Converting Demos into Signed Deals A five-person AI agency in Portland was delivering great demos. Their prospect feedback was consistently positive: "Impressive technology." "Real...
Selling Ongoing AI Maintenance and Support Contracts An AI agency in Portland built a beautiful computer vision quality inspection system for a food manufacturing client. The $280,...
Selling AI to Telecommunications Companies A seven-person AI agency in Dallas signed a $560,000 engagement with a regional wireless carrier serving 1.2 million subscribers across e...
Selling Platform Engagements vs One-Off Projects An AI agency in San Francisco had a pattern. They would win a $150,000 project, deliver it brilliantly, collect the final payment, ...
Transitioning from Hourly to Outcome-Based Selling Two AI agencies in the same city were competing for a manufacturing client's predictive maintenance project. Agency A proposed 2,...
Selling AI Services to Private Equity Portfolio Companies Last November, a three-person AI agency in Chicago closed a $1.2 million annual deal with a mid-market private equity firm...
Selling AI Services During Economic Downturns A three-person AI agency in Phoenix watched their pipeline evaporate during the economic slowdown of early 2025. Three deals totaling ...
Upgrading Project Clients to Retainer Contracts A five-person AI agency in Atlanta had a revenue problem hiding behind impressive numbers. They closed $1.6 million in project reven...
Selling AI to Law Firms and Legal Departments A three-person AI agency in Chicago signed a $190,000 engagement with an Am Law 200 firm that had 280 attorneys across four offices. T...
How to Sell AI Services to Family Offices and High-Net-Worth Investors A colleague of mine who runs a seven-person AI agency in Miami landed a $480,000 annual retainer with a singl...
Building Your Sales Enablement Tech Stack A four-person AI agency in Austin was running sales out of a shared Google Sheets spreadsheet, the founder's personal email, and a pile of...
Selling AI Compliance and Governance Tools A four-person AI agency in Washington, D.C., pivoted to AI compliance after the EU AI Act came into force and their existing enterprise c...
Selling AI to Mid-Market Companies ($50M-$500M) A four-person AI agency in Charlotte closed $1.1 million in AI contracts in a single year by exclusively targeting mid-market compan...
Turning First Projects into Second and Third Deals An AI agency in Charlotte delivered a $160,000 customer churn prediction project for a mid-market SaaS company. The project was a...
Selling AI System Migration and Modernization A financial services company in Chicago spent $1.8 million building an AI-powered fraud detection system in 2022. Three years later, t...
Selling AI to Retail and Ecommerce Companies A six-person AI agency in Austin closed a $290,000 deal with a direct-to-consumer brand doing $85 million in annual revenue. The projec...
Non-Negotiable Terms in AI Contracts A five-person AI agency in San Francisco learned this lesson the hard way. They signed a $280,000 contract with a logistics company that includ...
Selling AI to Construction Companies A five-person AI agency in Denver closed a $230,000 engagement with a mid-sized general contractor doing $380 million in annual revenue across ...
The Sales-to-Delivery Handoff That Keeps Clients Happy A seven-person AI agency in Denver had a retention problem that showed up six months after every sale. Their close rate was s...
Pricing Enterprise Support and SLA Tiers A six-person AI agency in Seattle had built a successful practice delivering AI projects to mid-market and enterprise clients. Their proble...
Building an Effective Pre-Sales Engineering Function A ten-person AI agency in Austin was closing deals at a twenty-two percent win rate. Their founders, both strong business devel...
Nurturing Inbound Leads Through the Funnel A six-person AI agency in Boston was generating 340 inbound leads per month through content marketing, webinars, and organic search. Thei...
Selling AI Services to Venture-Backed Startups A three-person AI agency in New York signed four venture-backed startups in a single quarter. The engagements ranged from $60,000 to ...
Improving Proposal Win Rates from 20% to 50% An eleven-person AI agency in Atlanta sent forty-two proposals in 2025 and won nine of them, a twenty-one percent win rate. Each propos...
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