How can a PMM best keep their leadership (Sr. Director, VP-level) best updated on an iterative & volatile product development process for a venture bet? What's the best communication cadence and format so leadership has confidence in the team?

The best way is to help the product and engineering teams bucket and articulate their work and goals.

1. Bucket [or Theme] Product Development - Help your product managers and engineers create distinct buckets for their work. I have been a part of organizations with 40 features under development, but no one has gone through and asked how these are related to each other. Take what's being worked on and arrange them into 3-5 themes.

2. Partner with PM/Eng to Craft Vision for Each Bucket - Once bucketed, I ask, "Does this bucketing make sense?" then, "What are we trying to accomplish?". The goal is to develop a directional statement with what's happening in the workstream

3. Identify what 'so what' is behind each bucket - Identify what the impact on the project or business is for each bucket. Your Sr. Directors and VPs don't care about what's happening; they care about what each bucket means for the company.

4. Set Success Criteria - Ask your PMs/Engs about what success looks like. How will they know if they've achieved the stated goal of each bucket?

5. Set a Deadline and exit criteria - Now that you know the impact and success, partner with PMs/Engs to set a deadline for when to know if we should continue with that work stream. It's also essential to set what failure looks like up front so you can immediately move on.

Communicate to VPs every week the business impact, what success looks like, what the deadlines/exit criteria are, and any blockers/asks that you may have to continue to push forward.