Agile Product Roadmaps: AiSDR’s Strategy to Feature Planning

Product roadmaps offer a glimpse into a product’s future by answering the question “Where are we going to be in X amount of time?”

But for start-ups and SMBs, this can turn into a futile exercise. Product development moves at such a breakneck pace that roadmaps become outdated almost instantly, trapping teams in a constant cycle of replanning.

That said, roadmaps are an essential part of product development, so you can’t go without them.

So what do you do?

At AiSDR, we cracked this challenge by reimagining our product strategy. Instead of a static quarterly blueprint, our strategy takes the pros of agile work, merges them with a philosophy of continuous innovation, and applies the result to product roadmapping.

TLDR: 

• The goal: Map out the vision and direction of AiSDR
• The tactic: Build an agile product roadmap
• The result: Release ~1,200 new features in 1 year

Step 1: Plan based on your velocity

Traditionally, teams outline their product roadmap on a quarterly basis. But when you’re a start-up or SMB, life’s moving way too fast and a quarterly roadmap will turn obsolete.

This happens for any number of reasons in or out of your control:

• Rapid market shift to a new technology (AI, anyone?)
• Real-time market validation trumps pre-planned schedules
• Customer feedback loops suggest different needs
• In-demand software integration
• Resource constraints
• Urgency to find product-market fit

The key to overcoming the limitations of a quarterly plan is to create a living, breathing roadmap that reflects your current velocity and priorities.

This approach has several advantages:

• Flexibility – You can quickly adapt to any market changes, customer feedback, or opportunities.
• Realistic expectations – Quarterly roadmaps are tough to approximate, which can lead them to being too ambitious or too small. An agile roadmap matches your team’s actual capacity and speed at any moment.
• Continuous alignment – Quarterly roadmaps tend to be set aside and seemingly forgotten until it’s time to update them. Living roadmaps however are always current and reflect the most important work you’re doing.

As a result, you can make product decisions about what to build next based on your team’s capabilities and your customers’ most pressing needs.

Step 2: Create and prioritize a list of features

Here’s where you’ll need to do a bit of groundwork.

First, start ideating potential features. You can pull them from multiple sources, such as customer feedback, market research, team brainstorming, and competitor analysis.

One easy tactic for gathering ideas that teams overlook are exit surveys where you ask churned customers why they’re leaving and what they would have liked to see.

Once you have a reasonably sized list, you’ll need to start prioritizing. Consider these factors:

• Customer impact
• Strategic alignment with product vision
• Potential development effort
• Potential revenue or growth opportunities

Try to rank features as objectively as you can, and try not to fall for any hype.

One approach to this is to use a scoring system similar to how you’d score leads to weigh each of these factors so you can focus on features that deliver the most value.

Just remember that this list won’t be set in stone, and you can regularly review and adjust priorities as your product and the broader market evolve.

Step 3: Limit yourself to 20 features

Prioritization is harder than you think, but restricting yourself to 20 features is a powerful strategy for maintaining focus and preventing product bloat.

But why 20?

That’s because it:

• Forces prioritization
• Prevents teams from getting spread too thin
• Enables high-quality implementation
• Maintains clear product direction

Think of this feature list like a backpack on a hiking trip. You can’t carry everything, so you choose only the most essential items that matter most right now.

And if a new feature idea becomes critical, you can remove a less important one from the list.

Step 4: Divide features into “Committed” or “Planned”

After you’ve created a prioritized list of 20 features, there’s one more step – Deciding which you’re 100% committed to developing and which you want to develop but need more research.

Nothing stops you from adding a few more designations, but we like to keep things simple 🙂

Before determining your commitment, here are a few questions you might ask yourself:

• Do you have the skills and bandwidth to complete the feature?
• What other priorities might this displace?
• Do we fully understand the technical implementation?
• Do we have the necessary infrastructure?
• Will this generate measurable value?
• What are potential implementation risks, and can they be mitigated?

Here’s what our product roadmap looks like (names and descriptions have been redacted because spoilers 😉 )

Step 5: Create a separate list for tracking new feature ideas

Last but not least, it’s a good idea to set up a separate page or list for new feature ideas.

This allows you to construct an easy and valuable innovation pipeline that serves as a repository for potential improvements, ensuring no good ideas get lost.

Here are a few best practices for managing this list:

• Set up spaces to share new ideas, such as a dedicated Slack channel
• Capture ideas immediately when they emerge 
• Include some brief context or market research for each idea
• Note the source of the idea (everyone likes credit!)
• Assign a preliminary impact, feasibility, or priority score

This list should transform into your product’s garden of ideas where you can encourage ideas that might bloom into future features.

Result

Our agile approach to AiSDR’s product roadmap has helped us:

• Release 1,197 new features in just 2024 (averaging over 3 per day)
• Empower team members to drive innovation
• Enable fast response to customer needs
• Foster a culture of continuous improvement