Founding Head of Sales

Founding Head of Sales

Full-time | Hybrid or Remote | Reports to Founders

Introduction:

• Join us at Fastino as we build the next generation of LLMs and agentic systems. Our team, boasting alumni from Google Research, Apple, Stanford, and Cambridge is on a mission to develop specialized, efficient AI.

• Fastino has raised $25M (as featured in TechCrunch) through our seed round and is backed by leading investors including Microsoft, Khosla Ventures, Insight Partners, Github CEO Thomas Dohmke, Docker CEO Scott Johnston, and others.

• The Head of GTM will own the entire GTM and Sales engine from day one: owning strategy and execution across sales and growth channels, working closely with the founders to define and scale our growth initiatives and build our future sales organization.

What You’ll Own:

• Full-Cycle Sales Execution: Run the entire sales process end-to-end; from outbound prospecting, qualification, demos, proof-of-concepts, negotiation, and closing. Expect to be an IC with the founders until we scale.

• Pipeline Generation & Outbound Motion: Work with the Fastino marketing lead and own pipeline creation using a modern GTM tool stack (e.g., Clay, Apollo, Gong, HubSpot, Zapier, Notion). Build highly targeted outbound campaigns with agentic, automated workflows.

• Customer Discovery Assessment: Work directly with customers to understand their workflows, pain points, and success metrics - and collaborate with Fastino’s engineering team to translate those insights into Fastino’s product roadmap.

• Onboarding & Customer Success: Shepherd early customers through onboarding and activation, ensuring they get value fast. Build repeatable customer journeys that reduce time-to-value and improve retention.

• Channel Strategy: work with founders to manage sales channels (cloud providers, hyperscalers) and additional acquisition levers - outbound, partnerships, events, community, etc.

• Operational Excellence: Set up first class GTM systems: CRM workflows, automation, dashboards, forecasting, and reporting. Ensure operational excellence in every customer interaction.

• Team Building & Leadership: As traction grows, build and lead a high-performance sales team. This includes hiring AEs, CS, defining roles, setting quotas, mentoring talent, and owning GTM org design.

What We’re Looking For

• 7-8 years in B2B SaaS or AI go-to-market roles, including carrying a quota and closing meaningful deals.

• Demonstrated success selling AI, ML, automation, or technical products to startups, scale-ups, mid-market or enterprise buyers.

• Experience operating as a player-coach - willing to own IC responsibilities at first while laying the foundations for a future team.

• Experience with PLG sales processes - Proven ability to build pipeline from scratch and create repeatable sales motions.

• Strong understanding of LLMs, agentic systems, AI workflows, and the modern AI tooling ecosystem.

• Ability to communicate technical concepts clearly to both engineering and business stakeholders.

• Comfortable collaborating directly with founders, engineers, and researchers.