Siena

AI

TechnicalAccountManager,AIAgentDeployment

Toronto FULL TIME Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Senior candidates.

The Brief

“Technical Account Manager, AI Agent Deployment at Siena. Skills: Technical account management, AI Agent Deployment, Customer experience, Commercial acumen. Own technical account health. Diagnose automation performance issues”

What You'll Achieve.

Automation rates; Resolution rates; Account is actually working; Retention; Growth

Industry & Context.

AI
Problems you'll solve

Diagnose problems; Diagnose automation performance issues; Fix problems first and explain later

What They're Looking For.

Must Have

5+ years in technical account management, customer success engineering, or a hybrid technical/commercial role, Technically fluent: you understand how integrations work, can read a configuration, and can diagnose common deployment issues without escalating every time, You lead with outcomes - automation rates, resolution rates, and whether the account is actually working, Commercially aware: you understand ARR, renewal risk, and expansion signals, and can position additional value without it feeling like a pitch, AI fluency - you use AI tools actively in your workflow and can enable and guide, confidently customers who are new to the space, You're proactive with data: you know what the numbers mean and you act on them before customers ask, You build relationships that outlast onboarding - customers want more access to you, not less

Nice to Have

SaaS, CX platforms, or e-commerce strongly preferred

What You'll Do.

Own technical account health

Diagnose automation performance issues

Configure improvements

Drive resolution rates without always pulling in engineering

Be the primary point of contact for your accounts

Run regular business reviews with customer stakeholders

Partner with the deployment team during onboarding

Translate what you hear from customers into structured product feedback the team can act on

How You'll Work.

Team & Collaboration

Partner with the deployment team during onboarding; Share knowledge about AI workflows

Communication Scope

Bring data, tell the story, and drive clear next steps; Bring clarity to customers

Full Job Description

MEET SIENA Siena is the first intelligence layer for customer experience. We're creating an operating system of AI agents that learn, remember, and act across every customer touchpoint—from support conversations to shopping experiences to voice and social media interactions. Siena doesn't just automate support; it powers shopping agents, builds persistent customer memory, generates actionable business insights, and creates empathetic interactions that feel human. We're transforming how businesses understand and connect with their customers, turning every interaction into intelligence that makes the next one better. THE TEAM We're a small, distributed team that punches way above our weight. Every person here has outsized impact because we've built leverage into everything we do. This philosophy makes us faster and, frankly, more fun to work with. If you're excited about building something that doesn't exist yet, keep reading. We're building agents that don't just respond to customers—they remember them, learn from every interaction, and connect experiences across channels. The role As a Technical Account Manager, AI Agent Deployment, you own both the technical and commercial health of your accounts. You master how Siena works under the hood to diagnose problems and drive outcomes - and you're commercially sharp enough to turn those outcomes into retention and growth. You're not a pure CSM and you're not a support escalation point. You're the person customers trust to own their results, and who turns that trust into a longer, larger relationship. Who you are - 5+ years in technical account management, customer success engineering, or a hybrid technical/commercial role - SaaS, CX platforms, or e-commerce strongly preferred - Technically fluent: you understand how integrations work, can read a configuration, and can diagnose common deployment issues without escalating every time - You lead with outcomes - automation rates, resolution rates, and whether the account is ac

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