The highest predictor of customer retention is an early success. Use AI in your onboarding to ask new clients, "What's the fastest, smallest win we can create for you?" Then, use automation to build and deliver that specific solution, ensuring immediate progress and long-term loyalty.

Instead of a broad onboarding, focus the entire initial user experience on achieving one specific, "brag-worthy" value event as quickly as possible. Structure this as a sprint: define the event, remove all friction, design a "click, click, value" path, and use alerts to nudge users along to that singular 'win'.

Standard questions like 'What's your biggest pain point?' often yield poor results. Reframing the question to what work a customer would offload to a new hire bypasses their pride or inability to articulate problems, revealing the tedious, high-value tasks ripe for automation.

To win over skeptical team members, high-level mandates are ineffective. Instead, demonstrate AI's value by building a tool that solves a personal, tedious part of their job, such as automating a weekly report they despise. This tangible, personal benefit is the fastest path to adoption.

To bridge the AI skill gap, avoid building a perfect, complex system. Instead, pick a single, core business workflow (e.g., pre-call guest research) and build a simple automation. Iterating on this small, practical application is the most effective way to learn, even if the initial output is underwhelming.

To bridge the gap between a product's long-term vision and its current state, focus on "progress, not perfection." Deliver a quick, meaningful win for the customer—like a single workflow or integration—to build the trust and momentum needed for them to stay invested in the unfolding roadmap.

To win over a high-profile client resistant to outsourcing, identify a small, specific gap in their current strategy (e.g., lack of carousels). Pitching a low-risk, targeted solution can be the 'foot in the door' that leads to a much larger, full-service engagement.

To gain organizational buy-in for AI, start by asking teams to document their most draining, repetitive daily tasks. Building agents to eliminate these specific pain points creates immediate value, generates enthusiasm, and builds internal champions for broader strategic initiatives, making it an approachable path to adoption.

Instead of launching a full platform, Canary Technologies began by digitizing a single, tedious process: credit card authorization forms. This "bite-sized" approach allowed them to solve a tangible pain point, build trust, and "earn their right" to sell more complex solutions to hoteliers later.