šŸš€ Should I add a pilot to my sales process?

3 tactics, 2 traps and 1 tool to run introductory sales calls

Hello founders!

Welcome to ā€˜Tactical Tips’ by Jerel and Shuo at DECODE, where we cover one new idea to help you build and grow your startup – every week in <5 minutes!

Today, we’ll be answering the question: ā€œShould I add a pilot to my sales process?ā€

And here’s advice inspired by Emery Rosansky, VP GTM at First Round Capital.

If you are near closing a deal and wondering whether or how to introduce a sales pilot, today’s newsletter is for you.

ā

A pilot in the right scenario is a sales superpower. However, when done poorly, it can be a major blocker.

šŸ”„ Inside this issue:

āœ… 3 tactics on adding sales pilots
āœ… 2 traps to avoid 
āœ… 1 tool to leverage 

šŸ‘‡Let’s dive in.

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3 tactics on adding sales pilots

šŸŽÆ Ensure pilots clear objections fast

  • Directly ask what’s holding the buyer back—get specifics about the objections, concerns, or hesitations (e.g. lack of trust, worried about integration etc)

  • Define the goal of the pilot clearly—whether it is technical validation, user adoption, change management, or use case fit etc 

  • Design pilots to ensure it eliminates specific objections and meets the goals—if it doesn't, it is a waste of time and resources

  • Set concrete success metrics that will enable a full roll out (e.g., 20% reduction in time, 40% increase in sales, etc) 

  • Match pilot length to time-to-value—long enough for the buyer to experience impact, but short enough to drive urgency

šŸ“‹ Set clear prerequisites before starting a pilot

  • Require a clear internal champion (e.g., someone committed to using the product X hours weekly, who will advocate for it internally)

  • Confirm alignment on pilot scope and success criteria

  • Ensure engineering resources are pre-allocated for integration work

  • Verify budget is approved for the post-pilot package being tested

  • Confirm decision-maker is aware of the pilot and comfortable with the decision timeline

  • Make all requirements explicit—don’t start until every box is checked

šŸ—“ļø Run a structured pilot with built-in checkpoints

  • Pre-schedule calls for kickoff, support, check-in and final decision:

    • Start with a kickoff call to align on pilot structure, success metrics and criteria as well as required prerequisites

    • Schedule a support call to set up real use cases, unblock setup issues, and address questions on specific flows (Eg. Configure a test flow or integration live)

    • Hold a check-in call to measure progress against success metrics, address objections, and discuss scope and pricing

    • End with a decision call that ties pilot results to success criteria, push for a go/no-go, and propose next steps

  • Put all meetings on the calendar upfront to avoid going dark or losing momentum after kickoff

2 traps to avoid

🚨Running pilots that create friction instead of removing it

  • Pilots should de-risk the deal and accelerate adoption—not add steps or slow it down

  • Don’t create hurdles where there were none—if the buyer is ready to say yes, having a pilot turns momentum into delay

🚨Letting pilots drag into endless stalls

  • Pilots prove the product works and value can be captured—not that value exists

  • If prospects don’t see value existing, skip the pilot and highlight the cost of inaction instead

  • Long pilots = resource-wasting stalls, not validation

  • Set hard boundaries on pilot scope to force real yes or no decisions

1 tool to leverage

šŸ“– Best practice on running sales pilots

  • Keep pilots under 90 days. If longer, make it a paid pilot.

  • Leverage tools like Google Analytics to capture user behavior for the pilot

Bonus: 1 trend to spark startup ideas

šŸ“ˆ Mishandled E-commerce returns are killing retail profits

  • Returns doubled to $890B/year since 2020, with 17–30% return rates

  • 70–80% of returned goods’ value are salvageable—but most are mishandled 

  • Legacy solutions are built for returns processing, not inventory value maximization:

    • Returns cost 20-65% of original item value

    • Brand-owned resale sites cannibalize full-price sales.

    • Third-party recommerce (buying and selling previously owned items) is slow and operationally complex.

    • Recycling offers too little per-unit value to be scalable.

  • Brands demand:

    • Time-to-restock under 1 month to maximize value for restocking in-season

    • AI-driven, ultra-accurate grading and processing to reduce labor and human error

    • Granular data on returns to forecast inventory and tailor marketing

    • Recommerce that maximize value while protecting brand equity

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