Careers

Join Our Mission to Transform IT Services in NYC

At Chief Second, we're not just another IT company. We're a team of passionate professionals dedicated to redefining how growing businesses experience technology support. Founded on the principles of radical generosity and genuine care for others, we're looking for exceptional individuals who share our vision of making a lasting impact in New York City.

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Why Join Chief Second?

We believe technology support can be different. While other MSPs focus solely on fixing problems, we're building lasting partnerships with our clients, helping their businesses thrive through proactive IT management and strategic guidance.

As a new but rapidly growing MSP launched in 2023, we offer you the unique opportunity to help shape the future of IT services while making a meaningful difference in our community.

Our mission goes beyond profit – we're committed to using our success to help others and foster positive change in NYC. If you're looking to grow professionally while being part of something bigger than yourself, we want to talk to you.

Tired of the Traditional MSP Grind?

We get it. We've been there too. Many IT professionals are frustrated with:

Reactive Firefighting

Being stuck in an endless cycle of reactive firefighting, never having the time or resources to implement proper long-term solutions

Not Sustainable

Working at companies that prioritize quick fixes over building genuine relationships with clients

No Opportunity

Feeling like their role lacks long-term significance, with no real opportunity to grow or contribute meaningfully to the business

Not Able to Truly Help

Being locked into rigid processes that don't actually serve the client's best interests

Bad Work-Life Balance

Your team is constantly hitting tech roadblocks. Simple tasks turn into hours of frustration. SupMissing out on work-life balance due to constant emergency responses and after-hours callsport tickets disappear into the void, and your current IT provider seems to operate on their own timeline – not yours.

Sound familiar?

We built Chief Second specifically to address these industry-wide challenges. Our founder spent 20 years in corporate IT, working his way up from engineer to leadership, and knew there had to be a better way to deliver IT services – for both our clients and our team members.

Life at Chief Second:  
IT Done Differently

When you join our team, you'll experience a workplace built around:

True Proactive Service

With dedicated Technology Alignment Engineers and structured monthly reviews, you'll have the time and resources to prevent issues before they impact clients.

Growth & Impact

From Support Engineer to vCIO, every role has a clear purpose and opportunity to shape our clients' success. You're not just fixing problems – you're helping businesses thrive.

Client Partnership Focus

We build genuine relationships through quarterly business reviews, strategic planning, and becoming a trusted extension of our clients' teams.

Work-Life Harmony

Our month-to-month contracts mean we earn our clients' trust through excellence, not lock-in. This allows us to focus on quality service during business hours rather than constant emergency responses.

Purpose-Driven Culture

Be part of a team that uses its success to make a real difference in NYC. Your work directly contributes to our mission of radical generosity and community impact.

Modern Tech Stack

Work with current technologies and best practices, with the freedom to implement proper long-term solutions rather than quick fixes.

Future Opportunities

While we're not currently hiring, we're always interested in connecting with talented IT professionals who share our vision and values. If you're passionate about transforming how businesses experience IT support, we'd love to hear from you.

Send your resume to careers@chiefsecond.com and tell us how you'd like to contribute to our mission.