Chief Information Security Officer (CISO) - Remote

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.

Location: Remote (U.S. or Canada) Type: US Applicants – Full-Time; Canadian Applicants – Independent Contractor About Human Agency At Human Agency, we are in a phase of rapid growth, driven by a continuous influx of opportunities requiring extraordinary talent across various disciplines. Our mission revolves around attracting exceptional individuals, ranging from creative producers to technical experts and entrepreneurial leaders, to help us navigate this exciting next chapter. We pride ourselves on being a company of action-takers. Our leaders are hands-on, our teams operate collaboratively, and every individual plays a vital role in delivering results. Here, titles do not shield us from constructive feedback. We embrace critique, learn swiftly, and consistently strive for excellence. The best ideas prevail, regardless of their origin, as our clients rely on us to provide the most effective outcomes consistently. The missions, products, and financial success of our clients are of utmost importance to us. We immerse ourselves in their environments, becoming dedicated stewards of their objectives and partners in addressing significant challenges. Every product, strategy, or asset we create must not only be aesthetically pleasing but also practical, usable, and designed for genuine impact. Our most valuable asset is our people, and we grow by hiring individuals who propel us forward. In the realms of strategy, engineering, design, data, and operations, we seek teammates who elevate our standards and enhance our capabilities. Our hiring philosophy is clear: always hire those who elevate us, never settle for less. We collaborate with organizations of all sizes to explore, design, and implement AI strategies that are secure, scalable, and human-centric. We believe that AI should enhance human potential rather than replace it, and we build with this conviction in every engagement. From advisory services and tooling to implementation and education, we meet our clients where they are and assist them in integrating AI in ways that align with their mission and values. Our aim is to empower teams to work smarter, move faster, and unlock new possibilities through thoughtful and responsible innovation. Above all, we lead with purpose, passion, and a sense of adventure. We undertake meaningful work with people we care about, making the journey an adventure worth experiencing. At Human Agency, our identity and our work are inextricably linked. The Opportunity This is not your conventional enterprise CISO role. You won’t inherit outdated infrastructure, manage a large team, or maintain the status quo. Instead, this is a hands-on, entrepreneurial position where you will be at the forefront of AI security. You will be tasked with designing systems that are yet to be created, tackling challenges that the industry is just beginning to recognize, and viewing security not merely as a cost but as a strategic and commercial advantage. We are deploying AI agents at scale across client environments, developing our own AI-driven tools, and advising organizations on safely integrating autonomous systems into their missions.

UniUni seeks an Information Security Officer to oversee security and governance throughout the organization. Reporting to the Chief Technology & Product Officer, this leader manages the full security program, covering cloud infrastructure, application and data security, compliance, and risk management. This position drives UniUni’s efforts toward ISO 27001 certification and SOC 2 Type II attestation. Close collaboration with engineering, platform, IT, legal, and executive teams is essential. The Information Security Officer also serves as the primary security contact for customers, auditors, and investors. As UniUni expands, this role will have the opportunity to build and lead a security team, influencing security practices and standards across the company. Key responsibilities Lead security and governance initiatives company-wide Manage cloud infrastructure, application, and data security Oversee compliance and risk management programs Guide the organization toward ISO 27001 certification and SOC 2 Type II attestation Collaborate with technical and business teams Act as UniUni’s main security representative to external stakeholders Location This role is based in Canada.

ABOUT CHALLENGEU ChallengeU is a pioneering Canadian B-Corp that operates virtual schools dedicated to dropout recovery students. Our mission is to empower every student to achieve a promising future, regardless of their circumstances. By integrating personalized coaching with cutting-edge technology, we effectively re-engage students who have become disconnected from traditional educational pathways.In Quebec, we successfully serve over 10,000 students each year through strategic partnerships with school districts, solidifying our position as a leader in dropout recovery education. Our Ohio Community School, which launched in 2023, has rapidly expanded from 250 to over 1,200 students, consistently achieving or surpassing state graduation standards.Ohio serves as our template for expansion throughout the United States. Unlike Quebec, where we collaborate with districts, in Ohio we have full operational control over our school. This unique setup presents an exceptional opportunity to innovate, rapidly iterate, and develop scalable systems that will revolutionize dropout recovery education across the nation.For more information about ChallengeU, please visit www.challengeu.com.THE OPPORTUNITY We are on the lookout for a Chief Schools Officer to guide ChallengeU Ohio through its ambitious next phase of growth: scaling from 1,200 to over 7,500 students while ensuring high-quality outcomes and creating processes that can be replicated across multiple states.This role transcends a conventional superintendent position. You will be instrumental in constructing the operational framework, leadership team, and processes necessary to support vulnerable students at an unprecedented scale. You will spearhead the development of AI-enhanced coaching tools, establish benchmarks for national expansion, and potentially impact over 100,000 students within the next decade.The ideal candidate will inherit a validated model, a dedicated team, and the support of an organization that has successfully scaled similar operations in Canada. We seek a leader who can systematize effective practices, enhance organizational capacity, and maintain an unwavering focus on student outcomes as we grow.KEY RESPONSIBILITIESStrategic LeadershipDrive the execution of Ohio's growth strategy: 2,000 students in Year 1, 4,000+ in Year 2, and 7,500+ in Year 3;Formulate and oversee annual operating budgets with accountability for financial performance;Create the organizational framework for multi-state expansion and spearhead efforts to secure licensure in additional states;Collaborate with Quebec leadership on shared services including HR, Finance, Technology, and Marketing.Operational ExcellenceEnsure full compliance with Ohio Department of Education regulations;Oversee all aspects of school operations: enrollment, student services, academics, testing, and records management;Implement data-driven decision-making across all operational areas to ensure continuous improvement.

TAG Software Group, part of Valsoft Corporation, acquires and supports software companies serving a wide range of clients, including SMBs, enterprises, and public sector organizations. The group focuses on long-term partnerships, providing stability for acquired businesses and supporting their teams and customers. TAG’s in-house experts manage acquisitions efficiently and connect portfolio companies with resources such as ValPay and Sadie AI. Unlike many private equity or venture capital firms, TAG operates as an owner for the long term. Businesses are not resold. Instead, the team builds strategic relationships with management, prioritizing employee and customer well-being over quick returns. The culture at TAG emphasizes people first. Employees are encouraged to grow and collaborate in a high-performance setting. Ambition and humility are valued, and achievements are celebrated, with the aim of keeping work engaging and energizing. Role overview The Chief Technology Officer (CTO) leads engineering teams with a range of specializations and experience levels. This executive shapes product direction and works closely with leaders from other departments. The CTO is expected to lead with empathy and a focus on results, helping teams develop while achieving business goals. What you will do Mentor and guide software developers at different stages of their careers Collaborate with leaders from other functions to align on product strategy Use data and user insights to inform decisions and drive product improvements Communicate effectively across the organization, setting clear expectations and encouraging teamwork Define roles and responsibilities within engineering to support growth and scaling Apply Agile methodologies to improve team performance and foster innovation Location This is a remote position based in Canada.

Join Rockstar 3, a rapidly growing consumer business with a strong brick-and-mortar presence, as the Chief Financial Officer (CFO). This pivotal role will see you collaborating closely with the CEO and Head of Operations to shape and implement strategic financial initiatives.We are looking for a highly analytical and proactive financial leader who will not only establish but also scale our finance operations. This role merges the disciplines of rigorous accounting, operational finance, and strategic leadership.As the CFO, you will ensure the accuracy and integrity of our financial information, develop scalable systems and processes, and serve as an essential partner within the leadership team to propel our business strategy forward.

Join System Canada Technologies as an Information Security Architect, where you will play a crucial role in enhancing our security posture by designing and implementing robust security architectures. In this contract position, you will collaborate with cross-functional teams to ensure the protection of our systems and data against emerging threats.

Numeris is seeking a dedicated and detail-oriented Information Security Analyst for a 1-year contract. In this role, you will play a crucial part in safeguarding our information systems and ensuring compliance with security protocols. You will be responsible for identifying vulnerabilities, responding to security incidents, and implementing effective security measures.Join our innovative team and contribute to the protection of critical data and systems while enjoying the flexibility of a remote work environment.

JYSK Canada is hiring a Chief Operations Officer to join its leadership team in Longueuil. This executive role shapes both the day-to-day operations and the long-term direction of the company. The COO works closely with teams throughout the organization to strengthen performance and guide growth. Key responsibilities Direct operational teams to boost performance and maintain consistency across the business Find and carry out improvements to streamline processes Foster a workplace culture that values and encourages innovation Contribute to strategic initiatives aimed at expanding JYSK Canada's presence in the retail sector Role focus This position emphasizes operational efficiency, process enhancement, and building an environment where new ideas are welcomed. The COO plays a central part in supporting the company's ongoing growth and success.

Aspire Software is hiring a Chief Operating Officer (COO) to lead operations for one of its software business units. This position is fully remote and open to candidates based in Canada. As COO, the focus is on operational and commercial leadership within a rapidly growing software vertical. The role involves shaping and executing a strategic plan that spans sales and marketing, customer support, and professional services. Success depends on an AI-forward mindset and the ability to align operational strategies with Aspire’s growth objectives. Key responsibilities Develop and implement an AI strategy for non-R&D departments Set and drive long-term, annual, and quarterly financial and non-financial targets Communicate a clear vision for growth, revenue, profitability, and customer care Engage directly in daily operations, including sales performance, opportunity management, forecasting, resource allocation, customer support, and project delivery Sales and marketing leadership Lead revenue growth initiatives by identifying new opportunities and executing strategies for cross-selling and market expansion Establish sales operations and infrastructure to support scaling and maintain process discipline Oversee competitive intelligence programs to inform feature and product development Improve use of CRM and internal tools to enhance forecasting, set targets, and deliver insights to the executive team and board Create and track KPIs for the sales team, such as CAC/LTV, and develop dashboards and reporting to monitor NRR and MRR trends Work with sales leaders to set quotas, budgets, compensation plans, and pricing strategies Manage key relationships with large accounts Represent Aspire Software at trade shows and industry panels Aspire Software is part of Valsoft Corp and manages a broad portfolio of software companies. The group delivers mission-critical solutions across multiple industries, focusing on growth through reinvestment and a decentralized operating model. Aspire emphasizes industry best practices and operational excellence as it scales its businesses.

WHO WE AREFounded in New York City, Take-Two Interactive Software, Inc. stands as a premier developer, publisher, and marketer of interactive entertainment, captivating consumers worldwide. Our diverse portfolio includes renowned brands such as Rockstar Games, 2K, and Zynga, delivering outstanding products across console gaming systems, PCs, and mobile devices, accessible through various channels including physical retail, digital downloads, online platforms, and cloud streaming services. As a publicly traded company on NASDAQ under the symbol TTWO, we pride ourselves on our dynamic workplace that fosters creativity, innovation, and efficiency while offering ample opportunities for individual and team growth.Our work environment—whether in-office or remote—embraces a casual and welcoming atmosphere. We believe in balancing hard work with enjoyment, making it a rewarding place to pursue your passions daily.

Join our dynamic team at Novisto Inc. as the Chief Financial Officer (CFO) and take the helm in shaping the financial vision of our rapidly expanding organization. In this pivotal leadership position, you will manage all financial operations, spearhead strategic initiatives, and collaborate closely with our executive team to drive growth and enhance long-term value. This is an exceptional opportunity to impact our business trajectory, optimize our financial performance, and contribute significantly to our mission within the ESG software industry.Key ResponsibilitiesStrategic Finance & LeadershipAct as a strategic advisor to the CEO on financial planning, growth strategies, and resource allocation.Build and lead a high-performing finance team that balances rigor with agility.Provide financial insights and support across all business units including Sales, Product, Operations, and HR.Oversee revenue management, including forecasting, pricing strategies, contract renewals, and compliance with accounting standards.Manage procurement strategies and vendor relationships to enhance cost efficiency and operational effectiveness.Fundraising & Investor RelationsLead fundraising initiatives including equity and debt processes, venture capital rounds, and strategic financing.Create and maintain investor materials such as pitch decks, financial models, and data rooms.Develop relationships with current and potential investors, lenders, and financial advisors.Manage board and investor reporting, ensuring clarity, accuracy, and strategic insights.M&A and Corporate DevelopmentIdentify, assess, and execute mergers, acquisitions, partnerships, and strategic investments.Conduct financial due diligence, valuation, deal structuring, and negotiations.Oversee post-acquisition integration from both financial and operational perspectives.Coordinate with legal, tax, and external advisors during transactions.Financial Operations & ExecutionOversee core financial operations, including accounting, payroll, and statutory compliance across various jurisdictions.Ensure robust internal controls, compliance, and audit readiness.Lead tax planning and regulatory compliance to support operational scalability and risk management.

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.

Deel develops a platform that helps companies manage global payroll and HR operations. The product combines HR information systems, payroll, compliance, benefits, and performance tracking. AI tools support teams working in over 100 countries. Deel’s team of 7,000 people operates remotely and speaks 74 languages. Role overview The Information Security Engineer will design, build, and refine core security platforms at Deel. This position is responsible for strengthening defense-in-depth strategies, safeguarding sensitive company and customer data, and ensuring compliance with international standards. The engineer manages the full lifecycle of multiple security solutions, translating best practices and regulatory requirements into effective technical controls. Location This is a remote role based in North America, Eastern Standard Time. Deel welcomes candidates located in Canada.

About Us:At Financeit, we are a leading point-of-sale financing provider dedicated to empowering some of the largest home improvement and retail organizations across Canada. Our innovative platform assists businesses in closing more sales by providing customers with affordable monthly payment options for significant home improvements, vehicles, or retail purchases.We pride ourselves on being a dynamic company where your contributions can make a tangible impact both within our organization and in the broader market. Here, collaboration, inclusivity, fairness, and respect are not just values we talk about—they are integral to our culture. If you are passionate about making a difference in a supportive workplace, we invite you to join our team.Role Overview:The Director of Cybersecurity & Information Security is responsible for offering specialized expertise and strategic guidance in assessing and mitigating risks, monitoring potential threats, and implementing effective security solutions to safeguard Financeit’s operations in both Canada and the United States. This role necessitates proactive engagement with business management, Legal and Compliance, Operations, IT, and regulatory bodies.This position reports directly to the Chief Compliance Officer.Your Responsibilities:Develop and oversee a comprehensive enterprise-wide information security risk management program.Set annual and long-term security and compliance objectives.Evaluate the effectiveness and compliance of Financeit’s information and data security framework.Generate regular reports for Senior Management and quarterly updates for the Board of Directors regarding privacy and security matters.Identify necessary controls to ensure the availability, integrity, and confidentiality of data related to customers, business partners, employees, and organizational information; assess control effectiveness.Analyze emerging security threats and aid Senior Management in recognizing and addressing potential security issues stemming from Financeit’s activities.Collaborate with business units to ensure uniform application of policies and standards throughout all projects, systems, and services.Oversee the remediation of cybersecurity threats and assist the Chief Compliance Officer in communicating these concerns to Senior Management and the Board.Coordinate Financeit’s information and data security audit programs, including SOC2 Type 2 and PCI-DSS compliance.Work closely with the development team to embed security practices throughout the Software Development Lifecycle (SDLC), ensuring secure coding practices are adhered to and vulnerabilities are addressed proactively.Support the organization’s incident management processes.

Team: Information Security Position Overview: Squarepoint Capital is looking for a highly skilled Senior Information Security Engineer to join our esteemed Information Security team. In this critical role, you will contribute significantly to enhancing our security framework by offering expert insights and spearheading improvements in vital domains such as network, cloud, data, and system security. As a key escalation contact for Security Operations, you will ensure that complex security issues are thoroughly analyzed and resolved efficiently. Your responsibilities will include supervising security measures in essential IT projects, leading threat modeling efforts for intricate systems, conducting audits to identify security vulnerabilities, and developing automated processes to continuously assess the effectiveness of security controls and system resilience. This position presents an exciting opportunity to lead security initiatives and influence the overall security strategy of the organization. Proactivity and self-motivation are essential for success in this role. Enhance security across key areas, including network security, email security, cloud security, and data protection. Act as a security consultant for IT projects, ensuring compliance with security requirements and risk mitigation strategies. Manage and optimize security tools, ensuring their effective deployment and maintenance. Lead the design and development of robust security solutions and architectures to safeguard critical assets. Provide second-line support to Security Operations. Conduct threat modeling and risk assessments to uncover vulnerabilities and implement proactive mitigation strategies. Oversee relationships with the Managed Detection and Response (MDR) provider to ensure service efficacy and continuous improvement. Implement initiatives outlined in the security roadmap, aligning with business objectives and emerging threats. Collaborate with cross-functional teams to boost security awareness and integrate security into business processes.

At 3Pillar Global, we are dedicated to developing innovative software products that empower digital enterprises. As part of our growth strategy, we are looking for a seasoned and proactive Field Chief Technology Officer (CTO) to lead our efforts in (a) providing visionary thought leadership and consulting on strategic customer and partner engagements, (b) supporting the sales team with technology and product development insights, and (c) advising product delivery teams on specific accounts where you’ve previously served as a billable subject matter expert.We recognize that the key to client satisfaction lies in aligning our services with their needs, simplifying their purchasing process, and enhancing their experience with us. Our clients increasingly require sophisticated technical expertise and support from product development partners to navigate complex architectural challenges. As a Field CTO, you will serve as a technical advisor to both internal teams and external stakeholders. Your collaboration with clients will involve understanding their technical requirements, offering solutions to technical obstacles, and guiding them in making informed technology investment decisions. You will join a consulting team of senior professionals in related fields, fostering a strong, collaborative environment that delivers strategic technology support to our clients. This role reports directly to the Chief Innovation Officer.

As the Chief Anti-Money Laundering Officer (CAMLO) at Alpaca, you will play a pivotal role in safeguarding our organization against financial crimes. You will be responsible for the development, implementation, and maintenance of our anti-money laundering (AML) program, ensuring compliance with all relevant regulations and standards. Your leadership will be crucial in fostering a culture of compliance and ethical conduct across the organization.

AIP Connect is collaborating with a prominent consulting firm that is committed to cultivating talent for the future within the Canadian market. This initiative represents a proactive approach to identifying skilled professionals who can contribute to their success.If you are a contractor seeking new opportunities and wish to be considered for future roles, we encourage you to submit your application. Please note that this is not an immediate opening.

Instacart is looking for a Senior Associate to join the Trust & Safety team, focusing on Information Security Operations. This is a remote role available to candidates based in Ontario, Alberta, British Columbia, or Nova Scotia. Key responsibilities Collaborate with teams throughout Instacart to safeguard customer data and enhance security practices. Monitor for security threats and contribute to strategies that address potential risks. Assist in ongoing projects to strengthen security operations and improve response processes. Location details This position is remote within Canada and open only to residents of Ontario, Alberta, British Columbia, or Nova Scotia.