The Unexpected Lever

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