Siena

Customer Experience

SeniorDeploymentEngineer,AIAgents

Toronto, Ontario, Canada FULL TIME
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Senior candidates.

The Brief

“Senior Deployment Engineer, AI Agents at Siena. Skills: Technical implementation, Integration engineering, Customer-facing technical problem solving, AI agent deployment and configuration. Embed with strategic accounts as the technical member of the deployment pod. Diagnose and resolve technical blockers: integration failures, Zendesk configuration issues, automation logic gaps, data sync problems”

What You'll Achieve.

Fixing one technical problem scales to ten accounts; Integrations live, data flowing, first automations configured for new accounts; Reduce ramp time for future accounts through documentation and playbooks

Industry & Context.

Customer Experience
Problems you'll solve

Diagnose and resolve technical blockers; Identify what's broken or misconfigured and drive a fix; Tackle hard technical problems

What They're Looking For.

Must Have

5+ years in technical implementation, integration engineering, or software engineering with a customer-facing component, Working knowledge of helpdesk and CX platforms - Zendesk, Gorgias, or similar - including API integrations, webhooks, and automation logic, Ability to read a customer's technical setup, identify what's broken or misconfigured, and drive a fix without needing to escalate every time, AI-fluency - understanding how LLM-powered agents work in practice, Comfortable in customer meetings when the conversation gets technical, Shopify, e-commerce platform integrations, and REST APIs are familiar territory

Nice to Have

AI-fluency. Make AI your second nature., Tackle unsolved problems. We’re redefining how customer experience will look like in the next decades.

What You'll Do.

Embed with strategic accounts as the technical member of the deployment pod

Diagnose and resolve technical blockers: integration failures

Zendesk configuration issues

automation logic gaps

Build account-specific automations and integrations that aren't yet supported out of the box

Own the technical setup of new accounts during onboarding

Surface patterns across accounts to the engineering and product teams

Contribute to shared technical documentation and deployment playbooks

Participate in technical scoping during late-stage sales

How You'll Work.

Team & Collaboration

Embedded with deployment pods alongside Deployment Managers and/or Forward Deployed PMs; Collaborate with engineering and product teams to surface patterns; Contribute to shared documentation and playbooks; Participate in sales scoping discussions

Communication Scope

Explain technical concepts without jargon; Comfortable in technical customer meetings

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 Senior Deployment Engineer, AI Agents, you're the technical layer inside our deployment pods. You're embedded with accounts where the complexity goes beyond what a generalist deployment manager can unblock alone - integration failures, automation logic that won't behave, helpdesk configurations that need an engineer's eye. You're not a pure customer-facing role and you're not a pure internal engineering role. You're the bridge. You're energised by hard technical problems inside a customer context - and you know that fixing one well scales to ten accounts. Who you are - 5+ years in technical implementation, integration engineering, or software engineering with a customer-facing component - Strong working knowledge of helpdesk and CX platforms - Zendesk, Gorgias, or similar - including API integrations, webhooks, and automation logic - You can read a customer's technical setup, identify

Free ATS check

Applying for this Senior Deployment Engineer, AI Agents role?

Most applicants get filtered before a human reads their resume. See if yours makes the cut.

How to Apply on Ashby

  • Ashby is a fast modern ATS — most applications take under 3 minutes.
  • The resume parser is strong; verify parsed experience dates and job titles.
  • Custom screening questions are often scored algorithmically — answer completely.
  • Location field affects geo-based screening; use your actual metro area.

ANONYMOUS · UNFILTERED

What do employees actually say about Siena?

Real rants from real employees. Read before you apply.

Read Company Rants →