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Siena AI is hiring an Enterprise Account Executive to lead the scaling of its enterprise sales motion. You will own the full sales cycle for six-figure, multi-stakeholder deals targeting consumer brands with $100M+ annual GMV. This is a hunter role for someone who can command rooms with CFOs and CX leaders without scripts or hand-holding, navigate formal RFP processes, build defensible business cases, and spot expansion opportunities within existing accounts.
You will operate with total autonomy, managing complex, multi-SKU deals that can run six months. You'll shepherd internal resources (solutions engineering, leadership) through RFP processes, adapt your approach to different stakeholders, and develop a real point of view on the competitive landscape. The role requires someone who treats every deal as the only one that matters and finds ways to win when others find reasons they couldn't.
Siena is a fully distributed, global team building the intelligence layer for customer experience automation. The company serves brands like Spanx, FIGS, and Brooklinen with a multi-agent AI stack that handles sales, support, listening, social, and voice across the customer journey. The team is small, operates at startup speed, and values ownership, directness, and fast execution.
This role is deliberately not for junior reps. Siena is paying top of market for someone already exceptional who wants to prove it again at a company small enough that individual work is visible across the organization. You'll have real ownership, work that ships fast, and the opportunity to help define what Enterprise AE means as the team scales.
About Siena AI
Commerce / Retail Tech; AI / Data / Infrastructure — AI customer service automation for commerce brands.
