Sales mistakes all startups make

We often think of Sales as the last step in a journey. You’ve spent years building a product, the website says what it does, there’s documentation and if that fails, there’s a drip campaign of emails.

But for your customers, Sales is the start of a process. And it takes work.

At Demo Gorilla, we’re nerds who’ve spent years learning how sales works and if you’re a nerd like us (or even if you’re just a normal person!) you’re probably making a few of these mistakes with your sales process.

You don’t understand your customer’s problem as well as you think

This is #1 with a <blink> tag, if you don’t understand why your product will get your champion promoted then you will fail.

You need to know the answers to:

  • What metrics is this department or role evaluated on? Over time you should become familiar with the most common ones in your customer base and what the most typical challenges are to hitting them.
  • What are the key strategic initiatives going on at this company. You don’t need to overdo this, but this should flavor all of your discussions; if they are looking to speed a process up, those are the kinds of examples you use – if they are expanding to a new market, you’ll use different examples.
  • What are they doing now & what are the drawbacks?
  • What other options are they considering? Obviously ask about competitors, but are they considering anything else: hiring, out-sourcing, building in house?

Your customer doesn’t have the context

You spend 80 hours a week thinking about your product, your company, and the future of your space. That’s great! But if your customers did that, they’d be you and wouldn’t need to buy anything.

That means it’s on you to:

  • Set the stage for every call: “Because of [strategic initiatives] and [challenges with old way], we’re looking at how we can [solution]”
  • Expect to repeat yourself
  • Know what are the ~3 takeaways you want everyone to remember.
  • Expect to repeat those takeaways
  • Keep notes in between sessions and remind everyone what was decided. People can change their minds, but in general the n+1 th meeting should be built on meetings 1 though n and if things have changed, that’s a learning. (We obviously love using Demo Gorilla’s notes and prepared notes for each call to help with this)

You don’t understand the market

When you learn they are considering a competitor, be ready to speak to how they can’t solve the customer’s problems as well as you.

Know their weaknesses and strengths, nothing is more convincing then “Competitor X is focused on different customer problems, they are great for companies who Y, but won’t work for you because of Z”

Don’t forget that your #1 competitor might not look anything like you, it might be a complicated Excel spreadsheet that’s constantly breaking, a subcontractor that does it manually at ten times the cost or even an competing internal project from their own engineers.

Have battlecards, and have them at everyone’s fingertips. Make sure it’s someone’s job to track all of your competitors and keep the battlecards up to date. Unfortunately your competition won’t make it easy on you :) Demo Gorilla does make it easy to track and share battle cards – and know when they are up to date.

Your customer doesn’t see themselves in your pitch

From start to finish, you’re telling one clear story: once the customer implements your solution, a specific problem will go away, their jobs will get easier

Does your decks start with slides about you or about customer problems? How many minutes of the call does that take up? When you get to the customers’ problems, how many really apply to that story for each and every customer? When they are listening to your story, do they see themselves as the protagonist.

You don’t connect emotionally

When you’re weaving your story, make sure to:

  • Refer to the metrics & strategic initiatives that your audience cares about and show them the features that solve their problems (we’re here to help with that)
  • If they have an existing account, demo from within that environment. Next best is a demo environment that matches what they’d see in production but whatever you demo from, make sure it has enough data to tell the story. (Demo Gorilla works from any environment: a sandbox, a demo account or the customer’s own account)
  • Use the closest possible customer case studies (Tip: Use Demo Gorilla actions to inject just the relevant examples)
  • If you have to use a deck, customize it to each customer (or use a tool like

You don’t know all your stakeholders

There’s a cliche in car commercials where one spouse surprises the other with a new car – and yet I’ve never met a couple that operates that way (though I’m sure they exist).

A B2B sale always involves multiple people, you need be able to identify the key ones to stand a chance of closing the deal.

Generally there are a few personas:

  • The champion: If they buy your product, their job gets a lot better – they may even get promoted. They’re the person who is investing their social capital to make the purchase happen. You generally enjoy talking to this person, and probably over-invest on average.
  • Detractors: These are people who either like the old way of doing things or are unsure if the new way will be better. Their level of push back could be anywhere from not wanting to re-learn how to do things all the way to worrying that your product will replace their jobs. You are almost certainly under-investing in understanding these people, you may not even know who they are.
  • The budget holder: There was a time when this was the person you wooed with steak dinners after you let them win at golf. Maybe some deals are still done that way but now it’s more common to go with the team’s recommendation. The days of buying crappy software and forcing the team to use it aren’t gone, but those rules don’t apply to you. You need to understand this person’s criteria: budget, timeline, where this sits in their priorities, and what the company initiatives are.
  • Technical experts: This could be a security review, or someone setting up a PoC. Generally they have a checklist of specific criteria and will verify that your product does them. Sometimes they’ll give you the checklist to fill out (e.g. security questionaries) but expect some back and forth. If they are doing the review, you must have this checklist and help them through it. You should have helped write it. Anything that is a common question should be on your website or in a document you give them. Nobody on either side likes this part, make it easier than your competitors.
  • Procurement: Generally by the time you’re talking to procurement, the deal is yours to lose. They are incentivized to cut some $$$s of the end price but you’ve earned this, don’t give out discounts lightly

Sometimes your champion doesn’t have the juice to get a deal done, or more likely doesn’t know all the steps in getting a deal through procurement. A key part of sales is figuring out how to navigate the org chart to make the deal happen.

You are in love with your product, they just want their problem solved

It’s easy to sell past yes, and for some reason it’s hard to end a meeting early.

Once they know what they need to, stop talking. Taking a breath will not kill the deal.

Don’t show every bell and whistle of your product, you want to convey two things:

  1. Giving you money now will make their problem go away
  2. You are someone safe to partner with for the long term

Once you’ve shown that the product will solve their problem there is no benefit in walking them through every feature.

Beyond grinding the energy of a call to a halt you also invite questions about whether or not they need feature X. Is there a pricing plan without it? Do I need to understand & configure all of these features to see the benefit?

Obviously we’re biased but, depending on your product depth, some or most of your features should only be demoed upon request. Integrations are the canonical example, you only need to demo Slack OR Teams – or neither at all unless ChatOps is a key part of your use case.

Show value not features

Show don’t tell! And when you show, resist the urge to say “And now I click here”!

You know you should be using sentences like “we need to X because of challenge Y, you can see how feature Z allows us to do that”

That’s why Demo Gorilla has dynamic talking points that change as you go through the product. Keep the focus on the value in the talk track, while you re-enforce it on screen.

Let us help you sell more product