Why do so many sellers miss the mark in enterprise deals without realizing it?

In this episode, Jarod Greene talks with Wendy Petty, CRO at WorkFusion, about the lost skill that still drives the biggest wins in sales: meeting face-to-face.

Wendy explains why sellers who rely on video calls are often leaving trust, nuance, and real connection on the table. She makes the case that younger reps, shaped by Zoom culture, need coaching to develop the in-person skills that build long-term connections. Her approach? Show up, in person, and lead by example.

In this episode, you’ll learn:

• Why face-to-face meetings close more – Selling is still about people
• How leaders can reset team habits – Start by modeling the behavior yourself
• What field selling unlocks – Faster trust, stronger signals, and more seats at the table

Things to listen for: 

(00:00) Introduction

(00:18) Why remote sellers lose enterprise deals

(02:05) Common excuses reps use to stay home

(03:34) What video calls miss about real selling

(04:10) The social skill every seller needs today

Should the SDR role still exist in today’s sales environment?

In this episode, Jarod Greene talks with Kate VanLue, VP of Revenue at AudiencePlus, about why she believes AEs should own the full journey from meeting booked to closed revenue.

Kate shares how the traditional SDR model has shifted into pure volume work that adds little value for sellers or prospects. She explains why compensation plans should reward AEs for carrying opportunities end-to-end, and how AI, events, and human connection are shaping better ways to create pipeline. Her perspective is clear: the future belongs to teams that replace high-volume outreach with real relationships and accountability.

In this episode, you’ll learn:

• Why the SDR role struggles to add value – High activity doesn’t always equal revenue
• What happens when AEs own meetings – Better conversion rates, stronger relationships, and cleaner incentives
• How teams can rethink pipeline generation – Use AI for signals, invest in events, and keep humans at the center

Things to listen for: 

(00:00) Introduction

(01:30) Why AEs outperform when sourcing their own deals

(03:04) Rethinking SDR roles and sales comp strategy

(04:40) Building enterprise sales talent without SDRs

(05:13) How AI changes go-to-market entry roles

(06:09) Why real human connection still matters

Is hiring someone who’s “done it before” actually the safer bet?

In this episode of V5, Jarod Greene sits down with Lindsay Rios, Fractional CRO of PowerChord, Inc., to question the logic behind experience-based executive hiring.

Lindsay challenges the assumption that startup success requires a leader who’s already taken a company from $10M to $50M ARR. She points out how this mindset leads to overpaying for familiarity while overlooking talented operators who already match the company's values, pace, and potential. Rather than chasing repeatable playbooks, she makes the case for finding someone ready to grow with the role, supported by coaching and context instead of inflated credentials.

In this episode, you’ll learn:

• Why experience can backfire – Hiring for logos can blind you to the real risks
• How to find the right fit – The best candidate might be the one who hasn’t done it yet
• What to prioritize in your next hire – Pay attention to adaptability, not just the resume

Things to listen for: 

(00:00) Introduction

(00:24) Why experience isn’t always worth the cost

(00:57) The myth of repeatable success

(01:56) How flashy hires distract from true fit

(03:23) What top talent actually wants today

(04:14) The real risk of past success bias

(05:38) Late bloomers often outperform early picks

Most reps won’t get better with AI. They’ll just get lazy.

That’s what Mike Head, CRO at PartnerStack, tells Jarod Greene in this episode of V5, as he shares his two bold takes on the future of sales teams.

Mike argues that AI is creating a wider gap between top sellers and everyone else. With prep work and research now outsourced to tools, many reps are starting to lean too hard on automation and skipping the fundamentals. This results in many people doing just enough to get by, but those who still put in the work pull even further ahead.

Mike also shares why AI could finally fix the long-strained relationship between sales and partnerships. If machines can surface the right partner at the right time and handle the busywork, there's no longer an excuse to go it alone.

In this episode, you’ll learn:

• Why average reps won’t survive – AI may replace the ones who aren’t adapting
• How AI changes partnerships – Automation can remove friction and boost deal size
• What separates top performers – Effort still matters, even in an AI-assisted world

Things to listen for: 

(00:00) Introduction

(00:23) AI will expose who’s actually prepared
(01:30) Sales tech doesn’t automatically mean better selling
(02:44) Why most reps will be replaced
(03:51) The new traits of top performers
(04:31) AI’s unexpected impact on partnerships
(06:28) Three practical steps to align sales and partners

Is outbound selling still worth the effort in the AI era?

In this episode, we explore how AI tools are changing outbound sales, and what separates average reps from great ones. Jarod Greene sits down with Austin Hitchcock, Senior Director of Account Development at Highspot, to discuss the future of pipeline generation, how AI is being misused by sales teams, and why human-first, creative outreach still wins. Learn how to build a high-output SDR team, avoid AI crutches, and drive pipeline in 2025.

In this episode, you’ll learn:

• Why AI makes average reps worse – Some treat it like a crutch, when it should be seen as a copilot
• How to build a high-output SDR team – Think ABM strategy, not task execution
• What separates good outreach from great – Personal video, smart research, and real human effort

Things to listen for: 

(00:00) Introduction

(00:43) Why pipeline is everyone’s responsibility now

(01:45) AI isn’t replacing reps,  it’s widening the gap

(02:32) What great reps do with AI tools

(03:45) Breaking through with real human outreach

(05:04) SDRs as ABM quarterbacks, not task robots

(07:26) Why in-person events still outperform digital efforts

Is sales really a job or just the outcome of doing your real work well?

On this episode of V5, Jarod Greene chops it up with Mark Niemiec, CRO at Salesloft, to unpack what sales is when you strip away the pipeline noise and pressure to close.

Mark believes a sale serves as proof that you helped a customer solve a priority business problem. He shares why discovery, creativity, and empathy matter more than pitch decks. He believes the best sellers operate like curious business thinkers. Mark also shares how an internal debate over using AI for sales research showed the tension between doing the hard work and moving faster. It eventually led to a new product launch, and it showcased that sellers who are earlier in their careers are quicker to embrace change.

In this episode, you’ll learn:

1. Why sales is the measurement, not the mission – Reps solve real problems or they don’t sell.
2. How AI became a POV-building engine – What started as an experiment turned into a product.
3. Where teams get stuck – Time wasted on research could be spent on creativity and strategy.

Things to listen for: 

(00:00) Introduction

(00:35) Redefining what sales is

(01:15) Traits of great problem-solvers in sales

(02:11) Should AI be allowed in discovery?

(02:45) Building a POV engine with AI

(03:37) Why AI adoption varies by background

(04:48) Early-career reps are leading the shift

Are bold LinkedIn takes helping or hurting your sales motion?

In this episode of V5, Jarod Greene sits down with Todd Busler, CEO and co-founder of Champify, to question the certainty behind today’s loudest go-to-market opinions.

Todd sees a problem with the way leaders chase what’s trending, speaking in absolutes about which industries and approaches are 'dead,' without accounting for the complexity of different categories, motions, and stages of scale. He argues that most teams are too focused on cold outbound and not nearly focused enough on the rich first-party data already sitting in their CRM. From job changers to past champions, the real growth levers are often ignored.

In this episode, you’ll learn:

1. Why absolutes are misleading – Confident hot takes can distract from the nuance your business needs to succeed.
2. How first-party data unlocks scale – Former customers and closed-lost context can become your best revenue source.
3. Where your team might be wasting effort – Outbound isn’t dead, but it’s definitely harder. Knowing who already knows you is the better play.

Things to listen for: 

(00:00) Introduction

(00:40) Why talking in absolutes misleads teams

(01:18) Social algorithms reward bad advice

(02:27) Why Todd avoids comment wars

(02:59) Outbound is getting less effective

(03:53) Companies misuse first-party data

(04:28) Retention and brand now matter more

Is your team still stuck in the old way of territory planning?

In this episode of V5, Jarod Greene is joined by Andrew Berger, VP of Revenue at Capchase, to challenge a long-standing sales tradition.

Andrew argues that quarterly and annual planning sessions waste more time than they’re worth. With countless hours spent on formatting, presenting, and guessing what will matter months from now, he believes the ROI just isn’t there. Instead, he’s pushing for a new approach that’s faster, more flexible, and powered by AI. By connecting systems and prompting smarter analysis, reps can spend less time preparing and more time selling.

In this episode, you’ll learn:

1. Why traditional planning slows teams down – Reps spend hours building plans that are outdated by the time they’re presented, creating more motion than momentum.
2. How AI can support better decisions – With connected systems and smart prompts, teams can surface relevant insights without digging through scattered data.
3. Where sales leaders can shift their focus – Moving away from rigid planning cycles opens up time to test, learn, and act on what’s actually working in the field.

Things to listen for: 

(00:00) Introduction

(00:24) Territory planning is broken

(01:11) AI changes sales strategy

(02:08) Presentations waste time

(03:01) Smarter account planning

(04:31) Speed over structure

(05:29) Building with new tools

Why do so many sales leaders fail before they even get started?

In this episode, Jarod Greene chats with Kelley Hippler, CRO at Briefly, about why people-centered leadership is the key to building sales teams that last.

Kelley explains how CROs fall into the trap of managing up, missing what their team really needs. She talks about the pressure leaders feel from day one and how it pulls them away from trust-building and coaching. Her mission is simple: leadership should clear the path, not block it. That starts with getting real feedback, removing friction, and making space for reps to succeed on their own terms.

In this episode, you’ll learn:

1. Why top ICs often flop as managers – The best sellers don’t always make the best leaders.
2. How to spot leadership red flags early – Lack of trust, poor coaching, and misaligned priorities are just the start.
3. What people-first leadership looks like – Focus on enablement, not activity metrics, and keep the spotlight on your team.

Things to listen for: 

(00:00) Introduction

(00:41) The real reason CRO tenure is shrinking

(01:09) What people-centered leadership means

(02:11) Why new leaders obsess over managing up

(03:58) Advice for aspiring managers in sales

(05:11) How to remove friction for your team

(05:50) The mistake top reps make as managers

Is your buying experience built for the customer or just convenient for you?

In this episode, Jarod Greene welcomes James Kaikis, CRXO at TestBox, to challenge how SaaS companies treat their customers after the deal closes.

James shares his frustration with buying software today, calling out the friction, the lack of follow-through, and the disappearing act many sales teams pull once a contract is signed. He makes the case that real value doesn’t come from the pitch but from what happens after. His fix? Rethink the roles we’ve boxed people into, especially Solutions Engineers and Account Executives, and bring their genuine expertise across the entire customer journey.

In this episode, you’ll learn:

1. Why trust breaks post-sale – Customers lose confidence when the people who earned their buy-in vanish at go-live.
2. How Solutions Engineers can drive value beyond the pitch – When SEs stay involved, buyers actually see what they were promised.
3. What sales teams should prioritize instead – Building credibility, sharing real proof, and sticking with the customer past the close.

Things to listen for: 

(00:00) Introduction

(00:36) Customers aren’t actually the priority

(01:08) Why buying software still sucks

(02:10) Building roles around buyer needs

(02:55) SEs hold untapped post-sale value

(03:53) Fixing the AE credibility problem

(04:33) Growth at all costs broke SaaS

Why does so much sales tech still feel like extra work? And how can AI actually make life easier for AEs and SEs instead of adding to the noise?

In this episode, Vivun’s senior selling team, Account Executive Mike Capitolo and Sales Engineer Clay Killgore, join Vivun CEO Matt Darrow to reveal where most sales tools go wrong and what it looks like when AI is built with the rep in mind. 

They share how agentic AI helps cut prep time, eliminate Frankenstack bloat, and support strategic selling without getting in the way.

In this episode, you’ll learn:

1. Why most sales tech stacks are bloated – Clay shares how disconnected tools create drag and why simplifying your stack can lead to faster execution.
2. How agentic AI helps AEs sell more – Mike explains how AI can act on your behalf, handling tasks behind the scenes so you can focus on strategic conversations.
3. What useful AI workflows actually look like – Real-world examples of how intuitive, rep-friendly AI is replacing rigid systems and enabling real productivity.

Things to listen for: 

(00:00) Introduction

(02:25) How Large Language Models changed the way sellers learn

(05:34) Why agentic AI finally works for reps, not just managers

(06:33) Clutter from the old sales process

(07:33) Your AI as your copilot

(09:09) No more prompting: what agentic AI automates

(13:06) Scaling strategic selling without sacrificing quality

(19:53) Final takeaways: no more Frankenstack, no more guesswork

Can AI make us more human in how we go to market?

In this episode, Jarod Greene sits down with Lucas Welch, VP of Corporate Marketing at Highspot, for a conversation about authenticity, AI, and the power of personal connection in modern marketing.

Lucas shares how AI isn’t replacing relationships but encouraging deeper ones, especially when go-to-market teams build experiences that reflect what people actually care about. He walks through how his team uses tools like intent data and Mentimeter to shape events that feel personal, not prescriptive.

Tune in to get insight on how the next generation will treat AI as a co-pilot, and why staying curious is non-negotiable if you want to stay relevant.

In this episode, you’ll learn:

1. How AI is reshaping B2B relationships – Technology is forcing teams to create more intentional, human-first interactions that break through digital noise.
2. Why co-created experiences work – Gathering input before events leads to stronger engagement, better conversations, and more shared insights.
3. The importance of AI fluency in your career – As new sellers enter the workforce fluent in AI, the ability to learn and adapt is now a competitive advantage.

Things to listen for: 

(00:00) Introduction

(00:43) Why AI may lead to more human connection, not less

(02:07) Using intent data and surveys to shape high-impact events

(03:47) How co-creating agendas keeps people engaged and sharing

(05:18) Building trust with enterprise AI through secure adoption

(07:27) Why mastering AI now matters for future career relevance

(09:14) How authenticity fuels better collaboration and ideas

(13:39) Advice for junior marketers on asking, growing, and doing the work

How do you scale a team without scaling headcount? And why are some companies still slow to adopt AI despite clear advantages?

In this episode, Vivun CEO Matt Darrow sits down with CMO and fellow podcast host Jarod Greene to discuss how marketing and sales teams can operate at a higher level using AI without losing the human element.

They share how a five-person marketing team can outperform teams four times its size, what gets in the way of broader AI adoption, and why the best enablement isn’t more training, but less friction. 

Human connection still closes deals. But the teams who move fastest with precision are the ones using AI to handle everything else.

In this episode, you’ll learn:

1. How AI helps lean teams scale up – Jarod breaks down the AI tools and workflows that power speed without sacrificing quality.
2. Why enablement needs a reset – It’s not about more content. You have to clear the clutter so reps can actually sell.
3. What’s slowing AI adoption – The blockers CMOs face and how teams are finding quick wins without waiting on perfect conditions.

Things to listen for: 

(00:00) Introduction

(02:14) Scaling faster without losing quality

(03:23) Breaking through the cold start problem

(05:00) Why some CMOs still stall on AI

(08:26) Rethinking SDRs with fewer tools, more output

(13:54) Enablement fails when content becomes noise

(19:13) Cutting through buyer fatigue with real value

(22:13) AI avatars can’t replace real relationships

Is the traditional sales model evolving with the rise of SEs?

In this episode, Jarod Greene sits down with Michelle Afshar, Global Head of Enablement at Darktrace, to unfold the shifting dynamics within B2B sales teams, focusing on the increasing importance of SEs.

Michelle explains why the future of sales belongs to sales engineers, emphasizing the need for sellers to be more technical. She argues that aligning SEs and AEs is essential for closing deals in today’s tech-driven landscape. 

Tune in to learn why modern sales roles are evolving.

In this episode, you’ll learn:

1. How sales roles are transforming – Michelle envisions a future where sales engineers are your best sales reps, adapting to the technical needs of modern buyers.
2. The challenges for AEs – Learn about the barriers organizations face in cultivating AEs with the technical prowess of an SE.
3. Redefining enablement – Discover Michelle’s strategy for equipping SEs with necessary sales skills, and AEs with necessary technical skills, emphasizing the importance of unified support across sales teams.

Things to listen for: 

(00:00) Introduction

(00:43) Successful sellers will be SEs

(02:36) The challenges of aligning AEs and SEs for better sales outcomes

(03:38) Understanding the modern buyer's journey and how it affects sales

(07:02) The role of enablement in supporting SEs

(09:50) The importance of training SEs beyond just product knowledge

(14:03) Strategies for structuring sales teams to foster collaboration

Are you using AI correctly for market research?

In this episode of V5, Jarod Greene sits down with Claudia Natasia, CEO of Riley AI, to discuss the evolving role of AI in customer insights.

Claudia breaks down how AI is transforming market research, but she’s quick to caution against a plug-and-play approach. Off-the-shelf tools or LLMs alone won’t cut it if you want a real edge. She shares why blending proprietary data with AI is the key to unlocking insights your competitors will miss. With Riley’s innovative approach, they're helping businesses uncover the kind of golden nuggets that actually move the needle.

In this episode, you’ll learn:

1. Why AI alone isn’t enough – To stay ahead, companies will have to use their own data alongside AI models to generate unique insights instead of blending into the field.
2. The value of proprietary data in gaining a competitive edge – Pulling from the same sources leaves you blind to opportunities others are missing.
3. How user research drives business success – Real customer stories not only shape product development but also fuel substantial revenue growth.

Things to listen for: 

(00:00) Introduction

(00:52) Using AI as a research tool

(02:00) The outdated GTM playbook

(01:47) Why AI tools fall short

(03:01) Riley AI’s data-driven approach

(04:27) User research’s business impact

Is the CRO role changing to meet modern sales demands?

In this episode, Jarod Greene connects with Kelly Lewis of  B2B Go-To-Market Strategy, to discuss the ever-evolving nature of the CRO role and B2B selling teams in general.

Kelly explains why today’s CROs need more than just sales skills. They have to master strategy, operations and even AI to lead teams effectively and scale success. She also predicts a rise in CRO educational programs to meet these needs.

Listen to learn how sales leaders can evolve into CROs and adapt to the growing expectations of this complex role.

In this episode, you’ll learn:

1. How the CRO role is expanding – Beyond sales, the role now includes responsibilities in operations and strategy, making it a more complex leadership position.
2. Why asking “why” matters – Sales leaders aspiring to be CROs must develop a deeper understanding of decision-making processes across their teams.
3. The shift towards a new breed of sellers – With AI transforming the industry, Kelly shares her thoughts on where the next generation of sales talent will come from.

Things to listen for: 

(00:00) Introduction

(02:25) Why scaling teams and adopting AI are key CRO challenges

(03:54) Balancing marketing, ops, and sales within the CRO role

(05:57) Why realistic expectations matter in revenue operations

(07:37) The role of behavior change in successful enablement

(13:09) How AI is reshaping the next generation of sellers

(14:17) The future of sales engineers transitioning to account executives

Is brand the last real differentiator?

In this episode of V5, Jarod Greene talks with Margaret Kelsey, CMO of Kodaris, about the shifting landscape of B2B marketing.

Margaret argues that software has become a commodity—AI has made it easier than ever to build and replicate products. Yet many companies still rely on outdated go-to-market strategies instead of investing in brand and creative distribution. She explains why personal brands, employee advocacy, and strong cultural alignment are the key to standing out in a crowded market.

In this episode, you’ll learn:

1. Why traditional GTM playbooks don’t work – Relying on paid demand gen and performance marketing is no longer enough to win.
2. How brand has become the ultimate moat – When technology and distribution look the same, differentiation comes from the values and authenticity behind a company.
3. The power of advocacy at every level – From founders to employees, building trust through personal branding and cultural alignment drives long-term growth.

Things to listen for: 

(00:00) Introduction

(00:52) Software is now a commodity

(02:00) The outdated GTM playbook

(02:37) Why brand is the last competitive moat

(03:17) Leveraging podcasts for brand-building

(04:16) Personal brands and internal advocacy

(05:03) Hiring for cultural and brand alignment

(06:07) The flywheel that drives real growth

What actually is an AI agent vs. a personal productivity tool? And how do you navigate the vast vendor landscape? 

AI is changing the sales game, but are leaders truly harnessing its potential? In this episode, Vivun CEO Matt Darrow and CRO Trevor Jett break down what sales leaders need to know about AI agents.

From cutting through vendor noise to understanding the real impact on sales productivity, they bring clarity to an often-misunderstood topic. With firsthand insights from scaling high-performing teams, they explore how AI can democratize expertise, not replace sales roles.

Deal velocity and quality relationships don’t have to be at odds in B2B. Listen in to learn how leading teams are bringing more power to sales with Agentic AI.

In this episode, you’ll learn:

1. What makes an AI agent different – Why most sales leaders get the definition wrong and how it impacts decision-making.
2. Avoiding AI tool overload – How to filter out distractions and focus on tech that truly moves the needle.
3. Rethinking enablement – Why top reps don’t rely on traditional training and how AI can level the playing field.

Things to listen for: 

(00:00) Introduction

(01:08) How CROs navigate AI vendor pitches

(02:45) Defining AI agents: What most sales leaders get wrong

(04:13) The real challenge of AI tool sprawl in sales

(06:14) The spectrum of AI experiences: three AI categories every sales leader should know

(08:47) Too much “AI,” not enough actual intelligence 

(12:00) Agentic AI’s role in accelerating sales enablement and ramp time

(17:19) The myth of AI agents replacing sales teams

Are sales engineers too focused on features instead of what customers really need?

In this episode, Jarod Greene connects with Tom Josephson, Senior Director of Solution Consulting at TCP Software, to explore the power of discovery in building solid relationships with buyers.

Tom explains why curiosity is a superpower for SEs, how the right questions reveal real customer needs, and why great SEs show less, not more.

This episode gets into how SEs can shift their approach from demonstrating technical prowess to being strategic partners who understand the customer's goals.

In this episode, you’ll learn:

1. Why curiosity is essential in discovery – the best SEs ask insightful questions to uncover what truly matters to the customer.
2. When less is more in a customer conversation – Saying “yes” and moving on can be more effective than over-explaining, and a well-placed “no” can actually build credibility.
3. How to keep prospects engaged – Letting them feel like they’re driving the conversation creates stronger buy-in and more powerful rapport. 

Things to listen for: 

(00:00) – Introduction

(00:54) – Why curiosity makes discovery more effective

(02:25) – Why SCs should resist the urge to show everything

(03:54) – When to say “yes” and move on (and when to ask follow-ups)

(05:57) – The power of a well-placed “no” in sales conversations

(07:37) – Helping prospects reframe the problem, not just the solution

(14:17) – How great SCs shift from demoing features to guiding decisions

Are sales engineers relying too much on technical expertise and missing what truly drives customer decisions?

In this special V15 episode, Jarod Greene sits down with Marjorie Abdelkrime, Head of US West and Healthcare Solutions at VMware by Broadcom, to explore what separates great SEs from those who get stuck. Marjorie shares why curiosity is the most critical trait for success, how Sales Engineers can build trust by admitting what they don’t know, and why AI-powered demos provide an opportunity to elevate the human element in technical sales. She unpacks the evolution of the SE role, from product expert to strategic advisor, and the mindset shifts required to elevate sales engineering conversations.

From leveraging AI to enhance—not replace—SEs to understanding the customer’s customer, this episode explores the nuances of modern solution consulting.

In this episode, you’ll learn:

1. Why curiosity is the foundation of SE success - The best SEs go beyond technical expertise by asking deeper questions, uncovering business needs, and connecting solutions to real customer challenges.
2. How admitting “I don’t know” strengthens credibility - SEs who acknowledge knowledge gaps and follow up with thoughtful insights build stronger trust with customers and internal teams.
3. The evolving role of AI in sales engineering - AI-powered demos can enhance efficiency, but SEs need to double down on soft skill development to drive meaningful business conversations and strategic decision-making.

Things to listen for: 

(00:00) Introduction

(00:58) Why curiosity determines SE success

(02:25) The danger of pretending to know it all

(03:54) AI’s role in demos and what it can’t replace

(05:57) How SEs can use AI to advance their careers

(07:37) Understanding the customer’s customer

(14:17) From demo expert to trusted business advisor