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Senior Manager, Engineering

Direct Supply · Milwaukee, WI · Full time

Posted Oct 1, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a third-party integration that caused trouble. How did you and your team handle it?

What they are checking: Experience with the risks of integrations that depend on outside partners.

How do you coach a team toward higher quality and more predictable delivery?

What they are checking: Concrete coaching methods, since the posting asks them to coach the team to high quality and delivery.

How do you support the career goals of engineers who report to you?

What they are checking: Commitment to professional development, which the posting lists as a key part of the role.

Tell me about leading a team through a period of change or uncertainty.

What they are checking: Ability to bring a team along through disruption, which the posting names.

How do you stay close enough to the technical work to make good decisions as a senior manager?

What they are checking: Balance between leadership duties and technical credibility with the team.

What would you do

Your team covers engineering, third-party integrations and platform creation. How do you balance those different kinds of work?

What they are checking: Ability to manage a broad scope without starving platform or integration work.

A release is slipping and stakeholders want a date. What do you tell them and what do you do?

What they are checking: Honest communication and recovery planning under schedule pressure.

How do you handle an engineer who is technically strong but hurts team morale?

What they are checking: Willingness to address behavior directly to protect the team.

About the work

Walk me through how you run Agile in practice to meet scope, schedule, cost and quality goals.

What they are checking: Practical Agile delivery knowledge, which the posting names under technology proficiency.

What do you look for when hiring an engineer for your team?

What they are checking: Clear hiring standards that draw in and grow top talent, as the posting describes.

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The full job description

As published by Direct Supply.

Position Summary: Direct Supply is building the future of healthcare technology with industry-leading products, solutions and platforms to help improve the lives of millions of seniors and those who care for them. In the Manager, Engineering position, you’ll lead a broad team of Partners focused on engineering, third party integrations, and platform creation. In this role, you’ll use your strong engineering and execution focused background to oversee the delivery of software solutions.. You’ll be expected to understand the process of software development and help coach your team to high levels of quality and delivery. You’ll also play a key role in the professional development of your direct reports. Competencies & Skills Needed: • Leads & Inspires Partner Owners - Energizes a team of Technology talent, creating an environment that draws in and grows top talent. Actively engages and develops Partners to perform their best and achieve their career goals. • Technology Proficient - Clearly understands the software development process and Agile methodologies and applying skills to meet scope, schedule, cost and quality goals. • Leads Through Change and Ambiguity - Leads with vision and agility during periods of growth, disruption, and uncertainty. Advocates for change, while bringing the team along and navigating through uncertainty to prioritize focus for the team. • Champions Innovation - Seeks out and adopts innovative new approaches and tech-enabled solutions to create value and transform work. • Fosters Inclusion & Diversity and Wellbeing - Acts as an advocate for and supports the wellbeing of all Partners. Willingly invites, acknowledges, and values different ideas. Encourages inclusion and diversity through word and action. • Drives Accountability & Results - Delivers quality and timely outcomes, driving business results through the team. Provides clear expectations and ensures follow through. • Effective Communicator - Delivers timely and helpful communication to teams and stakeholders. Provides clarity on decisions, ties back to the business, and outlines any actions or deliverables that are needed. What You’ll Do and Impact: • Lead multiple engineering teams in coordination with VP, Technology to support our growing business needs. • Participate in broad technology strategy in collaboration with other leaders across Direct Supply. • Build, grow, and lead a team of technology and engineering professionals focused on developing scalable, reliable, and cost-efficient products and platforms for Direct Supply. • Deliver software programs on-time and on-budget with high quality. • Facilitate relationships with external customers and coordinate work with their technology teams. • Establish and maintain a culture of team mentorship to build & continually strengthen core competencies in craftsmanship, platforms, and architecture. • Ensure teams meet project commitments across all areas on time, with quality, and within budget. • Balance resources and grow capabilities of the team to deliver business value. • Deliver Technology Platforms for use across Direct Supply. • Understand the business environment and align project goals and team to deliver on business outcomes. • Serve as a technical liaison between development teams and business stakeholders. • Maintain an understanding of the technology and development process of the team, to speak about quality at a deep level. • Provide oversight of the development process in conjunction with Development Leads, Architects, and Systems Analysts. • Prioritize efforts to reduce operational load, merge and eliminate projects that do not align to business goals, and align teams around skill/focus areas for productivity. Experience: • Bachelor’s degree in Computer Science, Software Engineering, or Computer Engineering • 6+ years of IT and Software Engineering work experience including software design and development • 1+ years of experience leading technical professionals and software development teams • Experience leading in a large technology platform and/or large organization • Experience with software and database design concepts • Strong technical experience in .NET, Web, and Mobile development as well as object-oriented design and coding skills (C++ and/or Java) • Track record of successful technology introduction and process improvement Additional Items of Interest: • Has experience leading delivery on large scale projects • Experience with distributed (multi-tiered) platforms, algorithms, and relational databases • Experience with leading technology teams developing platforms for use by external customers • Experience with managing support request ticket queues and transforming recurring requests into automated workflows Job to be performed in the location listed. Generous benefit package available. © 2013 to 2026 Direct Supply, Inc. All rights reserved.

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