7 Warning Signs Your Company Needs a Fractional Sales Leader (Money Monday)

0:01So going into a follow-up call, I want every important note right at my fingertips, not buried somewhere in a scribbled stack of notes. And with Plod Notepin S, I always have them because it's a wearable, portable note taker that lets me stay present and focused on customers during every single meeting. Plod captures the conversation and turns it into organized summaries and action items so I can follow up faster. And if I need a specific detail, Plod's recall has that ready for me. And that's why Jeb Sr. and I and all of Sales Gravy trusts our Plod Notepin S. Try Plod and stay focused on the conversation while it handles all of your notes.

0:34Go to plod.ai forward slash Jeb. That's plod.ai forward slash Jeb and use code JEB to get 10 % off your purchase.

0:48This is Jeb Blunt and it's Money Monday on the Sales Gravy Podcast. Say, make money, money, make money, money, money. Make money, money, make money, money, money. Money makes the world go round. I'm the talk around town. Remy gave me the sound. I need that strilla on the river.

1:14Welcome to another episode of Money Monday. My name is Duff Tucker, and this week I have the pleasure of filling in for Jeb. Now, let me start with a question. Who is running your sales team? And I'm not asking who has the title. I'm asking who's actually coaching the reps, inspecting the pipeline, setting the standards, managing the forecast, and making sure the sales process is working. Because here's what I've seen with a lot of growing companies. Sales can look pretty healthy from the outside. Revenue's coming in. The reps are busy. The founders are closing the deals. The CRM has opportunities in it.

1:48But underneath the surface, there can be some serious cracks. And those cracks usually start showing up before the revenue numbers do. That's why today I want to give you seven signs that it may be time to bring in a fractional sales leader. Not because your company's failing, quite the opposite. Sometimes you need sales leadership because the company's growing faster than the sales infrastructure can support. So let's get into it. Sign number one, the founder becomes the accidental sales manager. Now this one happens all the time. You're the founder. You close the first million dollars yourself.

2:19You know the product. You know the customers. You know how to handle the objections. You know how to close. So naturally, when you hire the first few salespeople, everyone looks to you. And before you know it, you're running the company and managing the sales team. Monday pipeline meetings? You. Reps need help with a deal? You. A proposal needs to be reviewed? You. A big customer is threatening to leave? You. And here's the problem. Every time you have to rescue a deal yourself, you're reinforcing the idea that the business only works when you are involved. Now that's not scalable. At some point, the founder has to stop being the best salesperson in the company and start building a sales organization that can sell without them.

3:00A fractional sales leader can step into that management role of handling pipeline reviews, coaching, deal strategy, and accountability so that the founder can get back to actually running the business. Sign number two, your reps are getting check-ins instead of coaching. Here's a question. When was the last time you actually coached one of your salespeople? And I don't mean how's your pipeline? How many deals are you working? Anything I can help with? That's a check-in. Coaching is different. Coaching sounds like, let's listen to that call. Walk me through what the prospect said. What do you think the real objection was?

3:34Who is the decision maker? What would you do differently if you had that conversation again? Now that's coaching. And here's the problem for a lot of growing companies. The reps are essentially managing themselves. They're sending proposals that no one has reviewed. They're walking into meetings unprepared. They're working opportunities without a real strategy. And eventually, they plateau. Your best reps get frustrated and leave. Your struggling reps continue struggling. And the company pays the price. Your people don't just need someone checking their numbers. They need someone invested in making them better.

4:07Sign number three, your forecast has become a guess. Here's another warning sign. You used to have pipeline reviews. Then they got pushed. Then they became monthly. Then they became, hey everyone, update the CRM. And now, no one really knows what's going on. So the forecast, it becomes a guess. Here's a simple test. Go to your CRM and look at your oldest open opportunity. When was the last meaningful activity? If it's been weeks, you have to ask whether it's really an opportunity. A real pipeline review isn't reading numbers off a spreadsheet. It's stress testing the deals. Who is the decision maker?

4:42Have we actually spoken with them? What's the compelling reason to buy? What's the next step? What's standing in the way? What could kill this deal? Is there a budget freeze? Is there a competitor? Did the decision maker leave? What's our backup plan? That's how you move from forecasting by optimism to forecasting based on evidence. Sign number four. Growth is stalling because your sales process doesn't scale. This one is especially common in founder-led businesses. Your first customers came from relationships. Your next customers came from referrals. Your network got you started and that's great, but eventually you hit a ceiling.

5:19Here's a simple exercise. Look at your last five deals. Where did they come from? If the answer is my network, someone referred them, I've known them for years, that's not necessarily a problem, but it may be a signal. because relationships are powerful, but they're not always scalable. And at some point, you need a repeatable system for finding new customers. Who are we targeting? What problems do they have? What's our message? How do we prospect? What's our sequence? What does a qualified opportunity look like? What happens after the first meeting? That's the transition from founder-led sales to a sales engine.

5:54Sign number five, your sales leader left and there's no bridge. This one is painful. Your sales manager leaves. Your VP gets promoted. Someone gets recruited by a competitor. Whatever the reason, suddenly there's an empty seat and you start looking for a replacement. But finding that right sales leader can take months. Meanwhile, who's coaching them? Who's running the pipeline reviews? Who's inspecting the forecast? Who's holding people accountable? Nobody. So the team starts drifting and then you finally hire someone. But they walk into a team that hasn't been coached in months. The pipeline isn't clean.

6:28The process isn't documented. the expectations, they're not clear. So instead of leading the sales organization, your new sales leader spends six months trying to figure out what happened. A fractional sales leader can act as the bridge. They can keep the team moving, keep the coaching happening, keep the pipeline reviews happening. When you eventually hire your full-time leader, they inherit a sales organization with structure instead of a mess that they'll have to rebuild. Sign number six, you're heading into an acquisition. This one gets overlooked. If you're preparing for an acquisition, a funding round, or an ownership transition, your sales organization is about to come under microscope.

7:06Investors aren't just going to look at revenue. They're going to ask, how predictable is this revenue? What's your pipeline? What's your conversion rate? What's your sales process? How accurate is your forecast? How dependent is the company on the founder? And here's where things get uncomfortable. If your CRM says one thing, your salespeople say another thing, and your financial reports say something completely different, you've got a problem. Because during due diligence, those inconsistencies, they get discovered. The goal should be for your CRM, your forecast, your reps, and your financials to all be telling the same story.

7:40That's what sales leadership should help create. Sign number seven, nobody sets the standard. This might be the biggest one. Walk onto your sales floor and ask two reps, what's your activity goal this week? If you get two different answers, you have a leadership problem. because you can't hold people accountable to a standard that has not been established. How many conversations? How many meetings? How many proposals? How much pipeline? What does a productive week actually look like? Without standards, people fill their time with whatever feels productive. Checking emails, updating CRM fields, researching prospects for three hours, creating the perfect proposal, and they feel busy.

8:19But being busy is not the same thing as being productive. A strong sales leader defines the activities that actually drive revenue and then creates accountability around them. You can't manage what you don't measure and you can't hold people accountable to standards that no one established. So do you need a fractional sales leader? Now here's the important part. You don't need to check all seven boxes. If you're seeing yourself in even one or two of these, there's probably a sales leadership gap that's already costing you something. Maybe it's lost revenue. Maybe it's stalled growth. Maybe it's reps leaving.

8:54Maybe it's an accurate forecast. Maybe it's simply the founder spending 20 hours a week managing sales when they should be running the company. And here's what I want you to consider. The answer doesn't always have to be hiring a full-time VP of sales tomorrow. That can be a six-figure decision. And if you haven't figured out exactly what the role needs to accomplish, you end up hiring an expensive person to walk in an undefined job. A fractional sales leader gives you another option. You bring in experienced sales leadership to diagnose what's actually broken. Build the process, coach the team, establish the standards, create accountability, and help build a sales engine that can eventually operate without them.

9:34But there's an important distinction. Don't just hire someone because they have VP of sales on their resume. Ask them, what have you actually built? What teams have you actually turned around? What numbers changed? Can you show me the results? Can I talk to your references? You want someone who has done the work, not someone who simply held the title. So let me leave you with this. Sales problems rarely appear overnight. They have clues. The founder becomes the sales manager. Coaching turns into check-ins. Pipeline reviews disappear. Forecasts become guesses. Growth stalls. Standards disappear.

10:10And eventually, everyone starts wondering, why aren't we growing faster? Now, the good news is you don't have to wait until the problem becomes expensive to fix it. Sometimes the smartest thing a growing company can do isn't to hire more salespeople, but to put experienced sales leadership around the people you already have. Because the goal isn't simply to sell more. The goal is to build a sales organization that knows how to sell more consistently, predictably, and without everything depending on the founder. That's when you stop having a collection of salespeople and start building a sales engine.

10:45This has been Money Monday. My name is Duff Tucker. And if you recognize your company in any of these seven signs, don't ignore the signal. Fix the sales leadership gap before it becomes a revenue problem. Thanks so much for listening. And until next time, keep learning, keep applying and keep winning. There's nothing like my American Express Platinum card. I love that I can earn hotel credits when I travel. I can also earn resi credits. So, you know, I'm hitting the restaurants everyone's talking about. Plus, with the digital entertainment credit, I'm even more excited to catch my favorite shows.

11:19All in all, I can access over$3 ,500 in annual value with benefits and eligible purchases across travel, entertainment, and more. Learn more at AmericanExpress.com slash explore dash platinum. Enrollment requirements, monthly, and other limits in terms apply. Most women have been there. Something feels off. You don't feel like yourself. Yet your doctor says everything looks fine. Spoiler, it's your hormones. Midi is a virtual care platform built for women by women and offers specialized hormone care from trained clinicians. Plus, it's covered by most major insurances. Getting started is easy. You can book your first visit with a clinician right away.

11:55It's not you. It's your hormones. Visit joinmidi.com to book your first visit. That's joinmidi.com. Insurance coverage varies. Check with your plan for coverage. Survival of the finish. You can sink or swim. I've been broke. I ain't never going back again. I need some C notes, some cheddar and a stack of ends. I need a bowl of dough. I don't need no Facebook friends. I need a pack of them snaps, a handful of Fetty wops and rubber band on my green backs. Look, dog, don't be playing with my paper. I need every red cent. That's why I brought my little scraper.