Engineering Manager

Summary

Join Guideline as an Engineering Manager to lead the Payroll team, responsible for building and maintaining robust API integrations with third-party payroll systems. You will define the technical roadmap, collaborate with third parties, drive technical decision-making, and establish engineering best practices. The role requires 7+ years of software engineering experience, including 3+ years managing a team of 5+ engineers, and expertise in designing scalable systems. The salary range is $158,000-$271,500 annually, depending on location, and includes equity in the form of Incentive Stock Options (ISOs). Guideline offers a comprehensive benefits package, including health insurance, paid time off, 401k matching, parental leave, and professional development opportunities.

Requirements

• 7+ years of software engineering experience, with 3+ years of experience managing a team of 5 or more engineers
• Extensive experience designing and building scalable, distributed systems, with a deep understanding of system architecture
• Experience with mission-critical backend systems, including performance optimization, fault tolerance, and horizontal scaling
• Proficiency in at least one server-side language (e.g., Ruby, Python, Node.js)
• Strong understanding of relational databases, caching, messaging queues, and event-driven architectures
• Strong understanding of API integration patterns, RESTful services, and data exchange formats (e.g., JSON, XML)
• Confident in spending up to 20-25% of your time contributing by writing code alongside your team as your time and priorities permit
• Competent in setting expectations, giving transparent feedback, and creating a culture of psychological safety

Responsibilities

• Lead and manage a team of engineers focused on developing and maintaining 3rd party API payroll integrations
• Define the technical roadmap and strategy for payroll integrations, aligning with overall product and business goals
• Collaborate with 3rd parties around integrations, including ownership of engineering ops regarding bugs, product needs, and general support
• Drive technical decision-making and partner with the rest of the organization to define processes and ownership responsibilities
• Establish and enforce engineering best practices, including code reviews, testing, refactoring, and documentation to maintain high-quality codebases
• Empower teams to provide high quality software by removing barriers and unblocking engineers in the team
• Support your engineers through empathetic leadership, mentorship, transparency, and accountability

Preferred Qualifications

Background in fintech, regtech, or HR-tech is a plus

Benefits

• Medical, dental, and vision insurance — We offer multiple plan options with varying company premium contributions
• Health Savings Account and Flexible Spending Account
• Company paid disability and life insurance
• Optional Voluntary life insurance
• Mental health benefit navigation with Rula for employees and dependents
• Paid parental leave for birthing and non-birthing parents
• Flexible time off in addition to company holidays — We observe the NYSE Holiday Calendar
• We use our own platform and contribute 100% of employee contributions up to 5%
• 1-month paid Sabbatical after 5 years of employment
• Annual learning and development stipend — We reimburse approved professional development expenses, up to $750 per employee per year
• Health Opt-out credit for waiving coverage