the end-to-end sales process and work with existing customers to expand the use of Betterview products over time.

Sales Operations Deal Desk Analyst

Company: Upwork

Location: Chicago, IL

Posted Feb 21, 2023

Upwork is a leading tech solution for companies seeking to hire top talent, maintain flexibility, and increase productivity. They are passionate about their mission to create economic opportunities worldwide. The company facilitates almost $2 billion in annual work through their platform, connecting top companies with exceptional talent globally. The Deal Desk Analyst role involves strategic partnership with sales, mentorship on business processes, and support in increasing deal velocity. The role requires analytical skills, attention to detail, and experience in sales, marketing, or customer success.

Product Marketing Manager

Company: SpotOn

Location: Chicago, IL

Posted Feb 18, 2023

This role involves working with various departments to build products that drive revenue for restaurants. The responsibilities include identifying product-market fit, defining engagement strategies, and launching new features. The role requires collaboration, ownership, and the ability to drive adoption and engagement among customers. The benefits package includes medical, dental, and vision insurance, 401k with company match, RSUs, flexible time off, and more.

Office Specific Posting

Company: West Monroe

Location: Chicago, IL

Posted Feb 20, 2023

Are you ready to make an impact? Ready to thrive in a foundational step on your sales career journey? With over 20% growth expected in 2023, West Monroe seeks a Business Development Representative. This is an inside sales position that works in a flexible office / remote setting and is responsible for generating new business through omnichannel communications with potential clients. The job involves identifying and originating new sales opportunities by executing follow-up on inbound leads as well as outbound campaigns, building and maintaining relationships with new and existing accounts, and achieving sales goals/quotas. Reporting to our Director of Business Development, the Business Development Representative will join our growing national sales team and operate out of our Chicago headquarters. Specifically, you will be driving new opportunities for digital strategy and product engineering consulting engagements. You will provide support to both our Marketing Team and our national team of Business Development Executives (field sales team). This is an outstanding role for aspiring sales and account management professionals who wish to advance their sales career on a high-performing team with advancement opportunities. We offer highly competitive compensation and benefits packages.

Associate Principal, Software Engineering: DevOps

Company: OCC

Location: Chicago, IL

Posted Feb 19, 2023

The job involves supporting the development efforts of the OCC Clearing Development team, enabling self-service build and deployment processes, designing and implementing process improvements, maintaining and configuring development environments in Kubernetes and AWS, and developing and supporting terraform, ansible, Harness, and Jenkins jobs. The role requires understanding of Kanban and Agile methodologies, ability to work in a fast-paced environment, and experience with CI/CD tools, cloud technologies, and monitoring related tools.

Senior Accountant, International

Company: Intelsat

Location: Chicago, IL

Posted Feb 19, 2023

The role involves leading operational accounting and governance compliance for the Commercial Aviation business of Intelsat. The Senior Accountant will work closely with various teams, supervise outsourced services, and manage monthly, quarterly, and annual accounting close processes. They will also review and approve local/statutory accounting reports, lead local annual audit requirements, and build financial reports/dashboards. The role requires strong communication skills, proficiency in Microsoft Office, and knowledge of US GAAP and NAV accounting system.

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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