Technical Career Coach | AI & Cloud |(Remote | Night Shift)

Career Outcomes Manager — AI & Cloud

Full-Time · Location-Independent · US-Overnight Shift (10 PM–8 AM local)

This is an ownership role. Unlike a monitoring or advocacy function, you don't just notice when a student is off track — you're accountable for getting them back on track and, ultimately, for the outcome: a placement, or a real step up into AI or Cloud. You'll carry a cohort of students end-to-end.

● Own a cohort of students end-to-end — their progress, their targets, and ultimately their outcome (placement or a documented upskilling step into AI/Cloud).

● Run regular group sessions and check-ins, primarily facilitating rather than lecturing — creating the space, keeping momentum, and knowing when to bring in a specialist.

● Identify when a student needs something you can't personally provide (deep technical instruction, a niche mock interview, etc.) and coordinate access to the right coach or expert — without losing ownership of the student's overall progress.

● Track and drive each student's progress against weekly/monthly targets and placement-guarantee conditions — not just observe them, but actively work to move the needle.

● Stay credible in technical conversations with working IT professionals — you don't need to out-code them, but you need to speak their language on cloud, DevOps, and AI career paths convincingly.

● Work a 10 PM–8 AM shift (your local time), giving you meaningful overlap with all major US time zones during their working day.

● Tell me about a time you were personally accountable for someone else's result — not just advising them, but owning whether they got there. What was the outcome, and what did you do when it started to go sideways

● Give me a specific number: in your last role, what result were you accountable for, and what was your actual track record against it

● Describe a time a plan wasn't working and you changed your approach mid-stream to still hit the outcome. What made you decide to pivot

● Walk me through how you'd explain the difference between a DevOps and an SRE role to a working developer considering the switch — at a level that would hold up in a real conversation with one.

● What do you actually know about AI/Cloud career paths today — certifications, in-demand skills, hiring patterns Where are the gaps in your knowledge, honestly

● Tell me about a time you had to sound credible on a technical topic you didn't deeply know, in front of someone who did. How did you handle it

● Tell me about a time you ran a group session where people had very different needs. How did you keep it useful for everyone

● Describe a time you brought in a specialist or expert to help someone you were responsible for. How did you decide it was needed, and did you stay involved afterward or hand off completely

● How do you keep ownership of someone's outcome when you're not the one delivering every session

● This role runs 10 PM–8 AM your local time, every working day. Tell me honestly about your experience with overnight or non-standard shifts — what's worked, and what hasn't.

● How do you stay sharp and personable with students at 3 AM your time versus your first session of the night

● This is a location-independent role. What does your ideal working setup look like, and what could disrupt it

● Placement rate (or documented upskilling milestone rate) for your owned cohort, against the qualifying-role threshold.

● % of students meeting weekly/monthly targets and placement-guarantee conditions on pace.

● % of stalled/at-risk students brought back on track within a defined window.

● Appropriate use of expert escalation — students getting the right specialist help without you losing ownership of their overall progress.

● Group session attendance and engagement rate.

• ● Student satisfaction / NPS for your cohort.