An Engineering Manager at Direct Supply is a strategic leadership role responsible for guiding high-performing software engineering teams, driving technical excellence, and delivering technology solutions that empower the senior living industry. In this role, you are not just managing tasks; you are shaping the digital platforms, e-commerce systems, and supply chain technologies that care providers rely on daily. Your work directly impacts the efficiency of senior living communities and the quality of care delivered to millions of seniors.

At Direct Supply, technology is a core business driver. As an Engineering Manager, you will lead efforts to modernize legacy architectures, integrate advanced capabilities like Artificial Intelligence (AI), and foster a culture of continuous improvement. You will act as the bridge between technical execution and business strategy, collaborating closely with product managers, operational leaders, and executive stakeholders to turn product visions into scalable, reliable software.

This position requires a unique blend of deep technical stewardship, people empowerment, and business acumen. Whether you are leading a team focused on transactional platforms, logistics, or emerging AI-driven solutions, your ability to inspire engineers, navigate complex organizational structures, and maintain a high quality bar is critical to the company's long-term success.

The questions you will encounter during the Direct Supply interview loop are designed to evaluate your situational leadership, technical oversight, and alignment with the company's collaborative culture. These questions are drawn from real candidate experiences and reflect the actual scenarios you will face during your conversations with peer managers, directors, and executives.

People Leadership & Team Management

This category assesses your ability to build, mentor, and guide engineering teams through challenges, organizational changes, and performance management.

• Tell me about yourself and your journey into engineering management.
• How do you handle a situation where a high-performing engineer is causing friction within the team?

Preparing for an Engineering Manager interview at Direct Supply requires a balanced focus on your technical foundation, leadership philosophy, and systemic problem-solving capabilities. You should approach your preparation by reflecting on concrete examples from your past where you successfully navigated complex technical and human dynamics.

To stand out, focus on demonstrating strength in these core evaluation criteria:

Technical & Architectural Stewardship – You must prove your ability to guide technical decisions without micromanaging. Show how you evaluate trade-offs, mitigate technical debt, and keep your team aligned with modern software engineering practices, including emerging trends like AI.

People Leadership & Talent Development – Direct Supply values managers who empower their teams. Be ready to discuss your coaching frameworks, how you build trust, and how you foster a diverse, inclusive, and high-performing engineering culture.

Cross-Functional Collaboration & Stakeholder Alignment – You will need to demonstrate how you partner with product, operations, and leadership to deliver business value. Focus on your ability to translate technical concepts into business outcomes and negotiate priorities effectively.

Executive Presence & Communication – Because the interview process involves senior directors and executive vice presidents, you must show that you can communicate strategically, handle high-level scrutiny, and present a clear vision for your engineering organization.

The interview loop at Direct Supply is thorough, highly consensus-driven, and designed to evaluate your fit from multiple organizational perspectives. The process is extensive, often involving multiple stages that span several weeks to ensure alignment across engineering, product, operations, and executive leadership.

The journey begins with an initial phone screen with a recruiter to assess basic alignment, followed by a deeper conversation with the hiring manager. If you advance, you will enter an intensive onsite loop. This onsite stage is characterized by a series of back-to-back, 30-minute interviews with a diverse panel, including peer managers, staff engineers, and directors. You should also expect timed onsite tests or situational assessments during this phase.

Following the team interviews, the process moves to executive-level evaluations. You will meet with senior directors, the EVP of Operations, the Head of HR, and ultimately the EVP/CTO of Technology. Because Direct Supply places a strong emphasis on executive alignment, the final hiring decision requires consensus at the highest levels of the technology organization.

The timeline above outlines the typical progression from your initial application to the final executive reviews. Candidates should prepare for a marathon process that requires sustained energy, consistent messaging, and patience across several weeks of evaluations. Because the onsite loop is highly compressed with multiple 30-minute sessions, managing your pace and keeping your answers concise is critical.

To succeed in the Direct Supply interview loop, you must understand the specific domains where you will be evaluated. Each round is structured to test a distinct facet of your management capability.

People Leadership & Team Empowerment

This area focuses on your ability to build cohesive, motivated, and autonomous engineering teams. Direct Supply looks for leaders who do not dictate solutions but instead build frameworks that allow engineers to do their best work.

Be ready to go over:

• Conflict Resolution – Your strategy for identifying and resolving interpersonal or technical friction within your team.
• Career Pathing & Mentorship – How you help engineers grow from junior roles into senior and staff-level contributors.
• Team Autonomy – The methods you use to delegate decision-making authority while maintaining alignment with organizational goals.
• Advanced concepts – Decentralized decision-making frameworks, psychological safety metrics, and succession planning for key technical roles.

Example scenarios:

• Managing an underperforming senior engineer who is resistant to feedback.
• Transitioning a team from a top-down management style to an agile, self-organizing model.

Technical Vision & Emerging Technology (AI)

Even if you are not writing code daily, you must demonstrate strong technical instincts and an understanding of modern architecture. Recently, Direct Supply has placed a significant emphasis on Artificial Intelligence (AI) and how engineering leaders plan to leverage it.

Be ready to go over:

• System Modernization – How you guide teams through migrating legacy monoliths to scalable, modern microservices or cloud architectures.
• AI & Machine Learning Strategy – Your perspective on identifying high-value use cases for AI integration within business workflows.
• Technical Risk Management – How you balance rapid feature delivery with long-term system stability and security.
• Advanced concepts – Generative AI integration patterns, data privacy considerations in AI models, and managing technical debt in cloud-native environments.

Example scenarios:

• Assessing whether to build an in-house machine learning pipeline or leverage third-party AI APIs for a new product feature.
• Guiding a team through a major architectural migration when the destination stack is unfamiliar to you.

Executive Presence & Stakeholder Management

As an Engineering Manager, you will interact with non-technical business partners and executive leaders who focus heavily on operational metrics, ROI, and business outcomes.

Be ready to go over:

• Executive Communication – How you present complex technical challenges, project delays, or resource needs to C-suite executives.
• Cross-Functional Negotiation – Aligning competing priorities between engineering, product management, and operations.
• Change Management – Leading your team through organizational shifts, strategy pivots, or changes in leadership.
• Advanced concepts – ROI modeling for engineering initiatives, managing upward communication during high-severity outages, and establishing key performance indicators (KPIs) that map to business success.

Example scenarios:

• Defending a necessary technical refactoring project to an executive who wants to prioritize commercial features.
• Navigating a sudden shift in business priorities that requires shelving a project your team spent months building.