Heidi Helfand

Author and Consultant at Dynamic Reteaming

Author of Dynamic Reteaming, with two decades in tech including growing from employee 10 to 900+ people, now teaches workshops and consults on how to effectively reorganize teams, reduce attrition, and embrace change as an opportunity rather than a threat.

The Org Builder The Craftsperson

Dimension Profile

Strategic Vision 35%

Execution & Craft 45%

Data & Experimentation 20%

Growth & Distribution 15%

Team & Leadership 90%

User Empathy & Research 35%

Key Themes

dynamic reteaming and reorg best practices five types of reteaming transparent collaborative reorgs whiteboard reteaming methodology change as career opportunity RIDE framework for decision clarity

Episode Summary

Heidi Helfand draws from two decades of experience growing startups from 10 to 900+ people to explain why team change is inevitable and how to get better at it. She introduces the five types of reteaming, the whiteboard reteaming methodology for transparent collaborative reorgs, and the RIDE framework for decision-making clarity. The core insight is that the people layer of company building is just as important as building products customers love, and embracing change rather than fighting it creates both better organizations and better career opportunities.

Leadership Principles

→ Reteaming is inevitable so you might as well get better at it — the advice to keep teams stable forever doesn't match reality in fast-growing or shrinking companies
→ Transparency in reorgs is worth the risk — visualize future team structures on whiteboards and let people give input, identify mistakes, and express interest in new roles
→ Be clear on who's the decision maker using the RIDE framework — who's Requesting, giving Input, Deciding, and Executing the change

Notable Quotes

"Reteaming is hard. Reorgs are hard. If we could just build the software, deliver to the customer, get the product market fit — if only it could be that easy. No, we have the people layer, so let's focus there too."
— On why the people layer of building companies deserves more attention

"We rolled these whiteboards out and it had the team structure with everyone's names on it. People identified mistakes in the design. People had the opportunity to see opportunities within their own company."
— On the whiteboard reteaming methodology used at Procore

"Who's Requesting the change, who can give Input, who's the Decider, and who's going to Execute? Being clear on who the decision maker is in a change is really important."
— On the RIDE framework for decision-making clarity in reorgs

Want to know how you compare?

Take the Assessment