Head Of Operations Jobs in Chicago, IL

About Attain

Built for consumers and companies, alike. In a world driven by data, we believe consumers and businesses can coexist. Our founders had a vision to empower consumers to leverage their greatest asset—their data—in exchange for modern financial services. Built with this vision in mind, our platform allows consumers to access savings tools, earned wages and rewards without cost or hidden fees. In exchange, they give permission to use their real-time data for research, insights and targeted advertising.

At Attain, your contribution will help us build a more equitable and efficient data sharing ecosystem—whether helping consumers access modern financial services or businesses leverage data to achieve better outcomes. You'll have the opportunity to work directly with hands-on leaders and mission-driven individuals everyday.

About the role

Attain's consumer mobile apps are the front door of our data ecosystem: they deliver real value to consumers, and the permissioned data they generate powers everything our enterprise platform does. Each app has a different audience with its own acquisition and monetization approach, all running on a shared backend platform.

As Head of Data Apps Engineering, you'll own the engineering side of that portfolio and be the consumer voice in with our ad-tech leadership team. This is a player-coach role by design: you'll lead a deliberately small team of mobile and backend engineers, write and review code yourself, and set the technical direction that lets us ship new apps at a marginal cost that shrinks with each launch. You'll work in lockstep with our Head of Product for the portfolio. And you'll represent the data apps business at the executive level, where your consumer expertise fills a gap the rest of the room knows it has.

This role reports into the SVP of Engineering.

Attain Office Hybrid Schedule (where applicable):

• Redwood City, CA: Mondays (in-office for stand-ups, all-hands) and choice of three days between Tues-Friday
• Chicago, IL: 4 days in office

You'll be a great fit for the role if

• You've built and scaled a consumer app with real ownership (as a founder, CTO, founding engineer, or the technical lead who was accountable for the outcome), and you can speak to what worked and what didn't from firsthand experience
• You've held senior scope before and are excited to lead your team through hands-on building: you want a small, focused team and a big mandate, not a big org
• You instinctively seek to collaborate with your Product counterpart to ship great products
• You're a backend-heavy full-stack engineer who is genuinely fluent across the stack, including React Native, and you still love being in the weeds
• You think like a product engineer: you'd rather pressure-test an idea with your product counterpart before a line of code is written than build the wrong thing beautifully
• You're credible in an executive room: you can represent a business line to a leadership team, translate consumer strategy for an ad-tech-native audience, and hold your ground on what it takes to build for consumers
• You read retention and engagement data across a portfolio of products fluently, and you use it to prioritize with your Product counterpart; you don't wait to be handed a metrics brief before you know which app or feature needs attention
• You get energy from leverage: shared platforms, reusable components, and AI-assisted development that let a five-person team ship like a fifteen-person one
• You've experienced consumer scale (real production load, real users, real growth curves) and know which scaling problems to solve now versus earn later

What a typical week will look like

• Lead architecture and hands-on development across the app portfolio: React Native front ends on a shared, multi-app backend platform
• Partner daily with the portfolio's product lead on roadmap, feasibility, and sequencing: you are the engineering half of that partnership
• Track retention and usage across every app in the portfolio and use it to decide what gets engineering attention next
• Drive the "factory" economics: harden the shared components (onboarding, account linking, loyalty, receipt OCR) so each new app is a configuration and a skin, not a rebuild
• Manage a small team of mobile and backend engineers: line management, code review, and career development, not layers of management
• Represent data apps at executive and planning forums: portfolio status, investment cases, and the consumer perspective on company-level decisions
• Raise the bar on modern engineering leverage: agentic/AI-assisted development is how this team punches above its size

Preferred Qualifications

• 10+ years of software engineering experience, with several years building consumer-facing mobile products
• Founder, CTO, VP Engineering, or founding-engineer experience at a consumer startup, or equivalent demonstrated ownership of a consumer product's technical outcomes
• Track record taking a consumer app from zero to meaningful scale (users, load, or revenue)
• Deep backend expertise (APIs, data pipelines, cloud infrastructure) plus production React Native or comparable cross-platform mobile experience
• Experience managing small engineering teams directly (line management; this is not a manager-of-managers role)
• Comfortable presenting to and working with executive stakeholders
• Rewards/loyalty or data product experience is a strong plus

We're excited to hear from you.

At Attain, we are passionate about finding people to continuously help us grow our organization. We encourage you to apply, even if your experience doesn't match every detail of the job description. If we don't see something that immediately fits, we will keep your resume on file for future opportunities.