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