This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers.

She will pick the best candidates from Jack's network.

The next step is to speak to Jack.

Job Title

Enterprise Account Executive

Salary

$150k-$300k + Equity

Company Description

Uncork Capital-backed SaaS startup managing $10B+ in cloud spend for the Fortune 500

Job Description

Join a high-growth cloud cost management leader transitioning from boutique advisory to a powerful SaaS platform, Skyway. You will own the full sales cycle for enterprise cloud and AI financial tools. Inherit a trusted brand with 35,000+ newsletter subscribers and active demand while building scalable strategies for the AI-native economy.

Location

San Francisco, USA

Why this role is remarkable

Market Authority: Leverage a massive existing footprint including 5 million podcast downloads and 100k+ followers, ensuring you never walk into a cold room.
Proven Traction: Backed by Heavybit and Uncork Capital with $7.75M raised and a track record of negotiating tens-of-billions in cloud contracts.
AI-Forward Culture: Direct impact on a product solving the urgent complexity of Anthropic, OpenAI, and AWS commitments for world-class engineering teams.

What You Will Do

Own the full sales cycle from initial qualification and deep discovery through to managing complex stakeholder groups and closing high-value deals.
Proactively build a robust pipeline by re-engaging the firm's extensive customer network, referral channels, and outbound efforts alongside consistent inbound interest.
Collaborate directly with founders and technical teams to translate customer pain points into platform features for the newly launched Skyway product.

The ideal candidate

Proven closer with 2-3 years of AE experience, ideally with a background in high-volume SDR roles and a desire for true book ownership.
Technically curious professional who thrives in ambiguity and can navigate decentralized buying groups across engineering, finance, and infrastructure departments.
AI-native worker who actively utilizes AI tools for research and productivity, with the discipline to maintain accurate CRM data in HubSpot.

Who are Jack & Jill?

Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.

And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.

How does this work?

Jack's an AI agent for job searching and career coaching. He works for you.
Jill is the AI recruiter working for the company. She recruits from Jack's network.
If it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives.

We never post fake jobs

This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.

Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.

We appreciate this can make them look a bit suspect, but there isn't much we can do about it.

Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.

Jack & Jill

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