Career Journeys and Scaleup Challenges

“As a startup, as a scaleup, you often get one chance. If the first impression is something that’s slow, doesn’t work, is down entirely, people will move on and go find some other way to solve that problem."

Tim Cochran and Kennedy Collins are the co-authors of the “Bottlenecks of Scaleups” series published on Martin Fowler’s website. In this episode, we explore several key challenges faced by scaleups, such as product-engineering friction, service disruptions, accumulation of tech debt, and onboarding. Tim and Kennedy share their experiences and provide actionable advice on fostering collaboration, creating unified roadmaps, ensuring system reliability, and managing technical debt. They also emphasize the importance of efficient onboarding and developer experience in navigating the complexities of scaling up a startup.  

Listen out for:

• Career Journey - [00:02:02]
• Definition of a Scaleup - [00:05:29]
• Bottleneck #1: Friction Between Product and Engineering - [00:08:24]
• Healthy Product-Engineering Tension - [00:13:36]
• Unified Product-Engineering Roadmap - [00:18:54]
• Bottleneck #2: Service Disruptions - [00:22:16]
• Cross Functional Attributes - [00:27:09]
• Bottleneck #3: Accumulation of Tech Debt - [00:32:39]
• Systems Ownership - [00:38:37]
• Bottleneck #4: Onboarding - [00:41:01]
• 3 Tech Lead Wisdom - [00:46:35]

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Tim Cochran’s Bio
Tim Cochran is a Principal in Amazon’s Software Builder Experience (ASBX) group. He was previously a Technical Director at Thoughtworks.

Tim has over 20 years of experience working with both scaleups and enterprises. He advises on technology strategy and making the right technology investments to enable digital transformation goals. He is a vocal advocate for the developer experience and passionate about using data-driven approaches to improve it.

Kennedy Collins' Bio
At Thoughtworks, he leads product and design for the Central Market of North America. A product manager by trade and a designer by training, he’s most interested in creating (and helping others create) useful and valuable things — be it software or organizational structures.

He’s also a bit of a nerd about strategy, human behavior, health and fitness, productivity, writing, coffee, cocktails, board games, and the history of product management.

Follow Tim:

• LinkedIn – linkedin.com/in/timcochran

Follow Kennedy:

• LinkedIn – linkedin.com/in/kennedycollins
• Twitter / X – @kennedycollins

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Show notes & transcript: techleadjournal.dev/episodes/179. Follow @techleadjournal on LinkedIn, Twitter, and Instagram. Buy me a coffee or become a patron.