Kevin Gaither's Linkedin Analytics

Sales reps think their manager's job is so easy, "Sittin' in their office refreshing dashboards all day," but they're wrong. Here's 7 things sales reps are clueless about when it comes to the realities of being a sales leader: 1️⃣ You're the shock absorber between your team and the exec team. You take the hits so they don’t have to. 2️⃣ You don’t just own the number...you own every excuse why the number doesn’t get hit. 3️⃣ You can’t play favorites. Even when your favorite is the one crushing quota. 4️⃣ You’re held accountable for things you don’t fully control. That's not fair but that's the job. 5️⃣ You give more feedback in a week than most people give in a year. Or at least you should be. 6️⃣ You’re expected to inspire others while dealing with your own burnout. 7️⃣ You have to fire people you really like personally. If you’ve never led a team before, don’t judge the job from the cheap seats. Sales leadership looks easier from far away. What did I miss? What's one other thing your reps don't understand about your role as sales leader? 👇

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. 😊

I once had to fire a sales leader who was hitting their number. Not because of performance but because they were toxic as he||. 🔴 They took credit for wins they didn’t earn. 🔴 Micromanaged top reps into quitting. 🔴 Avoided hard decisions. 🔴 And let bad culture spread like wildfire. Sure, the board liked the revenue. But inside the team? It was a culture-less cesspool. Top talent started quitting. And no one trusted this sales leader. But that was my fault. I hired the sales leader and I I ignored the signs for too long because I needed short-term results. But here’s what I’ve learned: 💡 The right to lead a sales team is not given. It's earned. And if a sales leader: – Steals credit from the team – Controls every move – Stays out of the trenches – Defends or ignores toxic behavior – Avoids real decisions ...they don’t deserve to be a sales leader...at least not on my watch. I don’t care how much "wood they're chopping." They’re doing more harm than good. ✅ Lesson: Sales leaders aren’t just measured by the number that they hit. They’re measured by what they build and the lives they positively impact.

You don’t truly know your sales leaders until the shit hits the fan. When everything's on fire, their real self show up. When things are going smoothly, almost any sales leader can look great. But in a crisis or in times of massive change? That’s when you can really see right through your sales leaders. I’ve been through a lot with my sales leaders and I've seen it all: - sales leaders freeze, - they point fingers at others, - protect their image, or - just shrivel up and hide. Wimps But then there's the great ones... - they lean in - they get super calm - they've got poker faces at times and - they just get going. Taking action. The difference isn’t experience. It’s emotional control, personal accountability, and clarity under pressure. You can’t fake that stuff. I used to think I could coach people into being that kind of leader during the crisis itself. Wrong. It was always too late. In times of crisis, people fall back into their normal state. That's hard for a boss/mentor to change. Now I look for it before I hire or promote someone. ✅ Lesson for Founders, CEOs, and Sales Leaders: If you’re not screening and vetting your sales leaders for how have behaved during times of crisis or extreme change, you’re gambling with your org’s future.

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.

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.

What I thought sales leadership was: -Giving direction -Delegating tasks -Calling out mistakes -Being the smartest person in the room What I learned sales leadership really is: -Teaching and empowering those around me -Delegating goals (coach them through the "how") -Praise in public, criticize in private -Hiring people smarter than me (not hard, LOL) Bottom line, it turns out, leadership is all about them and not about me. I wish I had learned that earlier in my career

When I read a sales leadership comment that is clearly from somebody who has no idea what they're talking about... It reminds me of the great quote by Mark Twain: "Never argue with stupid people. They will drag you down to their level and beat you with experience.” I just leave that comment sitting out there for all to see. There's no upside for me to get into a debate with somebody who has no clue how to build, fix or grow sales teams and hasn't done it repeatedly and successfully.

I once watched a sales manager blow up over his team's comp plan changes...in front of his sales team. He just had to show his team he had their back. But it didn’t get the plan changed. No. It just made the sales manager look weak and emotional. 🚫 After that, there was no way I was promoting that guy. I’ve learned there’s a better way. A more effective way. 👇 Here’s how I coach sales managers to handle comp plan disagreements like pros in 5 dead-simple steps: 1/ Stay calm. The second you react emotionally and get all worked up, you lose credibility. Nobody is going to listen to you. 2/ Get the facts. No, that's not "a lot of salespeople are unhappy." What’s the purpose of the new plan? What behaviors is it trying to drive? What specific flaws have you found in achieving that goal. WRITE THEM DOWN in a doc. 3/ Own your opinion. Don’t hide behind “my team won’t like it.” Speak for yourself. Be clear. Be direct. Bring the proof and facts you gathered in #2. 4/ Offer a solution. Heck, offer 3 different solutions. "I recommend" are the two most powerful words a future leader can use. But if you have no solutions, you're just a problem bringer. 5/ Do it privately. Not a knock down, drag out fight out in the open or on a team sales meeting. Do it one-on-one. No drama. No team gossip. That’s what real leaders do. What's one thing you'd add to this list? What's one thing you disagree with on this list?

After 25+ years as a sales leader, I've learned that standing out as a sales leader requires only 5 dead-simple moves: 1/ Be clear about what you expect. Ambiguity kills performance. Get specific. Set clear targets, and your team will know exactly where they stand. 2/ Be brutally honest with your feedback. Some call this "radical candor." Sugarcoating does more harm than good. Give it straight, with respect and care. 3/ Be humble when you screw up. And you will screw up. I’ve done it countless times. Own it, learn from it, and move on. This can be tough if your ego is high. 4/ Be bold and decisive. Waiting to make decisions kills momentum and your team loses confidence in you. Make the call, learn, and adjust. 5/ Be human. Treat your team like people, not resources. Listen more, empathize often, and celebrate wins. Don't be afraid to show love. I tried to practice these 5 moves every day until they became unconscious. They’re the backbone of effective sales leadership. What would you add to this list?

During the great recession of 2008, I turned over 100% of my sales team and it was the right thing to do. Prior to the Great Recession of 2008, my sales team was printing money. Sales were flowing in. Things were great! But then the Great Recession hit and buyer behavior and buying patterns changed VERY quickly (just like they are now). I had to move quickly too and I implemented a whole new Sales Methodology, retrained the team (about 30 reps at the time) and changed our hiring benchmarks and started hiring new reps into the new system. Unfortunately, the reps that were there before 2008, couldn't make the switch. Despite my best efforts to coach and train, change is hard. ➡️ ALL 30 of the reps on the team were gone by the end of 2008. I'm not proud of this. These are people whose lives were impacted negatively. ❇️ The result: Conversion Rates and ACVs increased year over year. The NEW team bought into the NEW methodology and made a material impact on the business during those tough times.. 💡 Learning Lesson: Sales leaders need to pivot quickly when the market changes like it's changing today. Unfortunately, despite efforts to retrain and coach, when reps can't pivot quickly as well, those reps must move on and be replaced with reps that buy into the new system. It sucks to have to make those decisions but as sales leaders, we have to make those decisions or the company will suffer or die. 2025 is proving to be as challenging as 2024. Are you prepared to make the tough decisions to make needed changes on your team this year?

Most sales managers don’t deserve the title. They were just the best rep or the last one standing. But great sales managers? They’re built, not just promoted. 👇 Here’s 14 things to look for in a great sales manager: ✅ They've built repeatable systems - not just followed someone else’s playbook. ✅ They ask great questions - not “check-the-box” ones. ✅ They read constantly - most sales managers haven’t cracked a book...ever. ✅ They bias towards action - and ask for forgiveness later. ✅ They give credit to the sales team - they don't look for credit for themselves. ✅ They’ve failed - but they don't hide it and they've learned a boatload from those failures. ✅ They’ve made unpopular but necessary calls - even when it's pi$$ed off their sales team. ✅ They eat their metrics for breakfast - the average ones "are good with people." ✅ They’re humble and confident - both matter. Not one or the other. ✅ They dig for root causes - average ones just fix symptoms. ✅ They always want growth - most are like "if it ain't broke, don't fix it." ✅ They talk about the people they've lifted up - not how great they themselves are. ✅ They want divergent opinions - most just want to be surrounded by Yes Men. ✅ They know that consistent results trump straight experience doing the thing If you hire sales managers that check these boxes, you'll be on your way to building an elite leadership team. What's one thing to look for that I'm missing?

I used to think my job as a sales leader was just to hit the revenue number. Period. So I pushed. I tracked every metric. I obsessed over pipeline creation. I managed inputs and performance like a hawk. 💸 Oh, we hit the revenue targets alright. ❌ But I didn’t build a team that people wanted to follow. I built a machine. I clearly had no idea what "sales leadership" actually was. What changed everything for me? When I realized that leadership is about helping the people you're working with to get better and improve their lives (not just in their job). Since then, my focus has shifted: -Coach people in their business AND personal lives -Promote generously but objectively (no favorites here) -Share everything I’ve learned (don't hoard it. leadership IS teaching after all) -Make the people who work for me better than me. ❤️ 𝙔𝙤𝙪𝙧 𝙨𝙖𝙡𝙚𝙨 𝙡𝙚𝙖𝙙𝙚𝙧𝙨𝙝𝙞𝙥 𝙡𝙚𝙜𝙖𝙘𝙮 𝙞𝙨 𝙗𝙪𝙞𝙡𝙩 𝙤𝙣 𝙘𝙖𝙧𝙚𝙚𝙧𝙨 𝙮𝙤𝙪 𝙝𝙚𝙡𝙥𝙚𝙙 𝙨𝙝𝙖𝙥𝙚 𝙡𝙤𝙣𝙜 𝙖𝙛𝙩𝙚𝙧 𝙩𝙝𝙚𝙮’𝙫𝙚 𝙡𝙚𝙛𝙩 𝙮𝙤𝙪𝙧 𝙩𝙚𝙖𝙢. Of course it's not pre-school working for me. I still care about results. But I care more about what those results create and the lives I can help to improve. 💡 Lesson for CEOs and Sales Leaders: If you want to build something that lasts, start thinking about the people you’re lifting up, not just the number you’re chasing.

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?

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?

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

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?

If I were 27 and wanted to become a VP of Sales by 31, here’s exactly what I’d do: This isn’t theoretical. It’s based on me doing nearly all of these things and watching the people who actually got promoted...and the ones who didn’t. Let’s go 👇 1/ Meet with 1-2 VPs or CROs outside your company every week. Talk with them. Ask real questions. Don’t just send cold connection requests. Most people love helping someone who's curious and serious 2/ Say YES to helping your peers. Jump on a call. Listen to their calls. Share a few things that helped you. If you say, “Let me know how I can help,” and never do anything... don’t bother 3/ Learn to read a company’s financial statements. I loved monthly exec finance reviews because I understood them and could ask smart questions. Most sellers have no clue. Be the one who does 4/ Master SaaS metrics. Know CAC, LTV, CAC Ratio, burn rate. Understand why these matter before you're managing a $20M sales team quota 5/ Learn how to interview. I read 5+ books on it early in my leadership career and wished I had done it years earlier. Want my top 5 recs? Drop a comment and I’ll share 6/ Ask to be part of hiring. Volunteer to sit in on interviews. Share what you’re learning. This shows initiative and earns trust with leadership 7/ Make sure your boss and their boss KNOW you want to lead. Don’t assume they can read your mind. Say it clearly. Then go earn it, don't wait for it to drop into your lap 8/ Get ridiculously good at spreadsheets. If you don’t know VLOOKUP, SUMIF, or pivot tables, fix that fast. You’ll use these almost daily in sales leadership esp at startups 9/ Get certified in your CRM. Learn how to create reports and dashboards. Most reps don’t do this. That’s why they stay reps 10/ Track your own funnel metrics, primarily conversion rates. Find weak spots. Write up a Google Doc with your own plan to improve them. Then… go do it 11/ Meet people in Marketing, CS, Legal. Learn how they work with (or against) Sales. Future VPs know how to navigate cross-functional bull$h|+ 12/ Practice clear, succinct writing. Execs don’t read 5-paragraph essays. Send the TLDR version. Rambling, bloated messages won’t cut it 13/ Read 12 business or leadership books a year. Apply just 5% from each. You’ll lap most people who "are too busy" to read. Ask me for recs in the comments 😡 There's nothing I hate more than a rep that asks to be promoted to sales leadership, sticks their hand out but then does nothing proactively on their own. Yes, these can be hard and take extra time esp when you're tired. But most salespeople won't even do 3 things on the list above & then wonder why they're not getting promoted. What's 1 other thing people should do to increase their chances of getting into sales leadership?

I once replaced this VP of Sales who everyone said was really smart and great with spreadsheets. But nobody wanted to work for him. The sales reps actually put a petition together to get him fired. It worked and he eventually got fired. But this helped me understand why sales leadership is so hard to master for so many. ✅ Great, modern sales leadership requires mastering both Arts and Sciences. Art ("soft skills"): -Communication -Empathy -Strategy Science ("hard skills"): -Math -Analysis -Decision-Making 👎 You can have the Art without the Science and your salespeople will probably "like you." 👎 You can have the Science without the Art and your salespeople will definitely NOT like you. If you want to be a great sales leader, learn to master both.

I once promoted a “nice” sales manager who everyone liked. Big mistake. 🤦♂️ His sales team loved him but he was a crappy sales manager. Being "nice" just doesn't cut it. Here's 13 Signs of High-Performing Sales Managers: 1. They embrace conflict - average sales managers want harmony. 2. They practice radical candor daily, not just at review time. 3. They're intolerant of toxic salespeople, no matter their production. 4. They optimize for daily progress, not perfection. 5. They create psychologically safe environments. 6. They proactively solve problems, not just identify them. 7. They're ruthless about a hiring process, not just putting butts in the seat. 8. They create repeatable systems and processes, not relying on talent alone. 9. If things go wrong, they own it and don't blame others. 10. They demand world-class and show you what that looks like. 11. They make tough decisions, even when it's not popular with their sales team 12. They encourage trying new things and failure (see psychological safety above). 13. They treat company money like their own and strive to never waste it. These aren’t “nice to haves.” They’re non-negotiables...if you want a great sales team. If you’re grooming your next sales leader, look past likability and listen for signals of courage, decisiveness, and discipline. The one who drives performance and accountability is the one who successfully scales sales teams. What’s one sign you look for in a high-performing sales manager?