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.

Communications Specialist - Entry Level

Company: Emerald Desert Promotions

Location: Peoria, IL

Posted Jul 29, 2023

The company is hiring entry-level communications specialists to join their growing team. The job responsibilities include communicating with customers, marketing and selling products, and maintaining a positive company culture. The company offers unlimited learning opportunities, virtual networking events, and growth potential.

Director, Technical Accounting

Company: Curaleaf

Location: Chicago, IL

Posted Jul 29, 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 is committed to taking corporate and social responsibility very seriously and has initiatives focused on education, national partnerships, state-wide initiatives, and local causes. The company aims to be the world's leading cannabis company by consistently delivering superior products and services and driving the global acceptance of cannabis.

Cloud/DevOps Engineer

Company: Halo Investing

Location: Chicago, IL

Posted Jul 28, 2023

Halo Investing, a leading Fintech company, has raised over $100 million in Series C funding. They are seeking a Cloud/DevOps Engineer to manage cloud infrastructure, automate operations, and ensure security. The company values collaboration, communication, and passion. They offer competitive benefits, a flexible work environment, and opportunities for professional growth.

Senior People Operations Specialist

Company: HealthJoy

Location: Chicago, IL

Posted Jul 27, 2023

HealthJoy is a remote-first employer offering a comprehensive compensation package, including medical, dental, and vision insurance, stock options, 401k match, paid parental leave, and flexible PTO. The company is committed to equal pay and diversity, and encourages applicants to apply regardless of their qualifications.

Manager, Database Administration

Company: OCC

Location: Chicago, IL

Posted Jul 27, 2023

The role of the Database Administration Manager involves managing day-to-day activities, providing data management guidance, and ensuring data integrity and recoverability. The manager is responsible for performing various tasks such as managing database department efforts, supporting project teams, and preparing progress reports. They also need to maintain a high level of leadership and management, develop performance review plans, and provide a supportive work environment.

People & Culture Manager

Company: Curaleaf

Location: Chicago, IL

Posted Jul 31, 2023

Curaleaf Holdings, Inc. is a leading international cannabis company with a mission to enhance lives by cultivating, sharing, and celebrating the power of the plant. The company operates in 19 US states and Europe, offering a wide range of cannabis products and services. Curaleaf is committed to corporate social responsibility, community involvement, and fostering a diverse and inclusive work environment. The People & Culture Manager role involves supporting retail and operations functions, managing HR administrative tasks, and leading complex employee relations investigations.

Collegiate Sales Manager

Company: Campus Ink

Location: Chicago, IL

Posted Jul 29, 2023

Campus Ink is a leading collegiate apparel company seeking a motivated and creative Collegiate Sales Manager to drive the growth of their campus-based design and sales initiatives. The role involves recruiting and managing a team of student designers, providing coaching and mentorship, and fostering a positive team environment.

Senior Manager of Growth and ABM

Company: Smartly.io

Location: Chicago, IL

Posted Jul 29, 2023

The text describes a job opening for a Senior Manager of Growth and ABM at Smartly.io, a global SaaS digital advertising platform. The role involves leading ABM efforts, designing and implementing marketing programs, and collaborating with sales, event marketing, paid media, and SDRs. The candidate should have 8+ years of B2B marketing experience in tech companies, with a focus on ABM campaigns. The role offers flexible work options, generous benefits, and opportunities for growth.

Lead Specialist, Content

Company: Grubhub

Location: Chicago, IL

Posted Jul 27, 2023

Grubhub is a company that values innovation, teamwork, and fun. They are looking for data-driven individuals to join their team and work together to achieve goals. The company offers a range of benefits, including PTO, health and wellness programs, and a generous compensation package.

Business Development Representative

Company: CancerIQ

Location: Chicago, IL

Posted Jul 31, 2023

The text describes a job posting for a Business Development Representative at CancerIQ, a company working on early cancer detection and prevention. The role involves outbound prospecting, qualifying deals, and building the pipeline. The ideal candidate should have sales experience, preferably in healthcare, and be interested in healthcare innovations. The company offers competitive pay, benefits, and a diverse work environment.

Manager, Virtualization Engineering

Company: OCC

Location: Chicago, IL

Posted Jul 31, 2023

The text describes a leadership role in managing a team of Virtualization engineers to administer OCC server environments, support a large computing environment, and drive an 'infrastructure as code' mentality. The role involves providing status reporting, creating process documentation, driving automation, and collaborating with other teams. The individual will also be responsible for change management, performance management, and developing the team. The role requires excellent communication skills, experience with VMware and UCS administration, and a bachelor's degree in Computer Science or a related field. OCC is a regulated financial institution offering clearing and settlement services for options, futures, and securities lending transactions.

Manager, System Engineer

Company: Ascent Global Logistics

Location: Chicago, IL

Posted Jul 31, 2023

Ascent is a recognized supplier of the year for multiple Fortune 500 companies and a partner to thousands of small and medium-sized businesses. They offer a wide range of logistics solutions and have a strong market presence. The company is looking for a manager to lead a team of engineers in managing and maintaining their systems, including Azure cost management, AD, Azure AD, Windows OS, VMware vSphere, M365, storage systems, and more. The ideal candidate should have strong leadership skills, technical expertise, and the ability to learn new technologies quickly.

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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