Roadmapping Towards Effortless Financial Health

Samar Shah
EPD at Digit
Published in
3 min readOct 19, 2021

The below questions were shared with Built In for a story published in July of 2021 focused on Weathering Change on a Product Roadmap. Our Head of Product, Samar Shah, shared how he and his teams stay in sync:

Interview Questions — Answer here
1. When developing a product roadmap, what steps do you take to ensure there’s alignment across teams from the get-go?

The first step is making sure everyone understands how our mission translates to our product strategy. At Digit, our mission is “To Make Financial Health Effortless for Everyone”. We intentionally opted for a business model that transparently maps to this mission: our customers pay a monthly subscription for Digit’s automated financial health platform.

This then drives our product strategy: to deeply understand the most important needs in our customers’ financial lives, build a roadmap of features that intelligently solve these needs with Digit’s effortless automation, and ultimately increase the impact our members receive from our subscription.

From there, we kick off each planning cycle by aligning on companywide product goals: a portfolio of metric-based and milestone goals to deliver product and business impact. We share out draft versions of goals early on to allow time to strengthen them based on cross-functional feedback.

Once everyone is aligned on our companywide strategy and goals, we rely upon each product team’s expertise to chart the roadmap ahead. Digit product teams are made up of dedicated product managers, engineers, designers, data scientists, and business stakeholders. Each team owns a different mandate and domain within our product experience and they work together to ensure that our collective roadmap will ladder up to reach our company goals.

2. How do you maintain that alignment throughout the development cycle? Cite a specific example of this process in motion.

I’ve found it most important to set up all teams to transparently communicate their progress and obstacles. If this information is readily available and well-consumed, teams will naturally lean in to support each other and adapt to the latest learnings.

We use Coda to maintain a collaborative hub that houses our “master product roadmap” and the status of each initiative. We operate our roadmap as a living, breathing stack rank, so mid-cycle changes to priority are immediately reflected. Dynamically linked team-level views allow each of our product managers and team leads to drive their own team-level planning, while automatically keeping the master roadmap in sync on the latest status.

Even then, it can be overwhelming to stay up to speed with everything in flight. To help with this information overload, we run a weekly heartbeat meeting that is broadly attended and allows each team to share their most important priorities and how they are trending towards their goals.

3. As project needs change, how do you re-prioritize the product roadmap and keep teams aligned?

Roadmap reprioritization usually occurs through a series of decisions based on new information: “We just learned X, so we should take Y action”. At Digit, our favorite way of getting from X to Y is with a written memo.

A well-written memo can lay out the new learning, how it changes our prior strategic assumptions (e.g., “early data suggests a gap in how our members are using a new feature” or “we underestimated the technical complexity of this project”), and how it impacts our ability to reach our goals. In most cases, we can still reach our goal if we shuffle prioritization or adjust team resourcing. Less frequently, the latest learnings may require us to revise our goals.

We ask our project leads to outline the different decision options and make a recommendation. This allows stakeholders to read and deeply understand others’ thought processes. We believe that async processing leads to stronger thinking and levels the playing field for everyone to express their opinions, so we wait to gather written feedback before holding live discussions. Similarly, we don’t force decisions in meetings and let project leads break from a meeting when they have enough input to ‘sleep on it’ and make a decision.

Interested in joining our team and working on our Financial Health roadmap? Reach out to recruiting@digit.co.

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