Hello {{First Name | founders}}!
Welcome to ‘Tactical Tips’ by Jerel and Shuo at DECODE, where we cover one new idea to help you build and grow your startup – every week in <5 minutes!
Today, we’ll be answering the question: “How to nail customer onboarding?”
And here’s advice inspired by Erika Anderson, Chief Customer Office at Storytell and former writer for Y Combinator and New York Times, who onboarded multiple Fortune 1000 companies like Paramount. She’s also hosting a Humane Tech Hackathon on June 28 in San Francisco. Join her there and discuss more tactical strategies!
If you want to turn customers who are unsure about your product into power users, today’s newsletter is for you.
🔥 Inside this issue:
✅ 3 tactics to deliver exceptional onboarding
✅ 2 traps to avoid
✅ 1 tool to leverage
👇Let’s dive in.
Need personalized advice on building your startup or just want to talk? Grab 30 mins with me here—happy to help and make intros if it’s the right fit or feature you in future newsletters.
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3 tactics to deliver exceptional onboarding
🤝 Know the customer
Map out organizational charts, identify key roles, and gauge familiarity with AI tools
Book 15-min pre-calls with key team leads and stakeholders to uncover 2-3 real use cases per role and identify pain points.
Understand any unique needs and the workflow by asking:
What are you working on right now?
What / who kicked off this project? Is that how requests usually come in?
Who else worked on this? What was their role?
What's the goal of this project?
Once you've completed your part, who do you pass this on to?
How can you tell it's complete?
How do you know it was successful?
🔥 Prepare before onboarding begins
Send a pre-onboarding checklist (e.g. create user accounts, share demo materials, and provide clarity on what to expect)
Request users to create accounts before the session—set up a dedicated live support room to assist those who haven’t completed this step
Prepare training environments to include tailored workflows, real content and deliverables, and role-specific AI prompts to generate desired customer outputs
Equip internal trainers with team-specific data, relevant materials, and tailored prompts for confident and effective facilitation
⏰ Host breakout sessions for hands-on learning
Segment by functional teams (Eg. content, sales, product, etc)—learn about each team and how they work
Limit each session to 30-45 mins, for 4 people or fewer
Have users set up their first project, navigate the application, and explore key features that are critical to experiencing value
Provide live support to guide usage and remove friction in real time
2 traps to avoid
🚨Not driving interactive use
Passive demos and feature walkthroughs ≠ real product experience
Direct time with the customer is invaluable—every minute should build a relationship through active use of the product
Ensure each user completes all core onboarding actions (e.g. first project setup) within the live environment; without hands-on setup and exploration, onboarding is ineffective
🚨Assuming one size fits all
Different teams = different workflows = different needs
Generic onboarding leads to shallow understanding and weak adoption
Map user journeys upfront and tailor demos, breakouts, and learning plans to reflect specific workflows
1 tool to leverage
📖 Best practice on successful onboarding
Aim for 50%+ of new users active on a core feature within the first week
If engagement is low, revisit pre-work, content relevance, and call-to-action clarity
Gather feedback from the champion—or find one—and ask what blocks usage
Leverage tools like Storytell to structure onboarding flows, populate team-specific content, and centralize training materials in one searchable hub
Bonus: 1 trend to spark startup ideas
🔨 Autonomous finance is reshaping every layer of financial services in fourth fintech wave
AI is poised to automate core financial workflows with minimal human input
Financial services rely heavily on knowledge work—$100B+ annually on outsourced labor and 7M U.S. jobs
54% of banking jobs are highly automatable, with global banks planning up to 200,000 job cuts
High-impact opportunities include:
AI financial analysts: Automating research, risk modeling, and compliance in a $100K+/yr job market
Onboarding/underwriting: Streamlining $30B+ in manual KYC/AML labor with fraud detection and due diligence AI
Voice-based services: Replacing up to 25% of contact center spend with AI-led customer support, disputes, collections, and financial advisory
Agentic payments: New infrastructure to process payments, addressing authentication, authorization, and liability
Startup Knowledge Check
Hint: Read our past newsletter on how to monetize effectively.
Continue learning
Featured event: Humane Tech Hackathon 2025
Build tech that puts people first. Join developers, designers, and product minds at the Humane Tech Hackathon on June 28, 2025 in San Francisco. Collaborate, create, and pitch to judges from Windsurf (acquired by OpenAI for $3B), Couchbase (NASDAQ:BASE), and a former YC visiting partner.
Other resources
Apply to participate in Founders Pop-up Board Advisory and receive startup feedback from execs at Microsoft, Google, Meta, Reddit (Free)
Schedule for a consultation on structuring your equity-based compensation plan (Free).
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