Crossing the $100K deal threshold transforms your AI agency's economics. This playbook covers exactly how to structure, sell, and deliver $100K+ AI engagements consistently.
VPs of Engineering are the most influential technical evaluators in AI purchasing decisions. This guide covers how to earn their trust, address their concerns, and turn them into advocates for your AI agency.
Some of your best future clients think AI is overhyped. Here is how to earn their trust, address their doubts head-on, and turn skepticism into your competitive advantage.
Selling AI to Sports Organizations: The Agency Guide to a High-Profile, High-Growth Vertical In January 2025, a four-person AI agency in Nashville signed a $340,000 contract with a...
Artificial urgency backfires with sophisticated buyers. Here is how to create real urgency that accelerates AI deals without damaging trust.
Your sales presentation is the single most visible moment in your sales process. This framework covers how to structure, design, and deliver presentations that win AI agency deals consistently.
Funded startups are uniquely attractive AI clients, they have fresh capital, aggressive timelines, and existential motivation to integrate AI. This playbook covers how to find, pitch, and close startup AI deals.
The hardest part of enterprise AI sales is not getting the meeting or writing the proposal, it is closing the deal. This step-by-step guide covers every tactic for moving enterprise deals from verbal agreement to signed contract.
Navigating CTO vs CIO Buying Dynamics: How to Sell AI When Two Tech Leaders Compete An AI agency in Washington, D.C., spent three months cultivating a relationship with the CTO of ...
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 ...
Selling AI to Chief Information Security Officers A five-person AI agency in Washington, D.C., closed a $420,000 engagement with the CISO of a mid-sized financial services firm aft...
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 Across Multiple Divisions in One Company A five-person AI agency in Philadelphia closed their first deal with the supply chain division of a $3 billion consumer products co...
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,...
Building a Structured Deal Review Process An AI agency in Boston had fourteen deals in their pipeline worth a combined $3.2 million. The founder reviewed the pipeline informally ev...
Cold Calling Strategies for AI Agencies A solo AI consultant in Atlanta picked up the phone 847 times over six weeks. Of those calls, 312 connected to a live person. Of those conne...
Winning Deals from Incumbent Vendors A regional bank in the Midwest had been working with a large consulting firm's AI practice for two years. They had spent $1.4 million on what w...
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...
Selling AI to Chief Data Officers A three-person AI agency in Boston closed a $340,000 engagement with the Chief Data Officer of a $2 billion specialty insurance company. The CDO h...
Selling AI to Insurance Companies A nine-person AI agency in Hartford landed a $620,000 engagement with a mid-sized property and casualty insurer. The project: an AI-powered claims...
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...
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 to Manufacturing Companies A four-person AI agency in Detroit signed a $340,000 engagement with a mid-sized automotive parts manufacturer last spring. The project scope ...
Selling AI Training and Enablement Workshops An AI agency in Portland added a workshop offering to their service lineup almost as an afterthought. A client asked if they could trai...
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