Job Search VA / Application Specialist (Proactive | Tech-Savvy | AI-Fluent)

I'm looking for a highly motivated, detail-obsessed, and assertive VA to manage my job search end-to-end. This is not a passive role. I need someone who takes ownership, drives the process, and holds me accountable — not the other way around. If I go quiet, I expect you to follow up. If a deadline is approaching, I expect you to flag it. If there's a better way to do something, I expect you to bring it to me with a solution, not a question.
You will research job opportunities, tailor application materials, submit on my behalf, and keep everything meticulously organized. You'll operate largely independently and be expected to manage your own workflow without hand-holding.
Responsibilities:

Search for relevant job listings daily across platforms including LinkedIn, Indeed, ZipRecruiter, Monster, Glassdoor, company career pages, and any other high-yield sources you identify
Tailor my resume and cover letter to each specific job description — this means thoughtful customization, not find-and-replace
Submit applications through job portals or email on my behalf, ensuring every submission is complete, accurate, and polished
Maintain a detailed application tracker in Google Sheets — logging company, role, date applied, link, application status, and any follow-up actions
Proactively follow up on submitted applications at appropriate intervals without being asked
Flag interview requests, recruiter messages, or any responses immediately — do not wait for a check-in
Remind me of any actions I need to take on my end; if I'm slow to respond, follow up
Continuously identify ways to improve the process and bring those ideas forward

What I'm Looking For:
Work Style — This Is Non-Negotiable
You are a self-starter. You do not wait to be told what to do next. You anticipate needs, solve problems before they become problems, and keep the process moving at all times. You are organized to a fault, proactive by default, and comfortable holding a client accountable. If something is overdue, you say so. If something could be done better, you say so. I want someone who is on top of this at all times — not someone I have to chase.
Experience

Demonstrated experience managing job searches and submitting applications on behalf of clients
A track record of success — clients who received interviews, offers, or landed roles as a result of your work
Prior experience with clients in the technology sector (software, product, data, IT, etc.) is a strong plus, as it signals familiarity with what tech roles require and how those applications are evaluated
Background in VA work, recruiting, or HR is advantageous

Technical Skills

Proficient in Google Workspace: Google Docs, Google Sheets, Google Drive
Proficient in Microsoft Office: Word, Excel
Strong English writing skills — you will be customizing professional documents and this must be impeccable
Familiarity with LinkedIn, Indeed, and other major US job boards is required

AI Proficiency — Highly Valued
The ability to leverage AI tools effectively is a strong differentiator for this role. Preference is given in the following order:

Claude (Anthropic) — highest preference; familiarity with Claude specifically is a meaningful advantage
ChatGPT / OpenAI tools — highly valued
Any other AI or LLM tools (Gemini, Copilot, Jasper, etc.) — valued, even if a lower preference
Applicants with no AI experience will be considered but ranked lower

To Apply, Please Include:

- A short note describing your experience with job boards and which platforms you know best
- One or two examples of client outcomes — did your clients get interviews? Offers? In what industries? Please be specific!!
- A brief description of how you stay organized and manage your workflow independently
- What AI tools you use and how you use them in your work?
- What is your earliest start date?
- What is your desired hourly comp for the role?

IMPORTANT:
- Provide scheduling windows for a 30min follow-up call that can be held same-day and/or within 1-2 days of submitting your application
- List what AI tools you use and how you use them in your work