Smaller, scrappier underdogs need to use all the tools at their disposal. 

It's the quintessential underdog story: The small, scrappy little company that goes up against the big guy, and despite setbacks, wins customers' hearts and minds. Today, we can't believe they were once us. 

Michael Dell did it. He took on big bad IBM and broke IBM's dominance on the PC market through his Dell Direct model. The Vermont boys behind Ben & Jerry's took on Pillsbury's Haagen Daz and won on the strength of both flavor, and brand. Steve Jobs' legend gets bigger with each retelling. 

Why am I talking about this? Because it's important to remind ourselves that every noteworthy business in the world was once where we are. Having said that, every business that didn't succeed, or stayed small, or has achieved only middling success was also once where we are. These are all possible outcomes for our businesses, unfortunately. 

So how do we ensure we're in the Ben & Jerry, Dell, and Apple camp? Well, there are entire books dedicated to the various things we can do in each area of our businesses. In this post, however, I want to talk about how small companies like us can leverage tools to give our sales teams the biggest productivity boosts possible. 

And no, this isn't a list that includes massive tools like Salesforce. If you're big enough to use Salesforce, you're big enough to have a sales army. What I'm talking about are teams like mine that comprise one entrepreneur, five sales reps, and one sales engineer. That's it. 

Sales Intelligence tools 

Especially if you're starting out with green new sales reps, this is a must. Sales intelligence software works by continuously crawling millions of publicly available websites, gathering relevant data, and matching it to profiles in its database… giving your team verified lists of customers with up-to-date contact information (often, with preferences!). The best ones even help you narrow this list to those customers who are ready to buy. I evaluated these 5 tools recently, and came away super impressed. 

For me, this investment was a no-brainer. I thought about how much time the team spends on cold emails and cold calling and how much of that effort goes down the drain. But now, my team goes in armed: they know who they're targeting, they know plenty about them, and they know (roughly) what sort of messaging and contact method would appeal to them most. Even if it is slightly expensive, this is an investment that pays for itself many times over. ​

Live Chat 

If you have a website and you don't have live chat, you're missing out on qualified leads who are already browsing your website! You've seen it in action yourself - you're browsing, and a little box at the bottom of the page pipes up and asks if you need help. Before you know it, you're engaging with this person (more likely, chatbot) and getting the assistance you need. Did it increase the likelihood that you'd purchase something from there? If the numbers are to be believed, absolutely yes. 

Aside from letting you chat with customers in real-time, live chat solutions can be configured (trained, actually) to identify and nurture leads, before passing them on to your team. This helps you capture even those late-night browsers, whom your team can connect with when they start their day. Moreover, all the interactions are ticketed, so no lead falls through the cracks. Also, you'd be surprised at how affordable they are. Here are a few I really like. 

Email tracking tools 

Again, think about the time your team spends on email campaigns - both for sales and marketing. Without email tracking tools, you're shooting into the void. You don't know how many of those emails reached the recipient or are languishing unopened, or worse, have been opened multiple times, but the client hasn't had a chance to respond. 

An email tracking tool would tell you. At SmartCue, we have an alert for when someone reads our email multiple times. When one of my salespeople sees that alert, they know this is an interested party. They look up their information in our sales intelligence tool and reach out using the mode of contact best preferred. The client, who was just reading your email is delighted to hear from them, and the conversation flows far easier. 

An email tracking tool gives you invaluable metrics (email open rates, the volume of clicks on links in emails, number of downloads of email attachments, etc), and allows you to eliminate busy work. Create an email campaign, and set it to run. Automate follow-up. Set up reminders. Take the busy out of work. Check out my list here

RFP Tools 

Have you noticed how much back and forth is involved in responding to an RFP? Everyone has an opinion on what needs highlighting, and it changes all the time. Not to mention how many times we change our mind on discounts, and how many times the configuration itself changes. Of course, this means mountains of rework (non-value adding, to boot!) and an inordinate amount of time spent getting approvals. Moreover, this is work that most sales reps find boring, so, of course, it takes longer to do. 

Now, the tool that automates RFPs doesn't exist, of course. But you can get pretty close. Proposal tools give you a very solid first draft, based on the rules, pricing, and discounts you've configured. Once you have that solid starting point, it gets easier to build from there. I've evaluated two types: CPQ software and proposal software. CPQ is overkill for small teams - get it when you hit your stride. For now, focus on good proposal software that is easy to use, comes with decent automation, and has plenty of templates (and allows you to customize them). 

Each minute you save from RFP drudgery, you get to invest in value-added tasks. 

Learning Management Systems 

Why would you need an LMS for such a small team? Precisely because they're small! It doesn't make sense to hire/outsource a training team (particularly if you don't have a lot of attrition). Given that it's 2023, you're probably all working from different parts of the globe, so buddying up with someone is hard (though it is easier to listen in on their demos and pitches). Also, people learn at different speeds - doesn't it make more sense to let them do it asynchronously, and at their own pace? 

Therefore: LMS. Most tools come with basic content libraries on foundational topics. Training consultants today are happy to design specific training materials for you, which you can then deliver through the LMS. Keep an eye on feedback from the tool on which modules are working, pass and fail rates, and other good data to keep refining training. 

Moreover, most of these tools come equipped with great features that can inspire learning. I evaluated a bunch of them here. Some let you practice conversations with an AI-powered conversation simulator. Some let you upload recordings (with or without commentary), so when you have a really good (or a really bad!) demo, you can turn it into a learning moment. Most of them offer gamification. 

And then, there are product walkthrough tools that give your sales reps hands-on time with the product, letting them get intimately familiar not just with the feature set, but the use cases and solutions you offer. The more your sales reps train on the product, the more confident they'll be and the more they'll shine during demos. 

Demo automation tools 

Now, this one is rather close to my heart. You see, like many sales leaders, I believe that the sale really happens in the product demo. Sure, there are a million things that feed into the demo and those that follow after, but really, the client decides whether or not your tool is worth fighting for, in that demo. 

So your team puts their best foot forward through research, a good discovery, creating custom demos that highlight the customer's pain point and your solution, and then they create scripts and practice practice practice. Ideally. 

In the real world, however, it's a scramble. Your sales engineer is near burnout: he's churning out custom demo after custom demo, and despite creating great scripts, is still pulled into demos at the last minute! He has no work-life balance. Your reps, on the other hand, don't like the scripts. Each time a product demo is customized, so is the script. How many scripts can one sales rep carry in their head before mixing them up? Moreover, the product team keeps adding new features and doodads. Do they have the time and headspace to absorb all these changes? No. 

The result? Stilted demos where the sales rep defaults to listing product features in a spray-and-pray approach, and on seeing something unfamiliar or facing a question they don't feel equipped to answer, pull in the sales engineer. Who in turn, comes in halfway through the demo, without context, and does his best to play catch up. 

Who wouldn't burn out like this? I most definitely did. And in the middle of that burnout, I dreamed up SmartCue

I wanted to create a tool that takes the grunt work out of demo creation - Sales Engineers, Sales Enablement Managers, or Product Marketing teams can rapidly create custom, personalized product demos with loads of contextual cues. Yep, no more scripts. So no more memorization for sales reps and no more stilted demos

Sales reps can, instead, simply follow the cues that Smartcue presents to them (and only to them!) based on where they are in the product. It also provides a step-by-step demo playbook or demo flow, so the sales rep can simply follow the flow. It doesn't matter how many updates the product team pushes into the demo environment - the sales engineer can update the demo in real time, and the sales rep just needs to follow the flow. 

SmartCue also helps keep track of the agenda - the client wants to explore functionality out of turn? No problem! No more madly flipping through slides or moving your demo video back and forth. The sales rep just goes into the demo as always, and SmartCue will cue them based on wherever they are in your product. When done, it will cue them into what they can cover next, based on the agenda. 

Without all this admin, without all the memorization, without worrying about not having the information they need to talk about a feature or functionality they haven't practiced on, the sales rep is free to interact with your clients. They're present in the room. They're listening to what's being said (and not said) and they're responding with unhurried, quiet confidence. They're bringing all their scrappy, young, underdog energy to the fore, in the best way. 

They're being David to the Goliath teams employed by your competition, and they're winning.