Head of Engineering (Player Coach), Chicago

Revenue3; Chicago (IL); On-site; USD 320,000 - 420,000; Full time

Benefits offered by this job

Equity ownership

Performance bonus

Health benefits

Ownership of delivery

Job summary

Revenue3, a next-generation payments platform, is seeking a Head of Engineering in Chicago to lead the engineering team and own day-to-day delivery in a highly regulated fintech environment.

You will stay hands-on in critical payment paths while mentoring engineers, setting architecture, and driving reliability and security. This role requires strong IC capabilities, ownership mindset, and experience scaling early-stage fintech infrastructure.

Qualifications

• Senior engineering leader who is still a strong, current IC and can hold their own in the codebase.
• Track record owning delivery for a team: shipping real product with accountability.
• Experience building process without bureaucracy; avoid unnecessary overhead.
• High bar for reliability, security, and correctness in regulated settings.
• Direct communicator; clear written communication and transparency.

Responsibilities

• Write, review, and ship production code on critical payment paths; stay hands-on.
• Debug production incidents, reliability gaps, performance and correctness issues.
• Set the technical direction and make architecture calls that matter.
• Mentor engineers, level up the team, and manage performance and growth.
• Own delivery: break work down, sequence it, ensure it lands.
• Manage and grow engineers: 1:1s, feedback, hiring, and hard conversations.
• Own the process: clear requirements, project ownership, and feedback loops.
• Be the point of accountability for the team’s output to the founders.
• Report to the CTO on personnel matters.

Skills

Senior leader

IC contributor

Delivery ownership

Regulated environment

Direct communicator

Blockchain experience

Early-stage startup

Job description

Our client is the next-generation payment service provider revolutionizing global financial infrastructure with stablecoins, AI-driven fraud prevention, and instant settlement. They enable businesses to grow faster with instant settlement, fraud & chargeback indemnity, global pay-ins, multi-currency FX, and unified payouts. Founded in 2023, the company serves marketplaces, fintechs, remittance providers, gaming platforms, and ecommerce merchants worldwide.

Since their seed round in 2024, they have achieved 23x revenue growth and scaled to multi-billion-dollar annual transaction volume. In response to this growth, the company announced a $25M Series A in October 2025, led by Pantera Capital, CMT Digital, Coinbase Ventures, Jump Crypto, and Reciprocal Ventures, accelerating their mission to power the world’s fastest-moving businesses with innovative, reliable global payments. Our client is proudly headquartered in Chicago, IL.

Role Overview

Our client is seeking a Head of Engineering to lead the engineering team and take ownership of day-to-day engineering, including prioritization, delivery, technical direction, and team health, which currently runs through the CTO. The company is white-label payments infrastructure: card acquiring, payin/payout across numerous methods, hosted and embedded checkout, and merchant onboarding, operating in a heavily regulated environment where the bar for correctness, security, and reliability is high and non-negotiable.

This is a player-coach role, not a hands-off management job. You’ll be in the codebase shipping real work on critical payment paths while building and leading the team. You own the team’s deliverables. When something is late, broken, or unclear, it’s yours to drive to done.

The first 6-12 months: this role is built around a handoff. Early on, you’ll work closely with the CTO and ship alongside the team to earn context and trust. As you prove out judgment and delivery, more of the day-to-day (planning, technical decisions, team ownership) shifts to you. Success looks like the team running confidently under you while the CTO steps back from operational engineering.

Key Responsibilities

In the trenches (player)

• Write, review, and ship production code on critical payment paths. You stay hands-on
• Debug the hard stuff: production incidents, reliability gaps, performance and correctness issues
• Set the technical direction and make the architecture calls that matter
• Raise the engineering bar through code review, standards, and example

Leading the team (coach)

• Own delivery: break work down, sequence it, and make sure it lands
• Mentor every engineer on the team, from senior to junior, leveling people up rather than just directing them
• Manage and grow the engineers: 1:1s, feedback, performance, hiring, and the occasional hard conversation
• Own the process: clear requirements before work hits engineering, real ownership per project (DRI), and a feedback loop that catches problems early
• Be the point of accountability for the team’s output to the founders
• Report to the CTO on personnel matters. Performance, team health, and people decisions run through you and surface to the CTO directly

Required Qualifications

• Senior engineering leader who is still a strong, current IC, able to hold your own in the codebase, not just review it
• Track record owning delivery for a team: shipping real product, on a real cadence, with real accountability
• Experience building process without bureaucracy. You know the difference between rigor and overhead
• High bar for reliability, security, and correctness. You’ve operated where mistakes cost money
• Direct communicator. You write things down and don’t hide bad news

Preferred Qualifications

• Stablecoin or blockchain infrastructure experience (Solana programs, EVM smart contracts, on-chain settlement)
• Experience working in a regulated, compliance-forward environment
• Early-stage startup experience

What We Offer

• Competitive compensation including base salary, performance bonus, and meaningful ownership
• Opportunity to own engineering delivery and team leadership at a rapidly scaling fintech company
• Collaborative and innovative work environment with world-class investors
• Direct impact on core product and company trajectory during a hyper growth phase

An equity grant allows you to share in the long-term success of the company. You will also have access to a wide array of benefits, including health and wellness benefits, 401(k) savings plan, and flexible time off.

Join the team rewriting how money moves worldwide, and become a driving force in the $194 trillion cross-border payments market.