About the role:

This is a high energy role in which you will bring the Internet of Things to small to medium size customers, building Samsara's business and bringing the benefits of sensor data to customers. Typical sales will be $5k to $20k, and typically involve proof of concepts, multiple stakeholders, multi-faceted pricing negotiations, and selling to owners, safety and operational managers.

This position is based remotely in Canada.

You should apply if: 

• You want to impact the industries that run our world: Your efforts will result in real-world impact—helping to keep the lights on, get food into grocery stores, and most importantly, ensure workers return home safely.
• Your mantra is #alwaysbeprospecting: The world of operations is vast. Your customers are often out in the field and the best way to catch them is live on the phone. Samsara’s top reps do constant research to find companies and contacts to expand their pipeline.
• You have innate curiosity in how businesses work: One day you’ll meet with someone in waste management and the next you may be learning about the inner workings of a food distribution center. Our top sales team members seek to learn the ins and outs of the businesses they support in order to make a larger impact. 
• You are a life-long learner: Samsara sales are complex. You will need to learn about businesses where you previously had little knowledge. The payoff is big but you have to be willing to put in the work. 
• You build genuine relationships with your customers: The industries we serve have relied on pen-and-paper solutions for years and haven’t been met with the type of technology we offer. Our customers value earned trust and human relationships built over time.
• You want to be with the best: Samsara’s high-performance Sales culture means you’ll be surrounded by the best and challenged to go farther than you have before.  

In this role, you will: 

• Own customer engagements end-to-end, from prospecting and qualification to close.
• Generate pipeline through strategic outbound prospecting, as well as receive inbound leads from our account development team.
• Target accounts with 11-30 vehicles. 
• Experience handling and owning transactional sales process with high volume demands.
• Champion, role model, and embed Samsara’s cultural principles (Focus on Customer Success, Build for the Long Term, Adopt a Growth Mindset, Be Inclusive, Win as a Team) as we scale globally and across new offices.

Minimum requirements for this role:

• 1+ years of experience in a closing sales role

An ideal candidate has:

• Proven track record of consistent quota achievement
• Experience selling in the commercial space - small to medium deals sizes
• Experience with high-volume cold calling
• Experience in fast-paced, transactional sales
• Must demonstrate a growth mindset and a willingness to be collaborative with your teammates and in your selling process
• SFDC familiarity

About the role:

This is a dynamic, high energy role in which you will bring the Internet of Things to mid-sized customers, building Samsara's business and bringing the benefits of sensor data to customers. Typical sales will be $20k to $100k, and involve POCs, multiple stakeholders, managing trials, multi-faceted pricing negotiations, and selling to executives and CXOs. 

This is a remote position open to candidates based in Canada

You should apply if: 

• You want to impact the industries that run our world: Your efforts will result in real-world impact—helping to keep the lights on, get food into grocery stores, and most importantly, ensure workers return home safely.
• Your mantra is #alwaysbeprospecting: The world of operations is vast. Your customers are often out in the field and the best way to catch them is live on the phone. Samsara’s top reps do constant research to find companies and contacts to expand their pipeline.
• You have innate curiosity in how businesses work: One day you’ll meet with someone in waste management and the next you may be learning about the inner workings of a food distribution center. Our top sales team members seek to learn the ins and outs of the businesses they support in order to make a larger impact. 
• You are a life-long learner: Samsara sales are complex. You will need to learn about businesses where you previously had little knowledge. The payoff is big but you have to be willing to put in the work. 
• You build genuine relationships with your customers: The industries we serve have relied on pen-and-paper solutions for years and haven’t been met with the type of technology we offer. Our customers value earned trust and human relationships built over time.
• You want to be with the best: Samsara’s high-performance Sales culture means you’ll be surrounded by the best and challenged to go farther than you have before. 

Minimum requirements for this role:

• 2+ years experience in a full-cycle, closing sales role
• Experience independently closing new deals larger than $10,000 in annual revenue.
• Must be located in Canada

An ideal candidate has:

• Proven track record of consistent quota achievement
• Experience selling in the midmarket space - medium to large deals sizes
• Experience with high-volume cold calling
• Must demonstrate a growth mindset and a willingness to be collaborative with your teammates and in your selling process
• SFDC familiarity

At Robots & Pencils, we build meaningful, scalable digital products that solve real business problems. We are looking for a Staff Product Manager who combines deep Generative and Agentic AI fluency with hands-on building ability to own AI product outcomes end-to-end. As a Staff PM, you're accountable for initiative-level outcomes, stakeholder satisfaction, and contributing to R&P's AI product practice. You think in systems, work backwards from the customer problem, and stay relentlessly curious about what's next in AI

Enterprise clients want to deploy Agents -  moving from a promising demo to a production system that works at scale, meets security and compliance requirements, and delivers measurable business value is hard. This role owns that problem. You'll be part of a GenAI initiative within the AWS ecosystem, building the evals, tools, patterns, and reference architectures that make AI deployment repeatable.  The mindset: prove it works, test assumptions early, and document while building.

Key Responsibilities

Product Strategy & AI Vision

• Define and drive the product vision, strategy, and roadmap for GenAI solutions - with agentic AI (agent orchestration, tool use, multi-step workflows) as the primary focus - connecting AI capabilities to enterprise business outcomes
• Translate enterprise problems into structured product requirements; reframe feature requests into outcome-driven priorities with explicit tradeoffs on invest in vs. defer
• Balance near-term deployment milestones with long-term platform scalability and sustainability
• Monitor the competitive GenAI landscape and emerging agentic patterns to inform roadmap and technology decisions

Discovery & Validation

• Research how enterprise users interact with AI agents and where they lose trust; frame the riskiest assumptions as testable hypotheses and de-risk them first
• Design and run experiments - POCs, pilot deployments, scenario-based testing of multi-step workflows, edge cases, and failure recovery - to validate agentic solutions where non-deterministic output makes traditional QA insufficient
• Distill research, experiments, and competitive intelligence into clear insights that pave the path for a successful product
• Agent Design, Prototyping & Production
• Define agent behavior and prototype system prompts and tool schemas; partner with engineering on context management - summarization, working memory, and information flow across multi-step tasks
• Drive multi-model architecture tradeoffs with engineering - define the quality, cost, and latency targets that determine which model serves each step in the agent workflow
• Build AI prototypes to validate hypotheses; define human-in-the-loop boundaries and guardrails - when the agent acts autonomously, when it escalates, and how to handle non-deterministic output
• Establish agent evaluation frameworks - task completion, reasoning quality, tool selection, failure recovery, safety - and partner with engineering on production readiness (observability, drift, responsible AI, prompt versioning)
• Define success metrics at the agent level - task completion rate, cost per task (not per inference), escalation rate, time to resolution, and customer trust alongside business KPIs
• Delivery & Execution
• Own the end-to-end product lifecycle from discovery through phased rollouts; establish the metrics framework (north star, input, guardrail metrics) and report product impact to leadership
• Manage the product backlog, scope, dependencies, and risks; drive agile ceremonies and produce high-quality PRDs, product briefs, and decision logs
• Evaluate technology and platform decisions from a product perspective; create deployment playbooks, reference architectures, and knowledge transfer materials so teams sustain solutions independently
• Use AI to accelerate product work - research, analysis, prototyping, documentation - with judgment on when it needs human oversight; onboard rapidly to new domains and support team members across the initiative

Stakeholder Management

• Build trusted relationships with stakeholders and executives; serve as the go-to product advisor and primary contact for AI product direction and deployment strategy
• Partner with AWS Solution Architects and account teams to align on technical approach, service selection, and go-to-market for GenAI solutions
• Manage expectations on scope, timelines, and tradeoffs; facilitate decisions across competing priorities using data, alternatives, and clear rationale
• Frame AI capabilities and limitations for non-technical stakeholders - manage hype cycles, set realistic expectations; surface unmet needs that deepen relationships and grow the account

Required Skills

• 8-12+ years in product management, forward deployment, or solutions engineering; must have shipped AI products from prototype through production at scale
• Strong product sense - ability to identify what matters to users and the business, make prioritization calls with incomplete information, and shape products that deliver real outcomes
• Deep GenAI fluency - LLMs, RAG, fine-tuning, prompt engineering, context engineering, evals - with hands-on experience building or shipping agentic systems (planning, tool use, HITL, guardrails)
• Proven ability to prototype AI solutions using AI tools (Cursor, Claude, Copilot) to validate hypotheses and de-risk product decisions
• Experience deploying AI solutions in enterprise environments with strong technical fluency - can read code, evaluate architectures, make product tradeoffs on technical constraints, and drive scalable deployment patterns
• Exceptional communicator - clear PRDs, technical specs, and decision logs; has led AI products through full lifecycle and driven alignment with Directors, VPs, and C-level
• Comfortable operating in ambiguous, fast-moving environments where the AI landscape evolves weekly
• PM-level fluency across the AWS AI ecosystem - Bedrock, AgentCore, SageMaker, Strands, Kendra, OpenSearch, Lambda, Step Functions - to make informed product and architecture decisions

Preferred Qualifications

• Software engineering or coding background (Python, JavaScript, TypeScript)
• Agency or consulting delivery experience
• Experience in Financial Services, Healthcare, or Life Sciences industries
• Familiarity with open-source LLM ecosystem (Llama, Mistral) for flexibility and cost optimization
• Prior experience leading time-boxed discovery initiatives or technical spikes with rapid validation cycles

Why Join R&P?

You'll work at the intersection of cutting-edge AI and real enterprise impact - helping clients deploy Generative and Agentic AI solutions that change how their businesses operate. R&P gives you the variety of consulting (new problems, new industries, new tech) with the depth of a product role - you'll build, ship, and measure, not just advise. The team is collaborative, technically sharp, and genuinely invested in doing great work for clients.

Elevate Your Career and Impact at Second Harvest

Location: Flexible, can be based in Vancouver, Calgary, Edmonton, Winnipeg, Ottawa, or Montreal.

Date: April 2026

Department: Volunteer Services

Reports to: Senior Manager, Volunteer Services

Status: Full-Time (New vacancy).

Salary: $60,000 - $70,000 Per Annum Plus Benefits

Work Type: Remote (with occasional in-person responsibilities)

Travel Required – Domestic & National: 30% (approximate)

The Opportunity Awaits—Where Passion Meets Impact!

Second Harvest is Canada’s largest food rescue organization and expert in perishable food recovery.

We rescue surplus, unsold food from across the supply chain and redistribute it to not-for-profits across the country to feed communities. Demonstrating our values of community, environment, integrity, and collaboration, we strive for No Waste. No Hunger.

If you are ready to bring your expertise and innovation to a mission-driven organization, this is your moment.

Enter Second Harvest…

Think we're just about redirecting food surplus? Think bigger.

Here's why Second Harvest is your next career leap:

• Pioneers in food rescue, we are a renowned leader in perishable food redistribution across Canada.
• With a mission fueled by a no-waste, no-hunger ethos, we're not just changing the game—we're rewriting the rules.
• Our strategic approach aligns with the United Nations’ Sustainable Development Goals (SDGs), making every day a step towards global change.

The Role:

As the National Volunteer Engagement Manager, you will work to engage volunteers across Canada and be responsible for supporting the growth of our national volunteer program, with a focus on scaling corporate & community partnerships across the country. The incumbent will work closely with our field operations staff, corporate partners, and community groups to ensure that all volunteer engagement activity is well-executed and meets the high-quality standards for Second Harvest’s volunteer experience.

Your Impact:  

Group Volunteer Engagement (50%):

• Collaborate with our Development Team and corporate stakeholders to co-create meaningful and measurable volunteer experiences.
• Oversee the planning and execution of volunteer logistics for any national Second Harvest initiatives, including but not limited to, community events, food collections, snack packing, Feeding Our Future, gleaning program, etc.
• Work with a network of suppliers and vendors to coordinate the ordering and delivery of event supplies for snack packing.
• Support Second Harvest regional teams with in-person delivery of corporate and community engagement events.
• Provide support with the planning and day-of logistics for any national volunteer appreciation events and National Volunteer Week activities.

Volunteer Coordination (40%):

• Recruit, screen, train, and supervise national volunteers as Second Harvest’s volunteer program expands nationally.
• Maintain an active and engaged roster of community-based volunteers in key markets to support the business goals of each department at Second Harvest.
• Act as liaison between Field Operations staff and volunteers, ensuring that proper volunteer management protocols are being followed
• Provide volunteers with feedback, monitor volunteer satisfaction, and resolve concerns in a timely manner.
• Participate in cross department meetings as required to remain apprised of volunteer requirements.
• Ensure that all volunteers are appreciated and stewarded to maintain a large and dedicated volunteer base.
• Support strategic planning by assessing and evaluating the national Volunteer Program in an ongoing capacity.

Administrative (10%):

• Regularly contribute to monthly/quarterly reports and support the creation of annual reports that include volunteer hours, number of volunteers, and program outcomes.
• Oversee data entry of national volunteers and placements into Raiser’s Edge.
• Perform other related duties as required or assigned to support the overall goals of the organization.

Who You Are:

• Partnership-Minded: you are a people person who can leverage existing relationships to build program success.
• Detail-Oriented: you are proud of your work and know that cutting corners isn’t an option.
• Energized: you are always ready to take on new things and have fun doing it.
• Flexible: constant change motivates you to adapt and grow.
• Technical: you have a high level of proficiency with Microsoft Office Suite of products; you also have experience working with Raiser’s Edge.
• Bilingual: Fluency in English and French is an asset.
• A minimum of three to five (3-5) years experience in the not-for-profit sector, with working knowledge of volunteer programs, community engagement, program management, CSR/employee engagement programs, or event management is ideal.
• Post-secondary education in volunteer management, human resources, social work, or similar field is preferred.

A Robust Compensation Package:

• A competitive salary paired with a robust benefits package.
• Comprehensive group insurance (health, dental, life, AD&D and Long-Term disability)
• Employer match contributions (3%) to a Defined Benefit Pension Plan.
• Access to parental leave top-up.
• 4 weeks of annual vacation & 1 additional day per year of service (max 30).
• 10 paid sick days & 3 personal days.
• Summer Half-Days to further extend long weekends & Winter holiday closure.
• Access to an Employee and Family Assistance Program.
• Professional growth in a role that makes a real difference.
• Flexible work hours and a commitment to work-life balance.

Apply For This Role:

Ready to lead at the forefront of food security and sustainability? Join us at Second Harvest and be part of a team that's not just meeting the standard but setting it. Apply today and be the change you want to see in the world.

Second Harvest uses AI tools to assist with application screening. We monitor these tools to reduce bias and ensure fair evaluation based on skills and qualifications.

Commitment to Equity, Diversity, and Inclusion:

Second Harvest is committed to fostering a diverse and inclusive work environment. We strongly encourage applications from all qualified individuals, especially those from equity-deserving groups, including racialized persons/persons of color, Indigenous peoples, women, persons with disabilities, and members of the LGBTQ2S+ community.

Accessibility & Accommodations:

If you require any accommodations at any stage, please contact us via humanresources@secondharvest.ca and we will work with you to meet your needs.