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