Win Long Sales Cycles Without Annoying Your Prospects
Sales reps often abandon prospects who are locked into multi‑year contracts, forfeiting future revenue. Harriet Mellor of Your Sales Co recommends a four‑step system: block the renewal date, use LinkedIn to stay visible, schedule meaningful 12‑week touchpoints, and multi‑thread across the organization. By turning an abstract timeline into concrete calendar events and leveraging low‑effort digital presence, reps can nurture hundreds of long‑cycle opportunities without annoyance. The approach shifts focus from immediate quotas to sustained relationship building, positioning the rep as the first choice when the contract expires.
How Do You Sell When You Have No Customers, No Reputation, and No Sales Experience in a Crowded Market? (Ask...
Robert Cekay, a developer of a home‑service CRM, faced the classic startup dilemma of selling with no customers, reputation, or sales experience. He was advised to ignore established platforms like Jobber and ServiceTitan and instead target owner‑operators who have never...
The Human Advantage: Enterprise Sellers Win or Lose on People Skills in the Age of AI (Ask Jeb)
Enterprise sellers face a new inflection point: AI equips them with unprecedented research and insight, but the decisive factor remains people skills. In long, complex deals, the relationship is the product, and trust outweighs features or price. Sales leaders who...
Moneyball for Sales: Why You’re Tracking the Wrong Metrics (Money Monday)
The article argues that the true leading indicator of sales success is the First Time Appointment (FTA)—a net‑new meeting with a prospect you’ve never spoken to—rather than traditional activity metrics like calls, emails, or LinkedIn touches. By treating FTAs like...
Buyer Resistance Is at an All-Time High with Colleen Stanley (OutBound 2026)
Buyer resistance has reached unprecedented levels as tighter budgets and AI‑generated outreach flood prospects with impersonal messages. Sales experts Jeb Blount Jr. and Colleen Stanley argue that the sellers who succeed are those who cultivate internal emotional‑intelligence skills rather than...
Why Prospects Jump Straight to Price and How to Take Back Control (Ask Jeb)
Sales trainer Jeb Blount explains why contractors and home‑service owners jump to price on cold calls and how reps can regain control. He notes that busy tradespeople use price as a quick filter when called at the wrong time, often...
Your Attitude Walks Into the Room Before You Do (Money Monday)
Sales experts stress that a seller’s attitude arrives before their words, shaping buyer perception within seconds. Whether on a phone, Zoom, or in person, tone, energy, and confidence dictate whether prospects stay engaged or hang up. The article illustrates this...
5 Hard Sales Lessons Most Reps Learn Too Late
The article distills five hard‑earned sales lessons that separate top performers from the rest. It stresses writing concrete goals, bringing in an external voice to break the "parent effect," mastering communication‑channel discipline, executing cold‑calling fundamentals, and leveraging self‑awareness through frameworks...
How to Coach Your Sales Team with Empathy without Losing Your Edge (Ask Jeb)
Jeb Blount explains that many sales managers mistake sympathy for empathy, which hurts team performance. He outlines how true empathy means understanding a rep’s perspective without agreeing, then holding firm on expectations. The core coaching technique is to listen fully,...
Why Your Daily Sales Meetings Aren’t Working (Ask Jeb)
Jeb Blount argues that most daily sales huddles are too long and poorly structured, draining reps' energy before they hit the phones. He recommends cutting the meeting to ten‑to‑fifteen minutes, holding it every single day without exception, and following a...
People Buy for Their Reasons, Not Yours (Money Monday)
The Money Monday episode of the Sales Gravy Podcast argues that buyers decide primarily on emotion, then rationalize with logic. Experiments with wine price tags and store music illustrate how subconscious cues shape preferences. Salespeople who open with features and...
The Power of Relaxed Assertive Confidence
Relaxed assertive confidence is the calm certainty that an ask will be answered with a yes, separating top sales performers from those who hesitate. Vera Stewart exemplifies this mindset, securing a refrigerated truck and a TV syndication deal by asking...
How to Get to the C-Suite Without Burning Your Existing Relationships (Ask Jeb)
Account manager Jeremiah Wren faces pressure to engage CEOs, CIOs, and other C‑suite leaders about AI, yet 75% of his 270 accounts lack executive contacts. He worries that bypassing his mid‑level contacts could damage those relationships. The article advises treating...
Q1 Sales Strategy Reality Check: How Top Sales Teams Finish Strong in Q2 (Money Monday)
The article frames Q1 as a feedback loop rather than a failure, urging sales leaders to conduct a focused strategy review before Q2. It stresses diagnosing whether a team faces an execution problem—consistent activity but spotty results—or a focus problem—low...
How to Rehearse a Sales Pitch So You Can Walk In and Win
The article argues that the most effective way to rehearse a sales pitch is to practice out loud in front of real people until the story is internalized, not merely memorized. Drawing on insights from Danny Fontaine of IBM, it...