Aspiring Sellers Summit 2026: Break Into Sales. Stand Out With AI.
The Aspiring Sellers Summit is back — and this year, we're taking you from Aspiring Seller → AI-Enabled Seller.
Join us for a powerful, full-day virtual experience designed for career switchers, recent grads, early-career sellers, and anyone ready to build a high-earning sales career with the advantage of AI.
You'll learn the foundations of selling AND the new AI workflows top reps use to research faster, prospect smarter, and close with confidence. The day is built on a 50/50 model — the morning is dedicated to the timeless human skills AI can't replace, and the afternoon is where you multiply those skills with AI tools and systems.
MORNING: Master the Skills AI Can't Replace
Opening Keynote: The AI Advantage — Chantel George, CEO, Sistas in Sales — Why now is the best time to break into sales, and how AI is giving new sellers an edge that took veterans years to build.
Keynote: The Modern Sales Skills Sellers Need for Modern Times — Shelton Banks, CEO, Re:WORK & Erica Franklin, Global Director of Sales, Sistas in Sales — The landscape has changed. This session breaks down the skills AI can't replace and why companies are still hungry for sellers who know how to connect.
Skills Labs (Choose Your Track) — Four concurrent, hands-on sessions so you can go deep on what matters most to you:
Prospecting Mastery — Jasmine Garrett, Account Executive, Salesforce — Practical frameworks to find and reach the right buyers, faster.
Discovery & Consultative Selling — Chris Tazewell, Account Executive, Genesys — Master buyer psychology and the art of asking the right questions.
Closing & Objection Handling — Terika Dilworth, Global Sales New Hire Onboarding Manager, VAST Data — Reframe objections and close with confidence, not pressure.
Renewals & Upsells — Keishla Ceaser-Jones, Managing Director, EAB — Grow accounts and build long-term revenue — the skill that gets you promoted.
Panel: The Human Skills AI Can't Replace — Lorraine Kamesha | Tanayia Buckner, Senior Enablement Specialist, ETQ | Gertrude Umeh, Sales Operations Lead, Big Cabal Media — AI can draft your emails, but it can't build trust. Hear how top sellers balance technology with the relationship skills that still win deals.
AFTERNOON: Leverage the Tools That Multiply Your Impact
Master Class: Building Your AI Sales System — This is the one you don't want to miss. You'll build a live, working AI sales workflow in real time — not a demo, not a lecture. Bring your laptop.
Map AI tools to every stage of your sales workflow — from prospecting to close
Live before-and-after walkthroughs showing how AI transforms the work top sellers do every day
Build your personal AI stack for lead research, outreach, follow-ups, and pipeline management — including free and low-cost tools you can start using today
Take home AI prompts and templates for prospecting emails, discovery prep, objection responses, and follow-ups
Learn the common mistakes new sellers make with AI — so you use it as a tool, not a crutch
How to talk about your AI skills in interviews — hiring managers are asking, and most candidates don't know how to position it
Fireside Chat: From Traditional to AI-Enabled — Amelia, Chief AI Officer, SaaStr, in conversation with Chantel George — A real conversation about what the shift to AI-enabled selling actually looks like, and how to make it work no matter where you're starting from.
Workshop: Your 90-Day AI Plan & Pathway — Petra Vincent — Map out exactly what you're going to do in the next 90 days to land your role, level up your skills, and integrate AI into your workflow. You leave with a plan, not just inspiration.
Meet with Gartner — A career-focused networking session with one of the most respected names in tech. Think of this as your warm introduction to opportunity.