IMPROVING ONBOARDING MILESTONES TO ENSURE FIRST VALUE

Onboarding isn’t just about setup—it’s the golden window to set the tone, deliver tangible wins, and reinforce the decision to work with you. By combining insights from Winning by Design, Alex Hormozi, and David Sandler, here’s a revamped approach to ensure First Value:

Key Principles:

1. Popsicle Moments: Create delight with small, unexpected surprises that make the customer feel appreciated and supported.
2. Gift Strategy (Hormozi): Reinforce goodwill and investment by giving personalized, thoughtful gifts during onboarding.
3. Reinforce the Sale (Sandler): Reassure the customer they made the right decision by highlighting early wins and restating the impact of the partnership.

Onboarding Milestones:

1. Build a DeWelcome & WOW

• Purpose: Create a memorable first impression.
• Actions:
  • Send a personalized welcome gift within 24 hours of kickoff. Example: A branded item paired with a thoughtful note about their specific goals or challenges.
  • Schedule the kickoff call within the first week to align on expectations and outcomes.
  • Popsicle Moment: Share a “Here’s what’s coming” video message to the executive sponsor or project owner.
• Reinforce the Sale: Celebrate their decision by sharing early data or customer success stories.

2. Kickoff Workshop

• Purpose: Align on goals, success metrics, and priorities.
• Actions:
  • Restate their objectives and key constraints as discussed during sales (reinforce the sale). paired with a thoughtful note about their specific goals or challenges.
  • Popsicle Moment: Send a summary of the workshop with a custom visual (e.g., their roadmap) to demonstrate immediate progress.
  • Highlight what “First Value” means for their unique use case, so everyone knows the first milestone.
• Outcome: Clarity on the path to First Value and mutual alignment.

3. Rapid Setup & Quick Win

• Purpose: Deliver tangible results within the first 2-3 weeks.
• Actions:
  • Prioritize a high-impact deliverable that solves a quick pain point (e.g., reporting automation, process improvement).
  • Use SPICED principles to connect the quick win to broader business outcomes.
  • Example: “This dashboard saves you 3 hours a week and helps you track CAC in real time.”
  • Popsicle Moment: Share a small “surprise” win they didn’t expect (e.g., bonus feature or efficiency hack).
• Reinforce the Sale: Recap the quick win’s impact and link it to their longer-term goals.

4. Enablement & Training

• Purpose: Empower the team to fully leverage the solution.
• Actions:
  • Deliver customized training sessions tailored to their role or use case. paired with a thoughtful note about their specific goals or challenges.
  • Share resources in digestible formats (videos, checklists) for self-paced learning.
  • Popsicle Moment: Host a surprise “office hours” session with a subject matter expert to answer their questions live.
• Reinforce the Sale: Remind them how their team’s efficiency and effectiveness are improving.

5. Milestone Checkpoint: First Value

• Purpose: Confirm and celebrate the delivery of First Value.
• Actions:
  • Present the tangible business impact achieved so far (e.g., reduced churn risk, improved visibility, increased pipeline efficiency).
  • Gather feedback to ensure alignment and validate the next milestone.
  • Popsicle Moment: Send a branded “First Value” badge or certificate to celebrate their success.
• Reinforce the Sale: Highlight their progress and reiterate how the partnership aligns with their long-term vision.

6. Long-Term Success Plan

• Purpose: Transition from onboarding to ongoing success.
• Actions:
  • Co-create a 90-day plan with KPIs and outcomes tied to their roadmap.
  • Ensure they know the rules of engagement for support and future initiatives.
  • Popsicle Moment: Surprise them with a “cheat sheet” of tips tailored to their goals or processes.
• Reinforce the Sale: Emphasize the foundation you’ve built together and the exciting outcomes ahead.

Additional Tips:

1. Repetition Builds Trust: Regularly restate their goals and remind them of the impact you’re delivering.
2. Personalization Matters: Use their industry, team size, or specific needs to make every touchpoint feel tailored.
3. Celebrate Early and Often: Recognize wins at every milestone to maintain enthusiasm and momentum.

Why This Works: By blending the emotional impact of popsicle moments, the goodwill of Hormozi’s gift philosophy, and Sandler’s reinforcement techniques, this onboarding process creates trust, builds excitement, and ensures customers realize value quickly. It’s not just about onboarding; it’s about creating advocates who are thrilled to partner with you.

References + Resources