Illinois · Applied AI
AI outbound sales in Chicago
Outbound that doesn't sleep, built for businesses operating in Chicago.
What AI outbound sales actually does
An AI sales agent that runs your outbound — researches prospects, personalises the pitch, sends the first 3 touches, and only hands a warm reply to a human. Hits the activity numbers no SDR can keep up with, without the spammy blast feel.
We've worked with enough operators in Chicago to know that the brief that arrives in our inbox is rarely the brief that ends up shipped. The first thing we do on any AI outbound sales project is sit with your team for a day before we propose anything.
- 01 Lookalike prospect lists built from your best existing customers
- 02 Personalised first-touch emails and LinkedIn messages — not templated
- 03 Auto-followups across email + SMS until they reply or opt out
- 04 Warm replies routed straight to your CRM with full context
Built on: Claude + GPT-4 for messaging Apollo / Clay for enrichment HubSpot or your existing CRM Twilio for SMS, Gmail / Outlook for email
Why Chicago businesses choose this
Chicago runs on logistics, manufacturing, finance and a genuinely diverse industrial base – AI here means fitting into operations that were already running lean before AI existed.
The Chicago context, plainly.
A major freight and logistics hub, a deep manufacturing base, and a futures and options trading industry with zero patience for anything slow. Chicago businesses want AI that respects an operation that already runs tight.
We work with teams across Chicago: The Loop · River North · Wicker Park · Lincoln Park · Evanston · Naperville.
How we build AI outbound sales for a Chicago team
We scope narrow, ship a working pilot, then harden it into production. The first slice is the highest-leverage workflow for your Chicago business, so value lands before the build is finished. Every engagement starts with a short call and a paid discovery if the brief needs one.
Outbound that doesn't sleep.
The outcome for Chicago teams
If we build the right slice first, Chicago teams feel the difference inside the first month. One NZ SaaS team replaced two outbound SDRs with an AI agent + one closer — 3× the meetings booked, same pipeline cost.
One NZ SaaS team replaced two outbound SDRs with an AI agent + one closer — 3× the meetings booked, same pipeline cost.
AI outbound sales in Chicago – common questions
When does AI outbound sales actually pay back?
Inside the first quarter, in our experience. We pick the first slice specifically because it's the highest-leverage workflow for a Chicago – so the savings start landing before the rest of the build is finished.
Do you do hourly billing or fixed price?
Fixed price for the pilot, every time. After that it's your call – fixed price per milestone or a small monthly retainer for ongoing iteration. We don't run open-ended T&M because it disincentivises us from finishing.
Can you walk us through a comparable build?
Yes – on the first call we'll pick the closest engagement we've shipped to what you're describing and walk through the outcome, the headcount and the time it took. One NZ SaaS team replaced two outbound SDRs with an AI agent + one closer — 3× the meetings booked, same pipeline cost.
Will this run on our own infrastructure?
Yes, where it makes sense. AI outbound sales can sit entirely in your cloud account, with model calls routed through endpoints you control. We default to Claude + GPT-4 for messaging, Apollo / Clay for enrichment, HubSpot or your existing CRM, Twilio for SMS, Gmail / Outlook for email but the architecture supports your existing platform choices.
The honest version of a sales call.
No deck. No discovery doc. Just whether this is worth building and what it would cost.
Get in touch
Talk to us about this
Tell us what you're trying to do and we'll reply with how we'd build it — no obligation.