How to surface hidden customer pain

Jake is the founder and CEO of Serval, an AI-driven IT automation and service management platform that just raised $47M in Series A funding this week. Before founding Serval, Jake spent over five years at Verkada, where he led multiple products from 0-1 and helped scale the company across hardware and software. His years at Verkada taught him that winning in enterprise means delivering consumer-quality experiences to business buyers — a lesson that shapes how Serval turns complex IT automation into something that feels magical.

In this episode, Jake and Brett dive into the lessons from Verkada that inspired Serval's founding, what it takes to disrupt entrenched enterprise categories, and practical tips for getting deeply embedded with customers and hiring high-quality candidates.

In today’s episode, we discuss:

• Why building “in existing categories” can be more powerful than creating new ones
• The lessons from Verkada that shaped Serval's platform strategy
• The customer interview question that unlocked the IT buyer’s hidden pain points
• How Serval's automation builder uses AI to generate code-based workflows
• Redefining engineering and PM roles with forward-deployed engineers
• Keeping the hiring bar high in an AI-native startup
• Why there’s a “land grab” moment right now in enterprise AI
• And much more...

Where to find Jake:

• LinkedIn: https://www.linkedin.com/in/jakestauch/
• Twitter/X: https://x.com/jakeserval

Where to find Brett:

• LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
• Twitter/X: https://twitter.com/brettberson

Where to find First Round Capital:

• Website: https://firstround.com/
• First Round Review: https://review.firstround.com/
• Twitter/X: https://twitter.com/firstround
• YouTube: https://www.youtube.com/@FirstRoundCapital
• This podcast on all platforms: https://review.firstround.com/podcast

References:

• Alex McLeod: https://www.linkedin.com/in/alexmcleodio/
• Clay: https://www.clay.com
• Cloudflare: https://www.cloudflare.com
• Cursor: https://cursor.sh
• Filip Kaliszan: https://www.linkedin.com/in/kaliszan/
• Hans Robertson: https://www.linkedin.com/in/hansrobertson
• Linear: https://linear.app
• Okta: https://www.okta.com
• Rippling: https://www.rippling.com
• Serval: https://www.serval.com/
• ServiceNow: https://www.servicenow.com
• Verkada: https://www.verkada.com
• Workday: https://www.workday.com

Timestamps:

(02:25) Lessons from holding different product roles

(07:29) Turning “hard mode” into a moat

(10:49) The early days of Serval

(12:59) Scratching the founder itch

(14:57) Unconventional interview techniques

(17:47) Solving core interview challenges

(21:10) Planning the early product roadmap

(23:03) The surprising power of patience

(26:12) Serval’s impressive technical advantage

(27:35) Disrupting legacy incumbents

(31:13) Building for mid-market and enterprise

(33:35) Serval’s enduring roadmap

(36:08) How to sell to an existing market

(39:16) The evolving role software plays

(43:55) Building for AI that didn’t exist yet

(49:49) Serval’s forward-deployed engineers

(58:31) The hybrid PM-GM

(1:00:27) “You can over-prioritize”

(1:02:48) The unexpected value of panic buttons

(1:04:50) What Serval looks for in new talent

(1:07:01) The ultimate hiring litmus test

(1:13:59) Building out Serval’s go-to-market function

(1:16:31) The evolving IT market in 2025