(AI-First) Engineering Manager

About this role

<div class="content-intro"><p data-pm-slice="1 1 []">Groupon connects 42 million customers with local experiences - restaurants, events, wellness and travel - and the million-plus merchants who deliver them. Our mission is to get people offline and into the real world at prices that make it possible. We're an AI-native company in the middle of a platform transformation, moving from a deals marketplace to an experience discovery platform that works for customers and merchants at the same time.</p> <p>&nbsp;</p></div><p>Groupon talks to tens of millions of subscribers through email, push and SMS — and changing a single transactional message takes two weeks, because each one is hard-coded into its own backend service in a ten-year-old stack. Your job is to make it two hours: replace ~120 of those one-off integrations with events a marketer can rearrange themselves in our customer-data platform, and move the whole channel onto Groupon's new TypeScript foundation as you go. You'd lead that turnaround — and still be in the code.</p> <h2>What you'd actually get to build</h2> <p>This is a turnaround, not a greenfield. Today the channel runs on a decade-old stack: each message wired by hand into its own delivery service, subscriber data spread across separate systems, a change measured in weeks. You'd move it — piece by piece, without dropping a single send — onto the modern foundation the rest of Groupon engineering is consolidating on:</p> <ul> <li><strong>From weeks to hours.</strong> Replace ~120 hand-built integrations with events a marketer can rearrange in our customer-data platform (Bloomreach) — so changing a message is a config, not a two-week deploy.</li> <li><strong>Onto one modern foundation.</strong> Groupon's new TypeScript platform (Encore, built by ex-Netflix engineers): declare a database or queue in a line of code and it's provisioned and observed for you; changes reach production the same day.</li> <li><strong>Why now.</strong> Groupon runs on infrastructure built for 2,500 engineers, maintained today by ~260. You'd be on the sharp end of fixing that — for a channel that reaches tens of millions.</li> <li><strong>AI is native to the new stack</strong> — a shared model gateway and coding-assistant rules wired into every service; agents write real code, and review keeps it safe.</li> </ul> <h2>Who you'll work with</h2> <p>You'll report to Nikash Ray (VP of Software Engineering) and own Managed Channel delivery end to end, leading a small team (~3 engineers) in Bangalore with stakeholders in Prague and London. It's a hands-on role: you run the cadence <em>and</em> stay in the system design and the code. Not for you if you want to review from a distance. Right for you if you like taking a critical, under-invested system and making it modern, observable, and boring to operate.</p> <h2>A week in the life</h2> <ul> <li><strong>The migration is the mission</strong> — wire offer and click events into our customer-data platform, retire the hand-built integrations one by one, and move live traffic onto the new foundation without a customer noticing.</li> <li><strong>Event-driven reliability</strong> — you design the message flow so a double-send is impossible by construction, not by luck.</li> <li><strong>AI-first incident response</strong> — during a recent traffic spike, an engineer used AI-assisted analysis to surface misconfigurations that only showed under load, shipped the hardening, then turned the diagnosis into a reusable runbook. That's the pattern you'd set.</li> <li><strong>Agents doing the toil</strong> — a code-quality gate and a PR-watcher keep routine reviews off people's plates, so attention goes to the hard calls.</li> <li><strong>The read stakeholders rely on</strong> — Prague and London know where the channel stands because you tell them before they ask.</li> </ul> <h2>Signals you're a fit</h2> <ul> <li>You've taken over a system nobody could fully explain and left it documented, observable, and boring to operate.</li> <li>You've moved live traffic off a legacy system without customers noticing.</li> <li>You've designed a messaging flow where double-sending was impossible by construction, not by luck.</li> <li>You've led a team four time zones away and it got stronger, not just managed.</li> <li>You've made AI agents part of how a team ships — and you can say exactly where they failed.</li> </ul> <p>We'll dig into these live — bring the specifics. <em>(You're still hands-on, so show us production code you've written recently.)</em></p> <h2>What success looks like</h2> <ul> <li><strong>Day 0–30:</strong> the pipeline is mapped end to end and written down for the first time; you've met every engineer and the Prague/London stakeholders; the delivery cadence runs on you, not on heroics.</li> <li><strong>Day 31–60:</strong> you own a real slice of the migration yourself, and the first hand-built integrations are retired.</li> <li><strong>Day 61–90:</strong> message lead time is measurably down (weeks → hours on the first flows), delivery is predictable, and the migration has real dates the whole channel can see.</li> </ul> <h2>How we operate</h2> <ul> <li><strong>Extreme ownership</strong> — you're the single point of accountability for the channel.</li> <li><strong>Speed over comfort</strong> — you make good decisions before all the information arrives.</li> <li><strong>Impact-obsessed</strong> — engagement, subscriber growth, and cost are the numbers you steer by.</li> <li><strong>AI-first and disciplined</strong> — agents do the toil, review keeps them safe. Agency, not brilliant-jerk.</li> </ul> <h2>How we hire — 14 days to a decision</h2> <ol> <li><strong>Recruiter screen (25 min)</strong> — career trajectory, role fit, comp alignment.</li> <li><strong>Foundry Challenge</strong> — a real-problem scenario from this role, done in your own time.</li> <li><strong>Hiring-manager interview (60 min)</strong> — walk through your Foundry Challenge, a deeper technical discussio