Location: REMOTE / Toronto, Ontario This job allows you to work remotely. PathPilot is on a mission to help millions of people unlock their potential by navigating and optimizing their careers through the power of AI. With 7‑figures in non‑dilutive funding and strong ecosystem partnerships, we’re scaling an AI Career Companion already being used by individuals, universities, workforce development organizations, and enterprises. We’re looking for a Head of Sales to own and scale PathPilot’s revenue engine. You’ll work closely with the founder and leadership team to define our go‑to‑market strategy, build the sales function from the ground up, and establish PathPilot as the category leader in AI‑powered career guidance. This is a hands‑on leadership role for someone who thrives in early‑stage environments where you’re just as comfortable closing strategic deals as you are building playbooks, hiring the first reps, and shaping how the market understands our value. Why join PathPilot? Own and build the sales function at a mission‑driven AI company Work directly with the founder on GTM strategy and revenue decisions Sell a product that delivers real, measurable outcomes for people’s careers Help define a new category at the intersection of AI, careers, and workforce development Build and mentor a team from the ground up Operate with autonomy, trust, and flexibility in a remote‑friendly environment Be backed by strong funding, partnerships, and real customer traction What are we looking for in a Head of Sales? You’re a builder, operator, and closer. You know how to design sales strategy—but you also know that early on, nothing matters more than getting in front of customers, learning fast, and closing deals. You’re deeply comfortable selling complex, consultative solutions to institutions and enterprises. You understand how to navigate long sales cycles, multiple stakeholders, and outcome‑driven buying decisions. Most importantly, you’re excited to roll up your sleeves and create something from scratch. What will you be doing: Define and execute PathPilot’s sales and go‑to‑market strategy Own revenue targets and drive consistent pipeline growth Close strategic accounts across universities, workforce organizations, and enterprises Build, hire, and mentor a high‑performing sales team (AEs, SDRs) Establish sales processes, playbooks, pricing strategy, and KPIs Partner with Marketing to refine positioning, messaging, and lead generation Collaborate with Product and Customer Success to ensure strong customer outcomes Build forecasting, reporting, and CRM discipline from the ground up Represent PathPilot in key sales conversations, partnerships, and market opportunities How will you spend your time: 40% closing deals and managing strategic accounts 20% building sales processes, playbooks, and operating rhythm 15% hiring, coaching, and developing the sales team 15% cross‑functional work with Product, Marketing, and Customer Success 10% forecasting, reporting, and GTM strategy refinement In your first 30 days, you will: Deeply understand PathPilot’s product, customers, and value proposition Close or advance key strategic deals already in the pipeline Assess current sales motion, tooling, and gaps Align with the founder on revenue targets and GTM priorities In your first 90 days, you will: Own and execute a repeatable sales motion Build and document sales playbooks and core messaging Hire or begin hiring initial sales team members Establish forecasting and reporting cadence Close meaningful new institutional or enterprise accounts In your first 180 days, you will: Scale a high‑performing sales team and operating rhythm Drive predictable revenue growth across multiple segments Refine pricing, packaging, and positioning based on market feedback Establish PathPilot as a trusted partner in AI‑powered career guidance Act as a key strategic leader shaping company direction Our hiring process: Intro Call – Align on mission, values, and expectations Sales Strategy Exercise – Walk us through how you’d sell PathPilot Leadership Interview – Deep dive into your experience and approach Final Conversation – Alignment with the founder on vision and culture Offer – We move quickly and collaboratively Must Have Skills: You might be the person we’re looking for if you: Have 8+ years of B2B sales experience, with 3+ years in sales leadership Have a proven track record of hitting and exceeding revenue targets Have sold SaaS solutions to higher education, government, or enterprise buyers Are strong in consultative, solution‑based selling Are comfortable navigating complex buying committees and long sales cycles Take a data‑driven approach to pipeline management and forecasting Are fluent in modern CRM and sales tech stacks (Salesforce or similar) Thrive in ambiguity, autonomy, and early‑stage environments Care deeply about mission, impact, and building something meaningful Nice to Have Skills: Bonus points if you’ve: Built a sales team from zero or early stage Worked in EdTech, HR tech, or workforce development Have existing relationships in higher education or workforce organizations Sold products tied to career services, learning, or talent outcomes #J-18808-Ljbffr
An innovative AI career guidance company is seeking a Head of Sales to lead and scale the revenue engine. This role involves defining go-to-market strategies, building a high-performing sales team, and directly engaging with strategic accounts. The ideal candidate must possess extensive B2B sales experience, particularly in SaaS, and be ready to thrive in an early-stage environment. This opportunity offers autonomy and the chance to make a significant impact in a mission-driven organization. #J-18808-Ljbffr
Location: Scarborough, Ontario We are seeking an experienced, results‑driven, and highly motivated Vice President of Sales to lead our North American sales organization. This executive will be responsible for defining and executing the sales strategy, driving revenue growth, expanding market share, and leading a high‑performing sales team while upholding our commitment to client service and our positive company culture. Responsibilities Strategy & Vision: Develop and execute a comprehensive North American sales strategy that aligns with the Company's overall business objectives, focusing on the unique value proposition of our technology solutions for complex engineering and design integration. Revenue Growth: Directly responsible for achieving and exceeding ambitious revenue and growth targets for all Company products and services. Team Leadership: Lead, mentor, and motivate the sales team, fostering a culture of accountability, continuous improvement, and high performance that reflects the company's strong, motivated work ethic. Market Expansion: Identify and capitalize on new market opportunities, competitive intelligence, and strategic partnerships to expand the Company's footprint across key building sectors. Client Engagement: Personally engage in key sales cycles, serve as a visible executive sponsor for major client accounts, and ensure the sales organization embodies our commitment to exceptional service and client delight. Operational Excellence: Implement best‑in‑class sales processes, CRM utilization, forecasting methodologies, and sales training programs. Cross‑Functional Collaboration: Work closely with Product Development, Marketing, and Client Services teams to ensure sales efforts are supported, market feedback is integrated, and the client experience is seamless. Must Have Skills Required Experience: 10+ years of progressive experience in sales leadership, with a minimum of 5 years in a senior leadership role (e.g., VP or equivalent). Demonstrated success in leading and scaling a B2B sales organization, preferably within the technology, engineering software, construction tech, or AEC (Architecture, Engineering, and Construction) sectors. Deep understanding of complex sales cycles and experience selling high‑value, enterprise‑level solutions to engineers, architects, and key decision‑makers on large‑scale building projects. Proven ability to define a clear sales strategy, develop accurate forecasts, and manage a substantial sales budget. Exceptional leadership, communication, and presentation skills. #J-18808-Ljbffr
Location: Montreal, Quebec
Job Description
Our client is a global investment management firm. As a technology and data-driven firm, they design and build their own cutting-edge systems, from high performance trading platforms to large scale data analysis and compute farms.
We are seeking an experienced Software Developer to join the backend system teams. The successful candidate will be an integral part of a team responsible for managing internal backend services, frameworks, and platforms utilized by quants, traders, and other development teams.
Responsibilities
Design, develop, and maintain scalable, tested, production-grade distributed systems.
Foster close collaboration and communication with investment stakeholders and other tech groups.
Assume full ownership for the systems developed by you and your team.
Provide support and troubleshoot live production systems.
Engage in all stages of the software lifecycle, from gathering requirements all the way through to production support.
Comfortable working with and/or picking up the diverse technology stack; Rust, Python, C++, K8s and more
Requirements
Must Have Skills
Bachelor’s degree in Computer Science, Engineering, or a related field.
Minimum of 6 years full-time software development experience.
Proficiency in C++
Desire to work with or previous experience in Rust
Hands-on experience implementing Docker/Kubernetes microservices in a production environment.
Experience with highly available distributed systems and/or working with large datasets.
Experience supporting and monitoring large production systems.
Excellent communication skills with comfort in directly interacting with stakeholders.
Familiarity with a Linux environment and version control software.
Experience working with and designing CI/CD pipelines.
Nice to Have Skills
Hands-on experience with Python
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Location
Toronto, Ontario
Overview
Our client is a leading technology solutions provider with 600 professionals across 14 offices in North America. They are at the forefront of technology, providing cutting‑edge solutions and maintaining a strong commitment to integrity, accountability, and skill. Their employees are our ambassadors, ensuring our clients and partners receive the best service.
They are seeking an AWS Connect Solution Architect to lead the design and implementation of enterprise‑grade Amazon Connect solutions for banking and public sector clients across Ontario.
In this role, you will be responsible for architecting end‑to‑end cloud contact center solutions, leading technical design discussions, and guiding delivery teams through implementation. You will work closely with clients, business stakeholders, developers, and engineers to translate business requirements into scalable, secure, and highly available AWS architectures.
This is a client‑facing, hands‑on architecture role requiring strong technical depth in Amazon Connect and broader AWS services.
Key Responsibilities
Architecture & Technical Design (40%)
Lead architecture and design of Amazon Connect solutions including:
Multi‑level IVR design
Skill‑based and dynamic routing strategies
Queue and routing profile architecture
High‑availability and resiliency planning
Define AWS infrastructure architecture including VPC design, IAM strategy, security controls, and service integration patterns
Design event‑driven integrations using Lambda, API Gateway, DynamoDB, S3, and Step Functions
Establish scalable deployment patterns across dev/test/prod environments
Conduct architecture reviews and validate technical feasibility
Technical Leadership & Governance (25%)
Provide architectural oversight to developers and engineers during implementation
Review code, Lambda functions, integration logic, and deployment strategies
Define logging, monitoring, and observability strategy using CloudWatch and related AWS services
Ensure solutions align with AWS Well‑Architected Framework principles
Support security reviews and ensure adherence to enterprise security controls
Client Engagement & Requirements Translation (20%)
Lead technical workshops and discovery sessions with client stakeholders
Translate business and operational requirements into solution architecture
Author and review High‑Level Designs (HLD), Low‑Level Designs (LLD), and System Requirements Documents (SRDs)
Present architecture decisions, trade‑offs, and risk considerations to technical and non‑technical audiences
Integration & Migration Strategy (10%)
Architect integrations between Amazon Connect and enterprise systems (CRM, data platforms, identity systems, APIs)
Support migration strategies from legacy contact center platforms (e.g., Avaya, Cisco, Genesys) to Amazon Connect
Design data handling and reporting strategies aligned with operational needs
Security, Compliance & Performance (5%)
Design solutions with encryption, IAM policies, network segmentation, and secure integration patterns
Ensure architecture aligns with compliance expectations typical in financial services and public sector environments
Optimize solution performance, latency, and scalability
Must Have Skills
AWS & Architecture Experience:
5+ years of experience in cloud engineering and solution architecture
3+ years of hands‑on Amazon Connect implementation experience in production environments
Demonstrated experience architecting multi‑queue, multi‑flow Amazon Connect deployments
Strong experience with:
AWS Lambda (Node.js or Python)
API Gateway
Amazon EC2
Amazon DynamoDB
Amazon S3
AWS IAM
AWS CloudWatch
Experience designing RESTful API integrations and event‑driven workflows
Contact Center & Enterprise Knowledge:
Strong understanding of:
IVR and call flow architecture
Skill‑based routing models
Contact center reporting and KPIs
Operational considerations (failover, resiliency, concurrency)
Experience contributing to or leading architecture documentation (HLD, LLD, SRD)
Comfortable operating in client‑facing, enterprise environments
Nice to Have Skills
AWS Certified Solutions Architect (Associate or Professional)
Experience supporting banking, financial services, or public sector clients
Familiarity with Infrastructure as Code (Terraform, CloudFormation)
Experience leveraging Contact Lens, Amazon Lex, and analytics services
Exposure to regulated environments and security review processes
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An innovative tech company is looking for a Software Engineer to join their remote team in Toronto, Ontario. You will help build and refine AI-powered features for their platform, taking ownership of core product features. Ideal candidates should have 3-5 years of experience in software engineering, familiarity with JavaScript/TypeScript, and a passion for delivering high-quality user experiences. The role offers a unique opportunity to work in a fast-paced environment and impact users' careers directly. #J-18808-Ljbffr
A technology company in Toronto is seeking a Senior Full-Stack Engineer to build innovative interactive character experiences. This role involves working closely with the founder to explore and develop new systems, integrating real-time interactions and AI. Candidates should have over 5 years of software engineering experience, strong full-stack skills, and the ability to work in a fast-paced environment. The position offers a unique opportunity to shape foundational technology in an early-stage project. #J-18808-Ljbffr
Location: Vancouver, British Columbia
Our client is looking for an exceptional Senior Frontend/UI Engineer to help deliver the customer facing application for their analytics platform. They are helping address the energy consumption and use from power intensive businesses focusing on Data Centers as their first market. The founding team helped solve these challenges in some of the worlds largest data centers, and are now taking that experience to build a best in class solution. As a Frontend Developer, you will play a pivotal role in shaping deeply impactful user experiences for their clean technology AI products. You will collaborate closely with product, design, and engineering teams to deliver scalable, high-quality web applications that translate complex data into intuitive, actionable insights for our users.
Key Responsibilities
Build user-friendly, visually appealing, and responsive web applications using modern frontend frameworks (e.g., React, Vue, or Angular).
Transform designs and wireframes into robust, high-quality code.
Enhance site performance, accessibility, and browser compatibility.
Integrate frontend interfaces with backend APIs, emphasizing real-time data and AI-driven functionality.
Collaborate with UX/UI designers and other developers to implement innovative features that empower climate action.
Optimize applications for maximum speed and scalability.
Maintain and improve the company's web platform, proactively identifying and fixing bugs.
Routinely test and validate web UI across browsers and devices.
Stay up to date with frontend trends and cleantech industry developments.
Must Have Skills
Experience: 5+ years developing frontend architectures and translating data into beautiful UI, preferably in startups or agile, mission-driven teams.
Tech Stack: Proficiency with HTML5, CSS3, JavaScript/TypeScript, and experience with React, Angular, or Vue.js.
Ecosystem: Familiarity with state management (Redux, Vuex, etc.) and integrating RESTful/GraphQL APIs.
Tooling: Experience with version control (Git), testing frameworks, and CI/CD pipelines.
Performance: Strong grasp of frontend performance optimization, accessibility standards (WCAG), and cross-browser issues.
Design: Keen eye for UI/UX, able to collaborate closely with designers and product managers.
Problem Solver: Excellent troubleshooting, analytical, and communication skills.
Nice to Have Skills
This platform will need to deal with visualization and interpretation of many disparate data points. Having been responsible for UI for similar platforms is a very nice to have (such as financial services, trading, weather, energy etc)
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Overview
Location: REMOTE / Toronto, Ontario. This job allows you to work remotely.
PathPilot is on a mission to help millions of people unlock their potential by navigating and optimizing their careers through the power of AI. We’ve secured 7-figures in non-dilutive funding and established key partnerships to help us scale our impact. Our AI Career Companion is already helping people clarify goals, access opportunities, and grow through personalized support. Now, we’re looking to take things to the next level—and that’s where you come in. We’re looking for a Founding AI Engineer to join us on this journey. You’ll be instrumental in bringing our future roadmap to life, working closely with the founder and team to design and build intelligent, user-friendly, and scalable systems. Think of this as a hybrid between a systems thinker, full-stack engineer, and data-centric AI builder — with strong coding instincts and a love for crafting elegant solutions, fast. We’re looking for a systems-savvy generalist with a data-first mindset, someone who values scale, modularity, and performance as much as iteration speed. You know when to let the model take the first pass—and when human logic needs to take over. You’ve worked with LLMs and agents and have fine-tuned models, or RLHF workflows, and are excited about applying that expertise in real-world products that make a difference. This role is ideal for someone who wants to move fast, own major decisions, and build AI-native software that couldn’t exist 2 years ago.
Why join PathPilot?
Work on something meaningful and mission-driven
Be a founding team member with real ownership and product influence
Build systems that support people’s careers and lives in transformative ways
Collaborate with a team that values vibe coding for rapid feature development and the intelligent use of tools like Cursor or Aider to boost developer productivity
Enjoy flexibility, autonomy, and the opportunity to work remotely
Shape the future of AI-powered career tools while being backed by major partners and 7-figures of funding
What are we looking for in a Founding AI Engineer?
You’re an engineer with a strong ownership mindset. You know how to go from ideas to production-ready solutions—and enjoy the messiness and thrill of early-stage building. You’re comfortable switching between big-picture architecture and in-the-trenches implementation. You use AI tools to speed up your workflow and build with velocity, but with a mind toward scalability, modularity and high quality secure code.
What will you be doing
Architect and implement core AI product features from end to end
Design backend and frontend systems using Node.js, React, and TypeScript
Integrate with and optimize the use of LLMs (OpenAI, Claude, etc.) for user interaction
Design and leverage agentic workflows for improved outputs and user experiences
Build vector search capabilities using Pinecone, Supabase, or similar
Fine-tune models and/or run RLHF experiments to improve user personalization
Lead or contribute to data ingestion pipelines and user context models
Collaborate with the founder and product team on scoping, prototyping, and iterative development
Push the limits of what's possible with AI in a career-focused product
Prioritize shipping value fast—without sacrificing long-term integrity
How will you spend your time
45% coding and system design (AI-first coding in React/Node/TS + AI integration)
20% LLM experimentation (prompting, agents, fine-tuning, evals, vector DBs)
15% data engineering and embedding strategies
10% product iteration and user feedback loops
10% collaboration, planning, and roadmap refinement
You might be the person we’re looking for if you
Have 5+ years of full-stack development experience, ideally with JS/TS and Python
Are fluent in modern frameworks like React, Node.js, and backend APIs
Are strong systems designer and thinking about scale, modularity and speed
Have deep comfort with LLMs, embeddings, vector DBs, agentic frameworks, fine-tuning, and RLHF
Have AI-native mindset - you lean heavily into tools like Cursor, Aider, RooCode, Cline by default backed by strong systems design
Have used tools like LlamaIndex, CrewAI, AutoGen, Pydantic, OpenAI Agents SDK or similar to build agentic workflows into software products
Are excited by fast iteration, lean experimentation, and building things that matter
Have a data-centric approach to product building with experience in data pipelines and/or ML deployment workflows
Are comfortable in environments with fast-paced iteration, autonomy, ambiguity, and high ownership
Have a customer-centric development mindset and are thinking in advance of ways to leverage the latest in AI to drive our mission
Bonus: Early-stage experience or having shipped 0•1 products
In your first 30 days, you will
Ship core feature improvements and test new LLM workflows
Implement a scalable vector search using Supabase or Pinecone
Pair with the founder to refine product and tech roadmap
Take ownership of AI tooling, prompt design, and experimentation environments
In your first 90 days, you will
Launch new AI modules that unlock personalized career guidance
Improve our fine-tuning and RLHF workflows to drive better user outcomes
Scale our data systems to support upcoming B2B pilots
Lead key decisions around architecture and product experience
In your first 180 days, you will
Build and ship agent-based tools that personalize user journeys in real-time
Expand and productionize our LLM stack with continuous evals and active learning
Drive improvements across our data and ML pipelines
Build agent-centric custom course creation and delivery engines
Mentor new contributors or collaborators as the team expands
Own key aspects of our AI infrastructure and establish scalable design patterns
Our hiring process
Intro Call – We’ll connect to align on the mission, values, and your goals
Async Challenge – You’ll complete a small AI-focused task using tools you prefer
Technical Interview – We’ll review your code and extend the challenge into real-world scenarios
Final Call – A deeper conversation with the founder to ensure alignment on vision, culture, and contribution
Offer – If it’s a fit, we move quickly and collaboratively to bring you on board
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A technology solutions provider based in Toronto is looking for an AWS Connect Solution Architect. In this client-facing role, you will lead the design and implementation of enterprise-grade Amazon Connect solutions. You will work closely with various stakeholders to translate business needs into scalable AWS architectures. The ideal candidate has over 5 years of cloud engineering experience, including hands-on expertise with Amazon Connect in production environments. Strong technical leadership and client engagement skills are essential for success in this role. #J-18808-Ljbffr
