Head of Sales

Modern AI

2d•Remote

About The Position

Modern is an AI-native data and intelligence platform for commerce brands, and an ai Residency that runs on it every day. The ai Residency team operates a portfolio of DTC brands using this exact platform, meaning features have already been tested against real P&Ls and clients. The company is now taking the platform to market independently. This role is the first dedicated seller for this effort, responsible for defining and executing the sales strategy for the platform. The role is a player-coach position, where the individual will carry the sales number, manage deals, and develop the sales playbook. A team will be hired later, based on growth, and the individual will lead this team. The focus is on building a repeatable go-to-market motion from the ground up, with a strong emphasis on rapid execution and adaptation within the dynamic AI landscape. Success is measured by establishing a working sales motion within the first quarter and demonstrating its repeatability in the subsequent quarter.

Requirements

5+ years of B2B SaaS sales experience with a proven track record of specific numbers, deal sizes, cycle lengths, and pipeline sourcing.
Genuine technical aptitude, including the ability to discuss APIs, data integrations, and attribution methodology without relying on an engineer.
Deep understanding of the AI landscape, including current trends and their business implications for non-technical brand owners.
Experience selling in ambiguous, early-stage environments with an undefined playbook and ICP.
Understanding of commerce metrics (CAC, MER, LTV, contribution margin) and their impact on operators.
A builder mentality, preferring to create new processes over optimizing existing ones.

Nice To Haves

Previous experience as an early or first sales hire, with insights on what would be done differently.
Experience selling both self-serve/PLG and enterprise motions within the same company.
Experience selling into agencies or having worked at an agency.
Background in martech, analytics, attribution, or commerce infrastructure.
Experience using AI tooling for prospecting or research workflows.
Direct DTC or e-commerce experience.

Responsibilities

Pipeline generation and strategy, including outbound, partnerships, communities, events, Modern's network, and affiliate/referral channels.
Selling across four motions: self-serve/product-led, mid-market brands, enterprise and strategic accounts, and agencies/partners.
Developing expert-level product fluency to conduct unscripted demos and handle technical objections.
Providing pricing and packaging feedback based on buyer reactions.
Establishing a product feedback loop by communicating reasons for lost deals to the product team.
Building the sales team and playbook once the sales motion is proven.