Strategy in Complex Multi-sided Products

Nacho Bassino
2 min readDec 27, 2022


Many of us work on consumer products, or B2B SaaS, or other products where the business model and the value proposition is strong and clear. But there are products and industries that need to connect a variety of different players, creating not only complex problems but also complex structures where the needs of different groups need to be constantly prioritized and considered to be successful.

Over his career, Jason Boast has had more than one of these situations, and he shares valuable tips and war stories of the challenges he faced that are also applicable to our “simpler” worlds.

My takeaways from this episode

  • Start by taking time to understand: “don’t make any assertion until you have asked all the questions”. If you are getting different answers, do a workshop and get people together in a room.
  • If you can’t define success in a short sentence, you don’t have it clear (and that is a problem).
  • The essence of Jason’s process: 1. Understand Everything, 2. Define success, 3. Simplify, 4. Over Communicate.
  • Discovery complements the understanding of “the basics” of the business, with the “outside” perspective.
  • As a leader, to empower product managers to say “no”, you should prevent any type of backchannel that might override the “no”, and be ready to go to battle with them. That requires previously having a strong alignment, so the “no” can be supported by you and the rest of your key stakeholders.
  • Anyone can use their own communication / management tools, but strategy lives with the rest of the “fixed” documentation in an official wiki (Confluence in this case).
  • Empowering teams, doing strong diagnosis and selection, over-communicating: all of that is the hard path. But it is the right path. Jason explains how he started with the “simpler” path: create a top-down roadmap of things to build. That is the easy way. But it is wrong and fails.

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Nacho Bassino

Working on online products, currently as Director of Product at XING. Passionate about technology and amazing web/mobile products.