Chicago, Illinois, United States · Remote OK
The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Maestro, an AI-native inventory-planning intelligence venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive r…
Skills: B2B SaaS Go-To-Market, Fundraising, Merchandise Planning, Inventory Management, Strategic Leadership
Chicago, Illinois, United States · On-site
$70k–$95k/yr
Company Description Fortune Brands Innovations, Inc. is an industry-leading home, security and digital products company. We’re focused on exciting opportunities within the home, security and commercial building markets. …
Skills: Outside Sales, Relationship Management, Account Management, Merchandising, Marketing Implementation
Chicago, Illinois, United States · Remote OK
The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Omnex, an AI-native operating system for multi-channel ecommerce sellers, currently in build at our studio. This is a co-founder partnership with meaningf…
Skills: Strategic Planning, Customer Development, Go-To-Market Strategy, Fundraising, Team Leadership
Chicago, Illinois, United States · On-site
$17/hr–$22/hr
Be part of an amazing story Macy’s is more than just a store. We’re a story. One that’s captured the hearts and minds of America for more than 160 years. A story about innovations and traditions…about inspiring stores an…
Skills: Customer Relationship Management, Upselling, Product Knowledge, Merchandising, Clientele Building
Chicago, Illinois, United States · On-site
Job Summary Full-Time. Open availability required for any shifts (open/close). Weekends required. $16.75/hour. The Cannabis Advisor is responsible for providing exceptional individualized customer service, educational co…
Skills: Customer Service, Cannabis Education, POS Systems, Inventory Management, Compliance
Chicago, Illinois, United States · On-site
$17/hr–$22/hr
HIRING IMMEDIATELY at Mendocino Farms! NOW HIRING FRONT OF HOUSE TEAM MEMBERS! Make $17.00 - $22.00 / hr including tips! We’re not just selling sandwiches and salads. We’re selling HAPPY! Restaurant Team Memb…
Skills: Guest Relations, Order Taking, Cashiering, Food Running, Bussing Tables
Chicago, Illinois, United States · On-site
$17/hr–$19/hr
Crafting the world’s finest coffee, one meaningful moment at a time We believe in creating a warm and welcoming space where every cup of coffee sparks connection. Every shift is a chance to brighten someone’s day. Whethe…
Skills: Customer Service, Beverage Preparation, Cash Handling, Interpersonal Skills, Teamwork
Chicago, Illinois, United States · Hybrid
$175k–$200k/yr
Description The Vice President of Operations will be responsible for developing and implementing the strategic direction for clinic operations by setting the standards and practices that support rapid growth, drive opera…
Skills: Multi-unit Operations, Strategic Planning, Talent Development, KPI Management, Revenue Growth
Chicago, Illinois, United States · Remote OK
$110k–$150k/yr
Rithum™ is the world’s most trusted commerce network, accelerating how brands, suppliers, and retailers work together to deliver seamless e-commerce experiences. We provide an unmatched platform for brands and retailers,…
Skills: Presales Consulting, Ecommerce Program Management, Value-Selling Framework, MEDDICC, ROI Analysis
Chicago, Illinois, United States · On-site
$19/hr–$29/hr
We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate…
Skills: Prescription Fulfillment, Customer Service, Inventory Management, Patient Care, Medical Communication
Chicago, Illinois, United States · Hybrid
$83k–$128k/yr
Instructional Designer Camping World Holdings, Inc. is America's largest RV retailer, dedicated to making RVing fun and easy. With locations in 42 states, we offer a comprehensive range of RV products, services, and cust…
Skills: Instructional Design, ADDIE, SAM Model, Articulate 360, PowerPoint
Chicago, Illinois, United States · On-site
VP of Finance / Head of FinanceAbout Local Eclectic Local Eclectic is a Chicago-based fine jewelry company operating five proprietary brands (Family Gold, For You With Love, Harvest Moon, Carried Jewels, Period Piece) wi…
Skills: P&L Management, Cash Flow Forecasting, Treasury Management, Banking Relationships, Financial Modeling
Chicago, Illinois, United States · On-site
$17/hr–$26/hr
The Starting Hourly Rate / Salario por Hora Inicial is $17.75 USD per hour. The Pay Range / Rango salarial is $17.75 USD - $26.65 USD per hour. ALL ABOUT TARGET Working at Target means helping all families discover the j…
Skills: Guest Service, Cash Handling, Inventory Management, Stocking, Merchandising
Chicago, Illinois, United States · On-site
$17/hr–$18/hr
APPLY https://recruiting.adp.com/srccsh/public/RTI.home?r=5001203913700&c=2211139&d=ExternalCareerSite&_dissimuloSSO=v0XFSTiSpGo:xkPnasH_wXkX_QUkRmd5uQwWkZo6gyWG5-4XAMfasW4 Merchandiser Our merchandisers are the heart an…
Skills: Merchandising, Retail Display Building, Plan-o-gram Implementation, Relationship Management, Organizational Skills
Chicago, Illinois, United States · On-site
About the RoleAs the General Manager, you are responsible for leading your team to deliver a profitable store business plan. You ensure your store achieves all key metrics and is meeting or exceeding goals. You are the l…
Skills: Retail Management, P&L Management, Talent Development, Forecasting, Scheduling
Chicago, Illinois, United States · On-site
We are so much more than a Parts Store and we are looking for even more great talent to join our NAPA family! As a NAPA Automotive Parts Specialist, you don’t have to be able to tear a motor down and rebuild it (however,…
Skills: Automotive Parts Knowledge, Customer Service, Parts Sourcing, Inventory Management, Communication Skills
Chicago, Illinois, United States · On-site
Overview Allied Universal®, North America’s leading security and facility services company, offers rewarding careers that provide you a sense of purpose. While working in a dynamic, welcoming, and collaborative workplace…
Skills: Customer Service, Security Patrolling, Incident Response, Access Control, Crowd Management
Chicago, Illinois, United States · On-site
$130k–$160k/yr
Overview When you join Hines, you will embark on a career journey fueled by vision and guided by leaders who set the standards of our industry. Our legacy is rooted in innovation and excellence, earning us a spot on Fast…
Skills: Property Management, P&L Responsibility, Budgetary Oversight, Hospitality Management, Mixed-Use Management
Chicago, Illinois, United States · On-site
$18/hr–$31/hr
Company Overview Bridgestone Retail Operations (BSRO) is part of Bridgestone Americas and employs over 22,000 teammates in North America. BSRO operates more than 2,200 company-owned stores, including Firestone Complete A…
Skills: Automotive Diagnosis, Electrical Systems Repair, Brake and Hydraulic Systems, Suspension and Alignment, Air Conditioning Systems
Chicago, Illinois, United States · On-site
Come join our family and become a Pizza GENIUS! Join the Little Caesars® Pizza!Pizza!® Family Do you like pizza? Do you like having fun? If so, we would love for you to join our family! Why We Are ExtraMostBestest: Weekl…
Skills: Customer Service, Food Preparation, Cooking, Teamwork, Time Management
Chicago, Illinois, United States • Remote OK
Sign up with Clera and we'll reach out the moment a role actually fits you — no more spraying applications into the void.
Lead the strategic direction and execution of Maestro, an AI-native inventory planning venture. Responsibilities include refining the ICP, leading customer pilots, managing the seed raise, and recruiting the founding team.
Requires previous founding experience at a venture-backed company and a proven track record in B2B SaaS sales and fundraising. Deep operational expertise in merchandise planning and multi-channel retail operations is essential.
FutureSight is seeking a Co-Founder & CEO to lead Maestro, an AI-native inventory-planning intelligence venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role.
Maestro is an autopilot planning intelligence for SMB operators managing physical inventory complexity without a planning team. It connects across channels and ERPs, handles routine decisions silently, and surfaces exceptions with context and a recommended action before they become revenue losses. The institutional memory that today lives only in a planner's head gets externalized, structured, and queried in plain language.
We didn't just build a thesis; we validated it directly with the market. We have spoken with founders, VP E-Commerce leaders, merchandise planners, and multi-channel operators at DTC and specialty retail brands across the US. The market signal is clear:
We are targeting a large, structurally underserved segment: SMB operators managing multi-channel physical inventory complexity at $5M–50M revenue — importers, distributors, Amazon aggregators, and specialty retailers. The beachhead SAM is estimated at $200M–$225M across approximately 15K–16K brands in the US and Canada. Excel is the universal incumbent! 5/5 buyers in our discovery sprint were on spreadsheets, with zero dedicated planning tools in use. EBITDA across the $10–50M DTC cohort is compressed to 7.25% in 2025 with revenue declining ~4.6% YoY. Planning waste attacks the margin stack directly.
About FutureSightFutureSight is a leading venture builder that co-creates world-class software companies with values-driven entrepreneurs from inception to exit. We are a team of founders, operators and designers with experience successfully bringing software to market at scale.
You’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 PartnershipAs Co-Founder & CEO, you will set the venture's direction and lead its execution.
Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate.
FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.
We co-found and fund vertical B2B AI companies. We are your full-stack co-founding team.
FutureSight is a leading venture builder located in Toronto and San Francisco. We cofound and fund vertical B2B AI software companies with values-driven entrepreneurs from zero to one. We are a team of founders, operators, investors, and designers with experience successfully bringing software to market at scale.
Offices: 2193 Filmore Street, San Francisco, California 94115, US · 101 College St, 250, Toronto, Ontario M5G 1L7, CA
There are currently 2,463 open retail positions in Chicago, IL listed on Clera. New openings are added daily as companies post roles.
Companies currently hiring include Albertsons Companies, Dollar Tree Stores, Starbucks, Domino's, AutoZone, among others. Browse the listings above to see every active employer.
Yes — 209 of the 2463 open retail positions offer remote or hybrid work (57 remote, 152 hybrid).
Each listing links directly to the employer's application page. Apply early — fresh listings get the most recruiter attention in the first two weeks.
