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

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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

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?

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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 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

TLDR: Founder-led sales got you to seven figures. It won't get you to eight. Gearoid Cox, founder of SalesPipeline, joins us to unpack why most founders can't let go of sales, why AI SDRs are more brand damage than productivity gain, and what it actually takes to architect a sales motion that scales without the founder in every seat.

Full Description:Every founder hits the same wall. The product is selling. The first ten clients came in on founder charisma and deep product knowledge. Then the business needs to scale, and suddenly the founder is the bottleneck nobody wants to name.

Gearoid Cox built SalesPipeline to solve this exact problem. His firm hires, trains, and runs sales and marketing teams on behalf of small companies that have outgrown founder-led sales but aren't yet ready for a full in-house GTM org. In this episode, Tiffany Jones sits down with Gearoid for a candid conversation about the gap between founder selling and scalable selling, what gets lost when founders pitch features instead of mapping buyer journeys, and why the new-logo obsession is robbing most revenue orgs of the easiest growth available to them.

They get into the AI conversation honestly: where AI is genuinely changing the game inside sales orgs (reporting, dashboards, enrichment), and where the AI SDR pitch is over-promising and damaging buyer trust at scale. If you're a founder, a fractional GTM operator, a head of revenue, or a RevOps leader trying to make sense of the moment, this one has receipts.

In this episode:

• Why founders cling to sales and what to do about it
• The difference between a sales process and a founder in their head
• Buyer journey thinking versus features-and-benefits selling
• Why AI SDRs are great products pointed at the wrong use case
• Where the real revenue lives (hint: it's not new logos)
• What "graduating" from outsourced sales actually looks like

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Guest LinksConnect with Gearoid Cox: https://www.linkedin.com/in/gearoidcox/| https://sales-pipeline.io

TLDR: Everyone tells sales managers to "be the CEO of your business," but nobody actually explains what that means. Sarah Bedwell does, and the gap between what most frontline leaders are doing and what's possible is staggering.

Sales managers have some of the hardest jobs in any go-to-market organization. They're managing seven to ten reps, sitting in on deals, running forecast calls, and still trying to figure out where their number is going to come from. But here's the problem: most of them have never been walked through the actual strategic planning process that turns a territory into a business they can run with confidence. In this episode of The Revenue Insiders, hosts Kelly Lewis and Tiffany Jones sit down with Sarah Bedwell, a seasoned revenue leader and sales enablement consultant with 20 years of experience spanning her time as employee number 70 at Tableau through building go-to-market programs across industries. Sarah breaks down exactly what it means to operate like a CEO of your own sales business, from identifying the go-to-market levers you actually control to building an operational cadence that gets you from spending 15% of your week on deals to 40%. If you manage a sales team or lead people who do, this one is packed with frameworks you can put to work immediately.

In this episode, you'll learn:

• Why most sales managers miss quota because they don't understand their own individual ICP at the territory level
• The go-to-market levers frontline managers control (and the ones they don't) and why knowing the difference changes everything
• How to build an operational cadence that protects your coaching time and eliminates the "booked 6am to 6pm" calendar trap
• The delegation framework that got one manager hours back in her week while making her reps stronger closers
• What second and third-line leaders should be inspecting to find out if their frontline actually has a plan

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/the-revenue-insiders/id1767256445Watch on YouTube: https://www.youtube.com/channel/UCNCx_Fge5kxBbKHev1C88CgFollow on LinkedIn: https://www.linkedin.com/company/the-revenue-insiders

Connect with Sarah Bedwell: https://www.linkedin.com/in/bedwellsarah