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 Engineer, Backend (Money Squad)

Company: SpotHero

Location: Chicago, IL

Posted Nov 06, 2023

SpotHero is hiring a Senior Backend Engineer for the Money Squad, responsible for payment processing and supporting internal teams with APIs. The ideal candidate has strong coding skills, system design understanding, and a proven track record of successful projects. They will contribute to the codebase, collaborate with teams, and ensure high-quality software delivery. Key responsibilities include designing and developing functionality, mentoring peers, and maintaining the codebase. The role requires experience in Python/Django/Postgres or JVM languages, knowledge of API paradigms, and understanding of double-entry accounting. SpotHero offers excellent benefits, a flexible PTO policy, learning budget, and a collaborative atmosphere. The position is in Chicago, IL or Toronto, ON, and is not eligible for visa sponsorship.

DevOps Sales Engineer

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Nov 06, 2023

Keeper Security, a globally expanding cybersecurity leader, is seeking a DevOps Sales Engineer for a remote opportunity. The role involves supporting the sales cycle from a technical perspective, demonstrating Keeper Security solutions, and providing technical assistance to customers. The ideal candidate should have 3+ years of experience with CI/CD pipeline tools, technical sales, and enterprise organizations. A B.S. in Computer Engineering or Computer Science is required, along with excellent communication and interpersonal skills. Keeper Security offers competitive benefits including medical, dental, vision, life insurance, 401K, and a generous PTO plan.

Manager, Customer Success Operations

Company: OpenGov

Location: Chicago, IL

Posted Nov 06, 2023

OpenGov is a mission-driven company that is transforming communities by providing cloud software for governments. The company is looking for a Manager, Customer Success Operations to join their team and help improve critical CS programs and drive customer journeys.

IT Systems Engineer

Company: Avant

Location: Chicago, IL

Posted Nov 06, 2023

Avant is seeking a Systems Engineer with 3+ years of industry experience in IT or Engineering, and a Bachelor's degree in a STEM discipline. The role involves managing internal core services, designing technical solutions, and ensuring adherence to security standards. The ideal candidate should have experience with SaaS/Azure AD environments, troubleshooting Active Directory, and working with enterprise systems like GWS, Intune, Jamf, Slack, AWS, and Tanium. Avant offers a flexible work environment, competitive benefits, and opportunities for professional development.

Vice President, Sales

Company: Smartly.io

Location: Chicago, IL

Posted Nov 06, 2023

Smartly.io is seeking a Vice President of Sales to expand and accelerate growth in the West and Central US regions. The role involves driving market growth, establishing sales processes, building brand awareness, recruiting high-caliber team members, and embodying Smartly.io's values. The ideal candidate has experience in building and scaling businesses, leading self-organizing teams, communicating with C-suite executives, and understanding the online advertising ecosystem. Smartly.io offers a comprehensive benefits package, including five weeks of paid time off, generous healthcare, wellness benefits, and equity grants.

Not-For-Profit Accounting Manager

Company: Quatrro Business Support Services

Location: Chicago, IL

Posted Nov 06, 2023

All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status. Process regular Accounts Payable and Accounts Receivable Support an accurate and timely monthly, quarterly and year end close Ensure the timely reporting of all monthly financial information Complete monthly allocations based upon time and effort reporting Ensure the accurate and timely processing of payroll and payroll updates Perform monthly bank reconciliations Track expenditures and revenues by function, activity, and grant Support budget and forecasting activities Monitor and analyze department work to develop more efficient procedures and use of resources while maintaining a high level of accuracy Work with the CFO to ensure a clean and timely year end audit Assist in development and implementation of new procedures and features to enhance the workflow of the department Support federal, state, city, local, and private grant compliance Contribute to team effort by accomplishing related results as needed Skills and Qualifications: Managing Processes, Financial Software (QuickBooks preferred), Payroll Software, Accounting, Tracking Budget Expenses, Financial Skills, Analyzing Information, Grant Management, Microsoft, Technologically Efficient Requirements: Must have at least 3 years experience in accounting Must hold at least a bachelors degree, accounting/finance focus preferred Must have experience with nonprofit organizations and grant compliance Must be able to travel to client sites across the Chicagoland area, primarily the city of Chicago and the northwest suburbs. Overview: Position: Nonprofit Accounting Manager Pay Range: $75,000 - $85,000 (based upon experience) Location: Chicago (city and suburbs) Experience/Expertise: Nonprofit Organizations and grant compliance Targeted Start Date: Ongoing Benefits: 401K Health, Dental, and Vision FSA/HRA 15 days of PTO, 5 days of sick leave, 10 holidays Employee Assistance Program Disability and Life insurance Professional Development Reimbursement Sales and Referral Incentives Responsibilities: The Accounting Manager works directly with clients to facilitate day-to-day accounting needs including accounts payable, grant management, accounts receivable, and payroll. EAB Solutions is an equal opportunity employer. We work either remotely from home or from the client site. We strongly believe in our values of people, excellence, and community and look forward to increased impact in the years to come. Obtain and maintain a thorough understanding of the financial reporting and general ledger structure. The successful candidate for this position will report directly to an EAB Solutions' CFO and play an instrumental role in the financial future of the client. Nonprofit Accounting Manager - We offer great benefits, flexible schedules, and fulfilling work. We are looking for a passionate individual to join our accounting team and provide direct accounting services.

Recruiting Coordinator (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Nov 06, 2023

Enova International is seeking a Recruiting Coordinator to join their team. The role involves coordinating interviews, maintaining the applicant tracking system, and assisting with onboarding. The ideal candidate should have 1 year of coordination experience, proficiency with an ATS, and strong communication skills. Enova offers a range of benefits including flexible work schedule, health insurance, 401(k) matching, and a sabbatical program. The company is committed to diversity, inclusion, and providing equal employment opportunities.

Customer Success Manager, Level 1-Portuguese Speaking

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Nov 06, 2023

Keeper Security, a leading cybersecurity company, is hiring Customer Success Managers for a high-producing team. The role is 100% remote with the option for hybrid work in Chicago, IL. The successful candidate will work with an established client base, grow revenue, and provide valuable cybersecurity solutions. Requirements include 1+ years of experience in Account Management or SaaS Customer Success, fluency in Portuguese and English, strong technical knowledge, and experience with Enterprise organizations. Benefits include medical, dental, vision, life insurance, 401k, and a generous PTO plan.

Statutory Reporting Accounting Consultant

Company: CNA

Location: Chicago, IL

Posted Nov 06, 2023

CNA is offering a job opportunity in the Statutory Reporting team, which is part of Corporate Financial Services. The role involves reviewing financial statements, overseeing intercompany accounting processes, and participating in process improvement initiatives. The ideal candidate should have a strong analytical mindset, excellent communication skills, and a Bachelor's degree in accounting or finance. CNA provides a comprehensive benefits package and a commitment to diversity and inclusion. The role is located in Chicago, IL and is a hybrid position.

Business Development Representative

Company: Hireology

Location: Chicago, IL

Posted Nov 06, 2023

Hireology is looking for a Business Development Representative to join their Sales team. The company has a unique culture and offers unlimited paid time off, health insurance, and other benefits. The ideal candidate will be driven, have great communication skills, and be metrics-driven.

Regional Executive (Outside Sales - Chicago, IL)

Company: Affinitiv

Location: Chicago, IL

Posted Nov 04, 2023

Affinitiv, the largest provider of data-driven marketing and software solutions in the automotive industry, is seeking a Regional Executive for the Chicago, IL territory. The role involves selling Affinitiv's products and services, maintaining a sales pipeline, and meeting revenue targets. The ideal candidate should have 5+ years of automotive software sales experience, proficiency in Salesforce, and strong computer skills. Affinitiv offers a flexible Work from Here program, comprehensive benefits, and a commitment to diversity and inclusion.

Senior Engineer, Backend (Integrations Squad)

Company: SpotHero

Location: Chicago, IL

Posted Nov 06, 2023

SpotHero, a rapidly growing company, is seeking a Senior Backend Engineer to join the Operator League for the Integrations Squad. The ideal candidate will have strong coding skills, experience in system design/architecture, and a proven track record of successful projects. Key responsibilities include identifying, designing, developing, testing, and releasing high-quality functionality, collaborating with the team, and providing support for the codebase. The company values humility, work ethic, flexibility, collaboration, technical curiosity, and constant learning. They offer excellent benefits, a flexible PTO policy, a learning budget, an annual parking stipend, and a collaborative atmosphere. SpotHero is an equal opportunity employer committed to building an inclusive 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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