← All roles

Head of Enterprise

TrainLoop· Sales
Apply on company site
Hybrid (San Francisco, CA)$150k - $250k + equityFull-timePosted 5d ago

About the role

Lead and develop the enterprise sales motion at TrainLoop. Personally open enterprise accounts, own the sales cycle from pilots to annual commitments, and drive pipeline and closure with founders and the technical team.

Responsibilities

  • 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.
  • 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 the first 90 days, take ownership of priority accounts and qualified pipeline, lead proposals and procurement, and establish pilot-to-platform conversion plans.

Qualifications

  • 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.

Skills

Required:Enterprise software salesCold outreach / prospectingNegotiation and closingDiscovery and needs assessment
Last updated Oct 21, 2026. Interested? Apply on the company site.
TrainLoop logo

About TrainLoop

Reasoning Fine-Tuning

TrainLoop makes it effortless for developers to supercharge LLM performance through reinforcement learning.

developer-toolsgenerative-aireinforcement-learning
Company profileWebsite

More open roles at TrainLoop