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.

Principal Database Architect

Company: iManage

Location: Chicago, IL

Posted Nov 10, 2023

iManage offers a flexible working policy that supports employee well-being and work-life balance. The Principal Database Architect role involves leading data architecture for a high-traffic SaaS solution, developing designs, and engaging with stakeholders. Responsibilities include overseeing data architecture, ensuring security, and fostering a culture of open communication and innovation. iManage values diversity and provides a supportive, inclusive environment with competitive benefits and opportunities for growth.

Associate Principal, Model Risk Management, Analysis

Company: OCC

Location: Chicago, IL

Posted Nov 11, 2023

The Associate Principal in Model Risk Management (MRM) is responsible for analyzing model risk across various financial models. They review and assess model risk, design and implement benchmark models, and perform model performance testing. The role requires strong quantitative skills, knowledge in financial mathematics, econometrics, risk management methods, and financial products. A Master's degree or equivalent in a quantitative field is required, with a PhD preferred. The candidate should have 7+ years of related experience in quantitative modeling in finance. Proficiency in programming languages, database technology, and technical documentation is essential. OCC, the world's largest equity derivatives clearing organization, offers a collaborative environment with benefits like a hybrid work environment, tuition reimbursement, and generous PTO.

Implementation Analyst (Procurement Expert)

Company: OpenGov

Location: Chicago, IL

Posted Nov 10, 2023

OpenGov is a high-growth, late-stage venture-backed startup that provides cloud software for state and local governments. The company is known for its exceptional team, mission to empower effective and accountable government, and transforming communities. OpenGov offers a rewarding career opportunity for an Implementation Analyst (Procurement Expert) to drive successful customer implementations, manage new customer deployments, and collaborate with cross-functional teams to improve customer workflows. The ideal candidate should have 2+ years of experience in government procurement and software implementation consulting, with strong analytical, communication, and technical skills. OpenGov is recognized for its leadership, funding, growth, culture, and product excellence, making it an attractive employer with competitive perks and benefits.

Product Marketing Manager

Company: Profitero

Location: Chicago, IL

Posted Nov 11, 2023

Profitero is seeking a Product Marketing Manager with 5+ years of experience in marketing, preferably in B2B, media, or technology. The role involves partnering with product managers, driving messaging strategies, and conducting market research. The ideal candidate should have strong writing skills, experience with video-based storytelling, and knowledge of customer success platforms. Profitero offers competitive benefits, including health plans, flexible PTO, and opportunities for professional development.

Technical Onboarding Specialist

Company: SpotHero

Location: Chicago, IL

Posted Nov 11, 2023

SpotHero, a Chicago-based Series D company, is seeking a PARCS Technical Onboarding Specialist. The role involves connecting SpotHero's software and services with PARCS via APIs, ensuring each integration is up and running, and collaborating with Product Managers and Senior Engineers. The ideal candidate should have 1-3 years of IT Networking experience, familiarity with API integrations, and the ability to troubleshoot firewall/networking issues. SpotHero values humility, strong work ethic, flexibility, collaboration, technical curiosity, and constant learning. The company offers excellent benefits, flexible PTO, an annual parking stipend, and a collaborative, innovative atmosphere.

Contract Specalist - Securities & Banking

Company: M1

Location: Chicago, IL

Posted Nov 10, 2023

M1 is a fintech company that offers a self-directed platform for clients to invest, borrow, spend, and save in one place. With over $6 billion in assets and 60,000 five-star reviews, M1 is recognized for its automated investing tools, high-yield savings accounts, margin loans, personal loans, and credit card rewards. The company aims to create a digital private banking experience, accessible with a click. M1 is looking for a Contract Specialist with 6-10 years of corporate paralegal experience, preferably in the financial industry, to provide legal and administrative support to the Assistant General Counsel. The role involves drafting and reviewing legal documents, managing contracts, assisting in corporate governance, conducting legal research, supporting litigation, ensuring compliance, and assisting in due diligence for M&A. M1 is committed to diversity, equity, inclusion, and belonging, and offers competitive benefits and perks.

Senior Software Engineer - Pangea (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Nov 11, 2023

Enova International is seeking a Senior Software Engineer with 5+ years of experience in C#/.NET, object oriented programming, and CI/CD pipelines. The role involves designing, building, and maintaining APIs and services for the Pangea platform, which is developed on C#/.NET and hosted with AWS. The ideal candidate will have experience troubleshooting production issues, writing software for consumer facing applications, and a willingness to participate in a periodic on-call rotation. The role is hybrid, requiring the individual to be open to coming into the Chicago office 1-3 times per month. Enova International is a values-driven organization that provides online financial services through its AI and machine learning-powered Colossus platform, serving non-prime consumers and businesses. The company offers a range of benefits including flexible work schedule, health insurance, 401(k) matching, PTO, sabbatical program, and more.

Implementation Consultant (Procurement Expert)

Company: OpenGov

Location: Chicago, IL

Posted Nov 10, 2023

OpenGov is a high-growth, late-stage venture-backed startup that provides cloud software for state and local governments. The company is committed to powering more effective and accountable government by transforming communities and assisting with various tasks such as helping small businesses open faster, ensuring tax dollars are accounted for, creating safer infrastructure, modernizing the permitting process, and aiding in disaster recovery. The Implementation Consultant role involves driving value to OpenGov customers, delivering complete and smooth implementations, and serving as a trusted advisor to both customers and team members. The company offers competitive benefits, a positive work culture, and the opportunity to make a significant social impact.

Sales Development Representative

Company: Cleo

Location: Chicago, IL

Posted Nov 10, 2023

Cleo is a cloud integration technology company that helps businesses connect and integrate their applications. They are looking for a Sales Development Representative to join their team and support their significant growth.

Systems Administrator II

Company: Grubhub

Location: Chicago, IL

Posted Nov 10, 2023

Grubhub is seeking a Systems Administrator II with experience in networking and system administration. The role involves managing current systems and network infrastructure, maintaining multi-site topology, and contributing to expansion to new locations and cloud providers. The ideal candidate should have a Bachelor's Degree, 3+ years of experience in corporate infrastructure management, and strong knowledge of Windows Server 2019-2022, Linux distributions, and virtualization concepts. The position offers a competitive compensation package, generous PTO, health and wellness benefits, free meals, and opportunities for social impact.

Engineer III, Backend (Money Squad)

Company: SpotHero

Location: Chicago, IL

Posted Nov 11, 2023

SpotHero is a fast-growing startup that empowers people to get everywhere easier. They are seeking a Backend Engineer III to join their Money Squad, which is responsible for powering all things money related. The role involves identifying, designing, developing, testing, and releasing high-quality functionality, as well as collaborating with the rest of the team to deliver quality products.

Channel Account Manager

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Nov 11, 2023

Keeper Security, a leading cybersecurity company, is seeking a Channel Account Manager for a remote position. The role involves building pipeline and channel revenue with existing partners and sourcing new relationships. The candidate should have 3+ years of security SaaS channel sales experience, a good understanding of Partner Incentive programs, and strong interpersonal and communication skills. The company offers a competitive benefits package and a fun, professional work environment.

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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