How do you determine how much of your roadmap should be focused on existing customers vs prospects?

Most roadmaps indeed focus on both. The balance of prioritizing prospects versus existing customers will depend on the business objectives your product roadmap is designed to support. For instance, if the business leadership team is leaning on you to improve customer retention or promote edition upgrades, it might be necessary to prioritize existing users.
On the other hand, if the goal is net-new user acquisition (in other words, the aim is to build a larger customer base), it might be more beneficial to focus on prospects.

I find that this type of division can be misleading. In many industries, there is little difference between what an existing customer would want vs what a prospect would want. Many times, the two would like to see the same kinds of capabilities built (but their priorities might be different). I think more about the buying centers I’m targeting, the use cases they have that my product can solve, and prioritize the roadmap based on the importance of those.

I typically start from what are the annual business targets set by the company to answer this question. Oftentimes, the sales organization, CEO, and professional services organizations have targets around expansion, new logo acquisition, and win rate which will help portion out what the backlog needs to be to support the business goals.
In absence of these targets set by leadership, I would use a RICE framework (https://www.intercom.com/blog/rice-simple-prioritization-for-product-managers/) to establish what is the highest value driver for the business. That way I am not really focused on driving whitespace or greenfield, rather on what will drive the most business results in total.

Great question! This is something most product teams wrestle with when only looking at the roadmap from a features perspective to balance what to build for existing vs prospective customers. What I’ve found very useful to address this is to revisit the product strategy and business drivers for the product and align the roadmap accordingly. For example, if you assess your product strategy and look at the data for your business drivers, you may see a trend that customers really start adopting your product in years 2-3 with 10x revenue from their initial purchase, what decisions would you make? One decision could be to build more features to get more prospects because you know it will pay off in years 2-3. OR, you could decide to focus on existing customers but learn from your customers why adoption is lagging and then focus on solving your customers needs to speed up adoption so they get value earlier from onboarding or within the first year and shift that 10x revenue earlier in the cycle for your business.
In short, I found it best to revisit the product strategy, and leverage data from customers and business drivers to make an informed decision on how to position the roadmap for existing vs prospective customers. Once you identify the customer or business outcome you want to drive, use the roadmap to deliver that outcome.

In a perfect world, you want at least 80% of your roadmap to be applicable to both! But, we don't live in a perfect world, do we?
Some startups focus on a small number of customers and really customize the product to the desired features of those early users, but I like to first go broad in appeal, and then deep into a few features that are highly impactful to as many users as possible.
If you want to reach a new type of user, solve a new use case, or enter a new market, you will have enough of a reason to build something exclusively for prospects. This is a strategic decision to expand your business or market footprint.
A great way to determine if your roadmap is mostly applicable to both prospects and existing customers is to build a way for existing customers to submit ideas for the roadmap, and let your entire customer base upvote their favorite ideas. The more votes, the more likely both existing and new customers will benefit from the roadmap idea.
Sometimes, however, you'll have a big customer needing something specific, and there will be many reasons to build something unique, often influenced by the size/revenue impact of the customer. I don't usually let more than 5-10% of the roadmapa focus on one-off, custom features.

Who to focus on often depends on the maturity of the product. At the beginning stages of the product, we focus heavily on prospective users. When the product is mature, we focus heavily on existing customers (the thinking is -- if you can deliver impact to existing customers then prospective customers will likely find the same features useful).
Additionally, who to focus on can depend on whether your company is driving to satisfy existing customers vs working to attract new customers.

The answer lies in the breakdown of how the organisation intends to hit it's goals.
See this answer for context - https://sharebird.com/h/product-management/q/how-do-you-handle-exec-input-in-the-roadmap-and-convey-a-point-of-view-while-also-accommodating-1
To take an extreme example, if 70% of the organisations revenue target is based on the acquisition of new customers then that's a good guideline for your investment levels, eg
65% - Prospects
25% - Existing customers
10% - Tech debt

In general, a product roadmap should be shaped by product strategy, vision, and goals rather than prioritizing initiatives or features based on whether they benefit existing customers or prospects. However, there are scenarios where a focus on existing customers may be justified.
- High-value customers at risk of churn, which could threaten the company or product's survival. In such cases, addressing the needs of these customers may take precedence over other priorities.
- Early-stage companies building a product with feedback from their customers. In this scenario, a focus on existing customers can help build out a product that is well-received by prospects and the broader market.
Related Ask Me Anything Sessions

Stripe Product Lead, Rishabh Dave on Product Roadmap & Prioritization

Atlassian Director of Product Management (Confluence), Paresh Vakhariya on Product Roadmap & Prioritization

HubSpot Group Product Manager, Lukas Pleva on Product Roadmap & Prioritization
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