3 ways to improve your team’s sales performance

A lot of the advice about improving sales team performance reads a bit “water is wet.” 

“Have a positive outlook,” they say. “Set clear sales targets,” they say. 

It’s not terrible advice, as far as it goes. But as a sales leader, you know all that already. That’s how you got this job in the first place. 

The challenge now is to figure out how to clone your best sales rep. 

Why are they hitting quota every time while the others aren’t? What are they doing differently? Or is it just that they’re doing more? 

And, more importantly, how can you make sure that every rep starts doing what those top reps are doing? 

In this article, we’ll get into the specifics of how to lift the performance of every rep on your team, how to uncover your own blind spots with better measurement, and solutions to the three most common causes of sales team performance issues. 

What makes sales performance management tricky? 

Not to get all ChatGPT on you, but the new B2B buyer journey doesn’t just make it harder to sell — it makes it harder to manage a sales team. 

Some of the biggest performance management challenges for sales managers today include: 

Lack of visibility 

Today’s B2B sales are so complex and drawn out that you might not even know a deal is floundering until it’s already too late.  

• Do you know where the rep is getting stuck in the deal? 
• Do you know what your best sales representatives are doing? 
• Do you know which messaging works best? 

If the answer to any of that is no, you probably need to add some tools to your stack to get the insight you need (more on that later). 

Remote work — with reps sitting across the world — only makes this more challenging.

Scaling what worked on a small team 

Back when there were just a few of you, you didn’t really need standardized processes because you were all in it together. And you, as the team leader, were close to the action. If your reps went off-script, you’d know about it. 

But, if you’re leading a larger sales organization, you have to be consistent. 

To quote Chris Orlob, former Head of Sales & Growth at Gong, “If you don't have the same language, the same stages and exit criteria, and nobody has a shared understanding of what you’re doing, then you are useless as a sales leader.”

Understanding activity vs. impact

Sometimes, the answer to the underperformance issue is pretty simple: your reps simply aren’t active enough. 

That’s not to suggest they’re not trying—they may be bogged down in manual processes or wasting time with deals that will never, ever close instead of moving on to the next prospect. 

Part of the challenge for sales managers is to figure out:

• a) what your team is really spending time on
• b) which activities drive sales results and which are just noise 

How to measure sales performance 

We’re going to assume you’re already measuring the usual pipeline and revenue numbers, and major CRM milestones—like total sales value, average sales, average contract value, average deal size, customer acquisition cost, and customer lifetime value.  

Those are important, of course. But to really understand your team’s overall performance, you’re going to need more granularity to pinpoint where reps are struggling and why. 

To get into the weeds on sales performance, here are some key performance indicators (KPIs) you might want to start looking at: 

1. Conversion metrics 

How’s your sales effectiveness? Is your sales pipeline healthy? How’s your win rate? Are your team members great at initial lead generation but then letting deals stall out? 

You’re probably already tracking the broad-strokes metrics here, but to drill into your pipeline health, you could also start looking at: 

• Conversion rate by funnel stage (to see where in the deal things are falling down) 
• Sales cycle length (to check on your sales team’s operational efficiency) 

Tools to track conversion metrics in detail

You should be able to do this with any solid CRM. Aside from Salesforce, our picks for SMBs and mid-market sales organizations include Hubspot, Pipedrive, Zoho CRM, and ActiveCampaign.

2. Conversation metrics

What messaging works best? What are your top-performing reps saying to prospects? Did your sales coaching help? 

To find out, you could track:  

• Talk-to-listen ratio
• # of questions per call
• Call duration
• Keyword frequency
• Duration of customer stories
• Duration of sales rep monologues 

Tools to track conversation metrics: 

The leader in this space is probably still Gong. 

On our Grow & Tell podcast, Conor Dragomanovich, 2X VP of Sales, now GTM leader at OpenAI, said he’s a big fan of Gong for analyzing sales calls and coaching his reps. He used to spend hours listening to recordings of his team’s calls, pulling snippets for later discussion and feedback. 

“It just amplifies the way you can work with an AE,” said Conor. “You understand their approach. You're seeing it from the perspective of the customer.”  

ZoomInfo (formerly Chorus) and Clari have similar features. 

3. Buyer engagement metrics 

How are your deals progressing? How good is your team at engaging the client? Are they getting them to start using the sales room or working on their to-dos in a mutual action plan? To figure that out, start tracking: 

• Prospect engagement metrics (DSR views, content views, time in DSR) 
• Engagement by each stakeholder (to check if your team is building multithreaded relationships with prospects) 

Tools to track buyer engagement

Our sales room platform, Dock, is extremely good at helping you see if your reps are engaging your buyers, which deals are progressing, and where reps might be dropping the ball. 

Dock lets sales professionals quickly customize and share deal rooms with customers. It makes it easy to create a white-glove buying experience for every prospect, bringing all the info they need together into one handy workspace. 

As a sales leader, Dock also helps you figure out how engaged your new customers are. With our reporting tools, you can track which stakeholders are looking at the resources in the digital sales room and how often.  

This means:

• You can jump in to coach any reps who aren’t engaging the buyer effectively. 
• You can spot if they’re not building multithreaded relationships (because you’ll see that only one account stakeholder is accessing the deal info). 
• You can spot deals that are stalling and make sure your team is in place to get things back on track. 
• And you can be confident that your salespeople are prioritizing the deals that are most likely to close. 

For instance, Andrew Hollis, the Sales Director at Nectar, explains:  

“With Dock, we're finding who the high-quality accounts are. It's helping us decide who we target, and, ultimately, now I can pop in and actually see if the buyers are serious. If an account executive thinks something's progressing, but the prospect isn’t really looking at the Dock — is it even possible?” 

Here’s a quick overview of Dock’s reports:

4. Sales activity metrics (by rep)

What are your reps spending their time on? How proactive are they? 

Note: more isn’t necessarily better. Reps who are frantically chasing the wrong deals are just wasting time. 

But these numbers will at least tell you if activity correlates with results. If not, you’ll know you need to look at your sales strategy to figure out how to use your team’s time better.  

Examples of relevant metrics here include: 

• # of leads created 
• # of outreach messages
• # of calls and conversations 
• # of meetings 
• # of proposals 
• # of sales rooms/client workspaces created 

Tools to track sales team activity

As well as tracking interactions in your CRM, you can use sales performance management software (SPM), like Salesloft, Outreach, or Hubspot, to monitor the number of calls, emails, and other interactions of each sales rep. 

Plus, with Dock, you can see how many sales rooms each rep has created. 

5. Sales enablement metrics 

Are your reps using the sales enablement materials they’re supposed to be using? If not, why not? Do they have the content they need? 

To track that, look at: 

• Sales content usage by rep
• Content engagement (e.g., time on page) by rep
• Sales training completion rate

📘 Learn more: Check out our guide to sales enablement metrics.

Tools to track sales enablement metrics

In general, the tools you use to share out learning resources and sales content also let you understand how your reps are using them (e.g., learning management systems or content management systems). 

Tools in this space include legacy enablement platforms like Highspot, Seismic, and Showpad, and newer market entrants like Workramp and Guru. 

Or you could skip all of those and just use Dock for this, too. Our content management system lets you organize your content, surface it quickly for your reps, and track how much use each asset gets. 

You can build an easily searchable and shareable library, organize it for customers in a personalized workspace (that they can access with one click), and make sure that your reps are using and sharing the right content with their prospects. 

How to improve your team’s sales performance

Dialing into your sales data should give you a clear picture of where your team is running into problems. Here are our tips for troubleshooting all the components of sales performance management: 

Problem #1: Your team just isn’t doing enough 

You might assume that underperformance is caused by poorly designed incentive compensation plans, but research from Gartner suggests that you’re more likely dealing with one of three less tangible issues: 

• Low motivation (potentially caused by a perceived lack of development opportunities or recognition)  
• Lack of manager feedback 
• Too much time wasted on low-value tasks (like admin, seeking approval for deals, etc.) 

If your team is unmotivated or underactive, try the following: 

Listen more actively

Start by listening closely to your team, suggests Conor Dragomanovich:

“Much as with helping a customer solve problems, I felt like the value of a leader is the ability to really and truly listen with the right intentions and ask meaningful questions to help both the AE and then yourself uncover the productive learnings and carve the right path out.” 

Shadow calls

If your team says they lack manager feedback, it may be that you’ve been too hands-off, says Peter Kazanjy, the co-founder of Atrium and author of Founder Sales. 

“‘Micromanage’ is the dumbest word ever,” says Peter — sales managers should expect to work closely with their team if they expect high performance. 

His recommendation? Each rep should shadow you for a while to get the hang of your sales process. Then, run mock calls before finally letting them lead calls with a more experienced rep riding along and giving feedback (or use Gong to spot areas of improvement after the fact). 

Empower sellers with easy-access resources

If your team is getting bogged down waiting for approvals, making and sending PDF proposals, and other tedious manual tasks, there are simple fixes that can help free up their time for actually selling. 

For example, with Dock, they could save hours by: 

• Using customizable templates for their sales rooms, proposals, and quotes instead of creating every asset from scratch every time 
• Creating proposals by using a product library with predefined rules, so they only need to wait for your approval occasionally
• Sending a single link after a demo with all the info the customer needs to make the purchase instead of wasting time emailing back and forth
• Using automation to populate the sales room, proposal, and quote with information from your CRM 

Problem #2: You have one or two star players, but the rest can’t keep up 

What if you have a couple of highly effective sales reps, but nobody else seems to be able to replicate what they’re doing? 

It may be tempting to assume you have a hiring issue, but there’s a good chance your new reps just aren’t being set up for success. 

Your earlier reps might have worked directly with you or the founder and learned their playbook from the horse’s mouth, so to speak. Newer reps are joining a larger, more complex sales organization, and they likely have less access to the founder (or first sales hire) and, therefore, less insight into your market and messaging. 

If you’re seeing a wide discrepancy in performance, then it may be time to create a standardized, repeatable sales workflow, suggests Lish Barber, Director of Enablement at Sigma Computing: 

“I have always found, even with enterprise sales teams, that as much tenure as they've got, a lot of time, it's just going back to basics. Making sure they know how to run that first call, and they know what good discovery looks like.” 

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Some areas you might want to look at are: 

Standardize your qualification process

Make sure your team is going after worthwhile leads by implementing a consistent discovery process, like the MEDDIC sales methodology, for instance.

The acronym MEDDIC represents the questions your reps need to answer before moving forward with a prospect: 

1. Metrics: How do they measure their success?
2. Economic buyer: Can they authorize spending?
3. Decision-making criteria: How are they evaluating your product?
4. Decision process: How will they reach a decision?
5. Implicate pain: What pain point or business goal is motivating them to buy?
6. Champion: Who will advocate for you on your buyer’s team?

Standardize your demo follow-up 

Using sales rooms for demo follow-up instead of long email chains with file attachments can help empower your new reps and get them sales-ready more quickly. 

For instance, Andrew Hollis and the sales team at Nectar use a templated sales workspace built in Dock for each new prospect, which includes their G2 reviews, an intro to the CS team, a quote builder, and everything the prospect will need to move forward with the deal. 

Before every demo, they create a personalized copy of the workspace. Then, all their demo follow-up happens in that workspace instead of over messy email threads.

The result, says Andrew, is a consistent and high-quality demo follow-up: 

“The first follow-up that a new rep gives is of the same tier as someone that's been here for two years…because they're copying that template." 

Standardize your deal process with a mutual action plan

Using a mutual action plan can help with the optimization of your sales process. This helps AEs to define clear timelines and milestones while also making it easier for your buyer to navigate the often complex purchasing process. 

💡 Pro tip: With Dock, you can embed an interactive mutual action plan in the same workspace as your quote, pitch, embedded demo recordings, legal documentation, and everything else your prospect needs to complete their purchase. 

Problem #3: Too many deals stall out

Research by Databox shows that most B2B deals take 1-3 months to close. Small wonder, then, that many sales teams struggle to keep momentum going. If that’s what your data shows, then these sales acceleration strategies might help your team bring their win rate up: 

Train your reps to partner with the buyer champion

According to Gartner, today’s buyers only spend 17% of the buying process talking to sales — and that’s split across all the competing products. As a result, there’s a limit to the impact even the best sales rep can have on the deal these days. 

Instead, you need to train your reps to identify the buyer champion quickly — the biggest advocate for your product or service within your prospect’s company. Then, reps should act promptly to give the buyer champion the resources they’ll need to help push the deal through. 

Stephen Ruff, Co-Founder of Champify, explains:

“You build a champion by connecting with them, helping them benefit personally, and tying your product to a problem they care about, but also by providing them the information they need to go internally and get buy-in and get their team excited.”

For example, your reps could provide curated resources (like ROI calculators or relevant case studies) to help the champion make your company’s case internally and work with them to map out all the stakeholders they need to engage with. 

📖 Learn more: Here’s a detailed guide to spotting and enabling your buyer champions.

Encourage reps to multithread relationships

You don’t just need one champion, of course — in B2B deals with multiple stakeholders, you need a whole team of champions. In other words, you have to make sure your team is multithreading.

They should be asking the main buyer champion to identify other key players who will make or break the deal — then engaging with those people and bringing them into your sales workspace. 

💡 If you’re using Dock, you can check that this is actually happening. Our People Analytics dashboard lets you track exactly which buyer contacts have engaged with a workspace to tell how well your team is multithreading deals.

Boost your sales performance management strategy With Dock 

If you’re keen to improve your sales team’s close rate, Dock can help. Our sales deal rooms can help your reps hit their revenue goals by: 

• Setting up personalized, collaborative workspaces with everything the buyer needs to get the deal done — all in one link
• Improving their sales forecasting accuracy with real-time data on buyer engagement, making sales planning and pipeline management easier 
• Streamlining sales operations with standardized mutual action plans and demo follow-ups so every prospect gets the same high-quality experience 
• Increasing sales productivity with predefined product pricing and discount rules, so they don’t have to wait around for deal approvals

Ready to hit more sales goals? Sign up for Dock for free.