
Head of Enterprise
San Francisco, CAFull-time$150–250K/yrSeen 1w agoStill listed 4 days ago
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Job overview
TrainLoop is seeking a hands-on Head of Enterprise to build its enterprise sales motion as an individual contributor. The role owns pipeline development and the sales cycle, from opening accounts and running paid pilots through procurement, annual platform commitments, and expansion. The hire will work with technical teammates to define pilot success criteria and conversion plans, while involving founders and technical staff where they add value.
Skills & qualifications
Skills
Qualifications
Full job description
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.
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