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 Web Developer

Company: Diagram

Location: Chicago, IL

Posted Jun 09, 2023

The text is a job description for a Senior .NET Developer position at Diagram, a digital consultancy. The role involves solving problems, architecting solutions, and contributing to strategic roadmaps for clients. The ideal candidate should have experience with .NET content management systems and be comfortable working in a collaborative environment. The position offers great benefits, a 401k plan with company matching, and an Open PTO Policy.

Underwriter I, Excess Casualty (Midwest)

Company: Argo Group

Location: Chicago, IL

Posted Jun 10, 2023

Argo Group is a specialty insurance leader with a culture centered on respect, equality, wellness, and opportunity. They are an innovative organization that values agility and impact. The company is seeking a talented Underwriter I to support the Excess Casualty team in the Midwest, preferably in Chicago or Kansas City. The role involves reviewing and pricing policies, interacting with wholesale brokers, managing underwriting territories, and overseeing endorsements. Qualifications include a Bachelor's Degree, related insurance experience, underwriting experience, strong communication skills, and proficiency in computer programs. Argo Group offers a comprehensive Total Rewards package, including competitive compensation, merit-driven profit sharing, flexible workplace policies, and extensive health, wellness, and financial planning options.

Corporate Strategy Analyst

Company: NinjaTrader

Location: Chicago, IL

Posted Jun 10, 2023

NinjaTrader, a growth stage FinTech company based in Chicago, is seeking a highly motivated Corporate Strategy Analyst. The role involves supporting the Chief of Staff and Office of the CEO, conducting complex analyses, industry research, and developing business/financial models. The ideal candidate should have 2+ years of relevant experience, advanced Excel and PowerPoint skills, and a strong analytical mindset. The company offers competitive benefits and is committed to equal employment opportunity.

Digital Marketing Strategist

Company: Diagram

Location: Chicago, IL

Posted Jun 09, 2023

The text is a job description for a Digital Marketing Strategist position at Diagram. The role involves leading marketing initiatives for multiple clients and industries, with a focus on strategy, marketing, design, and development. The ideal candidate should have experience in content marketing, web analytics, SEO, and presenting to clients. The company offers a fun, dedicated work environment with great benefits and perks.

Implementation Manager

Company: HealthJoy

Location: Chicago, IL

Posted Jun 10, 2023

HealthJoy, a high-growth company with over $100M in fundraising, is seeking a Technical Partner & External Data Source Operations professional. The role involves setting up new data integrations, maintaining existing ones, and serving as a point of contact for data feed troubleshooting. The ideal candidate should have 2-5+ years of professional experience in Benefits, knowledge of Health and Welfare benefits, and strong communication skills. HealthJoy offers a comprehensive Total Rewards package, including medical, dental, vision insurance, HSA contribution match, stock options, 401k match, paid parental leave, and flexible PTO.

Manager, Mergers & Acquisitions Advisory

Company: West Monroe

Location: Chicago, IL

Posted Jun 10, 2023

The job posting is seeking a Manager to join the Mergers & Acquisitions team, with responsibilities including leading transaction services, facilitating due diligence projects, and driving the development of M&A methodologies. The company offers a competitive total rewards package, including a bonus structure and benefits.

People & Culture Manager

Company: Curaleaf

Location: Chicago, IL

Posted Jun 11, 2023

Curaleaf Holdings, Inc. is a leading international cannabis company with a mission to enhance lives through the power of the plant. They operate in 19 US states with 150 dispensaries and in Europe as the largest vertically integrated cannabis company. Their corporate social responsibility is rooted in good, focusing on educational outreach, national partnerships, and local causes. The People & Culture Manager role involves HR administrative support, strategic responsibilities, and business partnering for retail and operations functions.

Sales Coordinator

Company: 8th Light, Inc.

Location: Chicago, IL

Posted Jun 10, 2023

8th Light, a global team of software, design, and technology professionals, is seeking a Sales Coordinator. The ideal candidate is a detail-oriented, analytical individual with a passion for sales and marketing. They should have experience in sales administration or coordination, managing reports and spreadsheets, and maintaining data integrity. The role involves building processes, enhancing systems, and supporting client-facing teams. The candidate will also assist in researching targets, coordinating with the sales team, and maintaining Hubspot data. 8th Light offers a flexible PTO, home office stipend, wellness days, and new parent leave. The company is fully remote and committed to supporting remote employees.

Senior Channel Alliance Manager

Company: Pricefx

Location: Chicago, IL

Posted Jun 11, 2023

Pricefx is a young and unconventional software company that has been in operation since 2011. They are a pureplay, native Cloud and SaaS provider in their industry and aim to be the leading SaaS Pricing (Price Optimization & Management) and CPQ (Configure-Price-Quote) vendor. They are an agile company that values market-driven innovation and flexibility. They have customers from diverse industries and sizes, including Michelin, Bosch, and Danone. They are a sustainable and globally growing company that is looking for a strategic partnerships manager to join their team.

HR Specialist - U.S., U.K., E.U

Company: Fairmatic

Location: Chicago, IL

Posted Jun 09, 2023

Fairmatic is a remote company with teams in the US and Europe. They are revolutionizing the insurance industry by using data and AI to offer personalized, risk-based insurance. The company has raised $88M from leading VCs and has a diverse, adaptable team. They are looking for an HR specialist to support their global, fully remote team as they scale.

Salesforce Business Analyst

Company: VTS

Location: Chicago, IL

Posted Jun 09, 2023

The text is a job description for a Salesforce Business Analyst position at VTS, a commercial real estate technology company. The role involves managing commissions, working as a Salesforce administrator, and interacting with various departments. The job requires being in the office 3 days a week. The position offers a unique opportunity to improve workflow and design integrated tools, and to have first-hand exposure to the inner-workings of a Revenue org at a growing SaaS company.

Product Marketing Manager

Company: Fairmatic

Location: Chicago, IL

Posted Jun 09, 2023

Fairmatic is a company that aims to make roads safer by using data and AI to introduce a personalized auto insurance option that incentivizes safe driving. They are looking for a Product Marketing Manager to drive the execution of their go-to-market strategies.

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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