macOS Support Engineer (Tier 2-Level, Client-Facing)

Second Son Consulting is looking for a thoughtful, people-smart macOS engineer who loves solving problems, learning constantly, and being part of a team that builds and supports real-world tech solutions. This is a client-facing engineering role - not a help desk job, not a sysadmin-in-a-cave gig.

You’ll take on escalated support issues, dig into thorny macOS platform challenges, and contribute directly to the engineering work that underpins our toolset. Along the way, you’ll collaborate with great clients and teammates who share your curiosity, attention to detail, and desire to make things work better.

We are looking to create a physical presence in the DMV (DC / Maryland / Virgina metro area) or the North Carolina research triangle as we broaden our reach to support teams across the country. Applicants in those regions are our focus for this role, but we will also consider fully remote applicants outside of this region who can work east-coast hours. Note that training will start as 9 am to 6 pm PT, and shift over the first 2-4 months to 9 am to 6 pm ET, which is the ultimate goal for this position.

Second Son is an MSP, which means we’re in the service business - and we love it. If you’re energized by variety, thrive on learning new systems, and like having each day bring something different, you’ll likely be a great fit.

One morning you might be troubleshooting Mail.app connecting to M365; by afternoon, you’re scripting custom deployments or helping a client sort out SSO with Box or Google Workspace. It’s not for everyone - and that’s okay. If you prefer working in a single, stable environment with one stack and one team, we get it. But if variety’s your thing, and you like the challenge of adapting your skills across industries and environments, you’ll find a lot to love here.

In addition to day-to-day support, you’ll also have the chance to contribute to platform engineering projects, including maintaining and evolving our internal toolset and open-source projects. If you’ve used tools like Munki, Nudge, or swiftDialog and get excited about what’s under the hood, we’d love to geek out with you. (We’re the team behind Baseline and Renew, and we contribute to others too.)

The ideal candidate will have a level of understanding of the following technologies that goes deeper than surface level. Candidates should be able to think critically about the domino effects of implementing changes to interconnected systems. We are looking for someone with experience contributing to and implementing strategy, not just pushing buttons. 

In this role you will…

• Provide day-to-day support in cross-platform environments for desktop, mobile devices, server, network, and cloud systems.  (75% macOS to 25% Windows).
• Deploy workstations and mobile devices using MDM/RMM tools and our custom scripts.
• Take escalations for complex technical issues from our Help Desk team.
• Identify, research, and resolve complex technical problems.
• Have the opportunity to learn new things on a daily basis, and cross-train with our other engineers.
• Identify opportunities for the implementation of new technology processes, procedures, or entire new systems. 
• Document, track, and monitor issues to ensure efficient and timely resolutions.
• Learn to recognize support needs and trends, and work with our Account Managers to address the specific needs of the teams and environments we support.

About Us:

We’re a privately-owned, Mac-focused consulting firm based in the Encino/Los Angeles area, supporting clients across the country — from local teams in LA to fully remote companies with no physical HQ.  We have fantastic clients who are fun and seriously committed to their wide-ranging industries. They are as small as a five-person real estate firm to a 50-person product design and manufacturing company to a 75-person non-profit social advocacy agency. Through collaborative, long-term relationships with our clients, we help them to maximize the return on their IT investment, sustaining measurable results with an eye on business strategy, practicality, pragmatism, transparency, a heap of creative problem-solving, and a sense of humor. We may be geeks, but we are geeks with social skills.  We are also partners, husbands, wives, involved parents, loyal friends, music and movie lovers, foodies, single-malt aficionados, and voracious readers.  We love learning new things and our skills and projects are continuously growing in scope and breadth. 

We’re an equal opportunity employer and we welcome candidates from all backgrounds, identities, and walks of life. We believe diverse teams build better companies - and better client relationships too.

Requirements

What you bring to the table…

• 5 or more years of full time IT experience.
• 1-2 years experience managing Macs with one or more MDM platforms.
• A solid understanding of Apple Business Manager and Automated Deployment Workflows.
• Knowledge of Apple’s MDM and DDM spec, including profile creation and preference domains.
• Experience with application deployments and patch management.
• A think-ahead, “ounce-of-prevention” mindset.
• A natural inclination to pay attention to the details.
• Excellent written and verbal communication skills, both within the team and across diverse client environments.
• A friendly, open personality.
• A commitment to business ethics and a client-first mentality.
• Proven ability to set customer expectations.
• Positive and collaborative team member who demonstrates initiative and tenacity.
• Keeps informed of technology trends, has an insatiable desire to learn new things, and follows best practices.
• Are looking for growth opportunities for platform engineering and Sr. System Administrator roles.
• 2+ years of experience doing real-time ticket management using a commercial ticketing system (ConnectWise, AutoTask).
• Strong follow-through and proactive task management.
• Understanding that Second Son is a service business, and that tracking time and efforts in “real time” are an essential part of what is required.
• You bring solid experience, but you're collaborative and open to learning how we do things as a team.
• You're looking for growth - not just in your technical skills, but in how you support people and build relationships

Candidates with skills in the following areas will be given priority consideration:

• Mosyle MDM experience
• Munki/Managed Software Center
• Knowledge working with Mac Admins open source tools like: Installomator, swiftDialog, MunkiReport, Erase-Install, Nudge, SOFA, Support App.
• Scripting knowledge (bash, zsh, python)
• An understanding of Application distribution methods and packaging principles
• Experience managing devices in an MSP environment
• Solid understanding of network and internet protocols such as DHCP, DNS, MX Records as pertains to troubleshooting client-side issues.

TO APPLY

Share your resume and a cover letter (in PDF format*) that explains why you believe you’d be a fit for Second Son and this position. Impeccable communication skills are essential to all we do, and we weigh cover letters heavily. We love a cover letter that shows us your personality, but don’t stress if you’re not a comedian. Just be yourself. We’re mostly interested in learning who you are, what you love to do, and why you’d love to do it here with us. A generic copy-paste won’t do you any favors — take a moment to show us who you are. We read every one.

*We will only be reviewing submissions in PDF format, due to security/macro concerns with .doc, .docx, and .zip file formats.

Benefits

What We Offer:

• Income competitive and commensurate with experience, projecting $40 to $45 per hour.
• Training, certification, and growth opportunities.
• An annual Learning and Development stipend equal to 1 week’s pay; it grows with you.
• Health insurance with Dental and Vision options.
• Paid time off consisting of:
• 6 days of sick leave
• 5 days of lifecycle leave (birth or death)
• 10 days of vacation (accrued)
• 6 paid holidays
• 5 days of paid Jury Duty service
• 401k with matching (after 12 months).
• On-call rotation bonus program.