Payroll Engineering Leader

Check is leading a revolution in the payroll industry. Payroll is the backbone of the US economy, and yet it has not undergone significant innovation in decades. We invented the embedded payroll space to change that (see: Check: Solving the $150 Billion Payroll Problem, Bank On It; Episode 438), both for the business owners who spend countless hours per week running payroll and for the millions of Americans who depend on their next paycheck. At Check, our mission is to empower the most innovative software platforms to create new payroll businesses, and enable those businesses to transform the way companies pay their employees.

Check’s culture is intensely caring: to each other as teammates, to our partners, and to the businesses and workers we serve. Our teams are made up of creative problem solvers and empathetic cross-functional collaborators who can simplify the complexities of payroll. We bring hustle and grit to our day-to-day, while building enduring solutions and relationships. 

This is a GM-type role, fundamentally accountable for the overall business results driven by the Payroll pod. The Payroll pod is inclusive of an engineering team and resources across product, compliance, and operations. This role is part of our Platform Leadership Team, offering close collaboration with company leadership. 

In this role, you will:

• Lead a cross-functional R&D pod to deliver a robust and compliant payroll infrastructure platform that supports Check and enables our partners' products as they scale
• Drive prioritization and balance against critical reactive initiatives and a long-term technical roadmap for deeper infrastructure improvements
• Build teams that execute at a high level of technical excellence and velocity and create a collaborative, unified culture within the pod across all functions
• Build new engineering capacity that appropriately leverages engineering spend for continued maintenance of our payroll systems
• Set the long-term strategy for the pod and system architecture, and conveying and advocating for that strategy to company leadership
• Recruit, coach, and develop engineers and managers that exemplify our shared values
• Do whatever is needed to ensure the Pod is successful, from the mundane (bringing food to meetings) to the the very difficult (making personnel recommendations)

Many backgrounds could fit this role, but ideal candidates will have:

• Hands-on experience scaling critical software platforms with low fault tolerance
• Excellence in navigating ambiguity: excelling at establishing prioritization frameworks and identifying the right work to meet business outcomes
• Experience growing managers and pulling up individuals  into successful leadership positions
• 10+ years of overall software development experience
• 5+ years of engineering management experience
• Experience building motivated, distributed teams that tackle challenging technical problems
• A record of growing individuals  into strong engineering leaders
• Thrived in highly cross-functional organizations
• Experience making business level decisions and evaluating tradeoffs
• Willingness and ability to travel approximately one work week per quarter
• Willingness and ability to attend our annual 3-day company offsite in the Fall

At Check, we value transparency and trust. It’s important to us that every employee and candidate feels confident that they’ll be treated (and compensated) fairly on our team. The engineering team specifically operates on a flat titling system, meaning everyone is either a Software Engineer or an Engineering Manager. We structure our titles this way to maximize equity, inclusion and opportunity within our team, and to minimize seniority bias. We want all engineers, regardless of job level, to feel empowered to lead projects they’re passionate about and to collaborate with their fellow Checketeers as equals. 

To that end, we will consider candidates with a variety of backgrounds and levels of expertise for this role, and we will determine the appropriate job level for each candidate based on their unique experience and qualifications. The expected annual salary for this role is between $240,000 and $264,000.

In the US, Check offers company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage to all full-time employees, effective on their first day of work. We also provide stock options, flexible PTO and sick leave, 16 weeks of fully paid parental leave for all new parents and