03 Nov
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Siena AI
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Toronto
It runs as a connected multi-agent stack on top of a shared intelligence layer: agents that sell, support, listen, handle social and voice across the entire customer journey, turning every conversation into signal you can act on. If you want to set the bar rather than follow one, keep reading. Our Enterprise customers are ecommerce and consumer brands doing $100M+ in annual GMV, and this seat is for someone who has already closed deals at that level. This is a hunter seat: you'll build your own pipeline and take six-figure, multi-stakeholder deals from first call to signature, with real RFPs and real competitive pressure. Build and own your enterprise pipeline into ecommerce and consumer brands doing $100M+ in annual GMV. Run the full enterprise sales cycle from first conversation to close: multi-stakeholder, multi-SKU deals with cycles that can run six months. Find and close expansion opportunities inside your own accounts. If you're missing any of these, this isn't the role for you. Experience selling to executive and C-suite stakeholders at ecommerce and consumer brands. A track record of closing accounts doing $100M+ in annual GMV, with named brands and named numbers. A track record of sourcing a meaningful share of your own closed pipeline. Bonus, not required. ~ Experience selling usage-based pricing,
with land-and-expand growth inside accounts you owned. Your experience is mainly mid-market or SMB, with deal sizes well below six figures. Your closed deals mostly came from inbound leads, not pipeline you created. Your enterprise experience is mostly supporting deals rather than owning and closing them. Work that ships and matters. The Agent of Record is current ground, with unsolved problems and cutting-edge models, not a crowded field to compete in. We hire adults and treat you like one. Excellent salary plus equity or stock grants. The people who thrive here are curious, customer-obsessed, and take ownership without being asked. They've built their own ecosystem of agents - some for research, others for debugging, writing, analysis, or writing code. Everyone gets premium accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) plus a quarterly budget for new tools. We use AI-assisted screening tools as part of our hiring process. Siena provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression.
📌 Account Executive - Sales & Account Management (Toronto)
🏢 Siena AI
📍 Toronto