How to Successfully Rebrand Your Startup: Key Takeaways from Our LinkedIn Live with Plane

On March 25, 2025, Chore went live on LinkedIn to host an insightful event titled "Rebranding Your Startup: How to Do It Successfully". This event brought together two seasoned founders, Adam Spector, CEO of Chore, and Matt Drozdzynski, founder of Plane, to share their hard-earned insights and practical frameworks on one of the most crucial yet misunderstood aspects of startup evolution: rebranding.

Rebranding is far more than a visual makeover. It's a strategic reset that aligns your company’s public perception with the current state of your mission, market, and model.  Rebranding touches every aspect of your business - messaging, visuals, operations, investor communications, you name it.

In the live session, Adam and Matt pulled back the curtain on their respective rebranding journeys: Chore’s transition from its former operational identity to a brand that speaks to startup founders, and Plane’s transformation into a forward-facing platform.

Why do Startups Rebrand?

Rebrands are often sparked by product pivots, customer evolution, or go-to-market shifts. Both founders highlighted how internal clarity, on who you serve and what makes you different, should precede any design or messaging changes. For Chore, the rebrand clarified that the company isn’t just a service provider but a strategic partner to founders drowning in admin. For Plane, it was about simplifying the brand to match its ethos of streamlined finance operations for global teams.  

How to Do It Right

Rebranding isn’t about a flashy logo; it’s about system-level changes. Matt emphasized the importance of narrative consistency, cross-functional alignment, and updating every touchpoint—internal and external. Adam shared how Chore invested in messaging architecture, UX design, and stakeholder communication to ensure a smooth, impactful rollout.

What Founders Often Get Wrong

A major mistake? Treating rebrands as cosmetic. Both founders advised against rebrands driven by aesthetic preferences or surface-level trends. Without substance, your audience will see through it, and your team won’t rally behind it. They also flagged timing: don’t rebrand in the middle of product instability or unresolved positioning issues.

The Aftermath: Measuring Success

It’s not enough to relaunch and move on. Post-rebrand KPIs discussed included:

• Website bounce rate improvements
• Lead quality
• Brand sentiment shifts via surveys and social media
• Internal adoption and morale metrics

Other Takeaways from the Session:

1. Timing Matters – Rebranding too early can confuse your audience; too late can lead to missed opportunities. The right time is when the current brand begins to hinder growth.

1. Data + Instinct – Use qualitative and quantitative signals: customer feedback, engagement metrics, and strategic goals should all inform your decision.

1. Story Before Aesthetics – A new logo or website means little without a compelling narrative. Start with your story.

1. Team Buy-In is Critical – Your internal team must understand and embody the brand before the world does.

1. Execution Takes Time – Rebranding is not a one-week sprint. It’s a thoughtful process that needs cross-functional collaboration.

Chore’s rebrand has already yielded measurable outcomes. Early indicators show improved conversion rates on landing pages, stronger engagement on branded content, and qualitative feedback from founders who now “get what Chore does” faster.

You can watch the full replay for more insights. We’re grateful to everyone who joined live, asked questions, and contributed to such a vibrant discussion.