It’s easy to keep saying yes to new features. It’s a lot harder to say no, especially when the customer is dangling a big contract.

In this episode of The Drafting Table, Danielle Leong (CTO at FireHydrant and former engineering leader at Twilio and GitHub) breaks down how to scale product and engineering without running your team into the ground.

We dive into the practical tradeoffs every founder faces between building what customers want and maintaining a healthy, high-functioning product team.

Together with Work-Bench General Partner Jessica Lin, Danielle shares tactical frameworks on:

• How to prioritize feature work vs. internal tooling

• Ways to avoid the “feature treadmill” while still closing deals

• How to use support tickets as early product health signals

• When to invest in design, implementation tooling, and debt paydown

• Why fast doesn’t always mean better and what to track instead

• How to build product that customers love without killing your roadmap

This episode is a must-watch for early-stage founders, engineering leaders, and PMs navigating the messy middle between MVP and maturity.

—

⏱ Timestamps

00:00 – Why “watching users struggle” is the best form of discovery

03:00 – Ruthless prioritization: building what users will pay for

09:00 – Feature parity vs. product identity

12:30 – What Twilio got right about customer empathy

17:00 – When internal tooling should take priority

22:00 – Why engineering estimates always go wrong (and how to fix it) - Also check out this blog post for more on this: https://www.rubick.com/steel-threads/

26:30 – How FireHydrant ties engineering effort to company goals

34:00 – How to align your whole team around cost-consciousness

37:00 – Implementation, margins, and the myth of “free” customers

40:00 – Where AI tools are helping and where they still fall short

44:00 – The one question Danielle asks every founder she advises

—

📌 For early-stage B2B founders, engineering leaders, and PMs building sustainable product roadmaps.

Hosted by Jessica Lin, General Partner at Work-Bench.