Anant Jain

Roadmapping for Startups

Tech

Introduction

Roadmapping is a critical process for any startup that has achieved product-market fit (PMF). While early-stage startups often operate in a highly experimental mode, post-PMF companies can start bringing a structured approach to planning their product and engineering initiatives. This guide outlines a practical framework for creating monthly/quarterly roadmaps that balance product development with engineering excellence.

The key challenge in roadmapping at this stage is maintaining the startup's agility while introducing just enough process to ensure the team moves in a coordinated direction. Too much structure can slow you down, while too little can lead to scattered efforts and missed opportunities.

Below is a step-by-step process I’ve found effective for quarterly planning, with a particular focus on balancing immediate product needs with long-term engineering investments.


The Roadmapping Process

Step 1: Create the Engineering Excellence Roadmap

  • Start with engineering initiatives before tackling the product roadmap.
  • Compile a list of engineering excellence projects the team wants to pursue.
  • Rate each project's Impact and Effort on a scale of 1 to 10.
  • Include brief justifications for each rating to facilitate asynchronous feedback.
  • Sort the table by Impact/Effort
  • The output for this step should look like as below:
Project Impact Effort Impact/Effort
Project 1 30 5 6
Project 2 50 10 5
Project 3 70 20 3.5

Step 2: Create the Product Roadmap

  • Identify key projects that should be prioritized for the next quarter.
  • Focus the team on one or two themes per quarter rather than spreading efforts across many projects.
  • Rate each project's Impact and Effort, including brief justifications to enable asynchronous feedback.
  • Sort the table by Impact/Effort
  • The output for this step should look like as below:
Project Name Tags Impact Effort Impact/Effort
Project A Product Bet 90 10 9
Project B Product Excellence 70 10 7
Project C Customer commitment 60 10 6

Step 3: Estimate team capacity

Account for these often overlooked time commitments:

  • Oncall and customer success work
  • Planned vacations and Holidays
  • Onboarding new team members
  • Any team offsites or planning days
  • Unexpected PTO

Step 4: Combine and draw a cutline

  • Bring the top projects from Step 1 into the doc for Step 2.
  • It’s okay to adjust Impact/Effort to fit better in the context of the table in Step 2.
  • Save at least 30% of the bandwidth for Engineering Excellence work, but this varies quite a lot startup to startup.
  • Based on the capacity in Step 3, you’ll be able to see the cutline of what you can realistically accomplish.
  • Based on the cutline, think about what’s below the cutline that should absolutely be done. If so, it’s okay to bump up its impact.
  • Alternatively, try to think of ways where you can break the work into two parts, where the first part requires less effort but meets the imminent need, and the second part can be deferred to later.
  • The output of this step should look like the following table:
Project Name Tags Impact Effort Impact/Effort
Project A Product Bet 90 10 9
Project B Product Excellence 70 10 7
Project 1 Eng Excellence 30 5 6
Project C Customer commitment 60 10 6
[Cutline]
Project 2 Eng Excellence 50 10 5
Project 3 Eng Excellence 70 20 3.5

Step 5: Make it official

I love using Initiatives and Projects in Linear to record and execute on the roadmap.