Strategy
Startups

How to Run a Software Pilot Program - B2B Do’s and Don’ts

Learn to create and run a pilot SaaS program. Andrew's shares best practices for B2B SaaS pilot programs to acquire your first paying software customers.

9 min
June 30, 2023
Andrew Verboncouer
Partner & CEO

If you have a B2B SaaS product almost ready, but you haven’t been able to onboard any customers yet, you’re in the right place.

These insights are gathered from all the different software pilots we have helped run over the past decade for my own startups or with Headway clients and their stakeholders.

If you have any questions, send me a DM on LinkedIn.

You'll learn how to

  • Acquire those crucial first customers
  • Create and manage your first software pilot plan
  • Understand what to measure and why
  • Structure ongoing calls for continuous feedback
  • Use your experience to guide your growth and pitch to investors with confidence

The goal: getting closer to your customers

“The greatest obstacle to discovery is not ignorance, it is the illusion of knowledge”

- Daniel J. Orsten

A common problem for first-time founders

They think they know

  • What customers want
  • What customers need
  • The problem that is most important to solve
  • That their solution idea is the answer they are looking for

For many founders, there is an illusion of knowledge

That their original solution idea is the answer. Rather than focusing on people and gaining a deeper understanding of their world.

Focus on people, not forcing your solution

Focus on customer problems more than your current solution is vital to making a software pilot program successful. This empowers you to adjust your product or even pivot to a more valuable opportunity.

Benefits of a software pilot program

Capture motivated early adopters

You want people who are willing to try new software. These are also people that are experiencing the pain product can solve today. “Curious” people aren’t usually a good fit. Find people who are excited to provide feedback and use what you have to offer.

Trying to seem bigger than you are isn’t a good thing early on

You will lose trust quickly with early customers with this dishonest approach. It may seem like a good idea to act like a big company, but lying will only create skepticism.

Develop deep empathy for the problem

Taking what you know and building upon it. Get deep into the weeds with the customers you are serving. The insights are valuable for every part of your business. Product marketing and messaging included.

Learn what aspects of your current solution hit or miss the mark

How do you challenge the assumptions around what people will do with your product or the way they get the job done?

  • Where were you wrong?
  • Where were you right?
  • Why?

Convert pilots into long-term customers and evangelists

You need to make money. A pilot program should be designed to understand how to create benchmarks and what’s working for customers. How has the pilot program benefitted these early adopters?

Capturing this data can help you gather powerful testimonials and case studies for when you want to scale up acquisition.

Inform roadmap, investment case, and market opportunity

You’ve either raised a pre-seed round or bootstrapped, but where do you go from here? 

You need to put forward proof that someone wants this and will pay for it.

Software pilots will help you gather the evidence you need to raise the next round, know what to do next, and see the best opportunities for growth.

Comparison of PLG vs SLG for pilot performance

PLG vs. SLG for early customer acquisition

Product-led growth has been getting a lot of attention lately, but the real question becomes, “Is PLG right for you, and what you’re solving today?”

Let’s walk through why product-led growth isn’t usually a good fit for B2B software pilot programs and why sales-led growth is a better option.

PLG pilot programs diagram

The problem with PLG for B2B software pilots

Lack of context

You only have assumptions here about who they are, what they care about, and what they hope to do with your solution. It is essential you learn as much as you can about who are the first users of your solution.

Lower quality leads

Getting too many of the wrong early users can cause more problems rather than help. You want to make sure you are learning from people that care about how your product could help them. Not just “curious.”

Lower activation

When you have lower-quality leads and a lack of context, you’ll likely see lower activation inside your product. And sadly, you might not know why.

Pilots are meant to create more clarity, not more confusion.

SLG pilot programs diagram

Why SLG is the way to go for pilots

With sales-led growth, you’re more likely to get the right early customers. Why is that?

Going sales-led with early users for your pilot gives you the clarity you need to understand what works, what doesn’t, and who is the best fit for your product.

How to run a pilot program for B2B SaaS

Never run free pilots

By doing this, your customers are automatically more invested in the process, and you’re more likely to avoid them signing up for an account and never getting back to you.

It also helps you screen for people who are motivated to act, and that’s what you should be looking for in a pilot program.

Never send new information over email, text, or PDF

Sharing new information via email is like sending it out into the abyss. You are limiting your ability to learn from that conversation, refine and craft your message better and get the raw, honest feedback from your customer that you would in person.

Never end a meeting without booking the next meeting

BAMFAM it. “Book A Meeting From A Meeting”

We recommend this practice to all of our startups. Make sure there is always a bookend of the process as you’re talking with someone in the pilot program, and they always know when that next point of contact will be. It’s important to remember this is an ongoing relationship you’re building - it’s not transactional.

You really have to be the concierge of your product and your business by setting up these regular cadences.

Don’t skip parts of the process

Slow is smooth, and smooth is fast.

When you’re talking to people in your network, it may be easy to skip ahead and assume the information you already know or assume problems they have.

In skipping parts of the process in discovery and understanding why they may or may not be the right fit for your pilot program, you lose the ammunition you need in that sales process.

Don’t expect customers to self-onboard, activate, and retain

Remember it is your job to guide customers on this journey, even as they’ve already committed to the process. The success of your program relies on how much care and attention you give your customers in the beginning stages. 

Ultimately, this will shape how you grow later by helping you have a greater understanding of the people that you are serving.  

Measure everything

Learn WHAT and WHY.


It’s important to make sure your product is metered, ensuring you have the right journey mapped out, discovering where people are dropping off, and then understand why.

This helps you build a better case moving forward or understand where you might be just plain wrong. Don’t forget the goal of the pilot program isn’t to grow and scale, but rather to gain a greater understanding of the customer and how your product meets their needs.

Your first 5 pilots

It can be intimidating to do this for the first time, but running a successful pilot program always starts with just giving it a try. This first batch of customers will share feedback and get your closer to the desired outcomes you want.

Start in-network. Ask, “Who else?”

If you’re starting a product in an area you don’t have the expertise, it could be a long journey for you.

I’ve seen many founders create innovations and products in spaces they aren’t really involved in, and that’s not a bad thing. The tough part comes when you can’t name your first 2-3 customers. When you don’t have anyone you can name that you think would be able to give you really great insights.

Knowing who those first few customers could be will ultimately help you build better case studies and inform running a successful pilot going forward. 

Limit to 3-5 customers

If you have worked in sales, you may be familiar with 100 Million Dollar Offers. A big component of that is the idea of scarcity and urgency.

If you’re pitching like you’re a big dog and want to compete with the who’s who in the industry, they’re going to compare you to them. But if you’re able to create a small scale pilot program where you’re limiting to 3-5 customers, you will create the feeling of scarcity and urgency that if they want to be an early adopter and part of the program, they need to act now.

Don’t hide that your product is new

Use it as a benefit and a feature of working with you. They get to help shape where this goes, and they get this tech-enabled service, the customer success calls you’re going to have, the understanding and hands-on approach you’re going to take to make sure they’re successful in the product. 

Focus on providing a tech-enabled service

Your software login doesn’t have to do everything. It just needs to be a viable option to help them solve a problem.

In the early days, it is really easy to set up recurring billing outside of the platform. 

Set up a regular cadence and commitments for both parties

When signing the pilot agreement there’s a price that they’re paying, which is probably a discounted price. Being clear about what that looks like and getting a commitment from them will help you gain the insights you need to help change your product over time. 

Selling your SaaS pilot

Understand what today looks like

Early on it can be attractive for first-time founders to say “I think our product fits what they do”. It’s easy to want that early revenue, but unfortunately it may not always be the right fit to provide you the right feedback you need. 

Get a benchmark of their tools, processes, and current state of performance

You need to track the progress of each lead and pilot user. Gather what you’re trying to change for them, the problems they are facing, and how that makes them feel. This data helps you learn how to resonate with customers faster for future sales calls.

This will help you have clear data on where they are before and after the pilot program

This is great for case study preparation! 

Set metrics for success against benchmarks and absolutes

As you get users into the pilots, you can now track against the benchmark data you gathered before they started. You can use this data to improve the product, know where to double down and create strong case studies.

Set the right expectations

Trying to sell yourself as this fully-buttoned-up company that is ready to scale is setting the wrong expectation for you and will lead to a lot of stress behind the scenes trying to keep up that appearance. 

It’s also the wrong expectation for your customer because they are going to hold you to that standard throughout the process.

Instead, provide more value through services, through your time, understanding, and digging into their needs. Then try to augment and change the roadmap where it makes sense.

Guide the process, share implementation timelines and steps

A lot of times in B2B and Enterprise depending on who you’re selling into, you can get bogged down with the steps from that initial yes to activating them on your platform.

The clearer you are about those needs, the better your program will run.

The worst thing you can do is get a yes from someone, and not know what the next step is. 

Example of a software pilot plan template

example of a software pilot plan with a 2 week schedule

Ongoing call structure

Typically, I think a 30-minute structure works really well for the ongoing call structure within your pilot program. This could be on a every two-week or even a monthly cadence depending on the involvement of your team and customers. Though early on, we had the best results sticking to a 1-2 week schedule. 

Here’s what that call structure looks like

5 min - Build rapport and catch up

5 min - Review the latest metrics and feedback

5 min - Identify key areas to support and improve

10 min - Share upcoming improvements and releases

5 min - Closing thoughts, next steps, schedule deep dive if needed

Creating a continuous impact loop to improve and prepare for public launch

Example: Focusing on customer activation

A pilot user agreed to join. But they aren’t using the product as expected.

What can you do?

Exploration can help you understand why.

Use customer data, shared feedback, and interviews to identify opportunities for improvement.

continuous discovery loop diagram

Testing improvements

Then, you can design improvements to reduce friction in the onboarding, test it with customers that can share feedback, and implement it into the product after refinement.

This is all a part of our continuous impact loop process that focuses on impact product and business metrics in a repeatable way. When you pilot SaaS for B2B it's important to stay focused.

Want help running a SaaS pilot?

If you have some quick questions for a pilot you are already running, feel free to send me a DM here on LinkedIn.

If you haven't started yet and would like to leverage our SaaS pilot process and coaching program, you can book a free consultation to learn more.

Actionable UX audit kit

  • Guide with Checklist
  • UX Audit Template for Figma
  • UX Audit Report Template for Figma
  • Walkthrough Video
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