Navigating the Challenges of Founding a Startup

Welcome to Growthmates with Kate Syuma — Growth advisor, previously Head of Growth Design at Miro. I’m building Growthmates as a place to connect with inspiring leaders to help you grow yourself and your product. Here you can learn how companies like Dropbox, Adobe, Canva, Loom, and many more are building excellent products and growth culture. Get all episodes and a free playbook for Growth teams on our brand-new website — growthmates.club, and press follow to support us on your favorite platforms.

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In this episode, Kate speaks with Benjamin Humphrey, founder of Dovetail, who opens up about his shift from corporate design roles to the challenges and rewards of startup life. Benjamin's story began as a designer at Atlassian before taking the leap into the unknown to create Dovetail, a user-focused product built to simplify research and UX processes. He delves into the defining moments that guided his journey, as well as the challenges of moving from a structured corporate environment to the entrepreneurial world.

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Dovetail’s mission is to improve the quality of every thing through the power of customer insights. In only six years, Dovetail has grown to drive research innovation at over 3,700 organizations including big brands like Harvard Business, Universal, Deloitte, Porsche, Starbucks, Shopify, Atlassian, Shell and more. Dovetail was deployed early at global design software company Canva, who set up its customer insights hub. Canva’s product team has used Dovetail since the very beginning to analyze customer research data, uncovering insights that improve their product’s user experience. Try out and start collecting your insights here → www.dovetail.com

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Key highlights from this episode 👇

* From Designer to Founder: Benjamin shares his path from the corporate world of Atlassian to founding Dovetail. Leaving a stable, rewarding job to pursue a personal vision, he discusses the mental shift required to step into a startup's uncertain world.

* Leadership and Team Building: Starting Dovetail required Benjamin to learn new skills quickly, from securing funding to making critical business decisions. Unlike his past roles where teamwork and large-scale collaboration were paramount, as a founder, he had to adapt to the demands of a smaller, more agile team.

* The Value of Progressive Disclosure in Design: Benjamin introduces the principle of progressive disclosure—gradually revealing features to users as they explore. He emphasizes that this approach not only optimizes user experience but also aligns with Dovetail's vision of helping users discover tools contextually, when they’re most needed.

* Insights on AI and the Future of Dovetail: With the release of Dovetail 3.0, enhanced with AI capabilities, Benjamin discusses the challenges and opportunities AI brings to his product. He shares his vision for responsibly integrating AI, ensuring it complements users’ research without sacrificing transparency or control.

Special announcement 🚀 Join the Design Career Accelerator on December 2-6!

How do you decide where to grow? IC vs Manager, in-house or solo? There are so many paths. For years, I’ve collected frameworks that helped me and my coaching clients from Loom, Intercom, and more. This year I want to share these practices with Senior IC Designers, Leads, and Managers who are on a cross-way in planning the next career step. To help you dedicate time for that at the end of the year, we created a special 1-week Design Career Accelerator — learn more about the program and grab your slot before December 2!

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Where to find Kate Syuma, Growth Advisor (ex-Miro):

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* Newsletter: katesyuma.substack.com

Where to find our guest — Benjamin Humphrey (Co-founder and CEO of Dovetail):

* LinkedIn: https://www.linkedin.com/in/humphreybc/

* Website: https://dovetail.com/

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Episode Timestamps:

[01:18] Introduction by Kate[02:28] Benjamin's Journey[03:49] Leaving the job at Atlassian[05:19] Command AI[07:24] Deciding to go in another direction with Dovetail[09:38] If you wanna go fast, go alone[12:16] What was extremely challenging for you didn’t have your skill set as a designer[14:26] How you uncovered the problem that your product is currently serving for[20:06] Product-led model for Dovetail[24:07] Progressive disclosure[33:03] Core values of the product[34:53] How to speed up time and get to the aha moment[35:52] Future of Dovetail and the element of AI[40:57] What one piece of advice would you like to give?[44:40] Outro

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📕 Useful Resources and other related Podcasts:

Revealing 3 myths about User Research and start easy | Jason Giles (VP of Product Design at UserTesting)

Making Decisions with User Research from Startup to Scale-up | Behzod Sirjani (Advisor & Partner at Reforge, ex-Slack)

Driving a Positive Behavioural Change with Your Product | Amy Bucher (Lirio, Author of "Engaged")

"How Dovetail CEO Benjamin Humphrey Scaled an Australian Startup to Global Success" on Fund/Build/Scale: Listen here

"Product Management with Benjamin Humphrey" on UI Breakfast Podcast: Listen here

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