Merchandising Operations Manager Jobs in Chicago, IL

OG.com is a fast-growing, CFTC-regulated Prediction Market platform powered by cutting-edge technology. We’re building an engaging marketplace where users trade on real-world outcomes - from major sports and elections to cultural and financial events. With a sleek mobile-first app and a passionate community, we’re redefining how people interact with news, probabilities, and financial markets. OG.com runs on the rails of North American Derivatives Exchange, Inc. (NADEX), a CFTC-regulated exchange operating since 2004 and was acquired by crypto.com in 2022.

The Problem You'll Solve

• A trader opens OG because something is happening right now - a game, a vote, a number dropping. They should land on the markets that match that moment, packaged so the next tap is a trade. Instead, too many prediction products bury the good stuff: stale modules, generic featured lists, packages that don’t match the narrative, a homepage that looks the same at 8pm on a Sunday as it did Tuesday morning.
• Every weak merch decision is volume left on the table. The wrong market in the hero slot. A parlay-style package that shipped after the story peaked. A module that still sells last night’s event. 
• You will own how OG presents live markets - not whether they exist or how they settle. That’s a different seat. You are the DRI for surface merchandising: homepage and discovery modules, featured and thematic hubs, packaged / multi-leg merch, calendars, live narrative swaps, and the experiments that prove what converts. You’ll build the merch operation that fixes this.
• You will run merch with independence. You make the call on what’s featured, how it’s packaged, and what comes off the board. You report to the VP of Product,  who sets OG product priorities. Market listing, rulesets, and settlement sit with Market Ops. You own the how and the when on the surface. No layers. No politics.

• Own the merchandised surface end-to-end. You are the DRI for homepage / discovery modules and featured market placement on OG web and mobile. You decide what sits in the hero, what rotates, and what never makes the cut. Nothing on this charter goes live without your sign-off on commercial quality.

• Build packaged, high-intent merch. You create and rotate packages (parlay / SGP analogs on event contracts) tied to real narratives - not generic “popular” lists. You make the go/no-go call on what ships to the module.

• Run live merch when the board blows up. You swap surfaces in real time during major events. You partner Trading / Risk when odds or inventory shift. You stay calm when the calendar is nights, weekends, and holidays. Speed without sloppiness - merch mistakes are public.

• Connect the calendar to the product. You own the merch calendar against sports, politics, culture, and marketing moments so launches aren’t a surprise to the homepage. You flag coverage gaps back to Market Ops before the story peaks.

• Prove it with experiments. You prioritize, QA, and read merch A/B (and multi-arm) tests with Product and Data. You know when a test is invalid. Winners become default. Losers get cut. You instrument your own funnel; you don’t wait for someone to hand you the analysis.

• Watch the competitive set and respond. You propose responses and you ship them - not a weekly screenshot dump.

• Handoff cleanly with Market Ops. You consume new listings the moment they’re live. You feed unmet demand and broken-resolution UX signals back. You don’t write rulesets. You don’t settle markets. You own presentation.

• Surface merch you’ve owned. You have owned sportsbook or marketplace merchandising (modules, featured, packages) end-to-end. You can point to a before/after - engagement or conversion - and what you did when the board blew up and dependencies broke down. We care what you’ve built and owned - not MBA, pedigree, or a certain number of years.

• Live / calendar ops under pressure. You have operated on event time (nights, weekends, holidays). You can describe a night you had to kill, swap, and re-feature in minutes - and how you kept the surface clean.

• Data-informed, not gut-only. You use SQL, dashboards, or a partner analyst to decide what features. You can walk through a merch call you reversed because the numbers said so.

• Experiment literacy. You have run or partnered on A/B (or multi-arm) tests for merch or discovery. You can explain a test you threw out because it was invalid - not just the ones that “won.”

• Cross-functional DRI, not a ticket-pusher. You align Product, Trading / Risk, and Marketing without owning their charters. You can describe a launch you coordinated and what you did when a partner slipped.

• Domain fluency or ruthless learning speed. Event contracts, odds, prediction UX - you are fluent, or you learn fast enough to debate power users. You ask “Show me how you currently find a market and tap into a trade,” not “Would you like more featured content?”

• MerchOps/ Sportsbook merchandising: shortest ramp; you already speak modules, parlays/SGPs, live swaps.

• Predicts / prediction-market merch: you’ve merchandised event contracts, not only traditional sportsbook lines.

• SQL / experimentation tooling: you move faster without waiting on a dedicated analyst for every read.

• Sports, politics, or culture vertical depth: you already know which moments deserve the hero slot.

• Speed. We don’t do multi-quarter merch strategy decks. If the opportunity is real, the homepage changes tonight.

• Access. You work directly with OG leadership, Product, and Market Ops. Your merch calls land where volume is made. No layers.

• Leverage. The merchandised surface is the front door of the trade. Your taste and ops cadence compound across every event on the calendar.

• Frontier. Prediction merch in a regulated U.S. event-contract product is still being written.