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Director, IT & Help Desk

March 12, 2026

About the position

We are looking for a Director, IT & Help Desk to lead and scale our internal technology infrastructure and employee support function. This is a strategic and hands-on leadership role responsible for building a secure, efficient, and high-performing IT environment that enables every team at Hello Heart to do their best work. Reporting into our VP of User Operations, you will define and execute our internal IT strategy, oversee help desk operations, and elevate the employee technology experience across our hybrid workforce with multiple locations. You will partner cross-functionally with Security, Legal, People, and Executive Leadership to ensure our systems are secure, compliant, scalable, and user-friendly.

Responsibilities

Define and execute a global IT strategy that supports a regulated healthcare environment to support 3x organizational growth across multiple locations around the world.
Lead and scale a high-performing global IT and Help Desk organization with clear SLAs, executive white-glove support, and standardized processes across all locations
Own IT risk, compliance, and audit readiness, including HIPAA alignment, access governance, endpoint security posture, logging, retention, and business continuity planning
Architect and optimize identity, device, and collaboration infrastructure, including MDM, zero touch provisioning, SSO, Google Workspace Enterprise, and least privilege access models
Own global office technology infrastructure, including networking, secure connectivity, A/V systems, and operational support for board meetings and company events
Manage IT budget, vendor strategy, contract negotiation, licensing optimization, and third-party technology governance in partnership with Security and Legal
Drive automation and modern workplace innovation, including secure adoption, governance, and enablement of Gen AI tools to improve employee productivity while mitigating data, privacy, and regulatory risk

Requirements

Ability to work hybrid from our Menlo Park office at least 2-3 days per week or as needed
10+ years of IT and Help Desk experience, including 5+ years in a leadership or management capacity
Strong expertise in Google Workspace Enterprise, MDM platforms, and SSO systems
Experience managing macOS, iOS, and Android environments in a hybrid or distributed workforce
Proven ability to design and scale onboarding, device management, and user lifecycle processes
Experience supporting executive leadership, including C-suite stakeholders
Demonstrated success managing vendor relationships, negotiating contracts, and optimizing technology spend
Demonstrated experience integrating AI-driven solutions into core workflows to improve efficiency, scalability, and decision-making
Strong project management and cross-functional collaboration skills
Data-driven mindset with experience building reports, dashboards, and operational metrics
Bachelor’s degree or equivalent work experience

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...