• Why Building Relationships in Sales Skyrockets Your Commission
    Jun 20 2025
    You know the drill. The quota clock is ticking, the pressure is mounting, and there's that relentless urge for a quick win. Every sales professional has felt that impulse to rush the process, to push for the immediate "yes," because, well, the numbers demand it. But here's the tough question you need to ask yourself: What if that very pressure is actively sabotaging your long-term success? What if chasing the fast buck is actually costing you the lucrative, lasting relationships that define an elite sales career and build a lasting book of business? As Sales Gravy Podcast guest Steve Pyfrom puts it: “Building relationships takes time and sales, teams need desperately to get off of this short-term win dynamic. The goal is long-term revenue for your company, lifetime value for the end user.” Focusing solely on the quick sale burns through pipeline leads faster than you can replace them, leaving you on a perpetual hamster wheel of prospecting just to stay afloat. It's time to talk about the long game, because building real relationships is where sustainable revenue lives. Why Churn Is Killing Your Commissions Let's talk numbers. According to SimplicityDX, customer acquisition costs have increased by 222% over the last eight years, while customer lifetime value has remained flat. It's getting harder and more expensive to find new customers, making the ones you have incredibly valuable. Yet most salespeople treat customers like one-time transactions. They close the deal, celebrate briefly, then immediately move on to the next prospect. This approach is financial suicide. Customers who feel rushed through the buying process rarely become loyal advocates. When a customer feels pressured into a decision or perceives the sale as purely transactional, their loyalty is paper-thin. They're constantly looking for better deals, questioning their purchase decision, and jumping ship when problems arise. When a customer churns, you lose all potential referrals, upsells, and cross-sells they could have generated. You're back to square one, hunting for new prospects to replace the revenue you just lost, all while acquisition costs keep climbing. The Trust Equation That Changes Everything Most salespeople think selling is about convincing, but selling is about connecting. When you rush a prospect, you're telling them their decision-making process doesn't matter. You're saying your timeline is more important than their comfort level. Real relationships are built on trust, and trust takes time. Think about your personal life. Your closest friends aren't the people who tried to fast-track the process. They're the ones who showed up consistently, listened without an agenda, and proved their reliability over time. The same principle applies in sales. The prospects who become your biggest advocates aren't the ones you pressured into a quick yes. They're the ones who felt heard, understood, and genuinely cared for throughout the entire process. The Compound Effect of Relationship Selling Consider Mary, a software sales rep who was in competition with 2 other software vendors for a deal with a manufacturing company. Mary's competitors immediately launched into aggressive pitches and discount offers to David, the CFO, hoping to close the deal quickly. Mary took a different approach. Instead of pitching, she spent two months understanding David's cash flow challenges and upcoming board presentation needs. She shared relevant case studies, introduced him to a supply chain consultant, and helped him think through his decision criteria. She never once mentioned her software. When David's team raised concerns about implementation timelines during their evaluation, Mary's competitors pushed back, insisting their solution was simple to deploy. Mary listened, then connected David with a similar CFO who had successfully managed a comparable rollout. That conversation addressed David's real concerns and kept Mary's soluti...
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    Less than 1 minute
  • Can AI Really Replace Salespeople? (Ask Jeb)
    Jun 18 2025
    That's the question every sales leader, CEO, and HR department is wrestling with as AI tools flood the market with promises to automate everything from prospecting to closing deals. Meanwhile, salespeople are panicking, wondering if their jobs are about to disappear to some algorithm that can write emails faster than they can type "Dear Valued Customer." If you're losing sleep over this, take a deep breath. The fear is real, but it's also completely misplaced. Here's the brutal truth: AI isn't going to replace you. But salespeople who understand how to leverage AI absolutely will replace those who don't. When Robots Try to Sell It's Not Authentic Remember when email prospecting worked? When a well-crafted subject line could get you a meeting, and personalization meant more than just mail-merging someone's first name? Those days are over, and AI killed them in about nine months. Here's what happened: Marketing departments discovered they could use AI to blast out thousands of "personalized" emails that sounded human but weren't. They could fake voicemails using voice cloning technology. They could create sales sequences that felt authentic but were completely artificial. The result? Complete market saturation with fake outreach that destroyed trust across every communication channel. Humans Have a BS Detector for Fakeness Here's what these AI-obsessed companies don't understand: People have an incredibly sophisticated BS detector. We can sense inauthenticity from a mile away, even when the technology is nearly perfect. When you receive an email that sounds too polished, too perfect, or follows a pattern you've seen before, your brain immediately flags it as fake. When you hear a voicemail that sounds just slightly off—even if you can't pinpoint why—you delete it. But here's the real killer: Once people realize you were too lazy to write your own email or leave your own voicemail, they lose all respect for you. They think, "If this salesperson can't be bothered to put in the effort to reach out to me personally, then why would I want to do business with them?" The One Thing AI Can Never Do This is where the magic happens, and it's where your competitive edge lies. AI can write emails. It can analyze data. It can even fake phone calls (poorly). But it cannot engage in real-time, empathetic, synchronous conversation with another human being. It can't read micro-expressions during a video call. It can't pick up on the subtle hesitation in someone's voice that signals an unspoken objection. It can't pivot in real-time when the conversation takes an unexpected turn. Most importantly, it can't build the kind of authentic human connection that makes people want to buy from you instead of your competitor. The AI + Human Intelligence Formula Smart salespeople aren't running from AI—they're running toward it—but they're using it as a tool to make themselves better, faster, and stronger, not as a replacement for actual selling skills. Here's where AI excels in sales: Research and Preparation: AI can analyze a prospect's 10-K filing, research their competitors, and create discovery questions in minutes instead of hours. It can build detailed company profiles and identify potential pain points before you ever pick up the phone. Data Organization and Analysis: That timeline your manager needs for a customer service issue? AI can pull data from your CRM, email, and support tickets to create a comprehensive summary in seconds instead of the hours it would take you to compile it manually. Writing Enhancement: Most salespeople aren't great writers. Don't shoot the messenger. AI can help you craft better emails, proposals, and follow-up messages, but only if you edit them, personalize them, and make them authentically yours. The Holy Grail: Intelligent Prospecting Lists: The biggest opportunity is using AI to build high-quality prospecting lists. Imagine walking into the office and having AI presen...
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    17 mins
  • Busting the Myth About Natural Sales Talent (Money Monday)
    Jun 16 2025
    Is there such a thing as natural sales talent? Are top level sales professionals born that way? Do they possess a gift from God that powers their ability to close sales? On this Money Monday I answer these age old questions. For the Love of the Game When I was 9 years old, after going to the Masters tournament with my Dad, I cut a limb from a tree that was shaped like a golf club, dug holes all over our back yard, and started playing “backyard golf” with a wiffle ball. I loved my little back yard golf course and played every day after school. One day though, my Dad who had been watching me said, "Why don't we just go play real golf?" My dad didn't know anything about golf. He didn’t grow up playing. But we went down to Walmart, bought some cheap golf clubs, and started chasing little white balls. We played at a legendary course in Augusta called The Patch - a municipal course with hard dirt fairways and patchy greens but a super fun place to learn the game. We were terrible. We never practiced or tool a lesson. But I loved going out with my dad to the course and we had fun! In high school I started playing on the golf team. That might have been a turning point for my game if we’d had a real coach but instead we had a math teacher who did not play golf assigned to baby sit us. So, we were on our own but we had fun. Those years, playing on my high school golf team were a blast! In college I continued to play golf for recreation - usually with my fraternity brothers. Golf was about going out, telling jokes, and drinking a lot of beer. I have so many fun memories from those days. The Myth of Natural Talent Stole My Joy After getting out of college I continued to play - mostly in business situations - and that’s when Golf stopped being fun. I would golf with clients and peers who were so much better than me. It didn't make sense that they could hit the ball so well and I could not. I would go out to the range and practice until my arms hurt but I never got any better. It never occurred to me to take a lesson. By my mid-thirties I was so frustrated with golf that I started to believe something that would haunt me for the next twenty years: I convinced myself that people who could play golf well were just naturally gifted. And because I wasn't naturally gifted, I would never be good at golf. So I quit. For two decades, I didn't pick up a golf club. A Massive Mindset Shift Leads to a Comeback If you have read my books and listened to my podcasts you know that I'm a big horse person. I've been involved in equestrian sports since I was a kid. I've had formal coaching and training with horses. On horseback, I thought I was naturally gifted. I believed it was something that God had imbued in me. So I forgot about golf and poured my time and energy into horses. Eventually, though, my son got older and started playing golf. And being an equestrian at my age became more and more dangerous. A bad day on a horse means you're in the hospital in traction. A bad day on the golf course means you go to soothe your wounds with a cold beer in the clubhouse. So I picked up the sticks again. But this time, I sought out a golf coach. A pro who could help me learn how to play the game. Starting over has been hard. It is difficult to learn new skills. But with lessons, I've gotten better. In fact, last week I shot my lowest score ever. Over the past two years of working on my golf game I’ve come to realize how much the story that I kept telling myself about not being naturally talented hurt me and how much it stole from my life. That story cost me twenty years of enjoyment of a game I loved. The difference between my success with horses and my failure with golf wasn't natural talent. It was coaching, instruction, and having someone teach me the right way to do things. The Power of an Open vs Closed Mindset Once you stop believing that you have to be naturally gifted in order to do anything we...
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    12 mins
  • The Alter Ego Advantage of Top Performers
    Jun 13 2025
    "I can't do that." How many times have you said those four words when facing a challenging sales situation? It could be picking up the phone to make that intimidating cold call. It could be asking for the close with a high-value prospect. If you say 'I can't do that,' guess what? You're absolutely right. You won't. But here's what’s surprising: The solution is simpler than you think. The Wisdom That Sounds Ridiculous (Until It Changes Everything) Thirty years ago, sales coach Steve Chandler heard a client say those familiar words: "I don't think I could ever do that." His response was four words that initially sounded absurd. "Then don't be you." When Richard Fenton, co-author of "Go for No!," first heard this concept, he had two immediate reactions: "That's the dumbest thing I've ever heard," followed quickly by "That's the most profound thing I've ever heard." Think about it. When someone says they can't speak in front of a thousand people, what's the typical advice? "Just be natural. Just be yourself." But if they’re someone who freezes up in front of crowds, why would they want to be that person in that moment? Although you can’t magically become a new person, you do have the power to choose which aspect of yourself shows up in any given situation. The Alter Ego Advantage of Top Performers Elite athletes and performers often adopt different personas to enhance their performance. When the game was on the line, Kobe Bryant would mentally shift into his Black Mamba persona, accessing a level of confidence and killer instinct that separated him from other players. "The Black Mamba is something I created to get through the lowest points," Bryant explained. "It's a mindset, a way of approaching challenges." Beyoncé morphs into "Sasha Fierce" on stage—a fearless, magnetic performer—but off stage, Beyoncé describes herself as naturally shy and introverted. Strategic identity shifting is the ability to step into a role that's equipped for the task at hand. Your 3-Step Transformation Process Ready to make it happen? Here's your simple framework: Identify Your Limitation What specific sales activity makes you feel uncomfortable or incapable? Be precise. Instead of "I'm bad at sales," identify exactly when you struggle: "I freeze up when asking for referrals from satisfied customers." Design Your Persona Who would you need to be to excel in that situation? Create a specific identity, such as The Referral Request Professional, who understands that satisfied customers want to help others access the same value they received. Make the Switch Before entering a sales situation that makes you nervous, consciously transition into your character. Use mental preparation (visualizing success), physical cues (changing your posture, adjusting your voice), or even simple props (a specific piece of clothing or accessory). Creating Sales Identities That Perform The beauty of the "don't be you" approach is that you're not manufacturing a fake personality. You're accessing different facets of who you already are or who you can become. Here are some examples of identities to cultivate in sales: The Cold Calling Champion When you need to make prospecting calls, don't be the version of you who worries about interrupting people or who fears rejection. Instead, become the professional who understands that you're offering solutions to real problems. Lead with confident conviction—like you’re doing them a favor by calling. Channel the mindset of a sales rep who is genuinely excited about helping prospects discover opportunities they didn't know existed. Before each calling session, take just two minutes. Visualize this persona. How do they talk? What's their vibe? How do they sit? Then step into that identity. The Confident Closer When it's time to close the deal, don't get stuck in the part of you that feels pushy or uncomfortable with money conversations.
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    52 mins
  • Stop Chasing Pipeline Multipliers: The Science of Building Clean a Sales Pipeline
    Jun 10 2025
    Here's a question that exposes one of the most dangerous myths in modern sales: How do you set the right pipeline creation target to consistently hit quota? That's exactly what Maryellen Soriano from New Jersey asked when she called into Ask Jeb. After crushing 134% of quota in her first year selling EdTech solutions—transitioning from owning her own childcare center to selling back into that same industry—she was being told she needed 11X pipeline to maintain her success. If that number made you cringe, you're not alone. The obsession with pipeline multipliers is creating more problems than it's solving, and it's time we had an honest conversation about what actually drives predictable revenue. The Pipeline Myth That's Killing Your Forecast Most sales teams are drowning in fake pipeline, and it's destroying their ability to forecast accurately. Leadership teams, especially in tech companies, consistently miss their numbers quarter after quarter because they're obsessed with one question: "How much pipeline do we have?" The real question should be: "How clean is our pipeline?" Would you rather have 11X pipeline filled with lottery tickets, or 2X pipeline packed with qualified buyers? The answer should be obvious, but somehow we keep chasing vanity metrics instead of focusing on what converts. Here's the brutal truth: All pipeline opportunities are not equal. Two Approaches to Pipeline Creation There are two ways to approach pipeline creation, and only one of them actually works consistently. Approach #1: Maximum Daily Prospecting (The Proven Method) Don't worry about how big your pipeline is. Worry about how much prospecting you're doing, and run on a daily cadence of prospecting that maxes out the time you can spend every single day. Prospect every day, every day, every day. I have a block of time every morning for prospecting. Then I'm prospecting during any gap during the day. If there's time between meetings, I'm doing outreach. Every single day I'm prospecting to the very max that I have time to prospect. When you do this, you don't have to worry about pipeline size because it takes care of itself. You never get on the desperation roller coaster because you never stop feeding the machine. Approach #2: Pipeline Multiplier Obsession (The Broken Method) This is where leadership teams fixate on having "5X pipeline" or "11X pipeline" because they think more is better. The problem? As soon as reps think they have "enough" pipeline, they quit prospecting. Then reality hits when half those opportunities were pipe dreams. The Science of Pipeline: The Law of Replacement If you want to look at pipeline like science rather than hope, you need to understand the Law of Replacement: You need to replace opportunities in your pipeline at a rate that is equal to or greater than your closing ratio. Let me give you a real example of how this works. In a previous role, I had my numbers dialed in perfectly: I knew I needed 10 first-time appointments every week About 50% would move to follow-up appointments (5 deals) I'd close about 20% of those follow-ups (1 deal per week) It took me about 20 prospecting touches to generate 2 first-time appointments Working backwards from one closed deal per week, I knew exactly what I needed to produce in terms of prospecting activity and first-time appointments to feed my pipeline consistently. If I didn't replace the deals that fell out every single week, I'd eventually end up with nothing. What Makes a Real Pipeline Opportunity Here's where most organizations get it completely wrong. They're stuffing their CRM with anything that moves and calling it "pipeline." A real pipeline opportunity requires a conversation. It's not a form fill or a marketing lead or something someone else talked to and dumped in your CRM. You need to have qualified it yourself and made a decision that it belongs in your pipeline. At Sales Gravy,
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    22 mins
  • Top Sales Pros Know When to Exit Bad Deals (Money Monday)
    Jun 9 2025
    Have you ever been working on a deal where you had this feeling, this intuition, this Spidey sense—something in the back of your mind telling you that this wasn't going to close? That you were going to waste your time? Maybe you had one of the stakeholders who was against you—an enemy. There was a naysayer who kept calling you out. Perhaps the stakeholders weren't engaged, or the incumbent vendor was so integrated into the organization that it would be very difficult to displace them. Whatever the case, you knew in the back of your mind that you weren't going to close the deal. But you kept working on it anyway. You rode that puppy to the ocean floor like the Titanic that it was. If you’ve done this, and I know you have, take heart because we've all been there. We've all had these situations, and we've later regretted them. Top Sales Pros are Quick to Walk Away From Bad Deals One of the traits of Ultra-High Performers that has always been true is that they're very quick to walk away from a deal they can't close—a deal where they've concluded that the probability of winning is so low it doesn't meet their threshold. The reason Ultra-High Performers walk away from deals like this is simple: They know that the greatest waste of their time is investing it with the wrong prospect. The time they invest in a prospect that's not going to close is money down the drain, because it's time they can't focus on a deal that will close. But average salespeople? They hang on—hoping against hope that somehow, miraculously, things will turn around. In sales, awareness matters. You must always know where the exit is. There are two primary reasons why salespeople work on deals that are never going to close. Understanding these reasons is the first step to avoiding the trap. Reason #1: The Failure to Qualify Properly Too often, qualifying is treated like a one-and-done activity. We qualify the opportunity against our ICP. We qualify the numbers, budget, timing, urgency, and whether we're talking to a decision-maker with buying authority. These are all quantifiable metrics that we can measure and check off our list. But Ultra-High Performers take qualifying to the next level. Rather than making it a quick process, they understand that qualifying is never done. It's an ongoing process of awareness that keeps you tethered to reality in every deal. And their top qualifier, once they've checked off the must-haves, is engagement. Are the stakeholders engaged? Are they leaning in? Are they matching your effort, answering questions, and working collaboratively with you? It's okay that there are some stakeholders who may be naysayers. That's normal in complex deals. But if you've got stakeholders who are enemies—people who are actively working against you—then your deal might be a bridge too far. Engagement is my No. 1 qualifier. I'm constantly asking questions and giving stakeholders things to do to see whether or not they're engaged. If they're not engaged, I walk away because lack of engagement is a clear signal that you are not going to close the deal. Reason #2: An Empty Pipeline This brings us to the second reason salespeople stay in bad deals—desperation born from an empty pipeline. On Friday, Dennis J. Walker, who is a benefits consultant with USI, posted something on LinkedIn that perfectly captures this dynamic. Here's exactly what he wrote: Jeb Blount regularly states that you can't be delusional about your pipe, your prospects, your efforts, etc and be successful as a salesperson. This week one of the larger deals in my pipe definitely didn't progress the way I wanted- and it turns out one of the executives is what I call a "deal enemy" - he was actively working against me and my team. The last two meetings I've had with him tipped me off this could be the case; this week we had an incident that indicated he was actively working against us. Because my pipe is full?
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    9 mins
  • 5 Ways to Sell More by Uniting Sales and Marketing
    Jun 5 2025
    Your sales team just closed a $50K deal. Marketing takes credit because the prospect downloaded three whitepapers. Sales takes credit because they nurtured the relationship for six months. Meanwhile, you're wondering why this kind of success feels so random—and why similar prospects are slipping away. Companies with misaligned sales and marketing teams waste more leads and see annual revenue decline. But businesses that achieve true alignment? They close more deals and grow revenue faster year-over-year. The difference isn't talent, budget, or market conditions. It's whether your marketing and sales teams are pulling in the same direction or accidentally sabotaging each other. Clashing Departments Can Crash Your Bottom Line The consequences of misalignment between sales and marketing are significant. One common side effect is sales teams complaining about the quality of leads generated by marketing, often dismissing them as "bad leads." Another issue is messaging. Marketing can be blind to the value propositions that are working for sales if they do not understand the sellers’ pitches and approach to closing deals. Their messaging is stale and ineffectual, completely disconnected from where sellers are finding success. When marketing and sales have different metrics or goals, it leads to a breakdown in communication and a lack of shared understanding. That misalignment hampers productivity, damaging morale and impacting your bottom line. Start With the Customer Journey The most important aspect that sales and marketing need to align on is the customer journey. This involves mapping out every touchpoint—from initial awareness to final purchase to customer retention. Map the customer journey together—then act on it. This shared blueprint reveals exactly when prospects are ready for direct outreach versus when they need more nurturing. The payoff is immediate: Marketing delivers leads at peak readiness, while sales focuses their time on prospects most likely to convert. When both teams operate from the same customer journey map, handoffs become seamless and conversion rates climb. Tackle Sales Objections Together Every sales professional understands that the path to a closed deal is rarely a straight line. It's often a zig-zag through questions, doubts, and hesitations from prospects. Marketing’s role is to help develop messaging and collateral assets that help the sales team deal with these objections. This includes essential resources like case studies, white papers, product demonstrations, and ROI calculators. With the support of marketing materials, sellers have the resources to back up their pitch, highlight benefits, and keep buyers engaged. Most teams fail to communicate. Marketing creates polished but generic materials that sales doesn’t know exist. Sales knows which objections are the hardest to overcome but doesn’t have specific collateral to counter them. The winning approach: Sales documents the top 5 objections that derail deals, complete with context about when and why they surface. Marketing then builds laser-focused tools to address these concerns. Think comparison sheets for "your competitor is cheaper," implementation timelines for "this seems too complex," or peer testimonials for "we're not sure this works in our industry." Close the loop: Sales reports back on which materials move deals forward and which fall flat. Marketing iterates based on real-world results. This feedback cycle shifts objection-handling from guesswork into a refined system that consistently converts hesitation into confidence. Get Sales and Marketing Aligned Now How can businesses foster a stronger cohesion between sales and marketing? Here are six key strategies: Establish Shared Goals and Metrics Sales and marketing should work together to define common objectives and key performance indicators (KPIs). Action item: Schedule a joint planning session within the next 2 weeks to agree on 3-5 ...
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    27 mins
  • Why Talk Time is the Worst KPI for Measuring Sales Performance (Ask Jeb)
    Jun 4 2025
    Here's a question that'll make your head spin: What do you do when your top performer is crushing quota but not hitting a required talk time KPI? That's the question posed by Josh Robich and Josh Nelson from Nashville. Josh Nelson ranked 18th out of 130 reps in his first full year at a new company, but he was consistently falling short of the company's sacred talk time metric of 3 hours per day, averaging only 2.5 hours instead. Meanwhile, his company is obsessed with using talk time as its primary KPI to measure sales effectiveness. If you're shaking your head right now, you're not alone. Obsessing over the talk time KPI rather than actual sales outcomes is one of the most backward approaches to sales management I see today, and it's costing companies their best talent. The Moneyball Problem: When Metrics Become Religion Remember the movie Moneyball? Billy Beane revolutionized baseball by focusing on on-base percentage instead of traditional stats that looked impressive but didn't correlate with winning games. He found a metric that predicted success. Talk time is the opposite of Moneyball. It's a vanity metric that makes leaders feel like they're managing performance when all they are really doing is measuring noise. Here's the brutal truth: Talk time means absolutely nothing if it doesn't drive revenue. It means nothing if the conversations are shallow, non-productive, or a poor buying experience. You can have reps talking for 4 hours a day who are dead last on your ranking report, while someone like Josh is closing deals left and right with only 2.5 hours of phone time. Which one would you rather have on your team? Why Talk Time Is a Lazy Leader's Crutch The reason companies fixate on vanity metrics like talk time is because it's easy. It requires zero investment in actual coaching, observation, or skill development. Think about it: It's much easier to look at a dashboard and say, "You need to talk more," than it is to actually listen to calls, analyze technique, and provide meaningful feedback on discovery questions, objection handling, or closing skills. But here's what happens when you manage this way: You drive away your best performers and enable your worst ones. Your top performers get frustrated because they're being penalized for efficiency. Your bottom performers get comfortable because they can hit their talk time numbers while producing nothing of value. What Actually Matters: KPIs That Move the Needle Instead of obsessing over how long reps are talking, and other vanity KPIs, smart sales leaders focus on outcome-driven metrics that actually correlate with sales performance and closing deals. First-Time Appointments How many new conversations is each rep having? In sales, FTAs are your Moneyball. If a rep isn’t setting enough first-time appointments, they are sub-optimizing their sales potential. Next Step Conversion Rates What percentage of first-time appointments convert to second appointments? This tells you everything about relationship building, discovery skills, and value articulation. If Josh is converting at a higher rate with less talk time, he's simply more effective per conversation. Show Rates How many scheduled appointments actually happen? This reveals qualification skills, the ability to create urgency and commitment, and the quality of prospecting conversations. Pipeline Velocity How quickly are deals moving through your sales process? This shows you who's truly building momentum versus who's just having long conversations that stall deals in the pipeline. Revenue Per Hour The ultimate sales efficiency KPI is who is generating the most revenue per hour of phone time. Stop Obsessing Over the KPI and Start Coaching When you shift your focus to outcome metrics, everything changes. Instead of telling reps to "talk more," you can provide specific, actionable coaching: For the rep who has great first-time appointment numbers but poor conversion rates:...
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    15 mins