Hi, I’m Kayla Sox. I sell a simple lead service (I tried lead generation for health insurance—what worked, what flopped, and what I’d do again) and CRM clean-up to small health insurance agencies. Mostly two to twenty agents. Medicare shops, ACA shops, and group brokers. (Back when I worked a single-carrier health insurance job from home in Texas, I wrote an honest review of the experience here.)
Cold outreach scares most folks (here’s a deeper dive on exactly what worked for me). You know what? It scared me too. For another real-world look at cold outreach tactics that resonate with health-insurance brokers, I recommend this straightforward playbook. But I needed meetings. So I tested a bunch of stuff. Email. Phone. LinkedIn. Short video. Even mail. I’ll show you the real scripts and the real numbers. No fluff.
And yes, I used all the tools I mention here myself. Some helped. Some wasted my time. I’ll tell you which is which.
Quick Game Plan (So You See the Flow)
- Who I reached out to and when.
- The list tools I used (mini reviews).
- The one email that got steady replies.
- A phone script that didn’t feel pushy.
- LinkedIn and a 45-second video move.
- A weird “mail” test that stuck.
- My 10-day cadence.
- What bombed.
I’ll drop real replies and call notes too.
Who I Reached Out To (Timing Matters)
I had the best luck with:
- Medicare agencies in Jan–Mar (after AEP cool-down).
- ACA shops in Feb–May.
- Group brokers right after Q4 renewals (Jan–April).
Best days and times for me:
- Tue–Thu, 8:10–9:30 a.m. local time.
- Fri at 8 a.m. was sneakily good too.
Why? Owners check email early. Phones aren’t ringing yet. Coffee’s still warm.
My List And Tools (Short, Honest Reviews)
I used these myself. Here’s what helped and what hurt.
- Apollo: Good for email lists of small agencies. Cheaper than ZoomInfo. Data was decent, not perfect. I always verified.
- ZoomInfo: Better for bigger brokerages and group teams. Pricey. Good phone numbers.
- NeverBounce: I ran every list through this. It saved my domain. Worth it.
- Clay: For matching websites and pulling “carriers we sell” lines. Helpful for custom lines.
- HubSpot CRM: Clean pipeline. Easy tasks. Free tier was enough to start. I’m a fan.
- Instantly: Simple sender rotation. Fewer bells. Better deliverability for me than Lemlist.
- Lemlist: Pretty UI. But I had more spam issues. Your results may differ.
- Loom: I made fast 45-second videos. Thumbnails helped.
- Calendly: Easy booking. I keep the link short and simple.
Side note: every now and then, I’ll sanity-check a direct dial or email by looking at public-facing classified directories—seeing how frequently contact details get refreshed there can clue you in on overall data hygiene standards. A hyper-local example is the Listcrawler board for Palo Alto (you can browse it here: Listcrawler Palo Alto ), and skimming a page like that shows just how rapidly phone numbers and ads rotate, which reminds you why regular list cleaning matters if you want your outreach to hit fresh, working contacts.
Little tech tip: I set up SPF, DKIM, and DMARC on my domains. I also used a sending domain like get.kaylasox.com. That kept my main domain safe.
Email That Got Replies (Real Example + Replies)
Subject lines that worked:
- “Quick idea for [Agency Name]”
- “Saw your [Carrier] page”
- “7-min idea, then I’ll go away”
Here’s my top winner (I sent this to Medicare agencies in January):
Subject: Quick idea for [Smith Medicare]
Hi [First Name] — Kayla here in [City].
I help small Medicare teams clean old leads and book warm calls.
I saw you list [Carrier A] and [Carrier B].
Would a 7-min chat be crazy?
If not, I’ll zip it.
— Kayla
Kayla Sox
[City, State]
If not a fit, reply “stop” and I’ll remove you.
Why it worked:
- Under 70 words.
- One clear ask.
- I used a line from their site (“We sell [Carrier]”).
- Tone felt human. Not needy.
Real replies I got:
- “7 min is fine. Tomorrow 8:30?”
- “We’re set for now. Circle back in May.”
- “How do you ‘clean’ the leads?” (This led to a call.)
Numbers from one run (287 contacts, Jan–Feb):
- Open rate: 64%
- Reply rate: 14%
- Booked calls: 5.2%
- New clients: 3 (two Medicare, one ACA)
- Spend: about $340 (tools + domains)
- New revenue in 60 days: about $12,400
Not bad for a simple note.
Cold Call Script That Didn’t Feel Gross (Role-Play)
I call after email, same week.
My opener (gentle, fast):
“Hey [Name], it’s Kayla. Super quick. I help small agencies turn old leads into booked calls. Did I catch you for 30 seconds, or bad time?”
If they say “bad time,” I say:
“Totally fair. I’ll email a one-liner. Best address?”
(Then I hang up. Respect helps.)
If they say “go ahead,” I go with:
“Cool. Two lines. I noticed you sell [Carrier]. We take your old leads, scrub bad numbers, and text a simple yes/no check-in. You get live calls booked. Worth a 7-minute chat next Tuesday morning?”
Role-play from a real call:
- Owner: “How do you scrub?”
- Me: “We validate emails and phones with NeverBounce and a carrier ping. Then we send a short check-in. No PHI. You see replies in your CRM. You approve the calendar slots.”
- Owner: “Cost?”
- Me: “Pilot is $900 for 30 days. If we don’t book at least 10 calls, we keep working free till we do. Fair?”
- Owner: “Book it. Send invite.”
That one closed in 11 days.
LinkedIn Message That Landed Meetings
I only messaged people who posted in the last 30 days. No mass spam.
Connect note:
“Hi [Name] — saw your post on [Medicare 101 in church halls]. I help small teams revive old leads. Would love to swap a tip or two.”
After they accept, I sent this:
“Thanks, [Name]. Quick idea: we run a 3-text check-in on 6-18-month old leads. It’s gentle: ‘Still looking? Y/N’. If that’s useful, I can show a live sample. If not, no stress.”
That got me 1–2 calls a week. Slow, but high quality.
Short Video That Punched Above Its Weight
I used Loom and held my phone. One take. No script on screen.
Before I settled on business-friendly tools like Loom, I spent an afternoon studying how the most attention-grabbing live-video platforms hook viewers in seconds—for example, this detailed CamSoda review lays out the interactive features and psychological triggers that keep an audience glued to a webcam performer. Skimming those retention tactics can spark ideas for making your own 45-second outreach videos irresistibly clickable.
My 45-second video:
“Hey [Name], I’m Kayla in [City]. I saw your page that lists [Carrier]. I love that you host Medicare 101 nights. We help small shops like yours warm up old leads and book live calls. No PHI. Here’s what it looks like in HubSpot (shows one fake contact card). If you want a 7-minute look, I can show this in real time. If not, all good. Thanks for doing right by seniors.”
I sent the Loom link as a reply to my own first email.
Video emails got 2x more replies than plain text in my Medicare test.
The Weird One: A Little Mail Kit
I sent a tiny “AEP Survival Kit” in early September to 20 Medicare shops:
- One yellow highlighter.
- One sticky note pad.
- A note card: “When the phones cool down in Jan, I’ll book you warm calls from your old leads. —Kayla, [number].”
Cost: about $7 each.
Results: 3 called me in January. One became a client in March. Slow, but sticky.
My 10-Day Cadence (Simple, Not Loud)
Day 1: Email 1 (the short one above)
Day