Drop Cowboy review for insurance agents: pricing, dialing and compliance
Drop Cowboy sends ringless voicemail and texts in bulk, then lets agents call back responders from a browser dialer. A built-in CRM holds contacts, consent and do-not-call lists.
Messaging + Dialer is the usual start, with one power seat included.
- Best for
- Agencies that lead with ringless voicemail and texts, then call back the people who respond
- Type
- Ringless voicemail and texting platform with dialer seats
- Price
- From $125 a month, seats from $29
- Dialing
- Click-to-call, power and predictive up to 3 lines
- Texting
- Bulk and one-to-one on messaging plans
- Recording
- Optional on dialer calls, with transcripts
- CRM connections
- Built-in CRM. HubSpot card, and Salesforce, Zoho and Pipedrive through Zapier
- Free trial
- 14 days for every new account
Our take
Drop Cowboy is a voicemail and texting tool first, with dialer seats added on. Its consent tools are among the most complete here, with evidence on file and a universal opt-out.
Ringless voicemail needs prior written consent for marketing. Drop Cowboy publishes guidance, but the agency carries the risk.
Its standard terms prohibit any mention of Medicare.
Pros
- Consent history with evidence and a universal opt-out
- Calling-hour checks by address and area code
- Bring your own carrier at lower seat prices
- Predictive dialing up to 3 lines
- No contract
Cons
- Terms bar Medicare use
- Data exports limited to a 90-day window
- No agency system connection
- Small money-back guarantee
Plans and pricing
| Plan | Billed monthly | What it adds |
|---|---|---|
| Just MessagingVoicemail and texts only | From $125 | Ringless voicemail, texts, voice broadcast, built-in CRM and inbox |
| Messaging + DialerMessaging with live callsWhere most agencies start | From $224 | Messaging plus one power dialer seat |
| Seat | Price a month | Lines |
|---|---|---|
| Just Dialer (manual) | From $29 | 1 |
| Power or predictive upgrade | Ask sales | Up to 3 on predictive |
| Voice Pro upgrade | $20 more | All-day talk time |
Prices as of October 2026, from Drop Cowboy's pricing pages. Bringing your own carrier cuts manual, power and predictive seats to $19, $49 and $79. No contract.
Usage and add-ons
| Item | Price |
|---|---|
| Compliance fee | $0.0039 a message |
| Local number | $3 a month |
| Toll-free number | $6 a month |
| Phone menu or forwarded call | $0.15 each in the US and Canada |
| AI voice cloning | $0.005 per 100 characters |
| Automation tasks | $2.50 per 1,000 |
Good to know before you buy
- Calls and messages are limited to 8 AM to 9 PM local time.
- Texting campaigns add registry fees by use case.
- Unused credits aren't refunded when you cancel.
Dialing modes
| Mode | What it does | Lines per agent | Plan |
|---|---|---|---|
| Click to Call | Dial one contact at a time | 1 | Manual seat |
| Auto | Power dials through a list | 1 | Power seat |
| Predictive | Dials several contacts at once | Up to 3 | Predictive seat |
- Dropped calls
- Ask for the abandon setting and report before you dial predictively
- Voicemail drop
- Plays a recording when a machine answers
- Ringless voicemail
- The core product. Messages go straight to voicemail with a press-to-opt-out line
- Contact limits
- Max contacts within a set number of days
Inbound calls and transfers
Callbacks from voicemail and text campaigns can forward to a phone or call center, with Slack and Teams alerts for new texts.
- Routing
- Forward callbacks, choose the return line and caller ID
- Phone menu
- Press-to-opt-out on ringless and callback flows
Phone numbers and spam labels
- Who supplies numbers
- Drop Cowboy, or your own carrier such as Twilio
- Bring your own carrier
- Yes. Numbers stay on your carrier at no platform rent
- Local presence
- Buy coverage by area code. The dialer picks the closest number
- Call signing (STIR/SHAKEN)
- Upload your own certificate on your own carrier
- Spam label monitoring
- FCC complaint badges when buying numbers, plus BLA, WebRecon and RND checks
Do Not Call, calling hours and consent
- National Do Not Call list
- Scrub tools and integrations. The terms keep the obligation on you
- State rules
- Federal and state calling hours applied automatically, covering 22 states
- Your own do-not-call list
- Per brand or all brands, up to a million rows
- Calling hours
- 8 AM to 9 PM by address and area code. Manual calls can warn or block
- Consent records
- Consent history per channel with evidence. Form capture with watermarked screenshots
- Opt-outs
- STOP clears text and phone consent. Universal opt-out revokes every channel, with an audit log
Medicare is off limits Drop Cowboy's standard terms prohibit any mention of Medicare. Medicare agencies need a written exception before using it.
Texting and registration
- Plans with texting
- Just Messaging and Messaging + Dialer
- Pictures
- Yes, except from toll-free numbers
- Carrier registration
- You file the 10DLC registration (US carrier registration for business texting) in Trust Center under your legal name
- Before approval
- Ringless voicemail can start while texting waits
- Opt-out words
- STOP and START
Call recording and Medicare
- Recording
- Optional on answered dialer calls
- Transcripts
- On or off with recording
- How long it's kept
- Content moves to archive every 90 days
- Export
- Self-serve within a 90-day window. Help with older exports costs extra
- After you cancel
- No duty to keep or return data
CMS's 2027 plan-year rule keeps Medicare sales calls for six years. Drop Cowboy's terms bar Medicare use in any case.
CRM and agency system connections
| Connects to | Type | How | What moves |
|---|---|---|---|
| Built-in CRM | CRM | Built in | Contacts, campaigns, inbox, consent and do-not-call lists |
| HubSpot | CRM | Built in | A card that sends messages and shows outcomes |
| Salesforce | CRM | Zapier | Send ringless voicemail and texts |
| Zoho CRM and Pipedrive | CRM | Zapier | Send ringless voicemail and texts |
| API and webhooks | Automation | API | Contacts, campaigns, messages, consent and do-not-call lists |
Zapier is billed separately. No agency management system connects directly.
Reporting and coaching
Reports
- Campaign results
- CSV export of contacts and reports
- Consent and opt-out audit log
Coaching
- Agent status view
- No listen-in or whisper tools
Getting started
Sign up and verify
Identity checks run through Vouched and Plaid.
Register for texting
File your brand and campaign in Trust Center.
Buy or connect numbers
Buy local presence coverage or bring your own carrier.
Load contacts and consent
Import lists with consent and run your scrub.
Launch voicemail, then calls
Send ringless voicemail and call back responders.
Support by phone, email, chat and a help center.
Contract and canceling
- Term
- Prepaid month to month
- Renewal
- Automatic. Cancel at least 5 business days before
- Refunds
- 48 hours on the first purchase, up to $125
- Canceling
- In settings, by phone, email or chat
- Your data
- Export within the 90-day window before you leave
Terms as of October 2026, from Drop Cowboy's terms and pricing page.
Drop Cowboy alternatives
- SlybroadcastFrom $8 a month for 100 voicemailsRingless voicemail on prepaid credits
- InterCloud9From $69 a user per monthPredictive dialer with texting credit packs
- PhoneBurnerFrom $140 a user per month, billed yearlyPower dialer with texting and email
- KixieQuote onlyMulti-line dialing with CRM logging
- JustCallFrom $29 a user per month, billed yearly, 2-user minimumPhone and texting, predictive on a quote-only plan
See every option in insurance dialers.
Frequently asked questions
How much does Drop Cowboy cost?
Messaging starts at $125 a month and Messaging + Dialer at $224. Dialer seats start at $29.
Can Medicare agents use Drop Cowboy?
Not under the standard terms, which prohibit any mention of Medicare.
Does Drop Cowboy have a predictive dialer?
Yes, a predictive seat dials up to three contacts at once.
Does Drop Cowboy store consent?
Yes. Consent history keeps evidence for each channel.
How we researched this review. We based this review on the pricing, terms and product pages published by Drop Cowboy, reviewed in October 2026, together with our team's experience working with insurance agents and agency owners since 2008.
Corrections
Vendors change their pricing all the time and they don't email us when they do. So if you see a price on here that's gone up, a plan Drop Cowboy quit selling or a contract term that reads different now, let us know and send the link to the page where Drop Cowboy has it. Somebody here pulls up that page and checks it before we change anything on ours.