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Edition 02 ยท October 2026

The monthly newsletter

The Revenue Insiders:The Brief

Planning season edition. Where 2027 plans break, how to make your SKO stick, and the AI reads that matter this month.

01

About The Brief

One read a month, built for operators.

One read a month for operators who design their revenue systems on purpose. The newest podcast episodes, what just happened in GTM, and thought leadership from Tiffany and Kelly, delivered to subscribers.

02

From the Podcast

New episode

The Seams Where Your Revenue Plan Quietly Falls Apart

Kelly Lewis and Tiffany Jones ยท Oct 15, 2026

The Seams Where Your Revenue Plan Quietly Falls Apart

Annual revenue plans rarely break inside one team. They break at the handoffs between RevOps, marketing, HR, enablement, and sales leadership. Kelly and Tiffany walk through the failure points they see most often, like territory changes that quietly undercut an ABM strategy, and share how to run a sales kickoff that actually carries the plan into the field.

Listen to the full episode
Listen and subscribe SpotifyApple PodcastsYouTube
Companion listen

Is AI Quietly Breaking Your Annual Planning? A GTM Midyear Check

Kelly Lewis and Tiffany Jones ยท Sep 24, 2026

Is AI Quietly Breaking Your Annual Planning? A GTM Midyear Check

Before you lock 2027, revisit where 2026 actually landed. Kelly and Tiffany score their January GTM predictions at the halfway mark: sales manager span of control, the gap between companies running AI agents and companies saying they are, consumption pricing, and what the Seismic and Highspot merger means for enablement.

Listen to the full episode
Listen and subscribe SpotifyApple PodcastsYouTube
03

Inside The Revenue Engine

Workshops, Courses, and Downloads

Free 60-minute workshop ยท Thursday, Nov 12, 2026 ยท 9 AM PT

Make It Stick: How to Build an Interactive SKO That Outlasts the Event

SKO shouldn't end when the event does. Join Kelly for a free workshop for enablement, sales, and go-to-market leaders who want their SKO to show up in deals long after everyone flies home. We'll cover how to prepare attendees before the event, run interactive sessions instead of lecture-style slides, and reinforce the material afterward so it lasts once your team is back in pipeline.

Save your seat

12-week cohort programs

A course, a cohort, and a coach

Self-paced modules, live group coaching with your cohort, and 1:1 coaching, with every framework run on your actual team and your actual business.

New process guide

The Modern Annual Revenue Planโ„ข

A 14-page guide to the seven phases of planning, from roughly seven months out to day one of your fiscal year. Includes the GTM Change Inventory worksheet and a rollout plan for getting changes adopted in the field.

Get the guide

Planning 2027?

Let's pressure test your plan.

If your plan is going to break, it will break at the seams between teams. We work with revenue leaders to find those gaps before the year starts.

Book time with us

Our Favorite New Tools

Weflow

A Revenue AI orchestration platform built on Salesforce. It captures email and calendar activity into the CRM automatically, analyzes customer conversations, and gives leaders deal visibility and forecasting, with an AI assistant and agent builder on top. CEO and founder Janis Zech joined us on the podcast this month to make the case that GTM productivity depends on connected context data more than on AI agents.

Visit Weflow Hear Janis on the podcast

The Latest AI News

  1. 01
    October 2026 RevOps News: Trends & Insights

    Seafoam ยท Oct 1, 2026

    Salesforce, HubSpot, ZoomInfo, Clari, and Salesloft all want to be your AI context layer. Before you connect agents to anything, decide which system owns each core fact.

  2. 02
    AI Update, October 02, 2026: AI News and Views From the Past Week

    MarketingProfs ยท Oct 2, 2026

    AI search is cutting clicks to external sites, so B2B marketers should judge content on citations, qualified traffic, and conversions instead of rankings.

  3. 03
    Aligned Introduces Seller Agent, the Industry's First AI Agent Built Inside the Deal Workspace

    GlobeNewswire ยท Oct 14, 2026

    Deal tools are moving from answering questions to doing the work, like revising mutual action plans and building decks. The question for leaders is what reps still own.

  4. 04
    Every AI Company Sells An Agent. They Are Not Selling The Same Thing

    Forbes ยท Oct 18, 2026

    The model is becoming interchangeable; the platform around it is not. When you buy an agent, you are choosing which system becomes permanent in your stack.

  5. 05
    Demandbase Launches New AI Agents to Lead the B2A Marketing Era

    Business Wire ยท Oct 20, 2026

    Buyers are asking AI assistants about you before they ever talk to you. Demandbase's new AEO Agent tracks what those assistants say about your brand to each buying group member.

04

Connect with The Revenue Insiders

Tiffany JonesTiffany JonesLinkedIn Kelly LewisKelly LewisLinkedIn The Revenue InsidersLinkedIn Tiffany on SubstackEssays on motherhood and revenue systems