Senior Engineering Manager Jobs in Chicago, IL (NOW HIRING)

Paylocity is an award-winning provider of cloud-based HR and payroll software solutions, offering the most complete platform for the modern workforce. The company has become one of the fastest-growing HCM software providers worldwide by offering an intuitive, easy-to-use product suite that helps businesses automate and streamline HR and payroll processes, attract and retain talent, and build a strong workplace culture.

While traditional HR and payroll providers automate basic HR processes such as payroll and benefits administration, Paylocity goes further by developing tools that HR and businesses need to compete for talent and deliver against the expectations of the modern workforce.

We give our employees what they need to succeed, including great benefits and perks! We offer medical, dental, vision, life, disability, and a 401(k) match, as well as perks that support you, your family, and your finances. And if it’s career development you desire, we provide that, too! At Paylocity, people matter most and have always been at the heart of our business.

Help Paylocity enhance communication and enable employees to connect, collaborate, and create from anywhere with a position in Product & Technology!

Want to develop the strategies and principles needed to deliver compelling software? Join our team and help us enhance our all-in-one software platform, elevate our one-of-a-kind technology, and improve the employee experience.

Take your career to the next level at one of G2's Top 100 Software Companies. Explore our Product & Technology positions to see where you fit!

This is a fully remote position, allowing you to work from home or location of record within the U.S. with no in-office requirements. You must be available five days per week during designated work hours. The work arrangement for this role is subject to change based on business needs and individual performance. This may include adjustments to on-site requirements or schedule expectations, as necessary.

About the Role

At Paylocity, Senior Software Engineering Managers are technology-focused leaders that act as the bridge between engineering teams and the business strategies driving their outcomes. It is a highly critical role in our Product and Technology organization. This key leader serves as manager of managers and is responsible for overseeing the work of multiple engineering teams in our Payroll domain, enabling them to achieve their highest level of performance, efficiency, and customer needs. This position requires commitment to exceptional results, a strong desire for continuous improvement, and the ability to build a collaborative culture within the team.

Who you are:

• Highly effective Senior Engineering Manager who will lead multiple teams in a remote-first environment
• An extremely proactive and in-depth technical communicator, both verbally and in Slack, and is highly skilled at explaining complex topics to many different audiences
• You have a very strong sense of what your teams are building, the underlying technology, and can pressure test the reasoning behind any tradeoffs made during development
• Quality is top of mind for you and all your teams, and is something you are never willing to compromise on
• Fluent in frontier AI tools in support of an AI enhanced SDLC (Anthropic, OpenAI, or Copilot)
• Plenty of experience and are comfortable leading highly critical products of immense scale with essentially zero margin for error
• Able to break down the boundaries of ambiguity, fully understand your domain, and push your teams to deliver the right outcomes for the customer
• A supportive mentor and coach for engineering managers with various levels of experience, as well as the individual contributors on their teams
• Able to independently initiate, plan, and execute projects of the highest quality which meets the velocity required by the business
• Skilled at building and presenting features and execution plans, as well as reporting progress to senior leadership
• Willingness to share your ideas in a collaborative environment with an open mind
• Are receptive to constructive feedback and unafraid to seek out suggestions from other categories within the organization

What will you do:

• Act as a direct servant leader for 4 teams and 2 principal engineers
• Support and influence the strategy of your teams through continuous collaboration with them and your leadership
• Delve into highly complex systems and concepts in the Payroll domain in order to guide your teams toward success
• Own the overall health and engineering quality of multiple products and demonstrate your ability to scale and improve upon these systems
• Maintain an understanding of the future direction of the business and how that impacts your strategy
• Break down the complexity of projects, services, and processes while communicating with other engineering teams and non-technical stakeholders
• Work with your teams to form actionable plans to modernize legacy applications
• Work closely with other leaders across the org to coordinate and slot priority for cross-functional development efforts
• Speak confidently about project timelines, system architectures, engineering practices, quality and more
• Raise risks immediately while proposing ideal directional solutions to mitigate
• Help guide your teams in the creation of properly leveled estimates in order to set realistic expectations with stakeholders and leadership
• Establish routines and frameworks for efficient communication and decision making
• Keep your teams informed of broader initiatives throughout the organization and help them integrate when needed
• Negotiate delivery tradeoffs with your Product partners to ensure tech debt and maintenance work is managed appropriately
• Help your managers grow their skills and experience
• Actively seek and hire globally distributed talent
• Conduct managerial interviews for candidates, and develop interview loops appropriate for the level of role being hired
• Contribute to the sense of psychological safety on your teams
• Hold regular 1:1's with all of your direct reports as well as occasional skip-levels to ensure the overall health of your organization
• Give regular and clear feedback around individual's performance
• Foster technical decision making on the team, but make final decisions when necessary
• Lead the team during operational incidents, root cause analysis, and identifying improvement areas to avoid repeat incidents through the creation of postmortems
• Create opportunities for individuals for growth, recognize team members publicly for achievements, and reward team members appropriately for high performance
• Hold self, engineering managers, and engineering teams accountable for delivering high quality, secure, reusable, and scalable software
• Build and maintain a healthy relationship with product counterparts in the domain

What you bring:

• BS degree or higher in Computer Science, Information Technology or equivalent experience
• 8+ years of experience in software engineering
• 4+ years in a management role overseeing multiple teams
• Experience leveraging observability and monitoring tools such as DataDog and Pagerduty
• Experience leading and scaling high-performing engineering teams in a SaaS or enterprise software environment
• A demonstrable level of successful strategy development along with proven outcomes
• Collaborative project planning capabilities that factor in risk/reward tradeoffs, assumptions and confidence levels
• An exceptional ability to communicate with a friendly and collaborative demeanor
• A history of both direct and indirect influence using data-driven approaches
• A basic understanding of enterprise financial planning and management tools
• Familiarity with working in cloud technologies (preferably AWS)
• Good understanding of various architectural patterns like SOA and Microservices and the related advantages and trade-offs
• Highly experienced in the design and development of large-scale .NET/SQL platforms with heavy emphasis on asynchronous processing and served by modern APIs in a React based ecosystem.
• Must show passion for the role and take responsibility for the team’s deliverables
• Able to work effectively in a team environment in an agile fashion
• Practical and creative in problem-solving

Physical requirements

• Ability to sit for extended periods: The role requires sitting at a desk or workstation for long periods, typically 7-8 hours a day.
• Use of computer and phone systems: The employee must be able to operate a computer, use phone systems, and type. This includes using multiple software programs and inquiries simultaneously.

Paylocity is an equal-opportunity employer. Paylocity is committed to the full inclusion of all individuals. We recruit, train, compensate, and promote regardless of race, religion, color, national origin, sex, disability, age, veteran status, and other protected status as required by applicable law. At Paylocity, we believe diversity makes us better.

We embrace and encourage our employees’ differences in age, culture, ethnicity, family or marital status, gender identity or expression, language, national origin, physical and mental ability, political affiliation, race, religion or spiritual belief, sexual orientation, socio-economic status, veteran status, and other characteristics that make our employees unique. We actively cultivate these differences through our employee resource groups (ERGs), employee experiences, perspectives, talents, and approaches to drive innovation in the software and services we provide our customers.

We comply with federal and state disability laws and make reasonable accommodations for applicants and employees with disabilities. To request reasonable accommodation in the job application or interview process, please contact accessibility@paylocity.com. This email address is exclusively designated for such requests, aligning with federal and state disability laws. Please do not send resumes to this email address, as they will be removed.

The base pay range for this position is $167k - $215k/yr; however, base pay offered may vary depending on job-related knowledge, skills, and experience. This position is eligible for an annual bonus and restricted stock unit grant based on individual performance in addition to a full range of benefits outlined here. This information is provided per the relevant state and local pay transparency laws for the location in which this position will be performed. Base pay information is based on market location. Applicants should apply via www.paylocity.com/careers.