Entrepreneur in Residence - Toronto

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.

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.

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.

Location: Remote (U.S. or Canada) Type: US Applicants – Full-Time; Canadian Applicants – Independent Contractor About Human Agency At Human Agency, we are experiencing rapid growth and are actively seeking exceptional talent across various disciplines. Our mission is to onboard individuals ranging from creative producers to technical experts and entrepreneurial leaders who can help us navigate this exciting phase of expansion. We pride ourselves on being a company of doers. Leadership is hands-on, teams operate collaboratively, and every member plays a crucial role in our projects. We embrace feedback at all levels, learn quickly, and continuously strive for excellence. The best ideas prevail here, regardless of origin, as we are committed to delivering outstanding outcomes for our clients. Our clients' missions, products, and financial health are of utmost importance to us. We immerse ourselves in their world, acting as stewards of their objectives and partners in tackling significant challenges. Every product, strategy, or asset we develop must be aesthetically pleasing and functionally effective, designed for real-world impact. Our greatest asset is our people, and we only grow by hiring individuals who challenge and inspire us. Across strategy, engineering, design, data, and operations, we seek teammates who elevate our standards and drive us forward. Our principle is to always 'hire up, never down.' We collaborate with organizations of all sizes to explore, design, and implement AI strategies that are secure, scalable, and centered around human needs. We believe that AI should enhance human potential rather than replace it, and we build with this belief in every engagement. From advisory services to implementation and education, we meet clients at their level, helping them integrate AI solutions that align with their mission and values. Our aim is to empower teams to work smarter, act faster, and realize new possibilities through thoughtful and responsible innovation. Through it all, we lead with purpose, love, and a sense of adventure. We engage in meaningful work with people we care about, making the journey an adventure worth undertaking. At Human Agency, our identity and our work ethos are inseparable. The Opportunity Human Agency is an AI-driven consultancy that actively collaborates with our clients. We do not merely advise from the sidelines; instead, we integrate into enterprise organizations and deploy production AI systems that drive real results. Currently, we are engaged with one of the largest privately held construction companies in the United States, focusing on LLM orchestration, document intelligence, workflow automation, and enterprise integration. We are looking for a Managing Director of Technology to lead these initiatives.

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.

Role Overview enable is hiring a Staff Engineer in Toronto, ON. This senior role sits at the heart of our engineering team, shaping the design, development, and delivery of new solutions that move our projects ahead. The Staff Engineer brings deep technical expertise and a collaborative mindset to guide product and service evolution.

Join Semperis as a Human Resources Business Partner! We are dedicated to being a Force for Good, starting with creating an exceptional workplace. Our employees are valued, supported, and empowered to perform at their best. With a focus on purpose, growth, and balance, Semperis has earned accolades such as being one of America’s Fastest-Growing Cybersecurity Companies by the Inc. 5000 and a multi-year Inc. Best Workplace awardee.Position Overview: This is a Hybrid role based in Toronto or Dallas, Texas, requiring up to 3 days in the office each week. We are in search of an innovative and experienced HR Business Partner to become a vital member of our People team.Key Responsibilities:Collaborate with People Teams to design and implement programs that attract, retain, and promote a diverse workforce.Establish yourself as a trusted partner for your client groups, focusing on revenue-generating teams (Sales, Operations, Marketing).Work alongside executive leadership to achieve People objectives.Address HR matters with compliance in mind and assist in managing global employee relations.Build strong relationships across the organization and the People Team.Lead initiatives such as Career Path development and Succession Planning, with opportunities to create new programs.

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 the Role Cohere is hiring a Manager of Technical Staff in Toronto. This role leads a team of skilled technical professionals, guiding projects that advance AI technology. The manager sets direction, supports team growth, and ensures projects meet Cohere’s standards. What You Will Do Lead and mentor a group of technical staff members Oversee project delivery, ensuring quality and timely completion Promote collaboration and a supportive team culture Help shape the direction of AI-focused projects at Cohere Location This position is based in Toronto.

Join DealMaker, a pioneering fintech company at the forefront of transforming the capital markets ecosystem. Our mission is clear: to make online capital raising a norm rather than an exception. We empower founders, CEOs, and business leaders to efficiently raise capital through innovative digital platforms, tapping into their communities and executing strategically designed campaigns. With over $2 billion raised across more than 1,000 campaigns, our platform stands unrivaled in offering an end-to-end solution. Our impressive portfolio includes notable clients like EnergyX ($88M), Green Bay Packers ($65M), Miso Robotics ($72M+), and Monogram Orthopaedics (Nasdaq:MGRM), with three IPOs accomplished in the last year alone. As we rapidly expand, we are on the lookout for talented professionals to join our mission of revolutionizing the global capital market.As a Staff Software Engineer, you'll be a key player in shaping our technical landscape and ensuring the successful execution of impactful projects. Your expertise in software architecture and design principles will be crucial in crafting robust and scalable solutions that not only address current business challenges but also anticipate future needs. Embrace the opportunity to lead architectural innovations, driving forward our vision for a more efficient capital raising process.

Okta builds secure identity solutions for both people and AI, providing trusted infrastructure that helps organizations manage access in a complex technology landscape. The company’s mission centers on delivering secure, reliable access for everyone. The Privileged Access Management (PAM) team at Okta uses an identity-first approach to tackle privileged access challenges. By applying Zero Trust principles designed for cloud environments, the team enables organizations to control access to sensitive servers, databases, and cloud resources. Their work ensures that only authorized users and systems can reach critical assets when needed. Role overview This Staff Backend Engineer position focuses on distributed systems and core software infrastructure. The role involves deploying code that safeguards real-world infrastructure for Okta’s customers. Contributions in this role support several feature teams and influence the speed, reliability, and usability of the product. Success in this position requires a strong understanding of how systems connect, an appreciation for solid abstraction, and the ability to adapt those abstractions as products change. What you will do Advance the core architecture of Okta’s PAM platform. Collaborate with product development teams to build scalable, modular components. Design and implement scalable architecture patterns. Develop APIs using the OpenAPI Specification to enable customer access to production infrastructure. Work with backend systems written in Go. Participate in rotational on-call duties alongside SRE and product development teams. Location This role is based in Toronto, Ontario, Canada.

About Emburse:At Emburse, we don't just envision the future – we actively build it. As a frontrunner in travel and expense management solutions, we are dedicated to creating an environment where technology enhances business value and drives remarkable outcomes. Our cutting-edge AI-driven platform empowers organizations to modernize their financial operations, enhance visibility, and optimize expenditures across the board.We are on the lookout for a dynamic and dedicated software engineer to join our team and contribute to the design and development of our innovative systems solutions. As a Staff Engineer at Emburse, you will collaborate closely with engineering managers, senior engineers, and cross-functional teams to establish the technical foundation of our products. Alongside this, you will have ample opportunities to engage in hands-on development of critical systems, taking charge of the successful execution of large-scale technical initiatives while also serving as a technical mentor and leader for other engineers.

About UsAir-tek is a dynamic software development company based in Canada, renowned for our innovative suite of unique products that have captured a significant share of a vast global market. Our strong product-market fit has led to a growing demand from clients worldwide, and as we enter this pivotal growth phase, we maintain an intentional stealth mode to enhance our strategic positioning.Our diverse and talented team is driven by a shared passion for tackling complex challenges, fostering innovation, and reimagining the passenger-centric travel industry. Situated in Toronto, our inclusive workplace culture prioritizes trust, collaboration, exceptional product delivery, and continuous personal development. We take pride in our work and are dedicated to supporting our colleagues.

About UsNubank, established in 2013, aims to liberate individuals from the constraints of slow and inefficient financial systems. By leveraging cutting-edge technology and exceptional customer service, we've redefined how people in Latin America engage with their finances. With operations spanning Brazil, Mexico, and Colombia, Nubank stands as one of the largest digital banking platforms globally. Our listing on the NYSE in 2021 and recognition as one of Time Magazine's 100 Most Influential Companies underscores our commitment to innovation. To learn more, visit www.nu.com.br. About the RoleAs Nubank continues its global expansion, it is vital to uphold high operational standards to empower our customers effectively. This position is pivotal in ensuring that as we scale rapidly, we maintain unwavering resilience. You will serve as the technical leader for our Resilience division. Your role will be instrumental in enhancing operational reliability through collaboration with product teams, implementing best practices, and designing deployment safeguards. You will tackle intricate architectural challenges, mentor fellow engineers, and influence the long-term resilience strategy for one of the world’s leading digital banks.

At Ripple, we are revolutionizing the way value is transferred globally, much like how information is shared today. Our ambitious mission is already in motion, as we provide cutting-edge crypto solutions for financial institutions, businesses, governments, and developers. By enhancing the global financial system, we strive to foster greater economic equity and opportunities for individuals worldwide. Join us as we embark on this remarkable journey, where you can achieve the best work of your career alongside supportive colleagues.If you are eager to make a significant impact and explore exceptional career growth opportunities, we invite you to join us in creating real-world value.THE WORK:As a Staff Software Engineer specializing in Platform, you will be instrumental in advancing Ripple's production infrastructure and release pipelines. Our Infrastructure Engineers are a unique blend of systems and software engineers dedicated to the design and lifecycle management of our hosted products. You will collaborate closely with product engineers to fulfill their infrastructure requirements, ideally within a self-service framework.WHAT YOU’LL DO:Design and implement platform features for computing, authentication, service discovery, observability, and redundancy.Lead architectural strategies balancing scale, cost, and maintainability.Mentor junior engineers on design, development, testing, and deployment best practices.Deploy and manage Ripple’s multi-region, multi-provider service platforms, with a strong focus on security and resilience.Create tools for automation, monitoring, and instrumentation to minimize operational friction and enhance engineering efficiency.Automate new and existing platform and application lifecycle services, leveraging data to achieve defined states with minimal human intervention.Propose scalable, maintainable, and cost-effective solutions.Participate in code reviews and contribute to a culture of continuous improvement.

Okta is seeking a Staff Backend Engineer in Toronto, Ontario, Canada, with a focus on Non-Human Identities. This position involves building backend systems that support secure management of digital identities for devices, services, and applications. The work contributes directly to Okta’s mission of advancing digital identity solutions for organizations. Key responsibilities Design and implement backend systems that manage non-human digital identities Collaborate with fellow engineers to deliver secure and scalable solutions Influence the architecture and direction of Okta’s identity products Team environment The engineering team tackles complex identity challenges together, using modern technology. Security, reliability, and innovation guide the team’s approach to each project.

"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 FaireFaire is a dynamic online wholesale marketplace driven by the belief that the future lies in local commerce. Independent retailers worldwide are achieving greater revenue than giants like Walmart and Amazon combined, yet remain relatively small in stature. At Faire, we harness the power of technology, data, and machine learning to connect this vibrant community of entrepreneurs around the globe. Imagine your favorite local boutique—we empower them to discover the finest products globally to stock their shelves. With the right tools and insights, we aim to level the playing field, enabling small businesses everywhere to compete against large box stores and e-commerce behemoths.By championing the growth of independent enterprises, Faire fosters positive economic impacts within local communities on a global scale. We are on the lookout for intelligent, resourceful, and passionate individuals to join us as we drive the shop-local movement. If you believe in the power of community, we invite you to be a part of ours.Role Description:Our Engineering organization is the backbone of our marketplace, responsible for the software that enables it to function seamlessly. The Product Security team empowers product engineering teams to create and deploy secure software solutions. We prioritize best engineering practices, striving to deliver software that is secure, thoroughly tested, easy to maintain, and capable of scaling to millions of users. We develop scalable, reusable frameworks, consult with product teams, leverage data-driven insights, and continually iterate on our practices.As a Senior Staff Software Engineer in Product Security, you will take on the role of technical lead for the Product Security domain. You will establish the long-term technical vision for integrating security within Faire’s application framework. Collaborating closely with Platform and Product Engineering teams, you will identify and mitigate security vulnerabilities, spearhead significant security initiatives, and mentor engineers across the organization to enhance secure engineering practices.Additionally, you will lead cross-functional programs to embed security deeply within our architecture, pipelines, and developer experience, effectively minimizing risk while maintaining development velocity.In this role, you will:Define the long-term technical strategy for application security at Faire, establishing scalable and developer-friendly frameworks and principles that facilitate secure development across all product areas.

Join Rokt, a leading force in hyper-growth ecommerce. At Rokt, we redefine the ecommerce landscape by delivering real-time relevance at pivotal moments. Our AI Brain and expansive ecommerce Network facilitate billions of transactions, connecting millions of customers, and earning the trust of the world's foremost companies.We are a passionate team of innovators dedicated to helping businesses discover transformative solutions to meet customer demands and boost revenue. Our partners experience a remarkable increase of 10–50% in additional revenue, often deriving their entire profits from the enhanced products or services they offer. This competitive advantage opens up vast opportunities for growth and innovation.Rokt values transparency in career progression and remuneration. Our clearly defined career ladder, alongside transparent compensation structures based on merit and capability, fosters an environment where Rokt’stars consistently strive to exceed expectations and redefine what’s achievable.We are on the lookout for a Partner Manager, SMB Agency Partnerships.The target total compensation for this role ranges from $192,000 to $252,000, which includes a fixed annual salary of $115,000 to $157,000, equity grants, and exceptional benefits. Equity grants are awarded in accordance with company policies, board approval, and individual eligibility.As the Partner Manager, you will enhance Rokt’s SMB Agency Partnership Program by recruiting and empowering top-notch agencies (including Shopify Plus agencies, development agencies, marketing agencies, and ecommerce consultancies) to facilitate substantial Rokt Thanks activations. These activations are characterized by 10K+ orders per month with high expected Activity Per Transaction (APT), applicable across both Shopify and off-Shopify platforms.Key Responsibilities:Recruit and cultivate a portfolio of high-quality agency partners capable of influencing merchants with a potential for 10K+ orders/month.Develop scalable agency enablement resources (playbooks, sales assets, and certifications) to ensure agencies effectively communicate Rokt’s value proposition and drive adoption.Collaborate closely with the SMB Business Development team to generate and advance partner-sourced opportunities that align with the large-activation profile.Coordinate cross-functional efforts with SMB Customer Success, onboarding, and implementation teams to ensure successful conversions of partner-sourced deals across various paths.Initiate and manage partner programs aimed at boosting adoption at scale (including referral fees, revenue sharing, co-marketing initiatives, and priority support).