Every Thumbtack lead costs you money — whether you win the job or not. And when a customer sends a request, it goes to up to 5 pros at once. The first pro to respond with a helpful, personalized message gets hired significantly more often.

But you can’t be glued to your phone all day. You’re on job sites, driving between appointments, or finally eating lunch. A Thumbtack auto responder handles the speed problem for you — replying instantly, even when you can’t.

What makes LeadWinner different from a basic auto-reply is the dual-channel approach: the AI responds through the Thumbtack platform and sends a direct SMS to the customer’s phone. That way your message reaches them even if they’ve already closed the Thumbtack app.

Here’s how to set it up. The entire process takes about 2 minutes.

What You’ll Need

An active Thumbtack Pro account
A LeadWinner AI account (sign up free here)

No technical knowledge required. No API keys, no code, no integrations to configure manually.

Step 1: Connect Your Thumbtack Account

After creating your LeadWinner account, you’ll see the Sources page.

Click “Add a New Thumbtack Account”
Click “Add an account from Thumbtack” in the modal
A new tab opens with Thumbtack’s authorization page
Log in to your Thumbtack Pro account and approve the connection
You’re redirected back — your Thumbtack account is now connected

The authorization uses Thumbtack’s official OAuth flow. You never share your password with LeadWinner, and you can revoke access at any time.

Step 2: Complete the Quick Start Wizard

The wizard walks you through the essential settings for your Thumbtack auto responder:

Notifications

Set up how you want to be alerted when a new Thumbtack lead arrives:

SMS notifications — instant text to your phone
Email notifications — lead details delivered to your inbox

Even with automation handling the response, you’ll want to know when leads come in so you can jump in for high-value conversations.

2-Way Auto-Dial

This feature is a game-changer for Thumbtack. When a lead comes in, LeadWinner can call your phone immediately. You hear the lead details, press 1, and the system dials the customer — connecting you both live.

Setup:

Toggle on “Enable 2-Way Auto-Dial”
Enter the phone number you want to receive calls on
Click “Verify” — you’ll receive a verification call
Enter the code shown on screen

With Thumbtack, the auto-dial works immediately because the customer’s phone number is available from the lead data. So the moment a lead arrives, the AI sends the text reply AND triggers the call to connect you live.

SMS to Customer

This is unique to Thumbtack. LeadWinner sends a direct SMS to the customer’s phone number — separate from the Thumbtack platform message. You’ll configure:

Your business phone number — this appears as the sender
ZIP code — for local number matching
SMS instruction — what the AI should text (kept under 160 characters for maximum delivery)

The default SMS template greets the customer by name, confirms their request, and includes a clear call-to-action — all in a concise text that gets read.

Business Phone Number

Enter the phone number you want the AI to share with customers. This is the number included in AI responses when customers ask how to reach you.

Continue Conversation

Choose whether the AI should keep conversing with the customer after the initial reply. When enabled, the AI handles back-and-forth questions — answering pricing inquiries, scheduling questions, and availability — until the customer is ready to book or you take over.

Activation

Toggle your business to active. LeadWinner immediately begins monitoring your Thumbtack account for new leads.

Step 3: Customize Your AI Messages

Click the settings icon next to your Thumbtack business to open the full settings panel.

Welcome Message

The AI instruction controls how the bot crafts its first response. You can specify:

Your business name, services, and service area
Pricing information or quote ranges
Your preferred call-to-action (“call us”, “book online”, “reply with your availability”)
Tone and personality (professional, friendly, casual)

You can use any placeholders you like — {customer name}, {their message}, {my business}, or whatever feels natural. There are no strict variable names. ChatGPT reads your entire prompt and figures out what each placeholder means from context, the same way a person would.

The AI uses this instruction combined with the actual lead message to generate a unique, personalized reply every time — not a template.

The key thing to understand: LeadWinner is powered by ChatGPT under the hood. All lead data is passed to ChatGPT, and every decision — what to reply, whether to qualify or decline, how to handle follow-ups — is made by it. So your prompt isn’t a rigid template with placeholders. You can write it exactly like you’d instruct a new hire on their first day: “If someone needs a same-day move, tell them about our express service. If the budget is under $200, politely decline. If they ask about insurance, explain our coverage.” ChatGPT understands these instructions the way a human would.

Services Not Offered

Thumbtack sometimes sends leads outside your specialty. List services you don’t provide here, and the AI will politely decline those requests instead of wasting your time (and the customer’s).

Follow-Up Messages

If the customer doesn’t respond, the AI sends timed follow-ups:

Follow-up 1 (10 minutes): Request phone number for a quick call
Follow-up 2 (1 hour): Re-engage with additional value or different angle
Follow-up 3 (24 hours): Friendly final check-in

You can customize the timing, content, and number of follow-ups (up to 10). Each follow-up is a fresh AI-generated message, not a copy of the first one.

Pricing Information

Share your pricing details with the AI so it can provide accurate quotes. Include hourly rates, flat rates for common services, minimum charges, and any pricing conditions. The AI will reference this naturally when customers ask about cost.

Step 4: Advanced Configuration

The Advanced tab gives you fine-grained control:

Response delay — introduce a short pause before replying (if instant feels too fast for your business)
Non-reply hours — block specific times when you want to handle leads manually
Timezone — ensure all timing (follow-ups, non-reply hours) matches your local time

What the Full Flow Looks Like

Once everything is configured, here’s what happens for every new Thumbtack lead:

Customer submits a request on Thumbtack — “I need my house painted, 3 bedrooms”
LeadWinner detects the lead within seconds
The AI analyzes the request and crafts two messages:
- A reply through the Thumbtack platform (~20 seconds)
- A direct SMS to the customer’s phone number
If the AI determines the lead matches your business, you receive an SMS/email notification with the details
If auto-dial is enabled, your phone rings — press 1 to connect to the customer live
If the customer doesn’t reply, follow-ups fire on schedule
If the customer replies, the AI continues the conversation (if enabled)

You just went from “lead received” to “customer engaged on two channels + phone call in progress” in under 30 seconds. Your competitors are still checking their Thumbtack app.

Why This Matters for Thumbtack ROI

Thumbtack charges you per lead regardless of outcome. If you don’t respond fast enough and lose the job, that money is gone.

With a Thumbtack auto responder:

Response time drops from hours to ~20 seconds
Conversion rate increases because you’re first to respond on two channels
Cost per acquired customer drops because you close more of the leads you’re already paying for
No leads slip through the cracks — nights, weekends, holidays, all covered

The AI pays for itself if it helps you win just one additional Thumbtack job per month.

Get Started

Start your free 7-day trial — live in 2 minutes. If you need help with setup, call (415) 604-0279 or email us. We’ll configure everything for you, free.