A Practical Guide to Running Effective Product Pilot Programs

Jon Schipp
Dec 13, 2025
14 min read

This article was written entirely by the author, and then polished using AI.

I love running product pilots. It’s one of the best ways, if not the best way, to test the value, viability, and scalability of delivering a solution and make corrections before it’s in-market. We will demonstrate how to do this with low-cost tools like spreadsheets, document writers, and surveys but first let’s start with the basics.

What is a Pilot Program?

Product pilot programs are small-scale, time-boxed experiments that let you validate a new product, feature, or service with a limited audience before committing to a full launch. They reduce risk, sharpen product–market fit, and help you operationalize how something will work in the real world.

A pilot sits between “we think this works” and “we know enough to launch confidently.” It is the last major validation gate before public release.

Now that we understand what a pilot is, let’s talk about the two types of pilots that are most commonly used.

Free Vs. Paid Pilots

There are two primary types of product pilots: free and paid. A free pilot typically drives higher participation, but often at the cost of depth and quality of engagement. These pilots tend to run longer, as participants are less incentivized to prioritize usage when there is no financial commitment. Free pilots are most effective in high-uncertainty environments, where the objective is to validate the core thesis and value of an early or immature product rather than refine usability. In this context, you are effectively selling a vision and gathering broad, directional feedback.

However, increased participation in a free pilot does not necessarily translate into a stronger signal of willingness to buy. Because customers are not paying, hands-on engagement is usually lower, and progress can stall without active leadership. Successful free pilots require significant effort from the vendor, including strong communication, proactive guidance, and ongoing coordination to keep participants engaged and moving forward.

Paid pilots, by contrast, validate true willingness to pay and naturally result in a smaller, more serious cohort. Customers have higher expectations and prioritize usage, which places greater operational demands on the vendor—particularly in areas like technical support and onboarding. Paid pilots are best suited for products that are closer to beta, where the focus shifts toward usability insights, workflow optimization, and maximizing customer value prior to a general release.

In both models, many of the inherent tradeoffs can be mitigated through a disciplined recruitment process that targets a strict ICP, or by running a highly structured, time-bound program designed to maximize learning efficiency.

Pilot programs are great options when

You’re entering a new market segment.
The stakes of failure in a broad release are high.
The product requires real-world environment testing.
You need evidence to justify further investment.

Pilots are optional for low-risk features and mandatory for products with large unknowns.

Pilot Goals & Objectives

As with any initiative, success starts with clearly defined goals. A pilot program should be intentionally designed around what you want to learn and validate, not treated as a loosely guided experiment. Well-crafted goals ensure the pilot drives meaningful outcomes. High-level examples of pilot goals are the following

Validate Product Value
Pressure Test Operational Readiness
Identify Areas of Friction Early
Hone GTM Before Launch
Create Reference Customers

I like the OKR format, and will show a few examples below.

Objective 1: Identify key customer & operational needs to address before launch

Average customer onboarding time ≤ 10 days from contract to first value
Define a support headcount model that scales to 20 customers per support FTE
Identify and resolve 100% of the top 3 product gaps prior to GA
Support ticket volume ≤ 2 tickets per customer per week after pilot completion

Objective 2: Test product market fit from existing customer base

Recruit 15 qualified pilot customers within 45 days
50% of participating pilot customers convert to paying customers within 30 days of pilot completion
2 reference customers willing to provide a testimonial or case study
Net Promoter Score (NPS) ≥ 30 among pilot participants

Pilot Structure

Now that the goals are set, you will want to design a pilot program that is aligned with, and aimed to achieve those goals. Structuring your pilot includes some thinking and then developing artifacts like RACIs, messaging, documentation, timelines, and slide decks. These will be used for leadership alignment, and enablement for team members which will be part of the program team.

One of the key things to determine is the structure of the pilot. Will a fixed number of say 15 customers provide you with enough learning? What if you want to run a larger cohort of 45 customers but only have a capacity to handle 30 at a time? Then you may need to structure a rolling pilot, where you can take on new customers as others end. What if you’re really geared for early market validation, and there’s a strong belief in the vision, and pressure for near-term ARR? You may want to try a more scaled pilot that can reach a larger number of customers but will require more investment and sales force mobilization. There’s no right answer. Determine what’s the best fit based on your goals, company strategy, and dynamics.

Some of the other key questions to answer that help drive the pilot structure are the following

Will this be a free or paid pilot?
Who is your pilot team, and what are their responsibilities?
What is your pilot customer capacity?
What are the pilot touch points?
How long will the pilot run for?
How and when will the pilot end?
How are customers going to derive value throughout the pilot?
How are you going to derive learnings throughout the pilot?
What is the process for enrolling customers in the pilot program?
How many customers will you be recruiting, and who owns the recruitment?
Who supports the customer?
How will you track and report out on pilot progress, and to which stakeholders?
What happens after the pilot ends? (hopefully pledges or conversions!)
Can customers convert to paid customers?
Are SKUs available, and is there a quoting process?

It’s best to develop an internal FAQ for these questions. For a pilot FAQ, I recommend the following questions in addition to what’s above:

Quick, what’s the most important thing for me to learn?
What is this pilot and why should I care?
How does this pilot help us achieve our strategy?
What’s the criteria for the pilot program and how can I get my customer into it?
What’s the Ideal Customer Profile (ICP)?
Do any of our key competitors have this capability?
Is there a planned public launch, and if so when is it?
Is the pilot offered globally, or for specific markets?
Is there a migration path from pilot to paid, or public launch?
How will customers be supported during the pilot?
I want to talk to my accounts about the pilot to gauge interest, how should I approach that?
How is this going to be sold?
What are the SKUs?
How is the product fulfilled?
Is there anything special I need to do on a sales order?
What currencies are supported?
Will I be getting compensated? What’s in it for me?
What can I do to help?

Now that we have a sense of structure, let’s dive deeper into some of the key areas starting with the Ideal Customer Profile (ICP).

Defining your Ideal Customer Profile

Before recruiting customers for a pilot, you must first clearly define your Ideal Customer Profile (ICP) along with any adjacent ICPs you intentionally want to include. This is not a formality; it is the foundation of effective pilot recruitment and the first question sales and marketing teams will ask when identifying candidates.Your ideal customer profile may look something like this:

Heavily regulated industries e.g. financial services, healthcare
Revenue above $500m, or greater than 3,000 employees
Geographic location in North America and EMEA
Product targeted to a team size of at least 5
Has x, y, z regulatory requirements
etc.

This definition should be explicitly documented and shared with sales, marketing, and customer success teams to ensure consistent qualification. Just as important, clarify how strictly the criteria should be applied. Does a customer need to meet every requirement, or is satisfying two-thirds of the profile sufficient? Make that guidance explicit to avoid ambiguity during recruitment.

In addition to your core ICP, consider defining one or more adjacent ICPs to deliberately test the boundaries of the opportunity. These might include customers that are slightly larger or smaller, less regulated, or operating in a neighboring vertical. Including these edge cases in a controlled way allows you to assess expansion potential without diluting the core learnings of the pilot.

Pilot Product Deck & Messaging

If you want customers to join your pilot, you first have to sell them on the vision. Clear, compelling communication is essential, which is why I strongly recommend creating an unofficial, customer-facing sales or GTM deck at the outset of the pilot. This deck becomes one of the most valuable early artifacts, not only for articulating the pilot, but also for continuous testing and learning.

I create this deck at the start of nearly every product initiative, with the expectation that it will evolve week over week based on real customer feedback. By the end of the pilot, it should closely resemble a polished, launch-ready sales deck. Along the way, it serves a dual purpose: aligning internal teams around the value proposition and clearly communicating that value to prospective customers.

The secondary, and equally important, function of this deck is feedback. When presenting it to customers, I explicitly frame it as a work in progress: “This isn’t a marketing-approved deck yet, and I’d love your honest feedback as we walk through it. What resonates, and what doesn’t?” This framing lowers the stakes and invites more candid discussion.

When reviewing customer reactions, pay close attention to:

Which slides do the most questions arise from?
Are there repeated questions that are not answered in the slides?
What facial expressions or movements (e.g. head nod) do specific slides elicit? (look for confusion, boredom, agreement, etc.)
Asking direct questions such as if they prefer slide A or B? Which one makes the most or least sense?

This qualitative feedback is invaluable for refining messaging. In practice, after five or so customer conversations, you’ll usually have a clear signal on what’s working, what isn’t, and how to improve the narrative.

Pilot Recruitment

Once the ICP and core messaging are defined, the most effective way to recruit pilot customers is by aligning closely with sales leadership. I typically start with an alignment session that includes a small group of sales leaders from the regions and segments I’m targeting. The goal is to walk them through the pilot overview, ICP definitions, success criteria, compensation considerations, and to gather candid feedback.

By the end of this session, you should be able to identify potential champions within the sales organization and determine which account executives or customer success managers you can partner with to support recruitment. Credibility and trust with sales leadership are critical here, without them, pilot recruitment will stall before it starts.

From there, work directly with account teams to build a list of customers in good standing who are strong candidates for the pilot. Track this list in Salesforce, a shared spreadsheet, or another system of record, and define a clear recruitment plan. If you’re leading the pilot from a product perspective, I strongly recommend that you personally run the initial customer conversations. At this stage, the product isn’t publicly available, and product leaders are typically best positioned to articulate the long-term vision and context.

This approach also reduces the burden on account teams, who may hesitate to recruit customers into a pilot they don’t yet feel confident “selling.” I usually position this as me doing the heavy lifting: account teams simply make introductions, while I handle scheduling, communication, pilot overviews, and demos.

Because customers are doing you a favor by participating, thoughtful incentives matter. Some customers will have an urgent unmet need and require little convincing; others will need more context to determine whether the pilot is worth their time. Be careful here—misaligned incentives can attract the wrong participants and undermine the pilot’s outcomes.

Incentives should reinforce the goals of the pilot, such as early-access pricing, below-market discounts, or priority influence over the product roadmap. Clearly communicate these incentives to both account teams and customers so expectations are aligned from the start.

For small pilot cohorts, word-of-mouth recruitment through trusted account teams is often the simplest and most effective strategy. If you need to recruit a larger group—or are struggling to generate interest—an email or product-led growth (PLG) campaign can be a useful next step. That said, pilot programs should be introduced carefully to avoid distracting account teams from quarterly revenue goals with a premature offering. This is why I prefer starting with targeted, relationship-driven outreach and expanding gradually.

As recruitment scales, you can widen the circle by engaging additional sales leaders, solution engineering leadership, or enabling select solution architects to help identify and qualify candidates.

Email or PLG campaigns don’t need to be complex. A simple banner or in-product message with a clear call to action—such as “Learn more” or “Express interest in the pilot”—is often sufficient. Once customers opt in, you can follow up with more targeted outreach and qualification.

When speaking directly with customers, showing is always more effective than telling. I typically structure these conversations with three phases. The first 10–15 minutes are spent learning about the customer: their business, team structure, pain points, and whether they’re actively seeking a new solution. This helps validate fit before moving forward.

Next, I move quickly into a demo, “Let me show you an early preview of what we’re working on”. Even a rough demo grounds the conversation and makes the vision tangible. Finally, if the customer is engaged, I introduce three to five slides that outline the pilot program itself, including time commitments, touchpoints, responsibilities on both sides, and the support model. Transparency here is essential for recruiting the right customers.

I close by asking whether they’d like to participate or need time to think it over, offering a follow-up call if helpful. Some customers will commit on the first call with a tentative start date; others may need two or three conversations. When a customer decides to move forward, I use a simple written sign-up form—either completed live on the call or sent immediately afterward—to ensure clarity and momentum.

As the program grows, you won’t be able to personally handle every recruitment call. To scale, document your messaging, record calls using tools like Gong, and turn early wins into enablement assets. Once you see initial success—such as multiple customer sign-ups—I typically run one or two enablement sessions with account teams. Seeing real customers commit builds confidence and enables others to help scale recruitment effectively.

Pilot Process

To run a smooth and repeatable pilot program, you need a clearly defined process that is documented, shared, and consistently followed. Pilots fail when ownership is ambiguous or execution varies from customer to customer. A well-structured process creates alignment, reduces friction, and makes the program scalable.

For simplicity, the example below assumes three primary facilitators of the pilot: the product leader, sales engineering, and the account team. The first step is to define ownership using a RACI model so everyone understands their role at each stage of the pilot.

Task	Product Leader	Sales Engineer	Account Team
Cust. Recruitment	Accountable	Consulted	Responsible
Pilot Overview Call	Responsible	Informed	Informed
Product Scoping Call	Accountable	Responsible	Consulted
Tenant Provisioning	Informed	Responsible	Informed
…	…	…	…

Once ownership is clear, document the end-to-end pilot workflow from initial account identification through final customer feedback

Account identified by Sales Leadership, E-mail Campaign, or PLG
Sales to Send Recruitment E-mail to Account, CC’ing Product Leader
Schedule Pilot Overview & Demo Call with Product Leader
Product Leader to send Pilot Next Steps E-Mail & any other details requested by customer
Receive confirmation of pilot participation
Schedule a Product Scoping Call led by Sales Engineer
1. Gather account info, necessary features, use-cases, define success criteria, and agree to start date
Sales Engineer to provision tenant to customer
Sales Engineer to schedule POC Kick-Off Call
1. Getting Started: initial configuration, access and guidance
Sales Engineer to schedule Weekly Check-in Calls
1. Driving value on use-cases and success criteria
Product Leader to schedule Final Pilot Call -
1. Gather feedback, review Success Criteria with customer
Product Leader to align with Account Team on Next Steps
Report out in Internal Monthly Leadership & Feedback Sync

In practice, this process should be fleshed out further with clear expectations for each touchpoint, example agendas, and lightweight email templates that account teams can reuse. The more explicit the process, the easier it is to execute consistently, and the more confidence teams will have in running pilots at scale.

Pilot Tracking & Learnings

The purpose of a pilot is not simply to run an experiment, it’s to generate insights that improve both your product and your GTM strategy. To do that effectively, you need a deliberate system for capturing, synthesizing, and reporting learnings. Without one, pilots devolve into anecdotes and opinions instead of actionable signal.

I group pilot learnings into two categories: qualitative and quantitative. Capturing both is essential for developing a complete picture of what’s working, what isn’t, and why.

Qualitative

Qualitative data helps explain why customers behave the way they do during a pilot. Common examples include:

Capturing feedback gathered from customer calls
Collect written feedback from e-mails and surveys
Customer health or sentiment scores
Feature requests and detailed bug reports

Quantitative

Quantitative data shows what is happening across the pilot cohort and allows you to measure progress objectively. Examples include:

Number of customer recruited into the pilot
Pilot activation & ongoing participation rates
Percentage of defined use-cases or success criteria achieved
Conversion outcomes, including committed or purchased revenue

Together, qualitative and quantitative signals create a balanced feedback loop

Tracking Every Customer Matters

Every customer offered the pilot, regardless of whether they accept, should be tracked. A “no” is just as valuable as a “yes.” Declines often reveal patterns around ICP fit, messaging gaps, pricing sensitivity, or timing issues that are critical to understand before launch.

I typically use a simple but robust spreadsheet to track pilot activity. As the product leader, I spend significant time maintaining this tracker and using it as the primary input for reporting and decision-making. It quickly becomes one of the most important tools in the pilot program.

What to Track

In addition to basic participation status, consider tracking:

Pilot start and end dates, including total duration
Number and type of customer touchpoints
Pricing estimates or calculators to quantify pipeline potential
Customer region or geographic segment
Existing products owned or in use, especially competitive notes
Potential expansion opportunities uncovered during the pilot (e.g., services, add-ons, or adjacent products)

In my most recent pilot, I tracked more than 30 distinct data points per customer.

While a tracker is necessary, it isn’t sufficient. You also need a structured way to capture feedback on the product, the pilot experience itself, and operational interactions with your team. These insights should be documented consistently and stored in a shared location that’s easy to reference and analyze.

Some example feedback questions include:

Operational feedback: Are you MORE or LESS likely to participate in future pilot offerings?
Product feedback: Are you MORE or LESS likely to explore solutions from other vendors?
Product feedback: How LIKELY are you to purchase the solution?
Strategic feedback: Should we continue launching this product?

These questions are particularly effective when delivered through structured surveys, allowing you to aggregate results and identify trends across the cohort.

Ultimately, the value of a pilot is only as strong as the learnings it produces. A disciplined approach to tracking and feedback ensures those learnings are visible, actionable, and directly tied to product and GTM decisions.

Pilot Completion & Next Steps

Every pilot program needs a clearly defined end. Without explicit exit criteria, pilots have a tendency to drift: customers continue using the product indefinitely, vendor expenses accrue, expectations blur, and learning velocity slows. To avoid this, you must establish a consistent and repeatable way to determine when a pilot is complete.

Pilot completion can be time-based, use-case–based, or triggered by a specific customer signal. While some flexibility is reasonable, it should be the exception rather than the rule. For example, if you define a three-month pilot as the standard duration and a small number of customers exceed that window, the priority should be understanding why and working with them on a clear exit plan. A short extension, two weeks or a month, may be appropriate if it aligns with your goals, but indefinite extensions should not become the norm. If that’s the case, you need to revisit your pilot structure and process to determine the root cause.

To recap

Time Based - The pilot ends after a fixed period of time has exceeded
Use Case Based - The pilot ends when defined use-cases or success criteria have been met
Milestone Based - The pilot ends after pre-defined customer milestones have been achieved
Hybrid - Criteria from all the above determines the end of pilot

Once exit criteria are defined, every pilot should conclude with a formal completion call. This is where you review outcomes, validate learnings, and align on next steps. It’s important to explicitly invite candid feedback during this conversation. Give customers permission to be direct: “We want your unfiltered, honest feedback. This is how we improve and avoid repeating mistakes.” These discussions often surface the most valuable insights of the entire pilot. Be sure to also thank the customer for their participation in shaping the future of your product and business.

If your goal is conversion, whether from a free pilot to a paid plan or from a paid pilot to a longer-term contract, commercial readiness is essential. Pricing and operational mechanics must be defined before you attempt to close.

Key questions to have answered include:

Is tentative pricing established and approved?
Are SKUs created and available?
Can sales and revenue operations generate a quote?
How is revenue recognized and allocated?

Failing to prepare these details in advance introduces friction at the moment of highest customer intent. You don’t want to be in a position where a customer wants to give you money but you can’t receive it.

Finally, continue tracking customers regardless of outcome. For those who don’t convert, document the reasons and assess whether re-engagement makes sense at general availability or a later stage. These signals are often just as instructive as successful conversions.

For customers who do convert, treat them as long-term design partners. Continue to invest in the relationship, monitor their health score, and stay ahead of renewal timelines. Early pilot customers are foundational to long-term success, and proactively managing their experience helps mitigate churn well before it becomes a risk.