Pilot Phase: Top 3 Reasons Pilot Projects Fail

3 reasons b2b startups fail in the pilot phase

The pilot phase is the most critical phase of your b2b sales journey.

So let’s talk about a topic that’s near and dear to every entrepreneur’s heart: pilot phase failures.

Nothing stings more than putting your blood, sweat, and tears into a customer pilot project only to watch it crash and burn.

So what’s the deal? Well, there are three big reasons why pilots fail: poor product, weak messaging, and wrong customer. But don’t worry, I’ve got you covered. In this post, I’m going to give you a deep dive into each of these reasons and share tactics that I used to flip the story and achieve > 80% pilot success.

Pilot Project Failure #1: Your product Just Isn’t Good Enough

This is an obvious reason why you don’t succeed in the pilot phase. If your product doesn’t do what you say it will do, then you don’t have a shot at winning a b2b customer. Remember your customer signed up for a pilot because you promised them X, now they are validating in the pilot phase that you can actually do X.

  • Is your product buggy?
  • Perhaps it only has some of the features that your customers need
  • The UI/UX is terrible and customers just can’t figure out how to use it
  • It’s a me-too product and there’s no real benefit to switching away from what your customer is currently doing
  • The value is so less that a customer would rather keep doing things the old way

If you’re in the early stages of building a product, I urge you NOT to get excited and overstate your product’s capabilities or benefits. Especially if you’re building a deep tech/hard tech product. Be clear on where you are in the product commercialization journey (alpha/beta/limited release/full commercial launch).

Overselling will initially get you a lot of positive hype and pilots lined up, but what you really do is set yourself up for failure because customers will surely be disappointed when your offering doesn’t match the pitch. Underpromise, overdeliver.

How to overcome product weakness in the pilot phase

  • State clearly What You Do, Who You Help, and How You Do it (1-sentence value proposition)
    • In my case, “SIERA.AI helps warehouse and factory managers digitize paper inspection checklists, reduce forklift accidents and track bad behaviors with our AI-enabled IoT devices and web dashboard.”
  • Tell your potential pilot customer what the product can do today and what immediate benefits it brings
  • Share what the next 6-12 months look like on your product roadmap and tease the future benefits (do not put specific dates)
  • Be careful not to focus too much on future features and value because it might give the customer an excuse to push a pilot by a few months
  • Ask your customer this, “Will it be a bad idea to run a trial for X in your business?”

Pilot Project Failure Reason #2: Your Messaging Is Weak

You might have a great product, but you’re not saying the right things to customers before, during, and after the pilot to convert the deal. Here are the top 3 messaging mistakes founders make in the pilot phase:

  • Not defining what success looks like before a pilot starts (only run the pilot if you’re at least 80% confident of meeting the criteria OR change the criteria). Remember, a pilot is a bridge to a deal. Make sure you build the bridge on day 1.
  • Not packaging and delivering value during the onboarding, execution, and closing of a pilot. You need to deliver a magical pilot experience. Go the extra mile to share training videos and documentation, handhold your customers, deliver weekly project updates with data/insights and finally wrap up the pilot with a beautiful presentation detailing the before and after transformation. Oh…btw, make sure ALL the stakeholders who are critical to buying your product are aware of the progress via an email chain or regular zoom calls.
  • Not planning for what a potential pilot conversion looks like. Ask this simple question, “If this pilot is successful, what does a potential rollout look like? And do you have a budget already allocated for it?”

Pilot Phase Failure #3: You’re Selling to The Wrong Person

When you’re doing b2b sales, you will end up selling to a committee of some sort. Make sure that the person (decision maker/ buyer) who signs the check wants the pilot, and is in on the demo calls and part of the pilot update meetings and email chain.

Many times, b2b deals are lost simply because the decision maker loses interest in your project and moves on to other critical areas in their business.

Here’s what I learned about titles and decision-making authority in mid-market/enterprise b2b sales:

  • Engineering/IT – Blocker, 0 authority, has the ability to block a deal if tech due diligence fails
  • Manager/Senior Manager – Influencer, no real authority, can help you navigate the deal
  • Director/Sr. Director – Mini decision maker, some authority, can sign small checks
  • VP/SVP – Major decision maker, has the authority to approve big purchases up to a limit
  • CFO/CEO – Final decision maker, for certain large deals, the project might have to be approved by the CFO/CEO


Traveling the pilot phase is a necessary evil for b2b startups. Nevertheless, startups can even get crushed under a pile of pilots. The path to success lies in having a strong product, a carefully crafted narrative, and a focus on your ideal customer profile (ICP) where you’re most likely to succeed.

BTW, If you’re looking to sign up your initial b2b customers, I wrote a quick article here on an exact framework to get your first 10 customers.

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