Product Manager, Agent Autonomy

Siena AI • $100K — $120K *

Toronto, ON M3C 0E3In-Person

Information Technology

Less than 5 years of experience

Today

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Job Overview by Ladders

Qualifications

5+ years of experience as a Product Manager in customer experience, ecommerce, helpdesk, or AI automation
Strong problem solver with a track record of navigating complex challenges
AI-native with hands-on experience using tools like Claude or Cursor
Experience conducting structured A/B testing to inform product improvements
Technical fluency to manage integrations and technical specifications

Responsibilities

Define and expand the autonomy spectrum for agents without human involvement
Develop and improve systems for autonomous resolution with measurable metrics
Create real-time visibility for customers regarding automation and escalations
Conduct A/B tests on agent workflows to guide feature development
Facilitate rapid onboarding for customers to achieve autonomous coverage quickly
Manage the full launch cycle for new autonomy features, including customer training
Engage directly with customers to showcase features and co-sell with the sales team

Benefits

Opportunity to lead and shape the product's autonomous capabilities
Work in a dynamic, customer-facing role with direct impact on user experience
Collaborate with a forward-thinking team focused on AI and automation
Access to ongoing training and professional development opportunities
Participate in a culture that values experimentation and innovation

Full Job Description

The Role

Siena needs a PM to own autonomy: the product surface where our agents act without a human in the loop. You'll decide where autonomy is safe to expand, give customers real visibility into what's automated versus escalated, and run the experiments that make autonomous resolution better over time. You're a strong problem solver first, and you've been a Product Manager in CX, ecommerce, helpdesk, or AI automation.
What You'll Do

Own autonomy end to end: define where agents can act without a human in the loop, and push that boundary as trust and evals allow
Build and ship the systems that make autonomous resolution measurably better: evaluation suites, automated testing, performance monitoring that catches issues before customers do
Give customers real-time visibility into coverage: what's automated, what's escalated, and why, so trust in autonomy compounds instead of eroding
Design and run journey-level A/B tests across agent flows, and use the results to decide what ships next
Own onboarding and automation so customers reach full autonomous coverage in days, not weeks
Run full launch cycles for autonomy features: internal testing, early access, GA, with customer enablement through webinars, docs, and training
Demo autonomy wins to customers directly and co-sell alongside sales
Act as forward-deployed PM when needed: sit with customers, scope live, and move fast from insight to shipped improvement

Who You Are

The Bar: If you're missing any of these, this isn't the role for you.

You're a strong problem solver, full stop
3+ years working as a Product Manager in CX, ecommerce, helpdesk, or AI automation
AI-native: you build with Claude, Cursor, v0, or similar as a daily part of how you work, not just something you've tried

Strong Signal: Not dealbreakers, but what separates a good hire from a great one.

Experience running structured experiments or A/B tests to improve a product metric, not just intuition-led changes
Technical fluency: you can scope webhook systems, OAuth flows, and complex integrations yourself
Customer confidence: you thrive talking with customers, running demos, and co-selling alongside sales

Nice to Have: Bonus, not required.

Experience building trust or visibility features (dashboards, coverage reporting, status pages) for a product customers rely on
Background implementing or rolling out complex systems for enterprise customers

Not a Fit If:

You want a narrowly scoped PM seat with a fixed roadmap handed to you
You're not comfortable being customer-facing or getting on a call to demo your own work
You'd rather stay behind the product than own the messy, ambiguous parts

About Siena AI

Siena AI is a developer of an autonomous chat platform that aims to transform the way it runs and interacts with consumers by combining human empathy and intelligent automation. The platform provides capabilities such as product information, order tracking, address changes, returns and product exchanges, subscription and retention management, allowing firms to conduct customer care and social media interactions autonomously.

Siena AI Careers

There has never been a better time to join the global team of Siena AI professionals, a leading force in the artificial intelligence sector.

Work You'll Do

Join Siena AI's market-leading team to assist some of the most innovative companies in mastering their technology-driven transformation journeys. At Siena AI, the fusion of technology, industry expertise, and digital innovation puts the company at the forefront of the AI industry. Lead in a unique market position, harnessing the power of AI to drive industry-wide changes and deliver unparalleled innovation. Engage with a global team of business and technology advisors, helping clients navigate through complex AI integrations and transformations. Collaborate with a dedicated group of AI experts, driving forward the boundaries of what's possible in technology and business.

Introducing the Siena AI Business Group Advisory

This team is dedicated to building a leading advisory service, guiding major companies through their digital transformation journeys using advanced AI solutions.

Innovative Work

Be part of the largest group of AI professionals, delivering targeted solutions through a depth of consulting experience and innovation that is unmatched in the industry.

Innovate and Grow

Deliver solutions that are trusted by enterprises worldwide, leveraging Siena AI's extensive consulting experience and innovative approaches.

Be Part of a Great Team

Join a team that works on cutting-edge Microsoft technology and harnesses the capabilities of a global scale operation to develop joint solutions.

Future-Proof Your Career

With Siena AI, go as far as ambition can take, with endless opportunities to advance careers through unmatched training, development, and certification support.

Explore Job Opportunities

Discover how Siena AI is moving industries towards more predictive and efficient practices with advanced AI solutions. From improving operational efficiencies to pioneering new industry standards, the impact is profound and rewarding.

The Siena AI Leadership and Innovation

With a commitment to leadership in AI and a culture that fosters diversity and professional growth, Siena AI is a beacon of innovation. The company's global scale and joint solution development enable clients to overcome challenges and lead transformations in their fields.

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Size

11 employees

Industry