Unlimited Pto Jobs in Chicago, IL

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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.

Technical Data Analyst - Remote

Company: Argo Group

Location: Chicago, IL

Posted Aug 26, 2023

Argo Group is a specialty insurance company looking for a Technical Data Analyst to join their Claims Operations Compliance and Data team. The role involves performing work under limited technical direction, solving difficult problems, gathering and manipulating claims data, supporting U.S. Claims compliance, managing the Reporting Calendar, and serving as the key Claims business contact. The ideal candidate should have good business acumen, a working knowledge of the claims business environment, at least five years of experience in data and compliance in a claims environment, and experience supporting specialty programs and partnering with TPAs, MGAs, or other outside vendors. The role requires proficiency in MS Office Suite, SQL, Cognos Business Studio, Power BI, and Snowflake, as well as excellent communication and time management skills.

Yelp - Inside Sales Representative (Remote - Central Region), application via RippleMatch

Company: RippleMatch

Location: Chicago, IL

Posted Aug 30, 2023

Yelp is seeking an Inside Sales Representative (ISR) to sell advertising space on Yelp to local businesses across the US and Canada. The role requires educating business owners about the value of Yelp's advertising platform and achieving monthly sales goals. The ideal candidate should have an appetite for learning, be multi-tasking, and have excellent communication skills.

Production Support Manager

Company: Beyond Finance

Location: Chicago, IL

Posted Aug 29, 2023

For eligible full-time employees, we offer:Considerable employer contributions for health, dental, and vision programsGenerous PTO, paid holidays, and paid parental leave401(k) matching programMerit advancement opportunitiesCareer development & trainingAnd finally, our team spirit and culture! You will work in a semi-autonomous and fast-pacedenvironment.What You'll Do:&9679; Lead a team to optimize the support of Operations users of CRM tools and dependent systems.&9679; Monitor production environments and proactively address alerts and escalations.&9679; Provide technical guidance and expertise to diagnose and debug production issues coming fromagents, alerts or other escalation paths.&9679; Design, maintain, and improve incident management and alerting processes as well as identifymonitoring opportunities.&9679; Drive automation initiatives to streamline operational tasks and reduce workflow inefficiencies.&9679; Increase incident report/resolution efficiencies and lower the human intervention time on relatedtasks.&9679; Lead and mentor a team of Production engineers, providing guidance and support in theirday-to-day activities and career growth.&9679; Provide comprehensive insights on product related trends, bugs and other system errors toProduct and Engineering teams.&9679; Perform problem & incident management, work with vendors and other technical personnel forproblem resolution.&9679; Lead cross-functional post-incident process reviews to ensure continuous improvement ofoperations, enabling the delivery of post incident reports to customers and stakeholders.&9679; Influence skills to create a culture of change, excellence and innovation while constructivelychallenging the status quo.What We Look For:&9679; Bachelor’s Degree or Master’s in Computer Science, Engineering, Software Engineering or arelevant field.&9679; 5+ years of experience Managing Production Support/DevOps/SRE Teams.&9679; 5+ years of experience in providing technical or infrastructure support.&9679; Experience with open-source technologies and cloud services (AWS preferred).&9679; Critical thinking/analytical leadership experience.&9679; Knowledge of scripting languages such as JavaScript, Ruby, Python, and Bash.&9679; Proven success driving monitoring projects and related initiatives.&9679; Ability to manage multiple complex projects - work prioritization, planning and task delegation.&9679; Strong SQL experience.&9679; Proven ability to work successfully with limited supervision.Why Join Us?While you make a difference for others, we’ll work to make a difference for you, providing an uplifting, collaborative work environment and benefits that reflect your value to us. You willprovide strategic, innovative, and cost-effective support solutions to increase efficiency, reliability, andintegration of our services and operations. We cultivate an environment of community, connection, and belonging across our entire organization.Beyond Finance does not accept unsolicited resumes from individual recruiters or third-party recruiting agencies in response to job positions.  No fee will be paid to their parties who submit unsolicited candidates directly to Beyond Finance employees or the Beyond Finance HR team.  No placement fee will be paid to any third party unless such a request has been made by the Beyond HR team. If you’re looking to join a forward-thinking, rapidly growing organization with helping people as its number one goal, we want to hear from you.About the Role:We are seeking a Production Support Manager to support Beyond Finance’s ambitious growth. Through compassionate, individualized care, supportive user-centric technology, and customized financial solutions, we’ve helped over 300,000 clients on their path to a debt-free life.While we’re proud of what we’ve already accomplished (over $2 billion in resolved debt), we're searching for new collaborators to help us get to the next level! At Beyond Finance, we’ve made it our mission to help everyday Americans escape the endless cycle of crippling debt and step into a brighter financial future.

Technical Product Owner

Company: BenchPrep

Location: Chicago, IL

Posted Aug 29, 2023

We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.We are looking for high performing and motivated professionals who are excited about the chance to leverage technology to impact the lives of millions of learners.  Join us.At BenchPrep, we pride ourselves on offering a great total rewards package to each employee, including medical and ancillary benefits, potential for yearly bonus, stipends for work-from-home expenses, flexible paid time off (our version of unlimited PTO), annual professional development stipend dollars, and of course, a competitive base salary.  The salary range for this position is being reviewed, and is set based on Chicago market data.  Please note this refers to the amount BenchPrep is willing to pay at the time of this posting. For information on how we collect and dispose of information, please view BenchPrep’s privacy policy statement here. Culture is our lifeline at BenchPrep.  We celebrate our people, both professionally and personally. We care about learning so much that we offer employees $1,200 annually to develop their skills so they can continue to operate everyday with new skills.  It’s no wonder we were selected in Inc’s Best Workplaces of 2020 and Crain’s 2020 Best Places to Work in Chicago lists.  We are an equal opportunity employer and value diversity at our company. We are strong, dynamic, and wear many hats. We are inspired by a shared mission to help millions learn better and faster through our unique platform.You should have: 3-5 years of experience in a technical product owner roleA demonstrated history of agile development methodologiesA demonstrated history of backlog management A demonstrated history of user story authoringA demonstrated history of project management skillsExperienced in the coordination of usability sessionsExperienced with training of internal stakeholdersCross-functional communication skillsFamiliarity with customer/market research Experience with MS Office, JIRA, Confluence, GSuite**Note: We know that excellent candidates can have all sorts of backgrounds and experiences, so please don’t hesitate to apply even if you don’t meet 100% of the listed requirements!Life at BenchPrep:  We work at BenchPrep because we’re dedicated to the mission and each day we have an opportunity to be challenged and learn.  We work hard and have lots of fun. True to startup culture, we aren’t afraid to roll up our sleeves to get the job done. We incorporate the latest in learner-centered technology, including personalization, gamification, data science, usability and omni-channel delivery.  We’re sitting in a pivotal time in the BenchPrep history. You’re a critical thinker who is analytical and collaborative, and you thrive on understanding and translating business objectives to inform and communicate clearly defined and strategically prioritized stories and acceptance criteria.  You have experience working in an agile SaaS product development environment, and concurrently leading frequent discovery, ideation, and development initiatives across multiple teams.What you'll do as a Technical Product Owner:Manage epics//feature backlog grooming and prioritizationManage user story development, sprint planning, and sprint reviews for 2+ developer teams and provide support for highly technical projectsDevelop user stories for assigned projects, ensure user stories are “ready” for development to start work, that each story has the correct acceptance criteria Provide support for client-facing teams and own major escalations and high value projectsTrain internal teams on new features and products Work with development teams to ensure committed user stories are completedCollaborate with Product Management leadership to understand and translate business objectives into actionable user stories and acceptance criteriaProvide regular development updates and insights to Product Management leadership Collaborate with Customer Success, Sales, and Development  team members, defining requirements for customer SOW engagements Engage with customers to gain a better understanding of their work and how BenchPrep products can assist themRetroactively review development initiatives and celebrate team successesAbout the team: Here at BenchPrep, the Product Management team is responsible for the growth of our business. The number of learners on our cloud-based learning platform has reached almost 7 million in 2021. We’re committed to helping people learn better, and that starts with our own people. This position is remote (along with all of our BenchPrep positions).About the role:We are looking for a dynamic and talented Technical Product Owner to join our growing team.  As a key player on our Product team, you are prepared to build productive cross-functional relationships and leverage your technical expertise to advance an ambitious product roadmap. Title: Technical Product OwnerReports to:  Director of Product ManagementAbout Us:  We deliver the most advanced and flexible learning experience for certification, credentialing, test prep, continuing education, and training.

Technical Product Owner

Company: BenchPrep

Location: Chicago, IL

Posted Aug 29, 2023

BenchPrep is seeking a dynamic and talented Technical Product Owner to join their growing team. The role involves building cross-functional relationships, leveraging technical acumen to advance an ambitious product roadmap, and managing stakeholder approval processes. The successful candidate will collaborate with UX Design and Technology teams, manage development initiatives, and provide regular updates to Product Management and cross-functional stakeholders.

Sr Product Manager (Loyalty)

Company: Grubhub

Location: Chicago, IL

Posted Aug 26, 2023

Grubhub is a company that values innovation, teamwork, and fun. They are looking for a Senior Product Manager to join their Loyalty team and create end-to-end diner experiences. The role requires a strong product management background, customer-centric mindset, and technical and analytical acumen.

Account Executive - ISR Public Sector

Company: Cisco Meraki

Location: Chicago, IL

Posted Aug 29, 2023

The text describes the company culture and values of Cisco Meraki, highlighting the importance of teamwork, innovation, and customer satisfaction. It also mentions the benefits and perks offered to employees, such as flexible work arrangements, paid time off, and opportunities for growth and development.

Enterprise Application Support Manager

Company: Enfusion

Location: Chicago, IL

Posted Aug 30, 2023

Enfusion will not discriminate on the basis of age, race, color, gender, marital status, sexual orientation, gender identity, pregnancy, national origin, religion, veteran status, physical or mental disability, genetic information, creed, citizenship or any other status protected by laws or regulations in the locations where we do business. *Note: This good faith pay range is provided in compliance with NYC law and the laws of other jurisdictions that may require a salary range in job postings.Perks of working for Enfusion • Competitive compensation • Company paid medical insurance • Generous PTO package • Entrepreneurial environment • Catered lunch every Wednesday • Small team with growth opportunity  Enfusion offers a competitive compensation and benefits package, retirement and pension plans, and generous Paid Time Off policy; and paid parental leave. Other perks include commuter benefits, and an employee assistance program.  All benefits and programs are subject to applicable eligibility requirements. Enfusion is fully committed to providing equal employment opportunity to job applicants and employees in recruitment, hiring, employment, compensation, benefits, promotions, transfers, training, and all other terms and conditions of employment. Along with having an in-depth understanding of how the product works. What You’ll Do:Deploy and provide application support for industry leading investment management platforms running on Unix/Linux platforms. Investigate issues and escalate to the proper development teams. Learn and become the technology expert behind how the system works. Will be the escalation point for major platform issues.Assess patterns in support tickets, requests and alerts helping increase efficiencies of training and support. Identify and implement areas for process improvement.Work with development to forecast severity of issues and throughput for fixing issues across teams. Maintain awareness of issue status after handing off to other teams.Provide root cause analysis as required internally. Oversee response to monitoring and support issues.Perform coaching and regular 1:1 with all members of your team.Maintain working relationships with other development teams and client facing teams.What You’ll Need:Computer Science/Engineering background (or related)Exposure and experience to finance (preferred)Strong critical thinking skillsComfortable with Linux CentOS and Linux Mint and Bash scriptingAbility to read and understand Java source codeBasic Networking (DNS, packet loss, etc)Ticketing system experience (Jira/Zendesk/Logs experience etc)Comfortable working remote during off hours and participate in shift rotations Good communication, both verbally and writtenAbility to work with global teams (EMEA, APAC, US)Process driven mentalityAbility to focus on incident response and management Keep track of incidents and support trendsProvide ongoing training and development to team6-8 years of experience managing production support of mission critical IT applicationExcellent leadership qualities to engage and manage stakeholdersSelf-motivated and thrive in a demanding work environment The salary for this position is $120,000 - $140,000 + bonus + benefits. This will require knowing how to diagnose, judge the criticality, and establish the scope of the issue in real-time. Imagine being a key member driving the shape and function of the platform which thousands of clients rely upon each day for their trading needs.  The Role:In this role, you will act as a liaison between our client-facing teams and internal development. In fact, we've been recognized as Best Managed Services Provider at the HFM EU Services Awards.  We help fund managers around the world streamline their operations, mitigate risk, and improve transparency and reporting so they can confidently focus on what they do best – invest.As a company, we’re absolutely committed to the growth, development, and well-being of our people. Enfusion is where you can pursue your passion, showcase and further develop your skills, and launch a meaningful and rewarding career.  If you're looking for a culture that is inclusive, collaborative, entrepreneurial, values diversity, fosters and rewards creative exploration, and strives to continually exceed client expectations then we're looking forward to hearing from you.   Learn more about Enfusion by visiting www.enfusion.com and apply today!Enterprise Application Support ManagerThe Team:We’re a team of technology centric individuals that strive to reduce the burden on our clients by providing a homegrown front-to-back platform that streamlines client processes in a single frame of reference. The purpose of this role is to oversee tier I & II technical support. We endeavor to maintain a drug-free workplace.

Software Administrator II

Company: Grubhub

Location: Chicago, IL

Posted Aug 26, 2023

Grubhub is seeking a Software Administrator II to join their Care Systems & Tools team. The role involves maintaining and supporting Care's software systems, managing business leader technology requests, troubleshooting software performance issues, and collaborating with various teams to implement software product enhancements. The ideal candidate should have a Bachelor's degree, 5+ years of related work experience, 2+ years of advanced administration experience for CRM solutions (preferably Zendesk), and experience as a systems administrator for telephony products. Strong communication skills, project management abilities, and the capacity to understand business processes and translate them into application functionality are also required. Grubhub offers flexible PTO, health and wellness benefits, competitive compensation, free meals, and opportunities for social impact.

Sr. Manager, Core US Strategy

Company: Grubhub

Location: Chicago, IL

Posted Aug 27, 2023

The opportunity involves connecting diners with a network of over 300,000 restaurants nationwide, offering innovative technology, user-friendly platforms, and streamlined delivery capabilities. The role involves developing city-specific strategies, leading their implementation, and working closely with the Head of Core US Strategy. The ideal candidate is a curious, problem-solving, analytical, organized project manager who is excited about working on complex projects. The role offers the chance to work on critical strategic questions, develop KPIs, and prepare executive recommendations.

Director, Core US Strategy

Company: Grubhub

Location: Chicago, IL

Posted Aug 26, 2023

The text describes a job opportunity for a Core US Strategy Director at Grubhub. The role involves building a new team to own the company's core strategic development and execution, including leading the Key City Strategy initiative. The ideal candidate is a strong leader with experience in consulting, corporate strategy, or investment banking/private equity. The role requires data and presentation expertise, ownership, curiosity, and project management skills. The successful candidate will work closely with the Head of Core US Strategy and SVP of North American Strategy to create, implement, and monitor Grubhub's annual strategic plan.

CRM Associate (Lifecycle Campaigns)

Company: Grubhub

Location: Chicago, IL

Posted Aug 27, 2023

We evaluate qualified applicants without regard to race, color, religion, age, sex, sexual orientation, gender identity, national origin, disability, veteran status, and other legally protected characteristics. You'll receive a great compensation package with eligibility for generous incentives, bonuses, commission, or RSUs (role-specific).Free Meals. Braze, Marketo, Hubspot, Salesforce Marketing Cloud).Working knowledge of HTMLComfortable working in Tableau and Google AnalyticsAnd Of Course, Perks!Flexible PTO. Excellent medical, dental and vision benefits, 401k matching, employee network groups and paid parental leave are just a few of our programs to support your overall well-being.Compensation. Please note that only those inquiries concerning a request for reasonable accommodation will be responded to from this email address.If you are a resident of the State of California and would like a copy of our CA privacy notice, please email [email protected]. If you're applying for a job in the U.S. and need a reasonable accommodation for any part of the employment process, please send an email to [email protected] and let us know the nature of your request and contact information. Brand, New Verticals, Enterprise Restaurants) to support/deliver CRM best practices and campaign strategy recommendations to drive key initiatives that ladder up to our company goals.Own development of key messaging points for CRM communications.Work with the Analytics team to manage weekly reporting for all CRM channels, including engagement metrics and business impact monitoring, elevating recommendations for next actions/strategies based on key results/insights.What You Bring to the Table : 2-3 years of experience in email, push, and in-app messagingBachelor's degree requiredEnd-to-end CRM strategic campaign planning and management/execution (including creative development) experienceExceptional written and verbal communication skills, with attention to detail and the ability to clearly communicate complex information to less technical audiencesStrong interpersonal skills, a positive attitude, and the ability to operate in a fast-paced environment with ambiguityExperience working with CRM Operations/Technical staff.Self-starter with a passion for marketing and the desire to deepen knowledge, someone with a "roll up your sleeves and dive-in" attitudeAnalytical mindset - Ability to understand, articulate, and make decisions based on how CRM impacts overall business goals and KPIsAbility to manage multiple projects while still ensuring all timelines and key milestones are metExperience working cross-functionally with Loyalty, Brand, Data Science, Creative Analytics, and Product teams, as well as Legal and ComplianceGot these? At Grubhub we believe in giving back through programs like the Grubhub Community Fund . Our employees get a weekly Grubhub credit to enjoy and support local restaurants.Social Impact. Grubhub employees enjoy a generous amount of time to recharge.Health and Wellness.

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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