Co-Founder & CEO - AI Communication Agents for Freight & Logistics FutureSightCo-Founder & CEO - AI Communication Agents for Freight & LogisticsChicago, ILRemoteYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. HawkAI deploys always-on, multi-channel "AI workers" that autonomously manage high-volume freight communications across calls, texts, and emails, integrating directly with core freight systems including TMS, load boards, and broker/carrier databases.
Co-Founder & CEO - AI Accounting Agents for CPA Firms FutureSightCo-Founder & CEO - AI Accounting Agents for CPA FirmsChicago, ILRemoteYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. Crossfoot is agentic accounting for small-to-mid CPA firms; a segment where accountant shortages are structural, client intake is capped by production headcount, and the manual close and tax prep workflow consumes the majority of senior staff capacity.
NewAI Engineer III TekWissen LLCAI Engineer IIIMettawa, ILRemote$90–$105Knowledge / Skills: Primary expertise (required): Possess deep, hands-on experience with the AWS Strands agent framework (or equivalent) building AI/LLM-driven agentic features: prompt design, tool/function design and calling, observability, retrieval-augmented generation (RAG), streaming responses, token/cost management, guardrails, and evaluation of model outputs. Demonstrate strong API development skills: designing and building robust, performant APIs (FastAPI strongly preferred), including async request handling, Pydantic data modeling, authentication/authorization, versioning, rate limiting, observability, and OpenAPI contracts.
NewAI Identity & Access Management Architect Artech LLCAI Identity & Access Management ArchitectChicago, IL$58–$64 / hourThe ideal candidate will have deep expertise in workforce identity security, modern authentication protocols, Zero Trust architecture, identity governance, and emerging agentic identity/AI architectures . Evaluate security technology choices covering cryptography, cloud-native services, secrets management, credential vaulting, data protection, and client-server communication.
AI Prompt Engineering Lead 1872 ConsultingAI Prompt Engineering LeadChicago, ILDesign and maintain a library of complex, production-grade system prompts for Claude Cowork and ChatGPT Custom GPTs tailored to legal tasks: contract review, clause extraction, due diligence checklists, legal research summaries, and matter intake. You'll partner with key business stakeholders to understand existing processes, workflows, etc., recommend AI solutions to automate existing business processes, and then deliver the solutions using tools like Claude Cowork and ChatGPT Custom GPTs.
NewAI Solution Architect Tekfortune Inc.AI Solution ArchitectChicago, ILTekfortune is a fast-growing consulting firm specialized in permanent, contract & project-based staffing services for world s leading organizations in a broad range of industries. Build enterprise Generative and Agentic AI platforms featuring high-performance RAG (Retrieval-Augmented Generation) pipelines and vector database integrations.
Co-Founder & CEO - AI Clinical Documentation Compliance FutureSightCo-Founder & CEO - AI Clinical Documentation ComplianceChicago, ILRemoteYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. The market signal is incredibly strong: Unprompted Product Pull: Every single lead described the exact product we want to build: a pre-billing, real-time, EHR-integrated flagging layer that checks documentation against payer-specific rules before claims are submitted.
Co-Founder & CEO - AI Healthcare Revenue Recovery FutureSightCo-Founder & CEO - AI Healthcare Revenue RecoveryChicago, ILRemoteYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. Reclaim AI resolves denied and aged claims end-to-end, embedding outcome-based contingency pricing—meaning practices pay zero upfront, and we only take a cut of the dollars we successfully recover, for our target ideal customer profile (practices with $80K+ in annual recoverable claims).
Technical Co-founder (CTO) - AI Collections Agent FutureSightTechnical Co-founder (CTO) - AI Collections AgentChicago, ILRemoteIn return for that level of commitment, you receive founder-level equity, founder-level authority with co-decision rights on product, technology, hiring, fundraising, and strategy, and a genuine partnership with the CEO on every material decision. Finance teams at B2B companies lose cash the same way every month: an invoice ages past 45 days, someone sends an email, no reply, someone calls, voicemail, they call again next week, still nothing.
Technical Co-founder (CTO) - AI Legal Front Desk FutureSightTechnical Co-founder (CTO) - AI Legal Front DeskChicago, ILRemoteStrongly preferred: prior founder or early-stage technical leadership experience; background in legal tech, healthcare, or another trust-sensitive vertical; capability to self-host custom models to meet legal and privacy needs. In return for that level of commitment, you receive founder-level equity, founder-level authority with co-decision rights on product, technology, hiring, fundraising, and strategy, and a genuine partnership with the CEO on every material decision.
NewAI Governance and Compliance Engineer / Lead VeeRteq Solutions Inc.AI Governance and Compliance Engineer / LeadChicago, ILYou will use Digital Experience Monitoring (DEM) and data insights to identify issues, drive improvements, and enhance the overall employee experience while partnering across Infrastructure, Operations, and business teams . Experience managing internal technology products or enterprise platforms within digital workplace or IT service environments (e.g., Microsoft 365, endpoint management, ServiceNow, or Ivanti) required.
NewAI Deployed Engineer Javen TechnologiesAI Deployed EngineerChicago, ILRemoteImplement and extend Model Context Protocol (MCP) servers and clients to connect AI agents with enterprise tools, APIs, and data sources. AI Agent Development Design, build, and deploy AI agents and multi-agent systems that automate complex workflows end-to-end.
Co-Founder & CEO - AI E-commerce Operations System FutureSightCo-Founder & CEO - AI E-commerce Operations SystemChicago, ILRemoteYou’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. Sellers operating across Amazon, Shopify, eBay, Walmart, and other channels constantly switch between dashboards, reconcile conflicting data, and make hundreds of operational decisions every day across pricing, inventory, advertising, fulfillment, and customer support.
Product & Technical Co-founder (CPTO) - AI Compliance Platform FutureSightProduct & Technical Co-founder (CPTO) - AI Compliance PlatformChicago, ILRemoteProduct Build — Ship a marketing review prototype into production with a design partner early adopter, then deliver communications surveillance, trading oversight, audit-ready logs and reporting; release GA v1 covering all core modules except regulatory filings within 9 months, and expand into regulatory filings and enterprise integrations through 18 months. In return for that level of commitment, you receive founder-level equity, founder-level authority with co-decision rights on product, technology, hiring, fundraising, and strategy, a board or board-observer seat as appropriate to the cap table and stage, and a genuine partnership with the CEO on every material decision.
AI Product & Innovation Sr. Consultant Mitchell MartinAI Product & Innovation Sr. ConsultantChicago, IL$105,600–$199,480 / yearBased in Chicago, IL, this full-time position involves end-to-end management of AI workstreams, requiring strong analytical and strategic skills. Data Pipelines | Model Evaluation Tools | Semantic Layers | Analytical Modeling Software | Presentation Tools.
AI Engineering Factory Lead Artech LLCAI Engineering Factory LeadChicago, IL$110–$120 / hourKey Phase 0 responsibilities: 1) Connecting across the Functional streams to support staffing and defining key skills 2) Defining the AI solutioning approach - what exists today, how do we leverage SAFE Methods 3) What is the responsibility of the AI CoE vs. AI Delivery Lead who designs and operationalizes a scaled AI Factory model, overseeing repeatable pipelines for use-case intake, model development, testing, and deployment across multiple parallel AI workstreams.
AI Engineer with Healthcare domain experience Thunderhawk Technology Partners LLCAI Engineer with Healthcare domain experienceChicago, ILDesign and prototype agentic AI workflows leveraging large language models (LLMs), retrieval systems, structured data, APIs, tools, and business rules to automate complex business processes. Strong understanding of large language models (LLMs), prompt engineering, retrieval-augmented generation (RAG), and autonomous decision-making frameworks within enterprise AI environments highly preferred.
Senior Java with AI Experience PozentSenior Java with AI ExperienceChicago, ILPractical experience personally implementing one or more AI capabilities such as LLM integration, prompt engineering, RAG, embeddings/vector search, semantic search, classification, summarization, AI-assisted workflow automation, or decision-support capabilities. Develop and integrate AI/GenAI capabilities hands-on, including prompt design, LLM integration, RAG pipelines, embeddings/vector search, semantic search, classification, summarization, and AI-assisted communication workflows.
AI Engineer III Artech LLCAI Engineer IIIMettawa, ILRemote$100–$110 / hourThe position involves designing, building, and maintaining a FastAPI (Python) backend that integrates large language models and other AI capabilities into enterprise production-grade services running on AWS. Substantial enterprise cloud experience, AWS preferred, with services like Lambda, ECS/Fargate, API Gateway, S3, RDS, Secrets Manager, IAM, and CloudFormation/SAM.
AI Lead/Architect eTeam Inc.AI Lead/ArchitectChicago, IL$70–$71 / hourAgent Development: Build and orchestrate autonomous AI agents with multi-step reasoning, tool usage, and workflow chaining using frameworks like LangChain, CrewAI, AutoGen, Semantic Kernel, or LlamaIndex. " LLM Integration & Optimization: Deploy, fine-tune, and serve open-source LLMs (e.g., Llama 3) using Databricks Model Serving; optimize latency, throughput, and cost.