Personal Assistant – Medicare Lead Follow-Up & Dating App Support (PST) + $10 Show Bonus

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TYPE OF WORK

Part Time

SALARY

$4.00 - $5.00/hour + $10 bonus per Quali

HOURS PER WEEK

20

DATE UPDATED

Aug 15, 2026

JOB OVERVIEW

We're looking for a sharp, fluent-English Personal Assistant for two connected parts of the role: helping activate and follow up with opted-in Medicare leads, and personally collaborating with me live on dating apps. This is a part-time, ongoing role (20 hrs/week, 4 hrs/day, with flexible timing between 9am–7pm PST) — and here's the headline: you can earn a $10.00 USD bonus per Qualified Appointment, on top of your hourly base.

PART 1 — MEDICARE LEAD ACTIVATION & SMS FOLLOW-UP (about half your time):
This is NOT cold calling or lead generation. Every lead you contact has already opted in — your job is speed-to-lead response and long-term nurturing, activating leads who raised their hand, not prospecting strangers.
- Speed-to-Lead Outbound Calling: call new Meta ad leads within 5 minutes of their form submission, any time between 9am–7pm PST, up to 5 times a day (via power dialer)
- Long-Term SMS Nurturing & GHL Inbox Management: GoHighLevel is already set up with an extensive Email/SMS/FB Messenger nurture sequence — maintain two-way text engagement, keep leads warm, and convert that engagement into a booked appointment once their enrollment window opens
- Multi-channel follow-up: move fluidly between phone, SMS/text, and app messaging depending on how each lead responds
- Re-engaging no-shows and cold/stalled leads via text to get them rescheduled
- Booking appointments and following up to maximize show rate (confirmation texts/calls, reminders, reschedules)
- Logging every interaction, lead status, and appointment detail accurately in GoHighLevel (GHL)

PART 2 — PERSONAL ASSISTANT: DATING APP COLLABORATION & CALENDAR (about half your time):
This is collaborative, not autonomous. I stay logged into and in control of my own dating app accounts at all times — you're not messaging or swiping as me, you're advising me live while I do it.
- Join live video calls (Zoom) where we go through matches and messages together in real time — you advise on who to prioritize based on my preferences, and can suggest message wording for me to review and send myself
- Help me spot red flags or inconsistencies in profiles, and flag the matches most worth pursuing
- Once we agree a date should happen, schedule and confirm evening dinner/drink dates on my personal Google Calendar, making sure times and locations work with my schedule
- Support broader executive calendar coordination — resolving conflicts and prioritizing my appointments across GHL and Google Calendar

YOU'RE A STRONG FIT IF YOU HAVE:
- Fluent English, spoken and written — this is required
- Personal or professional experience with dating apps (Tinder, Bumble, Hinge, etc.) and genuine comfort giving real-time opinions on profiles and messages over video
- Experience with speed-to-lead response, inbound follow-up, or SMS/text-based customer engagement — Medicare or insurance experience is a plus
- Hands-on comfort with GoHighLevel (GHL) — especially the unified inbox — power dialers, Google Calendar, and Zoom
- A quiet, reliable home office setup, dependable internet, and a professional headset/webcam
- Genuine, real-time reachability for speed-to-lead calls any time between 9am–7pm PST, Monday–Friday — able to drop what you're doing and call a fresh lead within 5 minutes, up to 5 times a day. Still a 4 hrs/day, 20 hrs/week role — the timing of those hours just flexes across this window rather than sitting in one fixed block
- A warm, natural communicator (by voice AND by text) who can keep a conversation going without sounding scripted, plus good judgment and discretion with personal matters

COMPENSATION:
$4.00–$5.00 USD/hour base pay ($5/hr is the top of this range), PLUS a $10.00 USD Qualified Appointment Bonus.

A "Qualified Appointment" is a scheduled Medicare consultation the lead actually attends during — or within 90 days of — their active enrollment window (Initial Enrollment Period, Turning-65 month, or Annual Enrollment Period), i.e. a window where a valid application can actually be taken. If a lead submits a form early (5+ months before eligibility), you'll keep them warm in the SMS/GHL nurture sequence — the bonus isn't triggered by that early info call itself, it's earned once you've kept the lead engaged and get them booked when their active window opens.

TO APPLY:
Please include a 30–60 second voice intro (Vocaroo, Loom, or a phone voice memo link) so we can hear your spoken English. Applications without a working voice link will not be considered.

SKILL REQUIREMENT
Customer Service Appointment Setting GoHighLevel
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