Chief of Staff for AI Innovation

Location: Toronto, Canada (US or Canada applicants considered)Type: US Applicants – Full-Time; Canadian Applicants – Independent Contractor About Human Agency Human Agency is growing quickly, building a diverse pipeline of projects that call for talent across creative, technical, and leadership roles. The team brings together creative producers, engineers, strategists, and entrepreneurial minds to shape the company’s next phase. Leaders stay hands-on, teams work closely together, and everyone contributes directly to results. Feedback is encouraged, learning happens quickly, and high standards are a constant. The best ideas win, no matter where they come from. Clients rely on Human Agency for consistently strong outcomes, so every product, strategy, or asset must be both practical and designed for real-world impact, not just visually appealing. People are the company’s greatest strength. The hiring philosophy is simple: bring on those who push the team forward, whether in strategy, engineering, design, data, or operations. Human Agency partners with organizations of all sizes to explore, design, and implement secure, scalable, and human-centered AI strategies. The goal is always to help clients integrate AI in ways that fit their mission and values, empowering teams to work smarter and unlock new opportunities through responsible innovation. Purpose, curiosity, and camaraderie shape the work. Human Agency values meaningful projects and a positive journey, linking company identity closely with its work culture. Role Overview: Chief of Staff for AI Innovation This Chief of Staff position supports the Managing Director of AI, combining strategic thinking in artificial intelligence with hands-on execution. The role is both a driver for growth and a builder of new solutions, designing AI-powered processes, setting up autonomous systems, and leading organizational rollouts. Responsibilities extend beyond traditional Chief of Staff duties. Expect to architect scalable AI processes, develop systems that support client transformations, and ensure smooth execution across the AI solutions practice.

About HeyMiloHeyMilo is a rapidly expanding AI recruitment platform in North America, supported by top-tier Silicon Valley investors and relied upon by leading staffing agencies, BPOs, and Fortune 100 companies.Our innovative AI agents streamline candidate engagement, mitigate fraud, expedite screening processes, and empower hiring teams to make informed decisions swiftly. As we scale, we seek individuals who are eager to grow with us.About the RoleWe are on the lookout for a Chief of Staff to collaborate with our founding team in Toronto. This pivotal role is ideal for someone experienced in navigating the startup-to-scaleup journey, equipped with the insight necessary to maintain smooth operations in a fast-paced, evolving environment.You will be positioned at the crossroads of strategy, operations, and execution. Your responsibilities may include preparing materials for investor updates one day and spearheading cross-functional initiatives or assisting the CEO in prioritizing key objectives the next. You will gain visibility into every aspect of the business and play a crucial role in shaping our scaling strategy.Given our focus on recruitment technology, a background in talent acquisition or experience with applicant tracking systems will enable you to quickly acclimate and gain a deeper understanding of our clients' needs.

Location: US or CanadaType: US Applicants - Full-Time; Canadian Applicants - Independent ContractorAbout Human AgencyAt Human Agency, we are experiencing rapid growth and are on the lookout for extraordinary talent across various disciplines. Our mission is to recruit individuals ranging from creative visionaries to technical specialists and entrepreneurial leaders, who can contribute to our next chapter of success.We pride ourselves on being a company of action-takers. Our leadership fosters a hands-on culture where teams collaborate closely, and every team member has a voice in the outcome. We value constructive feedback, learn swiftly, and constantly aim for excellence. Here, the best ideas prevail, regardless of their source, as our clients depend on us for optimal results.The missions, products, and financial goals of our clients are paramount. We immerse ourselves in their objectives, acting as guardians of their aspirations and allies in addressing significant challenges. Every product, strategy, or asset we develop must be aesthetically pleasing and practical, ensuring real-world functionality and impact.Our greatest asset is our people. We advance by hiring individuals who inspire us to improve. Whether in strategy, engineering, design, data, or operations, we seek collaborators who elevate our performance. We believe in hiring exceptional talent, never settling for less.We partner with organizations of all sizes to explore, design, and implement secure, scalable, and human-centric AI strategies. Our belief is that AI should enhance human capabilities, not replace them, and we instill this conviction in every project. From advisory services to implementation and education, we meet clients at their level and assist them in integrating AI in alignment with their core values. Our aim is to empower teams to work more efficiently, accelerate progress, and unlock new opportunities through responsible innovation.Throughout this journey, we lead with passion, purpose, and a sense of adventure. We engage in meaningful work with people we value, making the journey worthwhile. At Human Agency, our ethos and our operations are intertwined.The OpportunityThis role transcends the traditional chief of staff position. At Human Agency, the chief of staff embodies the ideal candidate for all our hires. You are an ambitious individual eager to take on a leadership role within a company — a dynamic C-suite leader — who opts to work closely alongside an executive, knowing this is the quickest route to achieving your goals. What sets us apart is that we provide you with that opportunity immediately.You will be involved in every aspect of the organization, from the ground up. Whether it's handling day-to-day tasks or leading board meetings, you will make impactful contributions at every level.

Join Alloy River as Chief of Staff (Director Level)At Alloy River, we are pioneering the future of finance with innovative applied AI technology. Our vision is to transform traditional accounting from a fragmented, manual process into a seamless, intelligent, and strategically decisive function. We aim to revolutionize finance, making it a proactive engine for profitability and operational control.Our approach involves re-engineering the general ledger from the ground up, integrating automation, workflow orchestration, and applied AI at its core. This results in a system that not only generates outcomes but also highlights exceptions and enhances leverage over time. This is not merely an incremental change; it is a complete overhaul of financial infrastructure for an AI-driven world.With over $30 million raised from esteemed investors such as Portage Ventures and Electric Capital, we are expanding our operations with some of the most talented builders, operators, and experts in the industry.Role OverviewAs Chief of Staff, you will be at the heart of our operations, collaborating closely with the CEO on strategy, execution, and operational improvements. You will possess the foresight and understanding to anticipate the company’s needs and act on them effectively.Key ResponsibilitiesStrategic PartnershipDevelop a comprehensive understanding of Alloy River’s business landscape, priorities, and operational framework to effectively represent the CEO's perspective.Integrate and analyze information company-wide, distilling critical insights and providing actionable recommendations.Identify potential risks, gaps, and opportunities proactively to avert issues before they arise.Excel in this role by alleviating the CEO’s workload, ensuring high trust and efficiency in operations.Cross-Functional LeadershipLead priority initiatives from conception to execution, ensuring alignment among stakeholders and removing obstacles to progress.Engage with external parties, including legal advisors and stakeholders during M&A and corporate development processes.Navigate uncertain situations and establish clarity and structure where it is lacking.

About Flywheel Digital Flywheel Digital partners with global brands to deliver digital commerce solutions that drive growth across major online marketplaces. Clients benefit from near real-time analytics designed to increase sales, market share, and profitability. With teams located in the Americas, Europe, and APAC, Flywheel Digital offers career paths with meaningful impact and opportunities for growth. Role Overview The AI Demand Innovation Specialist will join the Sales department in Toronto, Ontario. This role focuses on optimizing Flywheel Digital’s AI-driven technology stack, managing integrations, and supporting pipeline campaigns for the Sales team. The position also plays a key part in supporting data-driven decisions across the revenue organization. What You Will Do Optimize and manage AI-driven technology platforms and their integrations. Support sales pipeline campaigns by ensuring technology and data are aligned with business goals. Collaborate with sales, marketing, and revenue operations to improve operational processes. Promote data-driven decision-making throughout the revenue organization. Influence the way tools, data, and AI automation are used to accelerate growth. What We’re Looking For Extensive experience with Salesforce and HubSpot (both Marketing and Sales Hub). Strong background working with go-to-market technologies. Comfortable collaborating across sales, marketing, and revenue operations teams. Detail-oriented and proactive approach to building scalable processes. Interest in bridging sales and marketing through technology and AI. Location This position is based in Toronto, Ontario, Canada.

Tali AI is a rapidly expanding startup in Canada dedicated to enhancing healthcare accessibility through artificial intelligence. We are developing a pioneering AI platform designed to streamline clinical workflows by automating data collection, processing, and sharing. This allows healthcare professionals to concentrate on delivering quality care. Our platform is utilized by thousands of clinicians across Canada and the United States, spanning various specialties and seamlessly integrated with the complex landscape of North American health record systems. Our technical vision is to create a comprehensive operating system for clinical workflows, enabling healthcare teams to customize the platform to automate their data management tasks.We tackle genuinely challenging problems:Establishing real-time audio pipelines where latency impacts outcomes and accuracy is critical.Integrating with a diverse ecosystem of clinical software, including health records, billing, scheduling, referral management, and more.Creating reliable AI workflows and agents in a domain where errors can have significant consequences.Implementing a privacy and compliance framework that is robust by design.We operate in a fast-paced market that values rapid innovation, while building and maintaining clinician trust is paramount.

About UsNuBank is recognized as one of the largest digital financial platforms globally, serving over 127 million customers across Brazil, Mexico, and Colombia. Guided by our mission to combat complexity and empower individuals, we are transforming financial services in Latin America, marking just the beginning of the vibrant future we are crafting.As a publicly traded company on the New York Stock Exchange (NYSE: NU), we leverage proprietary technology, data intelligence, and an efficient operational model to provide financial products that are straightforward, accessible, and human-centric.Our contributions have been acknowledged in prestigious global rankings, including Time 100 Companies, Fast Company’s Most Innovative Companies, and Forbes World’s Best Bank. Explore more on our career page at NuBank Careers.About the RoleAs a Staff Software Engineer at NuBank, you will play a pivotal role in the AI Private Banker team, our intelligent financial partner designed to assist millions of customers in understanding their finances, making informed decisions, and executing actions effortlessly. You will be responsible for defining the technical architecture that supports conversational AI, recommendation engines, and tailored financial experiences across mobile and web platforms.Your expertise will span the entire stack, from developing Flutter mobile applications that engage millions of users to architecting distributed backend systems that facilitate real-time recommendations and conversational AI interactions. This role is not just about feature development; it’s about establishing a robust engineering foundation that democratizes financial empowerment at scale.Your technical decisions will have a direct impact on how millions of individuals navigate their financial journeys. You will be at the forefront of innovation, merging banking with cutting-edge AI technologies, crafting systems that are both groundbreaking and dependable. Join a team of inquisitive minds reshaping the possibilities in this space.

Role overview Harvey seeks a Staff Software Engineer in Toronto to drive the evolution of its AI Platform. The focus is on designing and building scalable systems that can adapt to business needs and deliver reliable performance. Key responsibilities Architect and develop essential components for the AI Platform, prioritizing both performance and scalability. Collaborate with engineers and data scientists to address complex technical challenges. Enhance the platform’s stability, speed, and overall functionality. Collaboration and impact This role works alongside a talented group in engineering and data science. Contributions will have a direct effect on the platform’s capabilities and support Harvey’s business outcomes.

Join humanagency as our Chief Information Security Officer (CISO) and be at the forefront of AI security innovation. This is not a conventional enterprise CISO role. Instead, you'll thrive in a hands-on, entrepreneurial position where you will design cutting-edge security systems, tackle industry challenges, and position security as a strategic advantage.As a CISO at humanagency, you will take the lead in deploying AI agents across various client environments and develop our own AI-powered tools. Your expertise will guide organizations on safely integrating autonomous systems into their missions, ensuring that every solution we provide is both aesthetically pleasing and functionally robust.We value collaboration, creativity, and a commitment to excellence. At humanagency, every team member is empowered to make impactful contributions, and every idea is valued as we work together to elevate our clients' success.

Role Overview Paytm is seeking a Lead Staff Platform Engineer focused on AI Infrastructure in Toronto, Canada. This position centers on building and scaling the systems behind Paytm's AI inference platform, which supports both internal teams and enterprise clients as they develop new customer-facing AI solutions. What You Will Do Own and manage GPU infrastructure, model hosting, and model serving for the AI inference platform. Enable multi-model routing across different modalities, including voice, vision, and fintech workflows. Oversee deployment of proprietary and third-party models on shared GPU and accelerator clusters. Develop self-service platforms that let teams provision compute, deploy, and customize models using APIs and control planes. Establish the AI control plane for Paytm Intelligence (Pi), with a focus on policy-driven routing, quotas, observability, and cost visibility. Impact Areas Accelerate delivery of AI agents and features across payments, risk management, fraud detection, collections, support, and developer tooling. Improve reliability and efficiency of hardware utilization. Give teams the tools to use AI infrastructure without rebuilding core systems each time. Location This role is based in Toronto, Canada.

"Embrace the power of rapid learning as an engineer in the AI era."What We Seek1. Strong Engineering FundamentalsAt Viggle AI, we believe in the versatility of our engineers, regardless of their specialization—be it frontend, backend, or algorithms. What truly counts is your robust engineering foundation and your capacity to simplify, refactor, and enhance complex systems.As AI transforms the tech landscape at a rapid pace, those with a strong grasp of fundamental engineering concepts can easily adapt and emerge as well-rounded, full-stack contributors. You will take the initiative in building intricate systems and engage closely with product and design teams to create exceptional user experiences.2. Outstanding Learning AptitudeIn an environment defined by swift technological advancements, past knowledge can quickly become obsolete. We prioritize your ability to swiftly learn new open-source tools, adapt to emerging technologies, and thrive in uncertain situations while executing effectively.We invite curious, agile thinkers who are enthusiastic about exploring technology and overcoming challenges to join our dynamic team.About Us:Viggle AI is an innovative startup supported by prominent investors such as a16z and TSFV. We are at the forefront of the Generative AI revolution, focusing on controllable video generation for content creators, providing cutting-edge technology that enables creators to bring their visions to life.Our rapidly expanding app is cherished by a diverse range of creators, from Hollywood professionals to TikTok influencers, and boasts a user base exceeding 30 million, along with hosting the second-largest Discord community globally.Benefits: Thriving startup atmosphere: build diligently, ship quickly, and grow continuously Competitive salary and equity package Comprehensive dental and health insurance Free meals and a vibrant, enjoyable office environment

About Fluent Software GroupFluent Software Group, a proud member of Valsoft Corporation, is a global leader in acquiring and nurturing vertical market software companies. We specialize in industries where deep expertise is essential for success.At Fluent, we provide founders and their teams with a lasting home—preserving their unique culture and momentum while opening up new avenues for resources, technology, and proven operational strategies that drive sustainable, long-term growth.The MissionWe are on a mission to develop AI startups within our established portfolio of vertical software companies—and we need innovative builders to bring this vision to life.Our goal is to collaborate with Fluent’s existing businesses to create new AI-driven products and market them to their specialized customer bases. The journey may begin by enhancing existing workflows that our business software already supports or by developing entirely new products. The core objective is straightforward—we aim to generate customer value by either improving operational efficiency or capitalizing on currently untapped revenue opportunities. Each of our portfolio companies possesses profound domain expertise and a dedicated customer base. What they require is a visionary who can transform AI potential into tangible products that customers are eager to purchase.This is akin to startup building with a significant advantage: you inherit established customer relationships, industry knowledge, existing infrastructure, and revenue to validate your endeavors—without the challenges of starting from scratch.The OpportunityThis role transcends traditional product or engineering positions; it embodies elements of both while remaining distinct. We are searching for an AI Product Builder: an individual who is constantly focused on customer challenges, engages in meaningful conversations with users, and is capable of delivering a working prototype within a week.You will spearhead the AI product vision and drive prototyping efficiency. The R&D team of the portfolio company will contribute domain expertise, production infrastructure, and engineering depth. Together, you will launch innovative solutions. Instead of training foundational models, you will be integrating AI APIs and leveraging tools such as Cursor, Claude Code, and bolt.new to deliver real, customer-facing solutions at an agile startup pace.This position is tailored for someone with the ambition to evolve into a startup CTO or CEO. As the product develops, your responsibilities and title will expand accordingly. Should you successfully build a viable solution, you will take the lead on it.

Who We AreAt Momentum Financial Services Group, we are dedicated to empowering individuals by transforming the way financial services are delivered to those in need. With over 40 years of expertise, we proudly operate Money Mart—Canada's largest non-bank branch network—leading the charge in providing financial solutions to underserved communities.Our offerings range from short-term loans to money transfers and prepaid cards, ensuring that millions of customers can access essential financial products when they need them the most.At MFSG, collaboration is at the heart of our operations. We work across various teams and functions to create impactful solutions that dismantle barriers and broaden access to financial resources. Whether you are innovating, strategizing, or problem-solving, your contributions make a difference in the lives of real people.

At Varicent, we're not merely changing the Sales Performance Management (SPM) landscape—we're revolutionizing how businesses achieve revenue success. Our state-of-the-art SaaS solutions empower revenue leaders worldwide to craft more effective go-to-market strategies, enhance seller performance, and tap into hidden potential. Recognized as a leader in innovation, Varicent shines in the 2025 Forrester Wave Report for SPM, 2023 Ventana Research Revenue Performance Management (RPM) Value Index, Gartner Peer Insights, 2024 Gartner SPM Market Guide, and G2. Our solutions are trusted by a diverse array of global industry leaders including T-Mobile, ServiceNow, Wawanesa Bank, Shaw Industries, Moody's, Stryker, and many more. Here’s why you’ll excel at Varicent:Innovate with Purpose: Create impactful solutions for customers globally.Join Excellence: Collaborate within a diverse and innovative team.Shape the Future: Lead initiatives in revenue optimization.Grow Together: Realize your potential in a nurturing environment.Join us at Varicent—where your talent and ambition converge with limitless opportunities for success!

Infrastructure Technical Staff MemberOn-site | Full-timeCompensation: CA$190K – CA$280KJoin our innovative team at mlabs as we create open-source browser infrastructure that drives the future of AI agents. With over 6,000 stars on GitHub and millions of browser sessions served monthly, our platform has experienced phenomenal growth, expanding 50x in 2025 alone. Our technology empowers developers to create seamless web interactions through our robust API.As one of the pioneering team members, you will collaborate with a high-performance group of four talented individuals, backed by top-tier investors, as we tackle the most challenging issues in distributed systems—from kernel-level debugging to global VM orchestration.The RoleAs an Infrastructure Technical Staff Member, your mission will be to build and enhance the distributed systems that support millions of browser sessions. Given the resource-intensive nature of browsers, your focus will be on optimizing performance, ensuring rapid startup times, and maintaining strong multi-tenant isolation across our infrastructure.Key Responsibilities:Global Orchestration: Design and maintain VM orchestration using technologies such as Nomad, Firecracker, and Kubernetes, with a focus on intelligent scheduling and achieving sub-second cold starts.Systems Engineering: Implement kernel-level observability with eBPF and enhance resource isolation through cgroup v2 and NUMA scheduling.Networking: Develop high-performance networking layers, including anycast routing and cross-region failover.Infrastructure as Code: Manage multi-cloud deployments across AWS, GCP, and Azure while overseeing customer VPCs with Pulumi.Product Ownership: Create developer tools for reliable browser automation and actively contribute to our open-source ecosystem.RequirementsExperience: A minimum of 5 years in operating production-scale distributed systems capable of processing thousands of requests per second.Linux Internals: Extensive knowledge of the Linux kernel, syscall optimization, and eBPF.Security & Isolation: Proven experience with multi-tenancy, resource limits, and security boundaries.Network Fundamentals: Competency in diagnosing complex production issues such as packet loss or routing failures at the protocol level.Execution: A proactive approach to ownership of outcomes from architecture through to deployment.

Caseware stands as a pioneer in Canada's Fintech landscape, redefining the global audit and accounting software industry for over three decades. With a robust user base exceeding 500,000 across 130 countries and support in 16 languages, we are a trusted ally for accounting and audit professionals worldwide. In fact, over 36,000 professionals proudly showcase their expertise in Caseware on their LinkedIn profiles!We are in search of a visionary and accomplished Chief People Officer to spearhead our People & Culture initiatives for a diverse, globally distributed workforce spanning 17 countries. This strategic leader will enhance our employee support systems as we continue to grow and will be responsible for architecting and implementing our comprehensive People operations strategy, which encompasses HR, Payroll, and Recruitment. This senior executive role reports directly to our Chief Executive Officer and is integral to our Executive Leadership Team.This is a permanent, full-time position (40 hours per week) based at our office located at 351 King Street East, Suite 1100, Toronto, ON, M5A 2W4. While occasional remote work is permitted, the Chief People Officer is expected to be present at our office 3 to 5 days per week.

"Harnessing the power of rapid learning is essential for engineers in the AI age." Join Our Team1. Strong Engineering FundamentalsAt Viggle AI, we believe in breaking down the barriers of traditional engineering roles. Whether your expertise lies in frontend, backend, or algorithms, what truly counts is your robust engineering principles and your proficiency in simplifying, refactoring, and optimizing intricate systems.As AI transforms technology, it brings forth innovative tools and methodologies. Engineers with a solid foundation can seamlessly adapt and contribute as versatile, full-stack team members. You will independently develop complex systems while closely collaborating with product and design teams to enhance user experiences.2. Outstanding Learning AptitudeIn a fast-paced AI landscape, prior knowledge can quickly become obsolete. We appreciate your capacity to swiftly learn new, unfamiliar open-source tools, adapt to emerging technologies, and navigate through uncertainty while delivering results.We seek inquisitive and adaptable thinkers who relish the exploration of technology and thrive in uncertain environments. If you are enthusiastic about ongoing learning and personal growth, we encourage you to apply.About Viggle AI:Viggle AI is an innovative startup supported by renowned investors, including a16z and TSFV. At the forefront of the Generative AI revolution, we specialize in controllable video generation, empowering content creators with advanced technology to bring their creative visions to life.Our rapidly expanding application is favored by creators ranging from Hollywood professionals to TikTok influencers, serving over 30 million users and hosting the second-largest Discord community globally.Perks of Joining Us: Dynamic startup atmosphere: Work hard, deliver quickly, and grow daily Competitive salary & equity options Comprehensive dental and health insurance plan Free meals and a vibrant office culture

About Alloy RiverAt Alloy River, we are pioneers in developing agentic applied AI specifically tailored for the finance and accounting sectors. In a world where accounting processes are often disjointed, manual, and reactive, we strive to create intelligent, structured, and decisively operational solutions. Our objective is to revolutionize finance, transforming it from a slow, labor-intensive reporting function into a dynamic, real-time strategic engine that drives profit and ensures control.We have fundamentally re-engineered the general ledger, integrating automation, workflow orchestration, and applied AI into its very core. Rather than having accountants shuffle data between various tools and manage tedious checklists, our advanced system generates outcomes, highlights exceptions, and amplifies leverage over time. This is not mere incremental enhancement; it represents a comprehensive redesign of financial infrastructure for an AI-driven future.With over $30 million raised to date from notable investors including Portage Ventures, Electric Capital, Elad Gil, and distinguished angels such as Tobi Lütke and Balaji Srinivasan, we are expanding our operations with the finest builders, operators, and craftsmen in the industry.Role OverviewIn this pivotal role, you will be the architect behind our foundational systems. The patterns you design will dictate the movement and settlement of financial data across the ledger, enabling others to build upon it rapidly and securely. Your responsibilities will encompass core system architecture, integration infrastructure, and the abstractions that ensure a cohesive and scalable codebase. Your work will be critical to product builders, agents, and future team members. Managing financial data requires meeting rigorous standards that most software does not encounter, and your contributions will set the benchmark.What You'll Work OnLead the development of the fundamental patterns that dictate the movement, matching, and settlement of financial data - the essential layer upon which everything else relies.Create essential primitives that product builders can leverage instead of reinventing: counterparty enrichment, object-arrival matching, and transaction reconciliation.Develop abstractions that empower engineers and agents to contribute effectively while navigating the complexities beneath.Serve as the architectural authority for the team - reviewing methodologies, guiding new projects, and maintaining the coherence of the codebase.What We're Looking ForThis position requires a robust technical foundation and a proven track record of developing systems that serve as the backbone for other engineers. This is not a role for generalists; we seek individuals with substantial experience in building reliable systems.

Role Overview Spectrum Healthcare is hiring an AI Developer in Toronto. This full-time position focuses on building AI solutions to support patient care and improve healthcare operations. What You Will Do Work with a team to design and implement machine learning models Optimize AI systems for efficiency and effectiveness Contribute to projects that directly impact patient care and operational processes Who Should Apply This role suits candidates interested in advancing their careers in healthcare technology and collaborating within an IT-focused team.

Role overview The University Health Network in Toronto is hiring a Postdoctoral Researcher to advance artificial intelligence in computational pathology. This position centers on research that explores how AI can improve pathology practices and contribute to better healthcare outcomes. Key responsibilities Participate in research projects focused on applying AI to computational pathology challenges Work closely with a multidisciplinary team of experts Support studies aimed at driving innovation in pathology and healthcare Work environment Join a group of researchers and clinicians dedicated to pushing the boundaries of computational pathology. Projects emphasize new methods and solutions that use AI to address real-world problems in the field.