Senior Systems Engineer

Deputy to the Chief Technology Officer

Position Senior Systems Engineer, Deputy to the Chief Technology Officer

Reports to Petru Gavril, Chief Technology Officer

Location 1120 Avenue of the Americas, Suite 1417, New York, NY 10036. Onsite, with regular client visits in Manhattan.

Status Full time, exempt

Compensation Competitive base plus performance bonus and benefits. Range provided on request.

The Short Version

Our Chief Technology Officer has run the technical side of this firm since 2007. He is very good at it, and he is one person. We are hiring the engineer who will stand beside him, learn how he thinks, and take real weight off his desk. Not a helper. A deputy.You will hold the work he hands you as if it were your own, because once he hands it to you, it is.

Why This Role Exists

Roark is a boutique firm. We serve investment managers, law firms, medical practices, and accounting firms across New York. Our clients pay for judgment, not for a call center. They know our names. They expect an owner to answer the phone, and one does.That model has one structural weakness. Excellence concentrated in a few people is fragile. This role exists to distribute that excellence without diluting it. You will become the second person in the room who can make a technical call and be trusted with it.

What You Will Do

Carry delegated ownership

• Take assignments from the CTO with a clear outcome and a deadline, then return with the outcome, not a status update about why it did not happen.

• Run client environments end to end. Standards, patching, backup verification, endpoint health, identity hygiene, network configuration.

• Serve as escalation point for our technicians before an issue reaches the CTO. Solve what you can. Escalate cleanly what you cannot.

• Represent the firm in client meetings. Explain technical decisions to a chief financial officer without condescension and without jargon.

Engineer and operate

• Design, deploy, and document Microsoft 365 and Entra ID environments, including Conditional Access, Intune policy, and tenant hardening.

• Manage endpoint and network infrastructure across our client base. Our stack includes NinjaOne, CrowdStrike Falcon Complete, Proofpoint, Bitwarden, and Ubiquiti.

• Lead migrations and buildouts. New offices, tenant moves, file platform transitions, hardware refresh cycles.

• Investigate security alerts, participate in incident response, and support our tabletop exercises.

Protect the Discipline

• Keep HaloPSA accurate. Time entered the day it is worked, notes a client could read, no ghost tickets.

• Keep Hudu current. If the documentation is stale, the next engineer inherits a guess instead of a fact.

• Uphold our SOC 2 Type II controls in daily practice, not only at audit time.

• Improve what you touch. Every recurring manual task is an invitation to automate it.

Build the bench

• Mentor junior technicians the way you were mentored, or the way you wish you had been.

• Turn your own hard won fixes into knowledge base articles so nobody solves the same problem twice.

What You Bring

Required

• Five or more years in a managed services or multi client IT environment. You have carried a ticket queue and survived it.

• Deep command of Windows, Mac, AWS, Azure, Microsoft 365, and Entra ID administration.

• Working fluency in networking. Routing, VLANs, VPN, DNS, firewall rules. You can read a packet capture without flinching.

• Practical endpoint security experience with EDR platforms, email security gateways, and 

MDM.

• Fluency with AI Tools, especially Claude. 

• You can automate rather than repeat.

• Writing that a client can read and a colleague can follow.

• Willingness to participate in an on-call rotation and to handle after hours cutovers when the work demands it.

Welcome, But Not Required

• Experience serving alternative investment firms, law firms, or regulated financial clients.

• Familiarity with SOC 2, Reg S-P, or investor due diligence questionnaires.

• Certifications such as Microsoft AZ-104 or SC-300, CompTIA Security Plus, Ubiquiti UEWA, or equivalent proof of craft.

• Exposure to Azure, virtualization platforms, or infrastructure as code.

Who You Are

The technical requirements above are teachable. What follows is not, and it matters more.

• A serious worker. You share our work ethic. The CTO has been here since 2007 and has never once been the reason something slipped. You want to be measured by that standard, not protected from it.

• A self starter. Nobody assigns your morning. You see the thing that needs doing and you do it, then you tell someone it is done.

• Relentless about follow up. You close loops without being asked. You circle back to a client before the client must wonder. You stay on a vendor until the matter is resolved, not merely acknowledged. You confirm that yesterday's fix held today, and when a client has gone quiet after a repair, you are the one who checks. Senior management hears from you before it mustask, and the team always knows where a thing stands.

• Comfortable asking for help. You ask early, precisely, and without embarrassment. Pridethat costs a client an hour of downtime is not pride. It is expense.

• In love with the work. You read release notes for pleasure. You have a lab at home, or a project you cannot leave alone. Technology is not merely your trade. It is one of your genuine enthusiasms.

• Honest under pressure. When something breaks on your watch, you say so first and fastest. We can fix any technical problem. We cannot fix a surprise.

• Presentable and professional. You appear before clients as someone they are glad to have in their office. Composed, courteous, unhurried.

• Quietly confident. You would rather be right than be seen being right.

The First Ninety Days

• Days 1 to 30. Learn our clients, our stack, and our standards. Shadow the CTO. Take ownership of your first accounts.

• Days 31 to 60. Run a project of your own from scope to signoff. Begin taking escalations from our technicians.

• Days 61 to 90. Hold a client relationship independently. Present a recommendation to the 

CTO and defend it.By day ninety, the measure of success is simple. The CTO can leave the country for two weeks and the firm does not notice.

What We Offer

• A seat at a firm where your work is visible to the owner and your judgment is wanted.

• Enterprise grade tooling and clients that are sophisticated enough to appreciate why it matters.

• Paid certifications, paid training time, and a direct line to a chief technology officer who teaches.

• A clear path. This role is designed to grow into senior technical leadership.

• Competitive base salary, performance bonus, medical coverage, retirement plan, and paid time off you are expected to use