Selling AI
The Podcast for Revenue Teams Selling and Using AI
Join us as we explore the intersection of artificial intelligence and sales, delving into the strategies, tools, and stories from professionals who are leveraging AI to sell smarter and selling AI products that are reshaping the future of go-to-market.
"We Had No Structure to Fully Structured" — Building Sales Process in Real Time
with Jim Robertiello
Jim Robertiello, Director of B2B Sales at Poppin, has spent 12 years transforming a colorful desktop supply company into a nationally recognized workplace furniture brand. This episode explores the unique challenges of selling physical products in a software-obsessed world. Jim shares tactical insights on managing channel conflict between direct and dealer sales, launching new territories through guerrilla marketing, and how AI is starting to track furniture utilization to optimize office layouts. Perfect for anyone selling in traditional industries trying to navigate modern sales complexities.
Jack Siney
with Jack Siney
Jack Siney, co-founder and CRO at FrontRace with five exits and $200M in sales built, argues that companies are failing with AI because they're missing a critical infrastructure layer. Despite 40 years of sales technology, forecasting accuracy hasn't improved since the 1980s — and most AI implementations are making the problem worse. Jack shares how his "metrics engine" approach analyzes the 20 small behaviors that separate 1x reps from 3x performers, including real examples like why one company never closed deals after sending a 7th text. Essential listening for sales leaders trying to get real ROI from their AI investments instead of joining the 650 million in failed pilots.
What Got You Here Won't Get You There — From Founder-Led Sales to Scale
with Kristie Jones
Kristie Jones, sales coach and founder of the Sales Acceleration Group, breaks down the hard transition from founder-led sales to building a scalable revenue team. Over two decades, she's hired and trained nearly 1,000 B2B SaaS reps and now coaches early-stage founders right before they try to scale. In this episode, we explore the specific mistakes founders make when hiring their first reps, how to identify true top 10% performers, and why the buyer's journey has fundamentally shifted—forcing sellers to build trust and credibility in a fraction of the time. If you're a founder moving from doing all the selling yourself to leading a team of reps, or a sales leader trying to figure out what actually separates great performers from the rest, this conversation is essential.
"95% of Buying Decisions Are Emotional" — Why Your Sales Team Is Still Selling Logic
with Sean Weafer
Sean Weafer is a sales coach, psychotherapist, and former marine engineer who's spent 30 years coaching sales teams on the behavioral side of selling. In this episode, we explore why companies claim to develop their reps, but win rates stay flat—and why the answer isn't more sales methodology training. We dig into how to identify what actually motivates your team, why promoting your best rep into management often fails, and how to shift from positioning as an expert to becoming a trusted advisor. If you manage a sales team, this conversation will challenge how you think about coaching, compensation, and what "development" actually means.
Great Marketing Should Reduce Your Sales Calls
with Jen Chaney
This episode explores how AI influences demand generation strategies, examining contemporary approaches to buyer research and the transition from pursuing lead volume toward accelerating pipeline velocity. The discussion covers AI's contributions to content creation, individualized outreach sequences, and the integration of marketing and sales functions for revenue growth.
A Champion Isn't a Person — It's a Behavior That Shows Up When There's Good Friction
with David Weiss
David Weiss challenges conventional sales approaches by distinguishing deal management as a separate discipline from sales methodologies. He reframes champions as behavioral patterns rather than individual contributors and examines how behavioral shifts manifest across sales cycles.
Buyer First Is a Behavior, Not a Statement — Carol Mahoney on What Most Companies Get Wrong
with Carol Mahoney
The episode explores buyer-first methodologies in sales, examines AI coaching applications for sales teams, and highlights mindset's importance in driving sales results. Carol Mahoney discusses understanding buyer perspectives, developing AI coaching technology, and how psychological orientation influences performance outcomes.
AI Will Happily Solve the Wrong Problem Very Efficiently
with Stephen Seers
The conversation delves into the power of storytelling in sales, emphasizing the importance of context, emotional response, and soft skills in the AI marketplace. It also explores the role of soft skills in business development and the relationship between process and context in sales.
"No Decision" Is Not a Close-Loss Reason — Why Your CRM Data Is Lying to You
with Liam Weedon
The episode examines RevOps evolution and conversational intelligence underutilization. It discusses shifting from traditional CRM data tooling toward genuine buyer signals, targeted outreach importance, and how conversation analysis might reduce CRM data dependency.
The Standardization Problem That Shipping Said Was Impossible Got Solved in Two Years
with Dylan Mace
This episode examines the intersection of AI technology and maritime industry sales. Dylan Mace discusses how bringing innovative AI solutions to traditionally resistant, relationship-focused buyers creates unique opportunities and challenges. The conversation covers how language models resolved a longstanding data standardization issue the industry believed unsolvable.
If Your Dashboard Isn't Changing Behavior, What's the Point?
with Chantel Hirschel
An exploration of Revenue Operations fundamentals covering practical first-90-day actions, why most dashboards underperform, tech stack evaluation, scaling revenue without expanding headcount, managing sales-marketing friction, and the emerging role of GTM engineers in the RevOps landscape.
We Are the Picks and Axes — Selling the Infrastructure That Makes AI Actually Work
with Joe Simpson
Joe Simpson discusses navigating enterprise sales through an IPO, private equity acquisition, leadership transitions, and product evolution toward AI-ready data infrastructure at Alteryx. The conversation covers positioning, buy vs. build decisions, and changing buying behaviors.
The Tools Changed, The Job Didn't: An Enterprise AE's Take on AI in Sales
with Richard Strom
The episode explores how enterprise sales has evolved over 15+ years, particularly through the lens of AI's impact on sales workflows. Rich Strom discusses his journey from cold calling to closing six-figure maritime deals, examining how sales tools have historically burdened rather than empowered reps.
How Enterprise Views Buying AI Products
with Dan Morgenstern
Dan Morgenstern discusses managing complex 12-18 month enterprise deals selling customer feedback software to major retailers. The episode explores stakeholder management across multiple departments, the balance between storytelling and data-driven pitches, and the importance of letting prospects speak.
Building a Custom GPT for Every Rep on Your Team
with Rich Lane
This episode explores innovative AI applications in sales coaching, examining both opportunities and challenges. The discussion covers how custom GPT tools can enhance coaching effectiveness, the distinction between coaching, training, and feedback, and critical implementation considerations for sales leaders.
Why ROI Isn't Always the Right AI Pitch
with James Lawler
James Lawler discusses why traditional ROI messaging fails when selling AI to legal professionals. The episode explores selling AI to change-resistant industries, privacy concerns superseding performance skepticism, using Copilot during calls for technical translation, and reframing the same product differently for different buyers.
Sales Enablement from Meeting Rooms to CustomGPTs
with Molly Sestak
Molly Sestak discusses leveraging AI and custom GPTs to streamline sales enablement processes. The episode explores how personalized onboarding plans can be created for new representatives beyond standard templates, and examines the strategic value of combining RevOps with enablement functions.
The Kickoff
with Warren Kucker
The Selling AI Podcast focuses on generating revenue with AI tools and simplifying decisions for buyers, as well as adapting sales strategies to navigate the AI shift in real time.
Your Host
Warren Kucker
A revenue leader and entrepreneur who founded Basiq.work, focusing on conversational AI for sales teams. Previously served as VP of Sales and CRO at Series B companies, scaling revenue to $2M+ quarterly bookings. His exits include Shelly.ai (ML email automation) and Boxton (digital freight platform). Started his career at Apple managing a $100M shipping efficiency program.