Case StudySmart Lists & Enrichment (AI Lists & Insights)
Helping new users see meaningful segments and insights from day one
Project Overview
Once we had a warm start from Gmail and enrichment, the next question was: how do we make that data feel actionable?
I led design on Smart Lists & Enrichment—a set of AI‑powered patterns that:
Automatically surface useful contact lists (e.g., prospects, customers, collaborators)
Attach clear attributions and confidence levels so users trust what’s happening
Provide insights and nudges that tie into activation (e.g., “Contacts you haven’t followed up with recently”)
This work fed both onboarding flows and ongoing usage patterns.
Problem
Even with data in the CRM, we saw that:
Users weren’t sure where to start – “Who should I email first?”
Static default lists (e.g., “All contacts”) didn’t help them segment or prioritize
AI‑generated suggestions risked feeling opaque or untrustworthy if we didn’t explain them well
We needed Smart Lists and insights that felt:
Immediately useful (not fake examples)
Editable and transparent
Integrated into onboarding and daily workflows, not hidden away
Role & Team
My role: Lead IC Product Designer for the Smart Lists & Enrichment track.
Partners:
Data / ML engineers defining signals and models
PM for AI‑First Onboarding
Designers working on contact layout, lists, and Global Home
Solution at a Glance
We designed Smart Lists & Enrichment as a layered system:
Default Smart Lists – auto‑created lists like Prospects, Customers, Internal Contacts, based on email behavior and enrichment.
Editable List Builder Experience – users can inspect membership, tweak filters, and save variants.
Attribution & Confidence Patterns – badges and tooltips that explain why a contact is in a list, where the data came from, and how confident we are.
Insights & AI Coach – inline insights (“High‑value contacts without recent activity”) and an AI Coach surface that suggests next actions.
Process
1. Smart Lists milestone & scope
Building on the Instant CRM Setup plan, I carved out a dedicated milestone for Smart Lists:
Scope:
Default Smart Lists and criteria
Smart List onboarding / education
Contact‑level signals and tags
Out of scope (initially):
Deep, multi‑object segments
Full reporting on AI segments
This kept the first version focused and shippable, with a clear path for later sophistication.
2. Smart Contact & List Builder prototype
I authored a Smart Contact & List Builder brief and prototype that defined:
Contact cards showing:
Key fields (name, role, company, recent interaction)
Enrichment tags and source badges
Relationship indicators (e.g., frequent collaborator vs. new contact)
Smart list suggestions:
In‑UI prompts like “Create a list of people you’ve emailed 3+ times in the last month?”
A preview step showing who’s included and why, before saving
List detail views that let users:
See per‑contact reasons (“in list because…” tags)
Adjust filters or remove individuals
Save variations as their own segments
The prototype served as both design direction and a communication tool with PM, Eng, and data partners.
3. Attribution & trust patterns
Because AI‑driven lists and enrichment can easily feel like a black box, I invested heavily in attribution patterns:
Source labels (e.g., “From Gmail”, “From enrichment service”)
Confidence chips (“High confidence”, “Needs review”)
Tooltips explaining which signals were used (frequency, recency, domain, titles, etc.)
A simple “Mark as wrong” / feedback mechanism to correct misclassified contacts
These patterns were designed to be reused beyond lists—anywhere AI‑driven inferences show up in the CRM.
4. Insights & AI Coach
To make Smart Lists more than a static segmentation feature, I explored:
Insights modules on lists and contact records (e.g., “Top engaged contacts this week”, “At‑risk contacts with no reply”)
A lightweight AI Coach sidebar that:
Explains what the system is seeing
Suggests next actions (e.g., “Send a follow‑up”, “Create a task”, “Add to nurture sequence”)
Integrates with review/confirm patterns established in Agentic Intake
Outcomes
A clear conceptual model for Smart Lists as editable, AI‑assisted segments rather than hidden system lists.
A reusable attribution and confidence vocabulary for enriched data and AI‑driven features.
Design direction that allowed engineering to implement a focused v1 while keeping room for richer AI insight work later.
Smart Lists & Enrichment (AI Lists & Insights) – Outcomes
Customer impact
Building on the Gmail Data Sync and Enrichment experiments, Smart Lists and enrichment were introduced on top of a CRM that now had more than 2× the “Data In” rate for synced cohorts, so new users saw immediately meaningful segments rather than empty lists.
Instrumentation around Smart Lists tracks how users who engage with at least one Smart List differ from non‑users on:
list‑based email sends,
reply / click‑through rates, and
follow‑up actions (tasks, deals, sequences).
Early cohorts show that Smart‑List users are more likely to send targeted emails and work from curated segments, not just “All contacts”.
Qualitative feedback from usability sessions highlighted higher trust and understanding of why contacts appear in each list thanks to clear attribution (“From Gmail”, “High confidence”, “In this list because…”).
Business impact
Enrichment on Data Sync demonstrated we could layer enrichment onto synced data while keeping value and monetisation essentially flat (e.g., “Data In” moving from 17.7% in control to 18.6% in the best enrichment variant, with total monetisation within ~0.1–0.2 points of control), giving us confidence to keep iterating on Smart Lists and insights without revenue downside.
The Smart Lists work established a shared attribution and explainability vocabulary—source badges, confidence hints, and “why in this list” chips—that other AI/ML features now reuse, reducing future design and implementation cost.
Together with Agentic and Data Sync, Smart Lists & Enrichment form one of the three core pillars of AI‑First Onboarding: capture intent, pull in the right data, then surface actionable, trustworthy segments that help new customers start using HubSpot meaningfully in their first sessions.
