Head of Enterprise

San Francisco, CA
Full-time
Visa Sponsorship

About the role

Lead and develop our enterprise sales motion. Personally open enterprise accounts and own the sales cycle through paid pilots, procurement, annual platform commitments, and expansion. This is a hands-on individual contributor role, with direct responsibility for building pipeline and closing business.

You’ll identify and reach prospective customers, develop champions and executive buyers, lead discovery and proposals, and negotiate and close deals. Work with the technical team to scope pilots with measurable success criteria, a clear buying process, and a path to an annual commitment.

In your first 90 days, take ownership of priority accounts and qualified pipeline, lead proposals and procurement, and establish pilot-to-platform conversion plans. The goal is to independently move enterprise deals forward while bringing the founders and technical team into the moments where they add the most value.

Requirements

• Typically 5+ years in enterprise software sales, primarily as a quota-carrying individual contributor, or equivalent demonstrated success.

• Personally sourced and closed multiple new enterprise contracts worth $1M+ in total contract value.

• Sold technical products involving AI, data, developer tools, or infrastructure.

• Personally owned outbound prospecting, discovery, proposals, negotiation, and forecasting.

• Converted a paid pilot or proof of concept into a larger production agreement.

About TrainLoop

Reasoning Fine-Tuning

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Job details

Salary

$150,000 - $250,000

Equity

0.5% - 1.5%

Location

San Francisco, CA

Experience

3+ years

Company

NameTrainLoop
IndustryEngineering, Product and Design
Team Size6

Funding

Total raised

$500K

Last stage

Seed

Investors

Y Combinator
MMarble Creek Ventures
MMoonfire
OOlive Tree Capital
Pioneer Fund

Founders

Mason Pierce

Mason Pierce

Co-Founder & CTO

LinkedIn
Jackson Stokes

Jackson Stokes

Co-Founder & CEO

LinkedIn

What happens next.

No applications, no recruiter spam. Just the intro.

01

Confirm the fit

A few questions to make sure this role is the right shape for you. Two minutes.

02

I pitch you to the company

I write the intro, send it to the founder, and handle the back-and-forth.

03

A meeting lands on your calendar

If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.