Show Notes
The salesperson of the future never forgets you. The only question is whether that feels like care or surveillance.
JP Grace has worked the floor. Publix bag boy, Breckenridge coffee shop, the whole tour. Now he's the CTO of Endear, the retail-first CRM powering one-on-one selling for brands like Reformation, Untuckit, Jones Road Beauty, AG Jeans, and Boll & Branch across more than 2,000 stores in 19 countries. And he's on a mission to give brick-and-mortar sales associates what B2B reps have had for decades: a system that actually remembers the customer.
Here's the problem Endear attacks. A sales associate gets maybe fifteen minutes at the start of a shift to message VIPs. Finding the right person, drafting the right note, picking the right template: it's all friction. So most outreach never happens, and the customer who walked away from out-of-stock shoes last Tuesday just disappears forever. Endear's brand-new AI Opportunity Engine, launched the day after this recording, flips that. It surfaces the five to ten biggest opportunities for each associate every morning, pre-drafts the message, and lets them review and send in seconds. Early results: 6x more outreach in six weeks and a 35x return on delivered messages.
JP's career arc is its own masterclass. He helped take LiveIntent from zero revenue to a valuation in the hundreds of millions, coached startup CTOs at AB InBev's ZX Ventures, and joined founders Leigh Sevin and Jinesh Shah after they'd spent years pivoting in stealth before catching their inflection point in March 2020, when the world went inside and brands scrambled for ways to keep selling without foot traffic.
Meanwhile, Ryan relives his entire retail past, from selling 30 electronic drum kits to Colorado Springs mega churches at Guitar Center, to leading the nation in Finding Nemo pre-sales, to a return-counter horror story at Nordstrom you will not forget. Underneath the laughs is a serious thesis: the companies that win the next decade won't have the best products. They'll be the ones who remember you the warmest.
Named Frameworks from This Episode
The AI Opportunity Engine Playbook
Turn the daily fifteen-minute VIP-messaging window from friction into a reviewed-and-sent routine.
- →Surface the top five to ten outreach opportunities per associate, per day.
- →Pre-draft every message so review takes thirty seconds, not fifteen minutes.
- →Process all the signals (purchases, browsing, restocks, milestones) so the human only approves.
- →Result: campaign-level scale with one-on-one human warmth.
The 360-Degree Customer Profile
One unified customer timeline so associates sell from context instead of digging for it.
- →Sync POS, e-commerce, marketing, loyalty, and support data into one timeline.
- →Give associates an Instagram-style feed of every brand interaction.
- →Surface AOV, color affinities, and interests at a glance.
- →Let AI summarize the signal so the associate sells instead of searches.
Online-to-Offline Commission Bridging
Align incentives so the floor and the website win together instead of fighting over the sale.
- →Credit associates for online sales their messages drive.
- →Turn store vs. site rivalry into one team with one scoreboard.
- →Make associates the loudest internal advocates for the tool.
The Willingness-to-Pay Test
Prove real demand with revenue from the very first customer, not promises.
- →Charge from day one, even with customer number one.
- →Work hand in glove on the floor with that first brand for six months.
- →Use paid traction as the foundation to raise and scale.
The Skip-the-Meeting Stack (JP's Personal AI System)
JP's personal agent stack for staying the most-informed person in the company without sitting in meetings.
- →Bots record and summarize every meeting you don't attend.
- →A 9 AM brief surfaces the three things you're blocking.
- →Slack triage compresses 400 unread messages into one scannable digest.
- →Follow up directly with people instead of sitting through hours of meetings.
Founder Experiment: Build Your Own Skip-the-Meeting Brief
Take the transcripts or notes from your last week of meetings (most AI notetakers export them), drop them into a folder, and write a script using the Anthropic API that runs every morning at 9 AM with this prompt: "From these transcripts and my unread Slack messages, list the three things I am personally blocking, the three decisions made without me, and the one conversation I should follow up on directly."
Pipe the output to email or Slack. You can prototype the whole thing in Cursor or Replit in under an hour. JP says it let him skip meetings entirely without losing the thread. Measure your reclaimed hours after one week.
Key Terms from This Episode
Clienteling
One-on-one relationship selling where associates use customer data to drive personalized outreach and repeat purchases.
CRM
Customer Relationship Management software; the system of record for customer data and interactions.
Omnichannel
A unified customer experience across store, web, email, SMS, and WhatsApp.
POS
Point of Sale; the in-store transaction system.
AOV
Average Order Value.
ICP
Ideal Customer Profile.
DTC
Direct-to-Consumer; brands that sell straight to shoppers rather than through wholesale.
Venture for America
A fellowship placing recent grads at startups, where Endear's founders met.
Opportunity Engine
Endear's AI feature that surfaces daily outreach opportunities with pre-drafted messages.
Q&A: What Founders Ask After This Episode
What is Endear?
Endear is a retail-first, omnichannel CRM and clienteling platform that lets brick-and-mortar sales associates have one-on-one conversations with customers over email, SMS, WhatsApp, and live chat, powered by AI.
What is Endear's AI Opportunity Engine?
An AI tool launched in May 2026 that surfaces each associate's top daily outreach opportunities and pre-drafts the messages. Early deployments showed 6x more outreach and a 35x return.
Who founded Endear and when?
Leigh Sevin and Jinesh Shah founded Endear in 2019 after meeting as Venture for America fellows. JP Grace serves as CTO.
How much funding has Endear raised?
A $2M seed led by Reformation Partners in 2022 and a $6M Series A led by Channel Equity Partners announced in January 2025.
How does clienteling compare to traditional marketing?
In the episode, JP cites 10x outperformance for manually written one-on-one messages versus marketing campaigns, and a 35x higher delivered return with AI-assisted outreach.
Which brands use Endear?
Reformation, Untuckit, Jones Road Beauty, AG Jeans, and Boll & Branch, among others, across 2,000+ stores in 19 countries.
Tools from This Episode
Endear
The retail-first CRM bringing AI-powered clienteling to 2,000+ stores worldwide. Home of the AI Opportunity Engine, which surfaces and pre-drafts each associate's highest-value outreach every morning.
Five Founder Questions This Episode Answers
- →How do I find my first customers when nobody knows my product exists, and why should I charge them from day one?
- →How can I use AI to multiply my team's output without replacing the human relationships that customers actually pay for?
- →What does it look like to build a "fit for purpose" tool in a market dominated by giants like HubSpot and Salesforce?
- →How do I align incentives so my team stops competing internally and starts winning as one unit?
- →How can I personally use AI agents to skip meetings, triage 400 unread messages, and still be the most informed person in the company?
Links from This Episode
- Endearhttps://endearhq.com
- JP Grace on LinkedInhttps://www.linkedin.com/in/josephpgrace
- AI for Foundershttps://aiforfounders.co
