The curiosity test in interviews

Eleanor Dorfman is the Head of Industries at Anthropic, where she leads enterprise go-to-market for Claude at the epicenter of the AI revolution.

Before Anthropic, Eleanor built and scaled GTM teams at some of the most talent-dense companies of the last decade. She started her career at Clever (where she turned multiple rejections into an eventual yes through sheer conviction and follow-through), moved to Segment, where she transitioned from customer success into sales and built the expansion motion, and then joined Retool as an early sales leader, helping scale the org through hypergrowth.

She also advises early-stage companies and has worked closely with venture firms like Thrive Capital giving her a front-row seat to how breakout startups are built and how early GTM hires play a mission-critical role in either accelerating or stalling that trajectory.

From public education to developer tooling to AI labs, Eleanor’s career looks less like the traditional “ladder” and more like what she aptly describes as a “jungle gym.”

Discussed In This Episode

• Why careers are a jungle gym, not a ladder and how to pivot on “one foot”• Getting rejected (and rejected again) and why persistence + conviction still win• The moment she realized sales was about energy, not personality

• What makes a seller truly AI-native and how top reps are using Claude today

• How to use Claude Code to build live prototypes (and why you may no longer need your sales engineer)

• Why “not technical enough” is often a lazy hiring critique

• The curiosity test: the one interview question that flipped her from “no” to “yes”

• Why early startup hires require a founder mentality

• The “ego death” principle and how ego hinders hypergrowth

• Why she doesn’t care about “productive capacity” in the AI era

• Learning vs. earning vs. values and the difference between Anthropic vs. other AI-natives

• Why Anthropic is enterprise-first and what that means for sellers

Timestamps

(00:00) From paralegal to public education to startup life

(05:10) Rejected three times by Clever and why she kept coming back

(11:30) Transitioning from customer success into sales at Segment

(16:45) Building the expansion sales motion and falling in love with sales

(24:46) Retool, hypergrowth, and scaling GTM in developer tooling

(29:30) How to break into an AI lab (and what actually gets a recruiter’s attention)

(32:09) Ego death, ownership, and what real commitment looks like

(39:00) The myth of “not technical enough” in early GTM hiring

(42:43) Claude’s personality: designed, not accidental

(44:30) How top reps use Claude Code to build live demos mid-cycle

(45:11) Managing in the AI era: throw out productive capacity, optimize for learning

(52:24) Why Join Anthropic

(58:26) Learning, earning, values and how to play for “the front of the jersey”

About The Vibescaling PodcastThe Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.

Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.

No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.

About VibescalingVibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.

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