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Added 1 hour ago
KS
Western Regional Sales Manager - Alberta
Kinetic Search Group
AB · Alberta, Canada
- $110,000 to $125,000 CAD / year
- Full-time
Backed by a larger international organization, our client combines the strength and stability of an established industry leader with the customer-focused approach of a specialized technical…
Added 2 hours ago
AL
Director of Operations
AlgoEdge Labs
Niagara Falls, ON
- Full-time
The business is planned to roughly double its revenue in 2027. The General Manager owns the P&L, customers, sales and engineering. The Director of Operations owns everything between order…
Added 4 hours ago
Retail Assistant Brand Manager, Sandro/Maje, (Holt Renfrew Ogilvy, Montreal)
SMCP NORTH AMERICA (US, CANADA)
Montreal, QC
As an Assistant Brand Manager, you’ll be a key leader in delivering an elevated client experience while inspiring and coaching your team to achieve excellence. You’ll lead by example,…
Added 5 hours ago
P
Executive Administrative Assistant
Popular
St. Thomas, ON
- Full-time
The Executive Administrative Assistant provides high-level administrative and operational support to the Division Manager and VI Region Division. This position plays a key role in…
Added 6 hours ago
NB
Wealth Associate
National Bank of Canada
London, ON
- Full-time
…400,000 clients in about 100 branches. Reporting to the regional manager, you will team up with a wealth advisor to offer an exceptional client experience. Collaboration and partnership…
Added 6 hours ago
NB
Wealth Associate
National Bank of Canada
Laval, QC
- Full-time
…400,000 clients in about 100 branches. Reporting to the regional manager, you will team up with a wealth advisor to offer an exceptional client experience. Collaboration and partnership…
Added 8 hours ago
B
Global Relationship Manager- 3
BrightClaim
ON
- Full-time
Responsibilities: Develop and strengthen relationships with sales organizations, creating effective go-to-market strategies for business growth. Design creative and profitable commercial…
Added 11 hours ago
LC
Assistant Store Manager, Dartmouth Crossing, Full Time
Laura Canada
Dartmouth, NS
- Full-time
Support the Store Manager in team management and merchandising to achieve sales goals.
Added 12 hours ago
K
Seasonal Sales Associate (Markville Mall)
Knix
Markham, ON
- $19.7 CAD / hour
- Temporary
As a Sales Associate at Knix, you play a key role in creating a warm, inclusive, and confidence-building experience for every customer who walks through our doors. From first hello to…
Added 12 hours ago
K
Seasonal Sales Associate (Square One)
Knix
Mississauga, ON
- $19.7 CAD / hour
- Temporary
As a Sales Associate at Knix, you play a key role in creating a warm, inclusive, and confidence-building experience for every customer who walks through our doors. From first hello to…
Added 12 hours ago
K
Seasonal Sales Associate (Rideau)
Knix
Ottawa, ON
- $19 CAD / hour
- Temporary
As a Sales Associate at Knix, you play a key role in creating a warm, inclusive, and confidence-building experience for every customer who walks through our doors. From first hello to…
Added 12 hours ago
K
Seasonal Sales Associate (Market Mall)
Knix
Calgary, AB
- $19.7 CAD / hour
- Temporary
As a Sales Associate at Knix, you play a key role in creating a warm, inclusive, and confidence-building experience for every customer who walks through our doors. From first hello to…
Added 12 hours ago
K
Seasonal Sales Associate (West Edmonton Mall)
Knix
AB · Edmonton, AB
- $19.7 CAD / hour
- Temporary
As a Sales Associate at Knix, you play a key role in creating a warm, inclusive, and confidence-building experience for every customer who walks through our doors. From first hello to…
Added 15 hours ago
G
Gestionnaire marketing produit / Product Marketing Manager
Genetec
Montreal, QC
- Full-time
Au sein de l'équipe Vidéo et Opérations unifiées, vous dirigerez la planification de la mise sur le marché des nouveaux produits, des mises à jour et des offres stratégiques couvrant…
Added 17 hours ago
CW
Account Representative / Account Manager / Project Manager
City Wide Facility Solutions
Burnaby, BC
- $55,000 to $80,000 CAD / year
- Full-time
This position is not cold sales. Success comes from owning the client experience, ensuring service quality, and acting as the trusted point of contact between clients, service partners, and…
Added 17 hours ago
TS
TDS Operations Analyst III
TD Securities
Toronto, ON
- Full-time
Global Business Services & Operations is at the core of TD Securities. We are a dynamic, multi-faceted division that partners with all parts of the Dealer, including Sales & Trading to…
Added 17 hours ago
TS
TDS Operations Analyst II
TD Securities
Toronto, ON
- Full-time
Global Business Services & Operations is at the core of TD Securities. We are a dynamic, multi-faceted division that partners with all parts of the Dealer, including Sales & Trading to…
Added 17 hours ago
CI
Banquet Assistant Manager
Canad Inns
Winnipeg, MB
- Full-time
Reporting directly to the Banquet Manager and General Manager, the Assistant Banquet Manager plays a key role in the planning, coordination, and execution of a wide range of events,…
Added 17 hours ago
L
Product Manager
Linedata
Toronto, ON
- Full-time
The Linedata Capitalstream Product Manager is responsible for managing Capitalstream product capabilities throughout the product lifecycle from initial concept and market research through…
Added 18 hours ago
BF
Bilingual Talent Acquisition Co-Op
Burnbrae Farms
ON · Mississauga, ON
- Full-time
…nutritious, and affordable eggs and egg products. Across our operations, spanning 7 farms, 8 grading stations, 3 processing plants, and 2 distribution centres, we collect, grade, boil,…
Added 18 hours ago
Store Manager - West Edmonton Mall
Laura Canada
Edmonton, AB
Privately owned and based in Laval, Quebec, with a strong vision for innovation and optimizing the employee and client experiences, we continue to help generations of Canadian women to look…
Added 18 hours ago
R
Branch Manager, Bayview & Wellington Branch
RBC
Aurora, ON
- Full-time
As a Branch Manager, you are a local market leader, motivating and coaching your team to create a memorable experience for clients. Inside and outside the branch, you capitalize on emerging…
Added 18 hours ago
JH
General Manager - Boutique Hotel
JRoss Hospitality Recruiters
Toronto, ON
- $120,000 to $130,000 CAD / year
- Full-time
Reporting to the CEO, the General Manager will oversee all aspects of hotel operations, working closely with an established management team to drive revenue growth, operational excellence,…
Added 19 hours ago
K
Seasonal Sales Associate (Polo Park)
Knix
Winnipeg, MB
- $17.9 CAD / hour
- Temporary
As a Sales Associate at Knix, you play a key role in creating a warm, inclusive, and confidence-building experience for every customer who walks through our doors. From first hello to…
Added 19 hours ago
Retail Store Manager - Place Montreal Trust
Laura Canada
Montreal, QC
Privately owned and based in Laval, Quebec, with a strong vision for innovation and optimizing the employee and client experiences, we continue to help generations of Canadian women to look…

Robots & Pencils

Senior Delivery Manager

Canada

The salary range for this role is $ 170.000 CAD - $220.000 CAD. · Full-time

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Job details

Pay: The salary range for this role is $ 170.000 CAD - $220.000 CAD.
Job type: Full-time
Experience: 5+ years of experience in software delivery, technical project management, or engineering leadership
Posting language: English
Posted: Oct 28, 2026

Original job description

Robots & Pencils is an applied AI engineering firm building the next frontier of business architecture. We design and ship AI co-workers that integrate into enterprise operations and deliver measurable results for our clients. We're all in on AWS, combining deep UX capability with senior engineering talent to get AI into production fast and keep it there.

We’ve earned the trust of leaders across Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, and Manufacturing and more, and earned a reputation as the nimble alternative to traditional global systems integrators. Founded in 2009, with delivery centers in Canada, the United States, Eastern Europe, and Latin America, we are smaller, faster, and more senior by design. Our teams average 15+ years of experience. We move fast, sweat the details, and build things that actually ship.

Position Overview

As a Senior Delivery Manager, you are the senior delivery authority on a cross-functional engagement: owning execution from kickoff through release, leading distributed onshore-and-offshore teams, and serving as the primary delivery partner to the client. You bring the judgment to navigate ambiguity, the discipline to keep complex programs on track, and the instinct to make every engagement a foundation for the next one.

Why This Role Matters

Senior Delivery Managers are where Robots and Pencils’ promise of “production-ready AI in 30 to 45 days” actually has to hold. On the engagements you run, you set the pace of delivery, the discipline behind it, and the trust that decides whether the client comes back for more. The work moves only as fast as someone is willing to own the plan, surface trade-offs early, and keep distributed teams pulling in the same direction.

What You’ll Do

Delivery

Lead end-to-end delivery of complex, multi-phase engagements, ensuring alignment across scope, budget, timeline, and quality to meet delivery commitments and achieve successful outcomes
Facilitate sprint planning, backlog refinement, and delivery execution across one or more cross-functional teams
Manage phased releases, production readiness, and transitions into operations and maintenance models
Identify and proactively manage dependencies, risks, scope changes, and escalations before they become blockers
Define, track, and report delivery KPIs, using data to guide decisions, manage delivery health, and inform tradeoffs across scope, timeline, and budget
Support QA and UAT efforts, ensuring quality is validated and outcomes meet agreed acceptance criteria
Bring an AI-forward mindset to your daily work, using tools like Claude to enhance delivery planning, reporting, and stakeholder communications

AI Enablement

Help implement the AI Development Life Cycle (AIDLC) across your engagements, and set the standard other delivery managers follow for standing it up
Use AI yourself day-to-day, and set the standard for how your engagements run an AI-augmented delivery process - modeling and coaching the delivery managers you mentor on how planning, building, and review change when agents are doing part of the work
Know observability for agentic and AI-driven work well enough to partner credibly with an AI product manager and AI engineers across your engagements - judge whether their approach is actually solid, catch risks early, and drive them to resolution - and hold the delivery managers you mentor to the same bar. You’re not the one building the instrumentation, but none of it should be a black box to you.
Define what “success” looks like for an AI-augmented delivery process and set the metrics standard across your engagements - quality, rework, review overhead, and velocity, not just tests passed
Build - or direct the building of - status-visibility tooling for complex AI-driven pipelines, using AI yourself, and expect the delivery managers you mentor to do the same
Understand context management and latency trade-offs deeply enough to make the call on when an agentic approach is the wrong tool for a client’s needs, and defend that call to the client
Set the standard for what infrastructure an agentic delivery pipeline needs - compute, orchestration, logging, guardrails - and know enough to hold engineering accountable for it, even though you’re not the one building it
Own the delivery approach for AI-native and agentic engagements: partner with AI/ML engineering leads on model risk, data readiness, and evaluation strategy, and translate technical uncertainty into a delivery plan and risk register the client can act on
Work with AI product managers and AI engineers to set the standard, across your engagements, for what a “definition of done” looks like for probabilistic or AI-driven features - evaluation thresholds, human-in-the-loop checkpoints, post-launch monitoring - well enough to judge whether it’s actually good, and hold the team to it
Coach delivery managers and delivery coordinators you mentor on the difference between shipping an AI product, using AI to accelerate a traditional delivery, and running an agentic development process to build the work itself - and help them adapt scope, staffing, and risk management accordingly
Serve as a credible voice with clients and internal leadership on what “production-ready AI” actually requires - setting realistic expectations for iteration, evaluation, and drift over time

Collaboration & Communication

Serve as the primary delivery contact for clients, building trusted relationships through transparency, consistency, and clear communication while identifying opportunities to expand value within the engagement
Lead stakeholder working sessions, roadmap alignment discussions, and delivery forums with confidence
Communicate progress, risks, and tradeoffs clearly to executive and non-technical audiences
Partner with Client Partners to spot expansion opportunities inside the engagement (scope, follow-on work, new use cases) and help shape the case for what’s next
Translate delivery progress into business impact for client stakeholders (ROI, milestones, decisions) so executives see ongoing value, not just status

Leadership & Influence

Lead distributed delivery teams across onshore and offshore locations, fostering accountability, collaboration, and delivery excellence
Coach junior delivery managers with concrete feedback and stretch opportunities, contributing to their development plans
Foster a culture of transparency, continuous improvement, and high performance across the engagement
Contribute to improving delivery practices, tools, and frameworks across engagements
Assess team strengths and gaps on your engagements, and partner with Client Partners to flag staffing needs and high-potential talent for the firm
Conduct executive interviews for engineers, designers, and other roles joining your engagements, and serve as an essential voice in go/no-go hiring decisions across the firm

What You’ll Bring

5+ years of experience in software delivery, technical project management, or engineering leadership
Strong understanding of agile delivery practices across complex, multi-team engagements (e.g., Scrum, SAFe, Kanban)
Experience managing distributed teams across onshore and offshore locations
Proven ability to deliver complex, multi-platform digital systems in agile environments
Strong client-facing communication and relationship management skills
Experience with delivery tooling (e.g., Jira, Confluence, GitHub, Azure DevOps, CI/CD pipelines)
Familiarity with cloud-native architectures and AI-enabled platforms
Demonstrable usage of AI tools to enhance delivery planning, reporting, and documentation (e.g., Claude)
Track record leading at least one engagement where AI/ML or agentic capability was core to the solution - including how you managed model risk, evaluation, and client expectations, not just how you used AI tools to work faster
Able to set delivery standards for AI-native work across an engagement or practice - evaluation criteria, human-in-the-loop checkpoints, monitoring - and coach other delivery managers on them
Track record leading a team through an agentic development/delivery process yourself - not just using AI tools personally - including how you approached observability, success metrics, and status visibility for a process that isn’t fully deterministic
Comfortable setting the standard, across engagements, for the infrastructure, context-management, and latency trade-offs an agentic delivery pipeline needs - enough to hold engineering and delivery managers accountable, even though you’re not the one implementing it
PMP, Scrum Master, SAFe, or equivalent certification preferred
Instinct for spotting where an engagement can grow, and the credibility with clients to bring those conversations forward with Client Partners

Helpful Extras And Unique Skills

Vertical depth in one or more of Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing
Experience delivering agentic, AI co-worker, or applied-AI initiatives in enterprise
Prior career experience in client-facing roles (engagement management, consulting, account leadership) that informs growth conversations

You’ll Do Well Here if You Are

A doer. You see something broken and fix it. You'd rather move on clarity than wait for certainty.
A fast learner who knows you don't know everything. The AI landscape changes weekly. You're senior enough to know better and curious enough to keep learning anyway.
Direct in a way that makes the work better. You give honest feedback. You'd rather have the hard conversation than blow smoke.
Obsessed with craft. You know genius is in the details. You ship exceptional, not perfect, and you don't put your name on work you wouldn't stand behind.
Built for ownership. You honor commitments, admit mistakes fast, and back your teammates when a decision costs something. No handoffs, no finger-pointing.
All in. You treat clients' businesses like your own. You take the work seriously without taking yourself seriously.
Resourceful when the budget, timeline, or team is tight. Constraints don't slow you down. They sharpen you.
Calm when it gets hot. When scope, timeline, and stakeholders pull in three directions, you slow the room down enough to make the right call. You’d rather raise the hard trade-off in week two than absorb it in week eight.
Glad to be in the room with people who care as much as you do. Our teams average fifteen-plus years of experience. We hire people who push each other to do better work.

The below range reflects the range of possible compensation for this role at the time of this posting. We may ultimately pay more or less than the posted range. This range may be modified in the future. An employee's position within the salary range will be based on several factors including, but not limited to, relevant education, qualifications, certifications, experience, skills, seniority, geographic location, performance, shift, travel requirements, sales or revenue-based metrics, any collective bargaining agreements, and business or organizational needs. The salary range for this role is $ 170.000 CAD - $220.000 CAD.  We offer a comprehensive package of benefits including paid time off, medical/dental/vision insurance and 401(k) to eligible employees.

An offer of employment may be conditional upon successful completion of a background check in accordance with local legislation and our candidate privacy notice. Your current employer will not be contacted without your permission.  We are committed to ensuring equal employment opportunities for all job applicants and employees. Employment decisions are based upon job-related reasons regardless of an applicant's race, color, religion, sex, sexual orientation, gender identity, age, national origin, disability, marital status, genetic information, protected veteran status, or any other status protected by law.

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More about this job

Responsibilities

Own complex, multi-phase engagements from kickoff through release, managing scope, budget, timelines, quality, risks, and production readiness while serving as the primary client delivery partner. Establish AI-augmented and agentic delivery standards, guide distributed teams and junior delivery managers, communicate progress and trade-offs, and identify opportunities to expand client value.

Requirements

Requires at least five years of experience in software delivery, technical project management, or engineering leadership, with strong agile delivery, distributed-team, client-facing, and complex digital-systems experience. Candidates must have led AI/ML or agentic engagements and be able to set standards for evaluation, observability, monitoring, infrastructure trade-offs, and AI delivery practices; relevant certifications are preferred.

Skills

End-to-End Delivery Management
Agile Delivery
Distributed Team Leadership
Risk and Dependency Management
Budget and Scope Management
Delivery Metrics and Reporting
AI-Augmented Delivery
Agentic AI Delivery
AI/ML Model Risk and Evaluation
AI Observability
Production Readiness
Stakeholder Communication
Coaching and Mentoring
Jira
Confluence

Benefits

Paid Time Off
Medical Insurance
Dental Insurance
Vision Insurance
401(k)

Visa sponsorship

Not detected in the job text

Keywords

AWS
Claude
Jira
Confluence
GitHub
Azure DevOps
CI/CD
Scrum
SAFe
Kanban
Agile
AI Development Life Cycle
Agentic AI
AI/ML
AI Co-Workers
Cloud-Native Architecture
Model Risk
Evaluation Strategy
Observability
Context Management
Latency Trade-Offs
Human-in-the-Loop
Post-Launch Monitoring
Production Readiness
Quality Assurance
User Acceptance Testing
PMP
Scrum Master Certification
Distributed Teams
Delivery KPIs

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