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.
More Is Not a Strategy: Selling AI in the Trust Economy
with Leslie Venetz
Leslie Venetz, founder of the Sales-Led GTM Agency and author of Profit Generating Pipeline, explains why she calls 2026 the year of the trust economy and why most B2B deals are now lost to the status quo rather than to a competitor. She and Warren Kucker discuss selling AI to a champion who fears it will replace their team, leading with the cost of inaction instead of ROI, why more activity is not a strategy, and a live audit of Warren's outbound sequence: segmentation, cadence by seniority, and voicemails that point to another touch instead of asking for a callback.
Your Buyer Doesn't Know What to Ask For Yet
with Michael DeLeonardis
Michael DeLeonardis, chief revenue officer at Verity, explains how selling autonomous warehouse drones differs from selling software, and why AI has pushed enterprise sales back into a demand creation cycle. He and Warren Kucker discuss deep discovery around physical constraints, win-loss analysis from call transcripts, deliverable-based selling that guides the buyer through each decision, a client success role that spans pre-sales and post-sales, and why industry expertise and a LinkedIn presence matter for sellers.
"You're Inspiring People to Mute Your Logo" — A RevOps Leader on AI Outbound.
with Jimmy Downing
Jimmy Downing, VP of Revenue Operations at NextGlass, explains how he went from an accidental Salesforce admin to running RevOps, and why the AI tools that work are the ones that solve one simple problem well. He and Warren Kucker discuss why AI-driven outbound damages brands, where to layer AI on clean data, why soft skills now matter more than ever for sellers, and the risks of features built too quickly with vibe coding.
Build Your Campsite Where the Buyers Live
with Morgan J Ingram
Morgan J Ingram, who went from sales development rep to sales trainer and now runs AMP Social, explains why outbound has shifted from sheer volume to creativity and intention. He and Warren Kucker discuss in-person events and experiences, pattern interruption in an AI-saturated inbox, how market shifts affect SDR and AE careers, building industry credibility, meeting buyers where they live online, and why deepening relationships will matter more as buyers grow less trusting.
"Motivation Is the Gas Pedal. Logic Is Just the Steering Wheel."
with Chris Gray
Dr. Chris Gray, a clinical psychologist turned consumer psychology consultant, explains why every purchase, including complex B2B deals, traces back to an emotion-based need. He and Warren Kucker discuss why B2B sellers default to logic, how a rational-sounding claim can carry an emotional message, his five Fs framework for resilient customer relationships, and why discernment becomes the edge as AI makes information abundant.
The AI Committee Is Step Two Now, Not the Last Gate
with Jean-Marc Chanoine
Jean-Marc Chanoine, Chief Sales Officer and GM of the Americas at Templafy, explains why selling AI into the enterprise has become a political problem more than a technical one. He covers how LLMs changed buyer expectations for document automation, why the AI committee now has to be engaged early in the sales cycle, and how vendors win when customers decide to build it themselves. The conversation closes with career advice for account executives and a prediction about smaller, localized software companies.
A New Approach to Sales Roleplay
with Neha Gupta
Neha Gupta, founder and CEO of Breakthrough AI, joins Warren Kucker to discuss how AI is changing sales role play. She explains why traditional role play and off-the-shelf chatbots fall short, how fine-tuned buyer personas and an objective scoring rubric make practice realistic and consistent, and how to roll out a practice program that reps actually use. The conversation also walks through rehearsing a 10 percent discount request and where role play is heading next.
The Surprising Way Personality Types Can Boost Outreach Response Rates to 30%
with Gary Sinderbrand
Gary Sinderbrand, a 35-year wealth management veteran, explains how he built the Rainmaker app to score psychological fit between financial advisors and prospects using Carl Jung's archetypes. He walks through how the app profiles an advisor, finds and researches compatible prospects, and mines existing clients' networks for warm introductions. He also covers Ask Archie, an AI coaching companion built on decades of his own training content, and where personality matching could go next.
Holding Complexity Under Pressure: What Your Meeting Transcripts Actually Reveal
with Logan Yonavjak
Logan Yonavjak, co-founder and CEO of Readiness Engine, explains how the platform uses AI and quantitative linguistics to measure leadership readiness from the way people talk in real work transcripts and assessments. She and Warren Kucker discuss why investors and executives still judge people by gut feel, what linguistic patterns reveal about stress, complexity and coachability, how team dynamics and psychological safety show up in meetings, and where generative AI could take leadership coaching next.
The Messaging Mistake Everyone Makes on LinkedIn (And How to Fix It in Two Sentences)
with Toby Blatchford-Tagg
Toby Blatchford-Tagg, founder of Lead Lab, explains how his business moved from B2B telemarketing to managing LinkedIn outreach at scale after COVID. He walks through the most common LinkedIn outreach mistakes: trusting Sales Navigator data, writing messages about yourself, and weak follow-up once a prospect shows interest. The conversation also covers why LinkedIn has replaced email outreach for his clients and where AI dialing does and does not belong in outbound.
Go for No: The Counterintuitive Path to More Yeses
with Andrea Waltz
Andrea Waltz, co-author of Go for No, explains why disqualifying early beats trying to persuade every prospect, and why reps should treat each no as progress rather than failure. She and Warren Kucker cover the origin of the Go for No philosophy, starting with what buyers want before what they need, using micro-commitments to keep deals honest, and how handling and nurturing a no creates future yeses. They also discuss setting no goals for sales teams and using conversation data to see why buyers really say no.
AI Just Accelerates Your Inconsistency
with Marvin J Martinez
Marvin J Martinez, an operations veteran who founded an AI consultancy for small and mid-sized businesses, explains why AI amplifies whatever sales process it is applied to, good or bad. He and Warren Kucker discuss mapping the manual process before automating, managing the change with sales teams, a hybrid outbound system built for a staffing firm, why authenticity matters more as automated messaging grows, and how to measure whether AI is paying off.
80% of the Deal Is Over Before the Buyer Talks to Sales
with Braydan Young
Warren Kucker and Braydan Young, co-founder and CEO of Slash Experts, discuss how B2B buyers do most of their research before they ever talk to sales, and why customer references should move from the end of the deal cycle to the beginning. Young explains how a streamlined reference process affects deal speed, deal size and trust, and the two discuss discovery calls, technical demos and the shift toward monthly and outcome-based pricing.
AI Can Finally Kill CRM Data Entry. That Might Be the Problem.
with Eddie Reynolds
Eddie Reynolds, CEO of Union Square Consulting, joins Warren Kucker to discuss what AI changes about CRM data entry and what it should not change. Drawing on 15 years of Salesforce implementations and three years as a Salesforce AE, he argues that automating data entry only pays off when reps still own deal judgment, qualification is rigorous and the go-to-market process has clear foundational definitions. The conversation also covers pipeline management, customer journey mapping and how the CRO role is shifting toward running a tech-driven, process-driven sales organization.
The Data Is Directional: Selling Into Domains Where You're Not the Expert
with Cash Monestine
Cash Monestine, Enterprise AE at AcuityMD, went from finance and SaaS to selling complex med device intelligence platforms to the most domain-expert buyers in tech. This episode explores how he built credibility as an outsider, how different med device verticals require entirely different sales approaches, and how he's using AI to collapse research time while staying consultative. If you sell into specialized domains or are moving from mid-market to enterprise, this is essential.
AI Made Human Connection More Valuable, Not Less
with Zachary Jones
Zach Jones, co-founder of Waffle, spent a decade in Army cyber command before building an agentic OS for non-technical businesses. Unlike most AI platforms that position themselves as faster assistants, Waffle positions AI as an operator that integrates into existing tools—and Zach still personally handles high-ticket discovery calls and cold outreach. In this conversation, we explore why automating everything disconnects you from your customer, how a three-person door brokerage saved $800K with agents, and why human connection becomes more valuable, not less, in an AI-driven world.
"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 Steers
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.