Ramp Up Your Team’s Sales Skills With This Closer’s Toolbox

Sales is a cut-throat industry, and even more so when you’re first starting out. To win over clients and blow your competition out of the water, you need sales skills, but you also need a game plan and tricks in your sales toolbox.

a tool box of sales skills

14 min. read

When I was a designer working at an agency early in my career, a senior designer mentioned that he was building up his ‘toolbox’. By toolbox, he meant different design styles and approaches that he could apply to specific circumstances; not literal tools, like say, InDesign.  

The hardest part when starting out in the design field is to know what ‘good’ looks like; your head is empty. The only way to fill it is to look at examples of great design and deconstruct them. Over time your design brain becomes like a well-trained muscle - you know instinctively what works and what doesn’t. You develop new styles, templates if you will, of what typeface/colour/image styles go well together in given situations.

Why am I talking about design when this post is supposed to be about sales?

Because whether you’re a salesperson by title or you just happen to fill that role in your company, you need a sales skills toolbox - a list of strategies that you know work.

Think of it like a magician's coat – full of pockets that contain tricks of the trade a salesperson can pull out to woo a prospective client and prove that their product/service is worth believing in. These ‘tools’ help your sales team move leads through the sales funnel, explain your product or service confidently, and allow them to close more deals, faster.


I recently sat down with Kevin Springer, co-founder of Proposify, to talk with our sales team about our current sales process and some issues the team was having. During our discussion we discovered that the sales reps who were finding the most success were using go-to statements, questions, and rebuttals they had built up over the years – a sales skills toolbox they could rely on to help them connect with their customers.

To get our entire sales team comfortable with the sales process, and to ultimately help them succeed, we knew they would each need to build their own sales toolbox. To do that, we decided to roleplay different scenarios. I played the salesperson while our salesperson played the lead. They threw objections my way, and I’d attempt to knock them down. Anytime either one of us was stumped, we stopped to discuss the situation.

Here’s what we uncovered during our sales roleplaying:

Qualification calls

Qualifying sales leads isn’t hard if you have a good process. No one wants to spend weeks nurturing a lead who ends up declining your proposal or doesn’t have the budget to work with you. On the other hand, you may pass on talking to someone because you thought they were too small, but it turns out they were a hot lead.

To quickly uncover whether a prospect is the right fit for a large-tier Proposify plan, we created a general qualification call approach.

What makes an ideal prospect?

It’s easy to think an ideal prospect is based on industry, company size, location, or job title, but those are just hints at who that prospect is, and the amount of work they do. To find this information quickly, sales automation and data-enrichment tools like Clearbit scan the internet and pull the data for you.

Even with this information, it’s still essential to examine your existing database of customers.

Sometimes you’ll find that your highest-value customers don’t fit perfectly into your qualified lead criteria. There may be smaller companies that value your product/services, for example. Or a prospect might use what looks like a personal email address, so you disregard it as a low-quality lead, but it turns out to be a CMO who’s logged into their personal laptop. Definitely a high-quality lead. You just never know.

For the same reason you can’t judge a book by its cover, you can’t judge a lead by only your base criteria. You need to dig deeper into what makes a good lead, and if possible, assign a value metric. For us at Proposify, it’s the number of proposals our leads write each month.

Our sales reps qualify a lead based on how painful proposals are to them. They ask questions like:

  • How did you find out about Proposify?

  • What caused you to look for a solution?

  • How many proposals does your team write each month?

  • What’s your average deal size?

These are the most important questions to ask because:

  • Knowing why a lead visited our marketing site, reached out to sales, or signed up for a trial tells us what problem they’re trying to solve.

  • Knowing how many proposals they create tells us how important writing and sending proposals or other sales documents is in their overall sales process. The more people writing and the more proposals they create, the more value we can provide.

  • Proposify helps companies close deals so knowing their average deal size helps us determine what closing one extra deal per year is worth to them. Helping them close a $2K deal is very different from a $500K deal.

Because we are able to pull base information (company size, location, and job title) from our sales automation and data enrichment tool, it allows our sales reps to spend more time figuring out if we can help each lead, and to what extent.

Handling objections

Your salespeople always know the least about your product or service; it’s just a fact. Your designers and developers can answer your lead’s questions about their design process or how an integration works better than you can.

Unfortunately, leads aren’t given the opportunity to talk to those experts. Instead, they are forced to talk to sales reps, which is why part of your salesperson’s toolbox should be knowing how to turn questions around and own the qualification call.

Bad Salesperson

Lead:  “Do you have feature X?”

Sales rep:  “Um, yes I think so.”

Lead:  “How does it work, does it work like this?”

Sales rep:  “Um, I don’t really know, but I can find out.”

Good salesperson

Lead:  “Do you have feature X?”

Sales rep:  “That’s a really interesting idea! No, we don’t have that specific feature, but just so I’m clear, what problem are you hoping to solve with that feature?”

Lead:  “Well, here’s my current situation…”

Sales rep:  “Oh, well in that case, here’s another way to solve that problem using our product.”

By turning questions around on the lead, it forces them to explain the reason for their question. Instead of the sales rep just answering yes/no questions, they can take command of the call and find opportunities to solve a customer’s problem.

The more detailed the answers, the faster the sales rep can determine whether or not the lead is a good fit.

What objections do your salespeople encounter?

Sit down with your sales team and make a list of every common objection they come across, then work on strategies to get around each one:

Objection: “You don’t have feature X.”

Rebuttal: “What problem are you trying to solve with feature X? OK, great. Here’s another way to solve that problem. I’ll also be sure to let our product team know why it’s an important feature to you.”

Objection: “Why should I choose you over competitor X?”

Rebuttal: “Competitor X is a great company, and we love them, but here’s why I think we’re a better fit for you: Our founders started [company_name] because they believe [mission statement]. Since [client’s core problem] is a big pain for you, it’s the thing we get out of bed to solve. If you’re looking for [unique selling point], then we’re the right product for you.”

Objection: “The price you gave me is high. I don’t have the budget for that.”

Rebuttal: “I can understand this is a decent size investment. We’re not the cheapest option around, but that’s because we believe, and our customers back us on this, that our product/service is worth it. Customers typically make back their investment within three months of engaging us. That’s because we do [unique value proposition] better than anyone else. Is that something you think is worth paying for?”

Your objection/rebuttal chart should be a document or spreadsheet that your sales reps can have open in a tab at all times. Eventually, each reply becomes instinctive; they will know the right moment to deploy each one.

Discussing price

Leads will often come calling with questions around pricing and usually, it’s about lowering the price or getting a deal. What tools are in your salesperson’s toolbox to deal with these situations?

During a qualifying call, if a lead says, “I was on your pricing page and was wondering if I can have feature X but only pay $Y for it?”, or “I’m just wondering how much you guys charge?”, your salesperson needs to own the conversation and put an emphasis on the value you can offer the lead.

Instead of just answering each question to land the deal – “Our pricing is X,” or “Sure, we could look at getting you on a cheaper plan and throw in that extra feature,” – you need to train them to ask qualifying questions, like:

“First, I need to know more. What does your current process look like? What caused you to reach out to us?”

Uncover the value and work back from there

Your sales rep’s first call to a lead is all about uncovering the value of your product or service.

Let’s say you’re a marketing agency and a lead calls to ask about pricing. You flip the script and start asking them about why they reached out, how they generate leads, and what their main problems are.

With the questions answered, the rep starts working out the math:

Sales rep: “OK, so right now you do $5,000/month in Google Adwords, and only get five leads per month. You’re paying $1,000/lead, and you can only close one deal a month. You’re paying $5K for a customer each month.

What if we could triple the number of leads for you and cut the cost of a lead down to $200? What would that do for your bottom line? Would you be able to handle more leads? Great, so doing the math quickly, that would translate into an extra $1 million in net new revenue within the first year.”

Now, because the sales rep focused on the value you can deliver FIRST, the lead will be fixated on the $1 million they can make instead of the $10K/ month you have to charge them to execute the project. They’ll look at that $10,000/month as a solid return on investment to get to the $1M in revenue.

Try this exercise with your sales team:

Give your team a list metrics to pull from the client, and show them how to then quickly calculate the value of your product/service based on those metrics.

For example, at Proposify we know that companies who write a lot of proposals and implement our software will save at least two hours per proposal. If a customer has a sales team writing 50 proposals per month, then they’ll save 624 hours per year using our software.

Multiply that by the average dollar per hour they pay their sales reps ($32/hr), and it works out that we could be saving that company nearly $20,000/year in hours alone.

Now, if their average deal size is $20,000 and we help them close even one extra deal per year, that could be a minimum $40,000 value we’re delivering the customer. So if a large tier plan costs a business $5,000/year to make $40,000, the value is pretty obvious.

Always uncover the value and work back from there.

Pitch meetings or demos

Demos are to product companies, as pitches are to service businesses. Whatever you call it, a pitch or a demo is something only offered to sales-qualified leads; ones who have shown a need for your service and have demonstrated an intent to buy.  

Here are things you need to document in your demo/pitch process:

  • Standard pitch deck or proposal template that you can customize

  • How to prepare for the meeting

  • Standard length and structure

  • How to address questions and objections

  • Standard value proposition

  • How to end the demo or pitch and CTA

A great resource for learning more about how to create a SaaS company demo is Product Demos That Sell, an ebook by Steli Efti from Serped also has a great post about How to Pitch To New Clients (And Actually Get Responses), which covers some deadly mistakes you could be making in your pitches.


We all know coffee's for closers because closing is the mark of a true salesperson.

It’s not about begging or nagging for the sale, but instead guiding the lead to move further down the funnel, and nudging them to make a decision.

I’m going to share two strategies for closing here, but you can probably create more.

Get the lead to tell you their hesitation for buying

To encourage your lead further down the sales funnel, you need to know all objections or obstacles holding them back from saying yes.

"So can you sign up for an annual plan today? No? What else needs to happen? You need to play around with the product? OK, let's say you love the product, what then? Oh, you need your marketing director’s approval? Then let's schedule a call with her for next week."

Asking the lead what the obstacles are to moving forward helps the salesperson understand how long the sales cycle will be and allows them to immediately overcome objections.

Use incentives and time constraints effectively

Often salespeople will offer clients special bonuses for closing, like an added feature that normally doesn’t come with the plan they’re on, or a shorter billing cycle. Give your salespeople tools they can use as incentives, but make sure they pair the incentive with a time constraint.

“I talked to my sales director, and I can get you on quarterly pricing, but I would need you to sign up to the plan by Thursday at 5 pm EST. After that, I can only offer you annual billing.”

This is really useful for add-ons that help close the deal.

“The regular deal is this, but I’ll throw in X, Y, and Z for the same price if you decide by [date/time].”

Don’t let your tools get stale

A toolbox is only as useful as the tools in it. When you first add that hammer or drill to the toolbox, it feels great; maybe it even inspires you to DIY everything in your life. But when that hammerhead starts flopping around, or that drill starts sounding like a dying cat, it’s probably time to replace them.

A sales toolbox is no different. Your sales team should be inspired by the equipment they have readily available to them. It should make them feel ready to sell and close every lead they speak with. When the materials in their sales toolbox start to feel stale (i.e., outdated qualifying questions, or incentives that aren’t incentivising), it’s not just uninspiring, it can be downright dangerous to the health of your sales.

Keep your sales toolbox updated, and evaluate the materials you have in it regularly to ensure they are still working for your salespeople, inspiring them to sell more, and empowering them along the way.

How to apply this to your business

Now it’s your turn to look at this framework and fill in the blanks. What are the most common things leads say to you on qualification calls? What works?

Put this into a shared doc with your team that you can all keep adjusting as you learn. The most important thing is to START documenting your process.

Is there an aspect of the sales process I’ve missed? Let me know in the comments below.

Ramp Up Your Team’s Sales Skills With This Closer’s Toolbox

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