Lead Account Executive (AI Services)

Very Big Things

12d•Remote

About The Position

Very Big Things is scaling a set of proven, productized generative-AI offerings for upper mid-market and Fortune 5000 organizations—anchored by Transform Work (TrackFrame-powered workflow transformation) and Modernize + AI (accelerated modernization with AI built in from the ground up). We are hiring a Lead Account Executive to convert strong market demand into a disciplined, predictable pipeline and closed revenue. This role is designed for a sales leader who can earn credibility with senior stakeholders, run a rigorous enterprise sales process, and consistently advance opportunities from discovery through contracting—without relying on ad-hoc solutioning to make the sale.

Requirements

7+ years of B2B sales experience, including meaningful time selling technology services (consulting/agency/SI/custom software) or complex technology solutions.
Demonstrated success selling into upper mid-market and enterprise stakeholders, including procurement and security stakeholders as needed.
Strong command of enterprise sales fundamentals: discovery, structured qualification (or equivalent), multi-threading, and negotiation.
Clear executive-level communication—written and verbal—with strong judgment and follow-through.

Nice To Haves

Experience selling or supporting solutions in generative AI, data, automation, or platform software (LLMs, RAG, agents, workflow automation).
Familiarity with enterprise security and compliance considerations (identity, access controls, auditability, data governance).
Prior exposure and/or network in target verticals: healthcare/life sciences, hospitality, manufacturing, or education.

Responsibilities

Own full-cycle sales execution:
Manage opportunities end-to-end: discovery, qualification, stakeholder alignment, proposal development, negotiation, and close.
Maintain a high-quality pipeline focused on upper mid-market and enterprise buyers; produce accurate, defensible forecasts.
Ensure consistent deal velocity through clear next steps, decision-criteria validation, and buying-group alignment.
Represent our offerings with clarity and confidence:
Lead with our core packaged solutions: Transform Work and Modernize + AI.
Communicate value, methodology, and expected outcomes in a structured manner; respond to technical questions with practical accuracy.
Partner with technical leadership during deeper technical evaluations and security/compliance discussions.
Build executive trust and long-term relationships:
Engage C-suite sponsors and operational leaders with clear, concise communication.
Establish credibility through thoughtful discovery and measured commitments—focused on business outcomes and ROI.
Coordinate with internal stakeholders to ensure clean handoffs and strong delivery continuity.
Contribute to a repeatable GTM motion:
Maintain exceptional CRM hygiene and deal documentation.
Improve playbooks, talk tracks, and qualification frameworks based on field learning.
Collaborate with vertical GTM initiatives (e.g., healthcare/life sciences, hospitality, manufacturing, education).