CoffeeMilk ConsultingCoffeeMilkConsulting
CoffeeMilk Consulting

SMB Consulting · Southern New England

AI-NativeBusinessConsulting.PlainEnglish.RealResults.

Strategy and operations consulting for SMBs across Southern New England, done the AI-native way. Whether that means implementing AI workflows or just thinking more sharply about your business, we bring both.

Founded by Tom Gleason  ·  Former clients: Google · GitHub · Atlassian · Snowflake · Cursor

No contracts · No jargon · Real results

🦞  Based in Rhode Island. Serving businesses across Southern New England (MA/RI/CT). Less hype, more help, all plain English.

Enterprise experience. SMB focus.

Our team has built and scaled operations at leading technology companies. We bring that same execution discipline to Rhode Island businesses.

In practice

What This Looks Like In Practice

AI workflows aren't abstract. Here's what we actually build for businesses like yours.

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Restaurant

Automated review responses drafted and ready to post in seconds.

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Retailer

Inventory reorder alerts triggered by sales velocity, not gut instinct.

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Professional Services

New client intake and follow-up emails handled automatically.

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Any Business

Meeting notes to action items to calendar blocks, without manual steps.

How we work

Services & Pricing

Published prices. No surprises. Start with a Clarity Session, then scale what works.

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Start here

Clarity Session

$500

90 min · recorded

A focused 90-minute conversation. We map your operations, surface your biggest opportunities, and deliver a plain-English report on exactly where AI can move the needle.

Book a Session
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Understand your options

AI Audit

$2,500–$5,000

One-time

A structured review of your current tools, workflows, and data. We identify the highest-ROI AI opportunities and deliver a prioritized implementation roadmap.

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Most popular

Quick Win Package

$5,000–$15,000

Fixed-fee project

A specific AI workflow scoped, built, documented, and handed off. One clear deliverable, one clear outcome. You own it completely when we’re done.

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Scale what works

Ongoing Retainer

$3,000–$8,000/mo

Month-to-month

Continuous consulting and AI implementation. We keep your automations running, check in regularly, and stay available as your business evolves.

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Exact scope determined in your Clarity Session. All prices fixed-fee — no hourly billing.

Why us

A Partner, Not a Vendor

Most AI advice comes from people trying to sell you software. We're the consulting partner who'll tell you what's actually worth doing.

Enterprise experience without the enterprise price tag

We’ll tell you when AI is the wrong answer for your situation

Small, proven bets compound faster than big transformation projects

Local and accountable: we show up, we deliver, you can reach us

Who's behind this

Tom Gleason, Founder

Tom Gleason

Founder · CoffeeMilk Consulting · Rhode Island

I've built my career in enterprise software, working with clients like Google, GitHub, Atlassian, Snowflake, and Cursor. CoffeeMilk brings that same level of strategic thinking and execution to small and mid-size businesses, without the enterprise price tag.

More about us

Ready to grow?

Find out what your business could be doing differently

60 minutes. A plain-English report. Serving businesses across Rhode Island, Massachusetts, and Connecticut.

Book Your Clarity Session