The Revenue Insiders

TLDR: AI should make you hire more sellers, not fewer. Zac Auger, a revenue leader who has run both sales and post sales at Square and Postman, makes the case that the companies cutting go-to-market headcount to fund AI are about to lose to competitors who are simply investing harder.Zac's path started at Framed Data, a Y Combinator startup he invested in and then joined. After Square acquired Framed, he applied its user behavior prediction models to Square's account management team, building an intelligent to-do list that told reps which customer to call, which product to recommend, and when to call. Connect and conversion rates jumped to roughly 50%, the team grew instead of shrinking, and Zac went on to lead one unified customer facing org. With planning season underway and every revenue leader being pitched AI SDRs, this conversation with Tiffany Jones and Kelly Lewis is a sharp reality check on sales leadership, RevOps, and where AI actually belongs in your go-to-market motion.In this episode:- Why hunters and farmers must be separate roles, even at a 20 person startup- How to segment customers by lifetime value and LTV lift instead of today's revenue- Why sellers often make better account managers than support reps- Why one customer facing org and one team psychology beats any handoff process- How Postman runs AI agents as teammates inside Slack, and why sales will be the last job automatedFollow The Revenue Insiders wherever you listen and leave us a rating. It helps more GTM professionals find the show.Listen on Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvLListen on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445Watch on YouTube: https://www.youtube.com/@TheRevenueInsidersFollow on LinkedIn: https://www.linkedin.com/company/the-revenue-insidersWork with us: https://www.therevenueinsiders.comConnect with Zac Auger: https://www.linkedin.com/in/zacauger

TLDR: Is AI a bubble? Mårten Mickos lived through the dot com boom and bust, scaled HackerOne from zero to roughly $100M in revenue, and now coaches CEOs through the AI shift. His answer: yes, a correction is likely, and it's still no reason to sit this out.

Mårten has been a CEO several times over, from MySQL to HackerOne, and today he spends his time building CEOs instead of companies. Tiffany (who worked on his team) and Kelly ask him the question every revenue leader is wrestling with: are we in an AI bubble, and what should CEOs and go-to-market teams do about it? Mårten compares AI to electricity, explains why the cost of AI compute could get more expensive before it gets cheaper, and shares why AI native challengers with weaker products are still beating established vendors. The conversation then turns practical for sales leadership, RevOps, and enablement teams: where to prioritize AI investment, why your CRM data matters more than your prompts, and why meetings full of AI notetakers are missing the point of getting humans in a room.

In This Episode:

• Why AI looks like the dot com era, only bigger and faster
• Experiment in three days, be patient for two years: Mårten's rule for AI investment
• How one founder stepped out of the CEO seat to rebuild his company as AI native
• Working Genius, Amazon six pagers, and setting the tone of a meeting
• The one question Mårten asks before every big decision

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Listen on Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvL
Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445
Watch on YouTube: https://www.youtube.com/@TheRevenueInsiders
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Work with us: https://www.therevenueinsiders.com

Connect with Mårten Mickos: https://www.linkedin.com/in/martenmickos

TLDR: Sales managers are being asked to coach 12 to 15 reps while carrying their own deals. Paul Burani, co-founder and CRO of Atlas Primer, joins Kelly and Tiffany to talk about where AI role play actually helps, why one practice rep is enough to start, and why the AI hype cycle is pushing companies into expensive mistakes.

Paul has spent 25 years across nearly every seat in a revenue organization, from cold calling and enterprise deals to leading global automotive strategy and planning at Google. We get into the bottom up value of practice for individual sellers, and the top down insight leaders never had before: what their teams actually say when they practice, and where messaging breaks down long before it shows up in pipeline. We also dig into the squeeze on middle managers, why executives need to practice staying on message after SKO, gamification that isn't cutesy, and how Enablement can finally connect learning to close rate, deal size, and renewal. This one is for every sales manager, RevOps and enablement leader, and CEO planning next year's go-to-market headcount.

In this episode

• Why competing on AI features no longer works, and what builds real customer affinity
• The bottom up and top down value of AI role play for sales teams
• What happens to the sales manager role as spans of control grow
• Why practicing once is enough to start, and how gamification drives adoption
• The hype cycle, AI layoffs, and the change in the revenue world nobody expects

Connect and subscribe

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Listen on Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvL Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445 Watch on YouTube: https://www.youtube.com/@TheRevenueInsiders Follow on LinkedIn: https://www.linkedin.com/company/the-revenue-insiders Work with us: https://www.therevenueinsiders.com

Connect with Paul Burani: https://www.linkedin.com/in/pburani/ | https://atlasprimer.com

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Europe is not one market, and treating it like one is the fastest way to burn a year of expansion budget. Iryna Begma, head of sales at LexisNexis in Brussels, breaks down how to pick your first country, what to localize, and how to sell under GDPR and the new EU AI Act.

Every US company eventually says "we're launching Europe," hires a few multilingual reps in London or Dublin, and points them at the whole continent. Iryna has lived on the other side of that plan. She started her sales career in Ukraine, built a sales community there that she still teaches in, and now leads new business across northern, southern, and central Europe plus French speaking Africa. Kelly and Tiffany dig into why Germany wants German solutions sold by German sellers in German, why Gong talk ratios mean something different in Madrid than in Munich, how outreach rules change country by country, and what European employment law means for sales managers trying to scale. If your go-to-market, RevOps, or enablement team has Europe on the roadmap, this sales leadership conversation belongs before your first hire.

In this episode:

• Why Benelux or Portugal might beat Germany as your first market
• When to localize your website, collateral, and outreach, and when English works fine
• How buyer behavior shifts by country, and why one Gong benchmark won't fit them all
• GDPR outreach rules in Sweden, Germany, and Belgium
• Probation periods, tax brackets, and work-life balance realities for European sales managers

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Listen on Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvL
Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445
Watch on YouTube: https://www.youtube.com/@TheRevenueInsiders
Follow on LinkedIn: https://www.linkedin.com/company/the-revenue-insiders
Work with us: https://www.therevenueinsiders.com

TLDR: Annual plans rarely fail inside one team, they fail at the seams between RevOps, marketing, HR, enablement, and sales leadership. Kelly and Tiffany break down where planning falls apart, why AI makes it riskier this year, and how to run a sales kickoff that actually lands.

With fiscal years closing fast, a lot of go-to-market teams are only now starting annual planning, and this year every team has its own AI building its own mini plan. Kelly Lewis and Tiffany Jones have lived through more than 20 annual plans between them, and they walk through what really breaks: territory changes that quietly blow up an ABM strategy, hiring plans recruiting can't support, enablement brought in six weeks before kickoff, and decisions that get "forgotten" in January. They share how to use a decision log, why you need named decision owners, how to drip change instead of dumping it, and why delivering comp plans and territories right before SKO costs you two weeks of selling. Whether you're a sales manager, an enablement or RevOps leader, or a CEO signing off on the plan, this is a practical guide to protecting revenue through change.

In this episode:

• The "seams" of annual planning and why cross functional handoffs make or break the plan
• Why enablement needs a seat at the table right after RevOps, not six weeks before kickoff
• Decision logs, decision owners, and how to handle a plan change after rollout
• Kelly's fast start approach: deliver territories and comp first, hold SKO for week three or four
• How to design an SKO around peer learning, customers, real deals, and actual breaks

Follow The Revenue Insiders wherever you listen and leave us a rating. It helps more GTM professionals find the show.

Listen on Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvL Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445 Watch on YouTube: https://www.youtube.com/@TheRevenueInsiders Follow on LinkedIn: https://www.linkedin.com/company/the-revenue-insiders Work with us: https://www.therevenueinsiders.com

Every board wants an AI plan, but most CRMs can't support one. Weflow CEO and founder Janis Zech joins Tiffany and Kelly to explain why the next leap in go-to-market productivity starts with connected context data, not shiny agents.

Janis spent more than eight years as a CRO and grew a company to roughly $85M before selling it. Through all of it he kept hitting the same wall: the CRM was supposed to be the system of truth, and it rarely was. In this conversation he explains how revenue operations teams can move from a system of record to a system of intelligence. That means capturing activity, conversation, and contact data automatically and mapping it back to the right opportunities. Tiffany brings the RevOps lens on garbage in, garbage out. Kelly brings the sales manager and enablement reality of coaching to MEDDPICC when nobody has time to review every call. Together they work through where automation should stop and where seller critical thinking needs to start. If you're building your annual plan right now, this episode is for you.

In this episode:

• Why tying activity to the opportunity, not just the account, changes deal reviews
• How AI can auto-populate MEDDIC and MEDDPICC and turn deal scores into coaching insights
• The human-in-the-loop debate: when reps should fill in fields and when automation wins
• Why Weflow's first AI forecasting model fell short until the data pipelines were fixed
• Janis's closing challenge: are you AI first or problem first?

Follow The Revenue Insiders wherever you listen and leave us a rating. It helps more GTM professionals find the show.

Listen on Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvL
Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445
Watch on YouTube: https://www.youtube.com/@TheRevenueInsiders
Follow on LinkedIn: https://www.linkedin.com/company/the-revenue-insiders
Work with us: https://www.therevenueinsiders.com

Connect with Janis Zech: https://www.linkedin.com/in/janiszech/ | https://weflow.ai

TLDR: Your end of quarter discount isn't speeding deals up, it's teaching buyers to wait. Todd Caponi, author of Four Levers Negotiating®, shows sales leaders and revenue teams a transparent way to negotiate that protects deal value and builds trust past the signature.

Todd Caponi is the founder and principal of Sales Melon, a seven time sales leader, and the author of The Transparency Sale, The Transparent Sales Leader, and Four Levers Negotiating. Kelly Lewis and Tiffany Jones sit down with him to unpack the moment he discovered his model: a Houston conference room in 2008, a procurement team asking for 35% off, and four words on a whiteboard. As Q4 discounting season kicks off, AI is exposing pricing models, and peers are comparing notes on what they paid, Todd makes the case that old school negotiating is running out of road for sales managers, RevOps, enablement, and go-to-market leaders. Tiffany brings the buyer's side as a RevOps leader who owns the software budget, and pushes Todd on how any of this works with AI consumption pricing.

In this episode:

• The four levers every B2B pricing model already runs on: volume, timing of cash, length of commitment, and timing of the deal
• Why fake expiring discounts slow deals down, and what to do instead
• What happens when an executive "closer" undercuts the rep at the finish line
• How the model holds up under consumption and usage based pricing
• The question every revenue team should answer: what do we give up to be great at our core?

Follow The Revenue Insiders wherever you listen and leave us a rating. It helps more GTM professionals find the show.Subscribe on Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvLSubscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/id1767256445Watch on YouTube: https://www.youtube.com/@TheRevenueInsidersFollow on LinkedIn: https://www.linkedin.com/company/the-revenue-insiders

Connect with Todd Caponi: https://www.linkedin.com/in/toddcaponi/ | https://toddcaponi.com

TLDR: Eight months into 2026, Kelly Lewis and Tiffany Jones put their January predictions on trial. AI isn't coaching your reps, most companies aren't running the agents they told their board about, and annual planning is about to get messy.

Season 3 of The Revenue Insiders opens with a midyear reckoning. Kelly and Tiffany revisit the go-to-market predictions they made in January and test them against what is happening now: sales manager span of control creeping toward 15 reps, SDR promotions falling off a cliff, the gap between companies that have deployed AI agents in RevOps and the ones that just say they have, and consumption pricing hitting annual plans nobody built for it.

They also get into the Seismic and Highspot merger, what an OpenAI hiring post and the EU ban on emotion recognition in hiring tools say about EQ in sales, plus why governance is still unsolved in revenue operations. If you lead sales, RevOps, or enablement, or you are early in your sales career, this is your 2027 planning prep.

In this episode:

• Why AI coaching inside the tools isn't the same as a manager developing a rep, and what happens when finance plans for 15 reps per sales manager
• The RevOps "haves and have nots" of AI agents, and why so many boards are being told a story that isn't true
• How AI assisted annual planning goes wrong when it's built on bad data and ignores the people, the buyer, and the go-to-market reality
• What consumption and outcome based pricing mean for comp plans, forecasting, net dollar retention, and the role of the CSM
• The future of enablement after the Seismic and Highspot merger, and why cutting your enablement team for AI is the wrong ROI math
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TLDR: Salesforce just acquired Contentful, and everyone is calling it a marketing story. Kelly and Tiffany make the case that it is actually a sales, enablement, and RevOps story about content becoming AI ready data. Here is what it means for your team before a Salesforce rep calls you this fall.

Full Description:Salesforce signed a deal to buy Contentful, a content platform used by more than 4,800 brands including roughly a third of the Fortune 500. The headlines filed it under martech. On this episode, Kelly Lewis and Tiffany Jones turn it into something far more relevant for go-to-market teams: a preview of what happens when your content becomes structured data that AI can assemble on demand. They unpack the strategic logic of the deal, the eye opening down round from a 3 billion dollar valuation in 2021, and why this fits the broader pattern of Salesforce buying its way toward an agentic, headless future. Then they get practical. What does this mean for the enablement leader, the RevOps team, and the seller on the front line? This is a candid, occasionally spicy conversation about clean data, content governance, the consolidation versus best of breed debate, and the human skills that get more valuable as AI takes over more of the revenue motion.

In This Episode:

• Why the Contentful deal is a sales and enablement story, not just a marketing one
• The data readiness problem and why garbage in still means garbage out, only faster
• Whether enablement platforms like Highspot and Seismic still have a role, and what survives
• How the enablement job shifts from making content to governing the truth
• Why critical thinking and discovery are the durable skills for every sales career
• The line in the sand: what should never be handed fully to AI

Connect & SubscribeFollow The Revenue Insiders wherever you listen and leave us a rating. It helps more sales leadership, RevOps, and enablement pros find the show.Subscribe on Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvLSubscribe on Apple Podcasts: https://podcasts.apple.com/podcast/id1767256445Watch on YouTube: https://www.youtube.com/@TheRevenueInsidersFollow on LinkedIn: https://www.linkedin.com/company/the-revenue-insiders

TLDR: While enablement teams everywhere are shrinking and the whole market is racing to automate, Clay is doing the opposite. Melina Giakas explains why her AI-forward enablement team makes reps earn the shortcut before any automation gets switched on.
Enablement is supposed to be the first thing AI replaces. So why is one of the most AI-forward companies in go-to-market growing its enablement team and deliberately pumping the brakes on automation? In this episode, Kelly Lewis and Tiffany Jones sit down with Melina Giakas, who leads GTM enablement at Clay, for a conversation that challenges almost everything you're hearing about AI in revenue right now. Melina shares how her team uses AI to compound competence instead of skipping it, why she makes go-to-market engineers prove a skill by hand for a quarter before automating it, and how Notion agents quietly handle content governance in the background. It's a practical, contrarian look at where AI actually belongs in modern sales enablement, RevOps, and the broader GTM motion.
In this episode:

• Why Clay is growing enablement headcount while the market cuts it
• The "prove it before you automate it" rule for go-to-market engineers
• Why AI roleplay keeps failing (and it isn't the technology)
• Moving beyond the LMS to measure behavior change, not course completions
• Using Notion agents for content governance with a human in the loop

Connect & Subscribe
Follow The Revenue Insiders wherever you listen and leave us a rating, it helps more GTM professionals find the show.
Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvLApple

Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445YouTube: https://www.youtube.com/channel/UCNCx_Fge5kxBbKHev1C88CgMore: https://www.therevenueinsiders.com
Connect with Melina Giakas: https://www.linkedin.com/in/mgiakas/ | https://www.clay.com