How to Move Your Sales Team from Winging It to Winning It

Let’s face it - sales is often seen as one of those departments where you can just wing it. Throw a couple of charismatic salespeople at some leads, promise them commissions, and sit back while the revenue pours in. Right? Wrong. This "winging it" mentality might work for a brief time, but it’s not a sustainable strategy, and it often leaves piles of revenue untouched.

If your company’s sales operation is running without clear leadership, defined processes, or accountability, you’re probably leaving money on the table - lots of it. And while it might seem like your sales team is doing well enough, you could be missing out on serious growth. But don’t worry, there’s a way to transform your sales team from winging it to winning it. One option you should consider is bringing in fractional sales management.

Let’s break it down.

The Casual Sales Culture: A Recipe for Missed Revenue

When a company’s sales operation is too casual, it often lacks three crucial elements: sales leadership, sales culture, and sales processes. Without these, you’re basically running a glorified lottery, hoping that enough deals fall through the cracks to hit your targets. Let’s dive into these common problems that plague casual sales operations.

​1. Lack of Sales Leadership
Picture this - your sales team is made up of enthusiastic reps who are great at talking to customers, but no one is guiding the ship. There’s no one analyzing data, setting long-term strategies, or making sure everyone is on the same page. It’s like a band with no conductor - everyone’s playing their own tune, and while it may sound okay in short bursts, it’s hardly a symphony. This leads to salespeople doing their own thing, without any overarching vision or direction, leaving them to operate in silos.

Without strong leadership, your sales reps will likely miss opportunities to upsell, cross-sell, or even close high-value deals that require more strategic thinking. Worse, without accountability, some reps may be coasting by, doing the bare minimum while still expecting top compensation.

If like many startups or small & medium businesses, you’ve promoted your best sales rep to be the Sales Manager, you could end up with a Sales Manager who falls short on proper management technique. In this case, many sales managers underperform as they learn that management requires a much broader skill set than closing deals.

2. Poor Sales Culture

When there’s no leadership or defined processes, the sales culture can turn into a free-for-all. You might find that some sales reps have become comfortable doing the minimum - hitting quota just enough to stay off the radar, but not going above and beyond. Why push harder when the bare minimum is enough?

In these environments, a sense of entitlement can creep in. Reps feel like they’re owed high commissions or rewards for just showing up, and the motivation to exceed expectations dwindles. This casual culture often fosters a sense of individualism rather than teamwork, where everyone is fending for themselves instead of working towards a collective goal. Ultimately, this culture leaves a ton of potential revenue on the table.

3. Lack of Sales Processes
You wouldn’t build a house without a blueprint, right? The same goes for sales. Yet, so many businesses run their sales operation without any kind of structured process. Maybe your team is hustling hard, making calls, sending emails, and having meetings, but without a clear sales process, they’re just throwing spaghetti at the wall to see what sticks.

The absence of a well-defined process makes it difficult to replicate success. What worked on one deal might not work on the next, and without a process in place, sales reps are left guessing. This leads to inconsistency in results, and more importantly, it makes scaling your sales operation a nightmare.

From Winging It to Winning It: Enter the Fractional Sales Manager

So, how do you go from a disorganized, wing-it sales operation to a fine-tuned machine that’s winning more deals? The answer lies in fractional sales management.

What Is a Fractional Sales Manager?

A Fractional Sales Manager is an experienced sales leader who works with your company on a part-time or project basis. Think of it like renting a top-tier VP of Sales, but without the full-time salary. Fractional Sales Managers bring a wealth of experience, often having worked across various industries and with sales teams of all sizes. Their job is to come in, assess your sales operation, and implement the strategies, processes, and leadership needed to take your sales team from winging it to winning it.

Why Fractional Sales Management Is the Perfect Solution

Here’s why a Fractional Sales Manager could be your best bet for turning things around:

1. Expert Leadership Without the Full-Time Cost: Hiring a full-time VP of Sales can be costly, especially for startups or small businesses. A Fractional Sales Manager gives you access to the expertise of an experienced sales leader without the hefty price tag of a permanent hire.

2. Immediate Process Implementation: One of the first things a Fractional Sales Manager will do is build out a structured sales process. They’ll set up systems for lead generation, pipeline management, and deal closing, ensuring that every salesperson knows exactly what steps to follow. This will eliminate the "winging it" mentality and ensure that your sales team has a repeatable process for success.

3. Accountability and Performance Tracking: With a Fractional Sales Manager in place, your team will have someone holding them accountable. No more coasting by or doing the bare minimum. Sales reps will have clear metrics and goals to meet, and their performance will be tracked to ensure they’re maximizing their potential. A good Fractional Sales Manager will also help you to properly reward high performers and push those who are underperforming to step up.

4. Improved Sales Culture: A Fractional Sales Manager can help shift the culture from entitlement to ownership. They’ll foster a sense of teamwork and shared goals, encouraging reps to take responsibility for their own success and contribute to the team’s overall performance. This shift can reignite motivation and drive within the sales team, leading to higher revenue and better results.

5. Faster Growth and Scalability: With the right processes and leadership in place, your sales operation becomes scalable. Whether you’re a small business looking to grow or a startup aiming to break into new markets, a Fractional Sales Manager can help you scale your sales team and increase revenue in a sustainable way.

Five Steps to Start Winning It Instead of Winging it

If your company’s sales operation is currently flying by the seat of its pants, it’s time to kick it up a notch. Here’s a quick five-step game plan:

1. Assess the Situation: Take a hard look at your sales team. Are they truly performing at their best, or are they just coasting? Where are the gaps in leadership, culture, and process?

2. Define Sales Goals: Make sure you have clear, ambitious, but attainable sales goals in place. You can’t win if you don’t know what game you’re playing.

3. Bring in a Fractional Sales Manager: Partner with a Fractional Sales Manager to get the expert leadership and process development your team desperately needs.

4. Implement Structured Sales Processes: Work with your Fractional Sales Manager to set up a sales process that defines every step from lead generation to closing deals.

5. Track Performance and Accountability: Start measuring everything. Set clear performance metrics and hold your team accountable for meeting or exceeding those goals. Reward those who go above and beyond, and provide support for those who need it.

If your sales team is operating too casually, it’s time to make a change. By bringing in a Fractional Sales Manager, you can take your sales operation from a disorganized free-for-all to a structured, high-performing, and competitive team. With strong leadership, defined processes, and a culture of accountability, your sales team will stop leaving money on the table and start winning deals that truly grow your business.

So, if you’re ready to stop winging it and start winning it, consider bringing in a Fractional Sales Manager from a company like Rev Sales Consulting. After all, there’s no shame in asking for a little help when it comes to winning.