Head of Enterprise

TrainLoopSan Francisco, CaliforniaOn-siteFull-timePrincipal, 12–15+ yearsListed 59 minutes ago

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About this 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.