Kevin Gaither's Linkedin Analytics

14 pieces of non-obvious advice after two decades of sales leadership: -Your salespeople are not your friends -Sales Kick-Offs are a waste of time and money -SPIFs and Sales Contest aren't effective -Conditions of termination should be crystal clear in writing -PIPs should last 9 months and not 30-90 days -A sales leader's mission should be to see their reps quit and go someplace better -My best ideas come from people other than me, especially the salespeople doing their job -Do not give any rejected sales candidates any feedback post-interview -Commission Plans are not "motivating" -Curiosity can't be taught, hire curious people -Motivation isn't something done TO salespeople -Hiring people from "within the industry that have the Rolodex or relationships" is usually a huge, expensive mistake -Elite sellers are not "money-motivated" -Hiring "sales athletes" is a flawed strategy Anything I've missed or you'd add?

Hot take: you're wasting your time if you spend your time equally with all of your salespeople. I've been in sales leadership for >25 years & learned that leaders shouldn't spend their time equally with all of their salespeople. There's only 4 types of salespeople and you should spend your time with only 2 of these types: 1. The Eagles. they march to the beat of their own drum, never follow the playbooks, hate the training and for some reason, they still hit or exceed their goals. Leave them alone. Most of the time they want to be left alone. NEVER let new people sit with them for "call shadowing." They are not examples you want other people to follow. 2. The Unsalvageables: they don't follow the playbook, never take direction, rarely hit goals. Spend ZERO time on these people over the long haul. 3. The Try-Hards: they're following the playbook but just not having the success just yet. Work with these people for a defined period of time, like 90-180 days. Some of these people will make it through, come around and start hitting goals but many will not. But give these people attention because they're trying. 4. The Boy/Girl Scouts: they follow the playbook and training, they're highly coachable and they hit goals regularly. Spend the vast majority of your time with these people. It's where you'll get the best ROI of your time. What do you think?

One of the kindest, most empathetic things a sales leader can do for a sales rep who is not cutting it? Inexperienced leaders should learn this technique earlier rather than later. "Redeployment" Despite the extra training and coaching you'll give an under-performing rep, you just can't keep investing in them forever. ❌ That's just not smart. 🪓 But you don't have to be a jerk either and kick them to the curb right away either. Great, empathetic sales leaders seek to find homes within the company for a sales rep who isn't cutting if the seat they occupy on the bus isn't working out for them. 🚍 Find them another seat on your bus where they can be much more successful! I've done this several times in my career with failing and successful sales reps and it's good for everybody involved. Wouldn't you agree? Have you ever done this before? How did it go? How did it FEEL?

ZipRecruiter went from 0 salespeople in 2013 to over 100 2 years later. We had a HUGE competitive advantage NOBODY would guess, but looking back, it was a KEY reason why we grew so fast. Our secret to hiring great salespeople was less about finding the salespeople who "were experienced" and more about finding the diamonds in the rough. 💎 ✅ Sales reps with raw potential, drive, and a relentless desire to learn and succeed. We learned to dig deeper, beyond resumes, credentials and so called "experience" to find great salespeople. We focused on hiring for traits like Drive, Need for Achievement, Optimism and Competitiveness. That strategy paid off in a huge way. Our “secret” was a competitive advantage that allowed us to scale quickly and gain massive marketshare from the leader. So here’s my lesson for CEOs, Founders, and Sales Leaders: Don’t just hire for experience. Hire for potential. Your next top performer might be the one with the most to prove, not the most experience. The results will speak for themselves.

After building sales teams at 8 startups over 25 years, we finally figured out, "do Vertical Territories improve sales performance?" The question of whether salespeople should be in vertical or geographical territories has been a hotly contested debate for decades. But I've never read about anybody who tested it and actually measured the results. Just opinions. As usual. Opinions. Some background: ➡️ the product had an ARR of about $5k ➡️ sales cycle of less than 45 days ➡️ typical customer was SMB. ➡️ We distributed accounts using a highly refined scoring system and it was working well. But one of my smartest sales leaders had a hypothesis that if we further segment the leads/accounts by industry and create Vertical Sales Territories we'd see a lift in Conversions Rates and Quota Attainment. And so we ran a test for 2 months where 10 of our reps are JUST calling on accounts from select Vertical Industries (the Test Group). 💡 Learning Lesson: In our environment, Vertical Sales Territories produced NO lift in conversion rates or quota attainment. It didn't hurt it either BTW but there was no meaningful lift in the test vs. the control. Has anybody else tried Vertical Sales Territories and truly measured the results in a Control vs. Test scenario to truly measure the results?

I've made this mistake and so have you. This is the #1 mistake new sales managers make: Tolerating Underperformers 📉 I once had a rep on a PIP who worked just hard enough to get off the PIP but then asked me for a promotion. I couldn’t believe it. 🙄 Improving doesn’t mean they’re now a top performer. Effort matters. Improvement matters. But output matters more. Too often, new sales leaders unintentionally lower their standards instead of making hard calls. Some reps will improve, but not enough to meet your minimum standards. 😡 And they end up taking more of your time while delivering less than others. You don’t have to lower expectations, and you don’t have to give up on them either. Here are two tactics I’ve used to keep standards high: 1️⃣ Have them self-assess Ask them to rate their performance in key areas. Then compare their ratings with yours. If they can’t, don't or won't see the gaps, no coaching will work until they do. 2️⃣ Prioritize your team over individuals Your time is limited—spending it equally isn’t wise. Ask yourself: - Would a rockstar rep struggle in the same role? - Knowing what you know now, would you rehire them? If the answers are no, and you've put in the effort to coach the rep, you need to replace the rep. If you don't make the move, someone else will make the move for you and likely replace YOU because you're lowering standards on your team not raising them.

I used to think that the sales team *reported to* the VP of Sales or sometimes the COO but I was wrong. Who controls the pricing of the product that you sell? The Product team. Who determines who the product should be sold to? The Product team. Who helps determine what channel will sell the product? Sometimes the Product team. Who determines what features get built? The Product team. I don't care who you think you or your sales team reports to now. Technically, if you're a sales leader, you report to Product. 👉🏻 Not literally, of course, but as sales leaders, we work to serve the Product team to sell the product that they create for us to sell. 💡 Learning Lesson: Work closely with your Product team to understand why they built the product, for whom they built the product, why it's priced the way it is and provide a continuous and productive feedback loop from the customers and prospects to Product. Do you see why I say that Sales "works for" the Product team? Agree or disagree?

Good morning to everyone except the folks who are still writing LinkedIn posts and comments with the phrases: • "it's all about" • "sales landscape" • "realm" • "in today’s competitive" • "In the fast-paced world of” thinking that we don't know that you used AI to write your Linkedin post/comment. Try harder.

I had this "middle of the pack" rep who landed himself on a 90 day PIP and worked just hard enough to get off PIP but then when he got off PIP, he asked me for a PROMOTION! WTF? And it was at that moment that I learned: 🤡 the Dunning-Kruger effect. The Dunning-Kruger effect, in psychology, is a cognitive bias whereby people with limited competence in a given social domain greatly overestimate their own knowledge or competence in that domain relative to the performance of their peers or of people in general. His argument was two-fold: 1️⃣ he had hit goal a few times before going on PIP 2️⃣ and then the ACCOMPLISHMENT of getting off PIP (and not getting fired) should earn him a promotion. SMH 🤦 But this was all my fault as the sales leader. 💡 Learning lesson: Make sure you've documented exactly and objectively what it takes to get promoted on the sales floor. If you don't, your reps will come up with their own reasons for promotion and surprise you with their reasons. 😂

My sales rep thought he had a "good relationship" with a client. But then he had a rude awakening when the client wrote: "Dance, monkey, dance." 🐵 He knew their favorite baseball team. Where they grew up. Knew the names of their kids. They laughed and laughed and laughed at each other's jokes...🎉 But then he accidentally intercepted an email from his potential client where the client was telling his peers "watch how I can get this rep to lower his price for me" and included a little "Dance Monkey, Dance" gif in the email. 😳 My rep was humiliated. This is why I get passionate when I hear people say: 💩 "KG, KG, you don't understand, sales is ALL ABOUT the relationships!" 💩 "People buy from people they like!" This kind of 8u||$h|+ results in salespeople who think that in order to win business, they should be nice and make friends with their potential clients. This couldn't be further from the truth. 💡 Learning Lesson: Teach your reps that it's better to be respected than it is to be liked. Teach your reps to look for ways to bring insights to their client and teach the client something they didn't know already. Doing that will develop trust and respect and THAT will be the basis for the relationship. Anybody else been in a situation like this? You thought you had a "great relationship" with a client and then you had a rude-awakening? Drop it in the comments

Taking over a sales team is like walking into a room full of anxious people expecting you to have all the answers. But the best leaders know that the first week isn't the time to start bragging about your successes and making immediate changes— It's time to build trust. And I've screwed this one up 6-ways to Sunday before. When I first stepped into a new leadership role, I learned quickly that leading from behind is the key to long-term success. Here’s my Week 1 playbook: 1/ Get an Intro: Let the person who hired you set the stage and sing your praises. It’s more impactful than self-promotion. 2/ Lead with Faults: Share your mistakes. Vulnerability builds trust faster than any success story. 3/ Look Everyone in the Eye: Build personal connections. Spend time getting to know your team one-on-one. 4/ Learn Everyone’s Name: It sounds simple, but it’s powerful. Knowing names shows respect and makes people feel valued. 5/ Ask 4 Key Questions: In 45-min, 1-on 1 Zoom calls, seek to understand what’s working, what’s broken, what’s hidden, and what it takes to get fired. This reveals the true state of the team. 6/ Over-communicate: At the end of the week, share your excitement, surprises, and next steps. It eases anxiety and sets the tone for the future. In Week 1, the smartest thing a new sales leader can do is listen more than they speak. The respect and trust you build now will be the foundation of your future success

I made such a rookie mistake. If you can believe it, I couldn't fire a rep, who missed goal 6 months in a row! 😕 Here's why: The rep had missed their goal 6 months in a row!! Time to let them go right? So I went to HR to get the paperwork finalized to fire them and she said: 👉 "Does he KNOW that he's not meeting your expectations?" My word....how could he not? They've missed goal 6 months in a row!!! 💡 My mistake: I never TOLD the team that missing goal consistently was grounds for termination. I didn't have ONE conversation with the rep warning them what would happen. The learning lesson here is ✅ make sure your reps KNOW in writing what it takes to get fired from their job and ✅ if they fall short of those expectations have frequent, documented conversations with them when they fail to meet your expectations.

I’m 54. I've had 3 successful exits in my sales leadership career & never have to take a W2 job again if I don't want one but... ...I still don’t know what the hell I’m doing most of the time. 🤪 Just a reminder that the people you may look up to, so-called "influencers," are still figuring it out. Life is the trip, there is no destination.

My 1st year in sales (1995), I made ~$100k ($200k today's $$) & my boss asked me what I was going to do with all that money? I told him that I was going to splurge and get a new BMW. What he did next is what every sales manager who cares about their people should do. ✅ He told me, "it's not what you make, it's what you keep." And handed me the book, The Millionaire Next Door. You see, real millionaires aren't the typical flashy types we see in the media. 📉 Real millionaires, the truly wealthy, keep their expenses low. Most sales managers want their reps to buy big houses and fancy cars and rack up lots of debt. That gives the manager a sense of perceived control. That sucks. 👉 My first sales manager cared enough about me to give me a life lesson that changed my life forever. It was cool of him to do that right? Imagine a world where all sales leaders cared about their sales reps like this right?

I received a job offer including a savage non-compete agreement. So I had a lawyer review it and she said: 🦈 "This non-compete has more teeth in it than Jaws. If you really NEED a job, go ahead and sign it. If you don't need a job, don't sign it." (wait there's more) 👇 But when I told the CEO why I was declining his offer, he said: "This is standard language. You know it's not enforceable." 🤔 When I asked him to remove it, he refused. So I declined and referred another friend who DID NEED a job and he got the job, signing the non-compete. 🚫 And years later, when he left the company, they sued him. He spent $60,000 to defend himself and then the company dropped the suit knowing the non-compete was not enforceable. 💩 They sued him just to mess with him AND to send a clear message to their current employees. This was 2008 and the FTC just banned non-competes in April 2024. How many other employees have been screwed by these vicious, legal instruments since then? Have you been screwed over or limited by a non-compete?

How can you spot terrible sales leadership in an instant? Look for these 6 glaring red flags. Years ago, I hired a sales manager who seemed like the perfect fit...competent, engaging, and a natural leader. But once on the job, his true colors quickly emerged. Within a week, I witnessed him berate a rep in the most unprofessional manner. The person we hired was nothing like the one on the sales floor. I was mortified. Not just by his behavior, but by my mistake in hiring him. Here are 6 red flags I’ve seen over the years that signal bad sales leadership: 🚩 Inconsistent direction - saying one thing Monday, changing it by Wednesday. 🚩 Micromanaging - suffocating the team with zero trust or delegation. 🚩 Triangulation - pitting team members against each other instead of addressing issues head-on. 🚩 Zero self-awareness - completely oblivious to how their behavior affects the team. 🚩 Never admitting they’re wrong - constantly deflecting blame. 🚩 Playing the blame game - never taking personal accountability. If you see these red flags, act fast. Your team’s success depends on it. What are some of the other red flags you've seen that we should watch out for in a poor sales leader?

"Just hire former salespeople that used to work for you." Sounds easy, but great sales leaders have a problem with this. 😕 Every time I've been tasked with building a sales team, the CEO always says that and then I have to explain why it's not so simple. 😥 You likely can't afford the salespeople that used to work for you any longer if you did a great job training and coaching them in the past. ✅ And honestly, if you aspire to be a great sales leader, that should be your goal. Train, teach and coach your reps so well that you can't afford them any longer. While you may not be able to hire them at future jobs, they'll think so highly of you that they'll send you plenty of referrals to hire. (Of course there's exceptions to this and I'd love to hear where you've seen that exception in the comments of course)

I inherited a salesperson who couldn’t sell his way out of a paper bag. And here's how I dealt with this train wreck. 🛠️ Just like all the others I inherited, I listened to his calls, provided curbside coaching, provided personalized training. Still no improvement. But I noticed something about this rep. They were incredibly analytical and were very, very good working with our CRM and other technology. So instead of firing this rep, I redeployed this rep into a much needed sales operations analyst role. And since then, this rep has gone on to move into Product Manager roles and be part of TWO companies that went public or were acquired and he started his own business and sold it! 💡 The learning lesson: before you discard a salesperson, look for the NON-sales skills they have that can add value to your company. ❤️ Then redeploy them. It will be great for them and great for you. Anybody else have great stories about redeploying salespeople into NON-sales roles?

I was in a $600k CRO role but I was 70 lbs overweight I was having chest pains I woke up nightly at 3am sweating I held my head in my hands "what am I going to do now?" but then I quit with no future job. Here's how I justified the decision (which was the right decision BTW): Normally, quitting your job without your next job is a bad idea but there's two dead-simple learning lessons here: 1️⃣ life is too damn short to deal with this kind of pain Yeah, the job market is tough, especially for high-paying jobs, but you know what's worse? A heart-attack, stroke or mental breakdown at an early age. 2️⃣ 6 months living expenses in the bank gives you freedom It was easy for me to look at my bank account and know I could live for 6 month with no job and make a decision to quit. Money isn't everything, but it helps. 👉 If you're in *one of those kinds of jobs,* it's time to quit and find something else. And if you don't have 6 months expenses in the bank, then it's time to develop a plan to build up that bank account to give you future freedoms.

When I became a first-time VP of Sales, I made a lot of mistakes. Here are the 7 biggest ones that cost me dearly: 1/ I didn’t manage up. Founders don’t have all the answers, and it’s okay to challenge them respectfully. It makes them better and your life much better too. 2/ I obsessed over results and ignored the process and inputs. But results without knowing how you got there and how to repeat them are useless. 3/ I didn’t lean on mentors. Your ego doesn’t matter—getting it right does. I figured they were paying me so much, I better not ask for mentors/advisors. Wrong. 4/ I didn’t create a structured interview process. Trusting my gut created a lot of mis-hires, that resulted in firing reps. That's not fun for anybody. 5/ I thought I could do it all—like configuring CRMs and building a sales process. I should’ve enlisted the help of a RevOps team instead. 6/ I used off-the-shelf sales processes, which rarely fit my team’s needs. It's great to continually improve your team but customize what you hear/read before implementing. 7/ I kept my mouth shut when I saw problems in non-sales teams. Wrong move. A VP’s job is to look out for the whole company. See something, say something. If you’re making any of these mistakes, stop now. It’ll save you a lot of time, money, and stress. And trust me—it’ll make you a better leader. 😊