Co Founder Ceo Ai Benefits Insuretech jobs in Chicago – Browse 243 openings on RoboApply Jobs

Co Founder Ceo Ai Benefits Insuretech jobs in Chicago

Open roles matching “Co Founder Ceo Ai Benefits Insuretech” with location signals for Chicago. 243 active listings on RoboApply Jobs.

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futuresight logofuturesight logo
Full-time|Remote|Remote — Chicago, Illinois, United States

As the Co-Founder and CEO of futuresight, you will be at the forefront of reshaping the AI benefits and InsureTech landscape. Your vision and leadership will drive innovation, create groundbreaking solutions, and ensure that our company remains a leader in the industry. This is an exceptional opportunity for an entrepreneur who is passionate about leveraging…

Apr 6, 2026
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futuresight logofuturesight logo
Full-time|Remote|Remote — Chicago, Illinois, United States

Join futuresight as a Co-Founder & CEO in the rapidly evolving AI WealthTech industry. We are seeking a visionary leader who is passionate about shaping the future of finance through innovative technology. As the CEO, you will drive our strategic vision, build a talented team, and lead the development of cutting-edge AI solutions to empower individuals in managing their wealth.

Apr 6, 2026
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futuresight logofuturesight logo
Full-time|Remote|Remote — Chicago, Illinois, United States

Join futuresight as a Co-Founder & CEO and lead the charge in revolutionizing AI-driven project proposals for the Architecture, Engineering, and Construction (AEC) industries. In this pivotal role, you will harness cutting-edge technology to create innovative project proposal solutions that streamline processes and enhance decision-making for stakeholders.

Apr 6, 2026
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FutureSight logoFutureSight logo
Full-time|Remote|Remote — Chicago, Illinois, United States

FutureSight is on the lookout for a dynamic and forward-thinking Founding CEO to spearhead the launch of a groundbreaking AI-driven reverse logistics orchestration platform. In today's commerce landscape, reverse logistics — encompassing all processes post-sale — has emerged as one of the most significant and least managed cost centers. High-volume workflows such as returns, warranties, exchanges, and recoveries are often handled through disparate tools, spreadsheets, and subjective decision-making.Operations, finance, and customer service teams invest substantial resources into enforcing policies, tracking evidence, managing returns, and reconciling results — frequently lacking visibility into lost value or the timeline for cash recovery. This inefficiency leads to margin erosion, protracted cycle times, and increasing operational burdens in a scaling workflow.Our mission is to create an AI-centric orchestration layer that integrates seamlessly between customers, fulfillment networks, and financial systems. Our platform will enforce policies at the entry point, capture evidence from the source, identify the most efficient return paths, and monitor outcomes until financial resolution — all without the need to replace existing ERPs, WMSs, or commerce systems.This represents a unique opportunity to establish critical infrastructure in a market exceeding $700 billion globally, paving the way for modern organizations to manage costs, risks, and recovered value post-sale.

Mar 4, 2026
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FutureSight logoFutureSight logo
Full-time|Remote|Remote — Chicago, Illinois, United States

FutureSight seeks a founding CEO to lead the launch of an AI-driven content intelligence and publishing platform. This is a remote role, with a preference for candidates in or near Chicago, Illinois. Role Overview Content remains the main channel for founders, operators, and businesses to reach their audiences. Yet, the process of turning fragmented information into high-quality, actionable content is broken. Professionals spend hours sorting through scattered data, feeds, newsletters, podcasts, articles, without a unified system to organize insights or produce consistent output. These gaps lead to lost insights, irregular publishing, and missed opportunities for audience growth. FutureSight is building an AI-centric content engine that ingests high-signal material, extracts and organizes insights, and generates drafts tailored to individual or brand voices. The platform aims to streamline the journey from raw input to structured insight to ready-to-publish content. This venture is not at square one. There is already an initial product, active users, and real feedback to support rapid iteration and market entry. The founding CEO will help define a new category at the intersection of creator tools, AI, and knowledge workflows, shaping a system of record for modern content creation used by individuals and teams. What You Will Do Acquire customers, starting with internal design partners and expanding to creators, teams, and agencies. Validate retention and willingness to pay. Drive product development in collaboration with FutureSight’s product and engineering team to launch Version 1. Lead seed fundraising alongside the initial investment. Recruit the founding team and build a strong company culture. About FutureSight FutureSight is a venture studio focused on co-creating and investing in B2B SaaS and Vertical AI startups. The studio partners with founders, offering hands-on support and early-stage capital to reduce risk and improve the odds of success. The leadership team brings together experience in venture design, product strategy, investment, operations, and marketing. Kevin Nguyen and Alan Smith guide venture design and product strategy. Prathna Ramesh leads capital strategy for new businesses. Dennis Ensing provides operational and strategic mentorship. Krista LaRiviere offers entrepreneurial and marketing expertise. Anupama Joshi supports founder development. John Carbrey, based in San Francisco, brings a track record of building and exiting multiple SaaS companies.

Apr 15, 2026
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Futuresight logoFuturesight logo
Full-time|Remote|Remote — Chicago, Illinois, United States

Join Futuresight as a Co-Founder & CEO, where you will spearhead innovative solutions in the AI Freight and Supply Chain sector. We seek a visionary leader who is passionate about transforming logistics through advanced AI technologies. In this dynamic role, you will guide strategic initiatives, foster partnerships, and drive company growth while working remotely from Chicago.

Apr 6, 2026
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futuresight logofuturesight logo
Full-time|Remote|Remote — Chicago, Illinois, United States

Join futuresight as a Co-Founder & CEO, where you will play a pivotal role in shaping our innovative AI RIA Compliance solutions. As a visionary leader, you will guide our strategic direction, foster a culture of excellence, and drive the growth of our company in the rapidly evolving landscape of regulatory technology.

Apr 6, 2026
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futuresight logofuturesight logo
Full-time|Remote|Remote — Chicago, Illinois, United States

Join futuresight as we embark on an innovative journey to redefine the future of technology and entrepreneurship. We are seeking a visionary Entrepreneur in Residence - Technical Co-founder (CTO) who is passionate about driving technological advancements and building groundbreaking solutions. In this role, you will collaborate with our dynamic team to develop and launch transformative products that will have a significant impact on various industries.

Apr 6, 2026
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Futuresight logoFuturesight logo
Full-time|Remote|Remote — Chicago, Illinois, United States

Join Futuresight as an Entrepreneur in Residence, where you will have the unique opportunity to shape the future of innovative business ventures. This remote role calls for a visionary leader ready to take on the challenge of potentially becoming a future CEO or founder. You will engage directly with our team and stakeholders to explore new ideas, drive strategic initiatives, and cultivate a thriving entrepreneurial ecosystem.

Apr 6, 2026
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accentedge, LLC logo
Full-time|On-site|Chicago, Illinois, United States

We are looking for a highly skilled and detail-oriented Executive Assistant to the CEO at accentedge, LLC. This critical position involves providing comprehensive support to the CEO by managing schedules, facilitating communication, and handling various administrative tasks to ensure the executive office runs smoothly. The successful candidate will possess strong organizational abilities and the capacity to manage multiple priorities with precision.Key ResponsibilitiesCoordinate and manage the CEO's calendar, including scheduling meetings and arranging travel to maximize productivity.Serve as the primary liaison between the CEO and both internal and external stakeholders.Draft, manage, and oversee correspondence, reports, and presentations for executive meetings.Prepare meeting agendas, take minutes, and track action items to ensure follow-up.Assist with project management and coordination of key initiatives, ensuring milestones are communicated and met.Organize company events, board meetings, and team-building activities as required.Uphold confidentiality and manage sensitive information with the utmost integrity.Actively seek opportunities to enhance efficiency and effectiveness within the executive office.QualificationsMinimum of 5 years' experience as an executive assistant or in a similar role supporting senior management.Exceptional organizational and multitasking skills, with the ability to effectively prioritize tasks.Strong written and verbal communication skills, exhibiting a high level of professionalism.Proficiency in Microsoft Office Suite (Word, Excel, PowerPoint, Outlook) and other relevant office management software.Proven ability to manage intricate schedules and work efficiently under tight deadlines.Strong analytical and problem-solving capabilities, with a keen attention to detail.Ability to work both independently and collaboratively in a fast-paced environment.Experience in technology or startup environments is an advantage.Preferred QualificationsBachelor's degree in Business Administration or a related discipline.Familiarity with project management tools and software.Experience dealing with sensitive and confidential information.Flexibility to work varied hours as necessary to accommodate the CEO’s schedule.

Feb 28, 2026
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IDEO logoIDEO logo
Full-time|$80K/yr - $90K/yr|On-site|Chicago, IL

Payroll & Benefits AdministratorAbout the Role:At IDEO, we leverage design thinking to shape innovative products, services, and experiences. As the Payroll & Benefits Administrator within our Talent team, you will play a vital role in enhancing the employee experience. Your responsibilities include overseeing payroll, retirement plans, and benefits programs to ensure they are executed with precision and care. Collaborating closely with the People and Finance teams, you will manage biweekly payroll, 401(k) administration, open enrollment, reporting, and logistics for global mobility—balancing meticulous attention to detail with a compassionate approach to our employees' needs.Your Responsibilities:Oversee biweekly payroll processing with a focus on accuracy and punctuality using ADP.Manage W2 preparation and year-end payroll processes.Conduct NDX testing and assist in payroll compliance audits.Handle quarterly payroll adjustments effectively.Administer the 401(k) program, including enrollments, compliance testing, and vendor management.Lead the execution of open enrollment, collaborating on communication and educational initiatives.Facilitate global mobility processes for employees relocating across different markets.Collaborate with Finance on payroll-related financial reporting, reconciliations, and forecasting inputs.Identify and implement improvements to streamline systems and enhance clarity in compensation and benefits processes.Conduct monthly benefits billing reconciliation.Manage approvals for expense reports.Engage in ad hoc projects as necessary.

Mar 5, 2026
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humanagency logohumanagency logo
Full-time|Remote|Chicago

Location: Remote (U.S. or Canada) Type: US Applicants – Full-Time; Canadian Applicants – Independent Contractor About humanagency At humanagency, we are in a phase of rapid growth and are actively seeking exceptional talent across various disciplines to join our team. Our mission is to onboard individuals ranging from creative producers to technical experts and entrepreneurial leaders who can contribute significantly to our next chapter of expansion. We pride ourselves on being a company of doers. Our leaders are hands-on, teams operate collaboratively, and every member has a voice in the projects we launch. We welcome feedback, learn swiftly, and continuously strive to elevate our standards. The most compelling ideas are what drive us, regardless of their origin, as our clients depend on us to provide outstanding results consistently. We treat our clients' missions, products, and financial outcomes with utmost respect. By immersing ourselves in their environment, we become stewards of their objectives and partners in tackling substantial challenges. Every product, strategy, or asset we develop must be both aesthetically pleasing and practical; it should be usable and designed to make a tangible impact in the real world. Our team is our most valuable resource, and our growth depends on hiring individuals who propel us forward. We actively seek team members across strategy, engineering, design, data, and operations who inspire us to reach new heights. We believe in hiring individuals who are better than us, ensuring our collective advancement. We collaborate with organizations of all sizes to explore, design, and implement AI strategies that are secure, scalable, and human-centered. We are committed to the belief that AI should enhance human potential rather than replace it, and we integrate this conviction into every client engagement. From advisory services and tools to implementation and education, we meet our clients at their level and assist them in integrating AI in ways that resonate with their missions and values. Our objective is to empower teams to work more intelligently, move more rapidly, and unlock new possibilities through thoughtful, responsible innovation. Throughout this journey, we lead with purpose, passion, and a sense of adventure. We engage in meaningful work with people we deeply care about, making the experience an adventure worth embarking on. At humanagency, our identity and our work ethos are intertwined. The Opportunity You are an entrepreneur at heart. We are looking for a dynamic individual who will primarily build and manage their own venture within the humanagency studio while also establishing the operational framework for how ventures are executed across the studio. You will lead weekly studio meetings, act as the primary critic, and hold accountability for project outcomes. You will be the persuasive force that verifies the success of projects or indicates areas needing improvement. This role combines the responsibilities of a CEO and product leader with strong sales capabilities. If you envision yourself as a driving force in shaping the future of our ventures, we want to hear from you!

Mar 11, 2026
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O'Hagan Meyer logo
Full-time|$70K/yr - $90K/yr|On-site|Chicago, Illinois, United States

O'Hagan Meyer is a vibrant and expanding law firm dedicated to delivering practical, innovative, and outstanding litigation and advisory services to our esteemed clients. We are in search of an enthusiastic and detail-oriented Benefits Administrator with substantial experience in managing employee benefits across various states, including but not limited to California and New York. The perfect candidate will have a robust foundation in benefits administration and compliance, featuring comprehensive knowledge of federal and state regulations such as the Affordable Care Act (ACA), ERISA, COBRA, HIPAA, and relevant leave laws. This role demands the capability to oversee the entire lifecycle of benefits administration, including enrollment, compliance tracking, audits, reporting, and employee assistance. Key Responsibilities:Administer and oversee employee benefits programs in accordance with ACA, ERISA, COBRA, and relevant state regulations.Manage benefits enrollment, qualifying life events, and annual open enrollment procedures.Ensure precise ACA tracking, measurement periods, and reporting (including 1094/1095 filings).Support ERISA compliance, including plan documentation, SPD distribution, and audit preparedness.Coordinate COBRA administration and vendor management.Oversee leave of absence programs, including FMLA, CFRA, state disability, and paid family leave.Assist with claims resolution and act as a liaison between employees and benefits providers.Maintain accurate records and uphold data integrity across HRIS and benefits systems.

Mar 18, 2026
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Akunacapital logoAkunacapital logo
Full-time|On-site|Chicago, IL

Join Akunacapital as a Compensation & Benefits Coordinator, where you will play a vital role in shaping our employee compensation structure and benefit programs. Your expertise will ensure that our compensation packages attract and retain top talent, while also aligning with our company's strategic goals.In this position, you will collaborate with HR and management to analyze market trends, oversee benefit programs, and maintain compliance with regulations. Your analytical skills will help us make informed decisions about compensation policies and employee satisfaction.

Apr 6, 2026
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Lewis Associates logoLewis Associates logo
Full-time|On-site|Chicago

Lewis Associates is seeking a dedicated Employee Benefits Attorney to join our legal team in Chicago. In this role, you will provide expert legal advice on employee benefits, including retirement plans, health benefits, and compliance with ERISA regulations. You will work closely with clients to ensure adherence to legal standards and help navigate complex legal frameworks.

Nov 12, 2014
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A. O. Garcia Agency logoA. O. Garcia Agency logo
Full-time|Remote|Chicago, Illinois

The Remote Client Benefits Representative at A. O. Garcia Agency supports clients in Chicago, Illinois by guiding them through their benefits and answering questions. This position is fully remote, allowing you to work from home while serving clients in the Chicago area. Responsibilities Respond to client questions and address concerns related to their benefits Communicate benefit details clearly and provide helpful support during each interaction Collaborate with a team while working remotely Location This role is remote, but applicants must reside in Chicago, Illinois.

Apr 20, 2026
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Abercrombie & Fitch Co. logoAbercrombie & Fitch Co. logo
Full-time|On-site|Chicago

Join Hollister Co. as a Brand Representative, where you will embody the spirit of our brand and engage with customers to create a memorable shopping experience. Your role will involve promoting our products, providing excellent customer service, and contributing to a vibrant store atmosphere.

Apr 13, 2026
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A. O. Garcia Agency logoA. O. Garcia Agency logo
Part-time|Remote|Chicago, Illinois

The A. O. Garcia Agency is looking for a Part-Time Benefits Services Representative to support clients remotely from Chicago, Illinois. This position centers on assisting clients with their benefits questions and providing clear guidance on available options. Key Responsibilities Answer client questions about benefits through phone and online channels Offer straightforward explanations of benefits options Maintain attentive and dependable customer service Work Arrangement This is a remote, part-time role. The position allows for working from home while helping clients and contributing to the agency’s service objectives.

Apr 20, 2026
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Global Elite Empire Consultants logoGlobal Elite Empire Consultants logo
Remote Client Benefits Advisor

Global Elite Empire Consultants

Full-time|Remote|Chicago, Illinois

Are you weary of the daily grind of requesting time off, enduring traffic, and facing income limitations? If so, this opportunity may be the change you've been searching for.We are looking for motivated individuals eager to take charge of their schedules and earnings by assisting clients who have expressed interest in their benefit options.Forget about cold calling and micromanagement. Our system is straightforward and will yield results if you put in the effort.Your Responsibilities:Engage with interested clients.Guide them through simple options.Assist them in setting up their benefits.Your Rewards:Work remotely from the comfort of your home.Enjoy flexible working hours.Earn a performance-based income with no ceilings.Receive comprehensive training and mentorship.Ideal Candidate: We seek individuals who are ready to invest in themselves and stop trading time for money.*All interviews will be conducted via Zoom video conferencing.(Global Elite Empire Consultants is a third-party recruiter, not an insurance agency)

May 1, 2026
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360 IT Professionals logo360 IT Professionals logo
Full-time|On-site|Chicago

Join our dynamic team at 360 IT Professionals as an Oracle EBS Advanced Benefits Module Subject Matter Expert. In this role, you will leverage your extensive knowledge of Oracle EBS to guide our clients in optimizing their benefits administration processes. You will collaborate with cross-functional teams to implement best practices and ensure the effective utilization of the Oracle EBS Advanced Benefits Module.Key responsibilities include conducting training sessions, providing technical support, and serving as a trusted advisor to clients. Your expertise will be integral in enhancing operational efficiencies and ensuring compliance with industry standards.

Apr 14, 2016

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