AMA: Notable Head of Product, Tom Alterman on Roadmap Planning

The simple answer here is prove that you're approach will make them more money. Here are some more tactical suggestions: * Build trust and credibility with sales leadership. This means showing them that you understand their business goals and priorities, and that you are committed to helping them achieve them. If they see that you're opinions make it easier for them to hit their quotas, they'll trust your judgement. * Frame the conversation in terms of business outcomes. Sales leadership is ultimately interested in driving revenue and growth. When you are discussing roadmap priorities, focus on how your proposals will help them achieve those goals. * Be data-driven in your prioritization decisions. Use data from customer surveys, interviews, and usage analytics to show how your ideas will lead to the business outcomes the fastest

When prioritizing your roadmap, focus on the initiatives that will have the biggest impact on your strategy and goals. If you have a retention problem, focus on improving that before worrying about new prospects. And if there is a lot of opportunity to expand with your current customers, focus on that as well. It's generally easier to expand existing accounts than land new ones. It's usually a warning sign if you need to build a very different set of features to meet the needs of prospects vs existing customers. That's usually a sign they are not the same audience. Not a problem in itself but be deliberate if you are pivoting your target audience

The short answer here is Mission -> Vision -> Strategy -> Goals -> Projects/Features. Focus on things that way round and it will be clear what features to prioritize. I'd recommend this fantastic article for a play by play with examples of how to run a great planning process using this structure

A roadmap is a conclusion to a story that starts with a mission and then continues with a vision, strategy and goals. If you're pivoting, I presume you've already shared why that's happening and the new vision you're pivoting towards. If not, then that's what you need to do first. After that you need to get the strategy and goals updated before roadmap matters. Bring your company along on that journey and you won't need to worry about expectations

Don't force them to say no, get them to say "Hell Yes!" If the leadership team is not willing to commit to one segment, and you believe that's needed to succeed, then don't make them choose. Get them excited about a specific segment and how it is the fastest path to achieving their goals. Once you have them excited, it will be easier to align them on funding the work that is needed to unlock the opportunities in that segment and pull resources from other projects.

My general rule is that you should only share projects with customers that you're at least 80% confident you're going to deliver in the timeframe you indicate. This could be even higher in an B2B SaaS company where customers might buy your product based on that roadmap. I'd therefore be very conservative on what you share publicly. You can share goals or strategies which are higher level that don't promise particular features but indicate the direction that you're going in. I find that usually delivers the impact you're looking for, getting your customers to buy into the vision, without holding you to a set of features you might learn are not the right ones to achieve that vision