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14.ai

Founding account executive

14.ai, San Francisco, California, United States, 94199

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We are an intense, tightly-knit team building the future of AI-native customer experience for B2C brands. Our customers range from fast-growing DTC brands on Shopify and TikTok Shop to established e-commerce companies, and we obsess over listening to each of them and helping them succeed. Our development pillars are security, reliability and performance, combined with pragmatism to always find working solutions and be ultra-responsive to customer feedback and requests. Working at the intersection of AI and commerce, we strive to build correct, future-proof solutions with great taste.

Blog post: https://14.ai/blog/why-ai-native-bpos-are-the-future-of-outsourcing-8f404ac6-7446-4708-8c7e-46576b8cd460

As a Founding Account Executive, you will be directly engaging with our customers and prospects. You will become the bridge between cutting‑edge AI automation and DTC brands scaling their support operations. You’ll run discovery calls, deliver tailored demos, close deals, and step in as the trusted advisor when complex buying decisions require judgment and empathy.

Our goal: reach $10M ARR by end of 2026.

What you will do

Own the full sales cycle

from prospecting to close for B2C brands looking to transform their customer support

Run discovery calls

that uncover real pain points around support volume, BPO costs, and scaling challenges

Deliver product demos

that show how 14.ai achieves auto‑resolution with sub‑10 second reply times

Build relationships

with founders, COOs, and CX leaders at DTC brands on Shopify, TikTok Shop, and other platforms

Shape our go‑to‑market strategy

based on what you learn in live customer conversations

Partner with our founders

to refine messaging, pricing, and product positioning

Become a product expert

who can speak fluently about AI agents, integrations, and e‑commerce workflows

Who you are

Hungry and scrappy : you thrive in early‑stage environments where you build the playbook, not follow one

Customer‑obsessed : you listen deeply, ask smart questions, and genuinely care about solving problems

Technical enough : you can learn complex products quickly and explain AI/automation to non‑technical buyers

Results‑driven : you love hitting goals and understand that revenue is the lifeblood of startups

Excellent communicator : you write crisp emails, run tight meetings, and build trust fast

Ambitious : you want equity, responsibility, and the chance to define a category

Bonus points

Experience selling B2B SaaS to e‑commerce or DTC brands

Familiarity with Shopify, TikTok Shop, or CX tooling

Prior work at an early‑stage startup (seed to Series A)

Why join 14.ai

Founding team role : real equity and the opportunity to build something from the ground up

Learn from the best

: work directly with experienced founders who’ve built and sold AI companies (video: https://www.youtube.com/watch?v=FedPUth6fQY)

Category creation : you’re not selling a commodity; you’re defining a new way brands think about support

Impact : every deal you close changes how a company operates and scales

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