#29 Ashley Smith, GP & Founder at Vermilion Cliffs Ventures: From Twilio to Venture Capital & the Future of AI

Feb 6, 2025

Ashley Smith, GP and Founder of Vermilion Cliffs Ventures, shares her journey from answering support calls at Twilio to leading growth strategies at top tech firms. She discusses what makes a successful founding team, emphasizing the importance of communication and customer engagement. The conversation dives into the evolving role of AI in boosting developer efficiency and navigating software complexities. Ashley also reflects on her approach to early-stage investments and what excites her in the fast-paced tech landscape.

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ANECDOTE

Ashley’s Humble Tech Start

Ashley Smith started at Twilio by answering support calls as her entry-level job.
She quickly learned go-to-market strategies and grew from that small start into a tech career.

INSIGHT

Hiring for Excellence and Ownership

Great teams consist of quirky, passionate people who own their work fully.
Hiring only 'great' candidates preserves long-term team performance and culture.

ANECDOTE

Startup to Big Company Transition

Ashley describes her challenging transition from startup Parse to big company Facebook.
She experienced cultural shift, management challenges, and resource abundance at Facebook.

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In this episode of Inside the Workflow, we sit down with Ashley Smith, GP and Founder of Vermillion Cliffs Ventures. With a track record of driving growth at Twilio, GitLab, and GitHub, Ashley has now turned her focus to investing in early-stage technical founders. We explore her journey from startup operator to venture capitalist, her leadership approach, and what she looks for in founders building the next generation of developer-focused companies.

From her early career answering support calls at Twilio to leading go-to-market strategies for some of the biggest developer tools, Ashley shares invaluable lessons on building strong teams, navigating competition, and the evolving role of AI in software development.

What You’ll Learn in This Episode:

Building High-Performing Teams – The key traits Ashley looks for in founders and early hires.
Founder-Led Growth – Why technical founders must embrace go-to-market strategies.
AI & Developer Tools – The latest trends in AI infrastructure and how startups can leverage automation.
Scaling Startups – Lessons from Twilio, GitHub, and GitLab on rapid product adoption.
The Future of Investing – Ashley’s approach to early-stage investing and what excites her in tech.

Key Topics Covered:

[00:00] Introduction & Ashley’s Background – From Twilio support to leading growth at top startups.
[05:00] The Transition to Venture – Why Ashley founded Vermillion Cliffs Ventures.
[10:00] Startup Team Building – What makes a great founding team and early hires.
[15:00] AI’s Impact on Software Development – The shift from hype to real-world applications.
[20:00] Founder-Led Sales – Why early-stage technical founders need to embrace GTM strategies.
[25:00] The Future of Venture – How Ashley sees investing evolving in the next decade.
[30:00] Leadership & Work-LifeBalance – Lessons from navigating startup intensity and VC life.

Whether you're a startup founder, investor, or AI enthusiast, this episode is packed with insights on building, scaling, and investing in the future of software and AI.

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