Chief Operations Officer

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 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.

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.

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.

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.

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.

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.

DOF Canada is a premier provider of advanced vessel and subsea services, operating in key oil and gas production zones worldwide. Our state-of-the-art Remote Operated Vehicles (ROVs), sophisticated survey systems, and a robust fleet of offshore construction vessels enable us to deliver comprehensive subsea solutions tailored for the offshore oil and gas sector.We are actively seeking driven and dedicated individuals for the role of Chief Officer to join our team on Canadian Flagged Offshore Support Vessels. The position entails working within a structured offshore schedule on a 28-day rotation. The ideal candidate will possess a strong collaborative spirit, enabling effective communication with both offshore and onshore teams. If you aspire to thrive in a dynamic environment while advancing your maritime career, DOF Canada offers an exceptional opportunity!Responsibilities include but are not limited to:Serving as Second in Command of the vessel;Assisting the Master during emergency situations;Supporting the implementation of Company policies and the Safety Management System;Acting as Senior DP Operator and Safety Officer as appointed, along with chairing the vessel safety committee when necessary;Taking on the role of Ship Security Officer (SSO) or Deputy as required;Managing navigation and bridge watchkeeping duties as Officer of the Watch, directly accountable to the Master;Ensuring logbooks are maintained accurately according to stipulated guidelines;Monitoring vessel stability and trim for compliance with statutory requirements;Overseeing fresh water management during sailing and coordinating with the Engine Room while at sea;Collaborating with the Chief Engineer for fuel consumption planning;Ensuring maintenance of lifesaving and firefighting equipment as mandated by law;Updating LSA & Fire Fighting Training Manuals with ship-specific information;Providing department-specific training for new personnel;Contributing as a member of the PEC Committee;Ensuring proper maintenance and certification of all lifting appliances and deck machinery;Maintaining the vessel's fabric excluding machinery spaces;Overseeing that all garbage is managed according to established procedures;Managing stock levels of deck supplies;Securing deck cargo and organizing cargo transfer operations.

Role Overview venn is seeking a Chief Anti-Money Laundering Officer in Toronto to lead efforts against financial crime. This leadership role manages the creation, execution, and ongoing oversight of the company’s anti-money laundering (AML) strategies and programs. What You Will Do Oversee the development and implementation of AML policies and procedures Manage ongoing AML program operations and improvements Ensure compliance with all relevant laws and regulations Promote a culture of integrity and transparency throughout the organization

Join us in crafting a more rewarding financial future for all Canadians!At Neo, we are committed to revolutionizing the financial landscape for Canadians. Our dynamic, rapidly growing tech startup environment is not for the faint-hearted; it is complex and fast-paced, yet immensely rewarding. Since our inception in 2019, Neo has rapidly ascended to become one of Canada's leading fintech companies.#1 on Deloitte’s Technology Fast 50 for 2023, 2024, and 2025 — the first company ever to achieve this remarkable feat!#1 Fastest Growing Company in Canada for 2024 by Globe & MailAward-winning mobile apps and credit card offeringsA vibrant team of over 500 professionalsMore than 1 million satisfied customersPartnerships with over 10,000 retail outletsPosition OverviewAs the Chief Marketing Officer (CMO) at Neo Financial, you will play a crucial role on our executive leadership team. Reporting directly to the President, you will be responsible for crafting and executing a cohesive marketing strategy aimed at enhancing brand visibility, driving user acquisition, and increasing revenue. This role is hands-on and strategic, requiring a leader passionate about merging innovation with marketing excellence.Key Responsibilities:Develop the Marketing Function: Create and execute a data-informed, impactful marketing strategy that aligns with Neo’s business objectives and organizational goals.Strategic Leadership: Oversee and guide all multi-channel marketing initiatives. Establish a vision for engaging target audiences, driving lead generation, and enhancing customer acquisition and retention. Build and mentor a high-performing marketing leadership team that fosters creativity and excellence.Brand Strategy: Develop and implement innovative brand initiatives that resonate with our audience and reflect Neo’s core values.

Range Group supports professional travel advisors by providing technology, dedicated support, and a focus on social impact. The company reports over $4.5 billion in annual travel sales and invests in resources that help advisors demonstrate their value to clients. Through the Range Foundation, 10% of group profits are directed toward projects in education, environmental conservation, and other social initiatives. Kensington Tours, a Range Group company, operates as a global luxury travel provider with $500 million in annual sales. The team designs personalized travel experiences, including tours, yachts, villas, cruises, air travel, and corporate services. Over two decades, Kensington Tours has maintained a 30% compound annual growth rate by blending destination expertise, attentive service, and a strong digital marketing engine. The company now aims to build a globally recognized luxury travel brand through digital innovation, cultural relevance, omnichannel marketing, and data-driven personalization. Role overview The Chief Marketing Officer (CMO) will lead global brand, growth, and digital innovation strategies for Kensington Tours. This executive position combines strategic brand leadership with the responsibility to deliver scalable growth. The CMO is tasked with modernizing the marketing ecosystem, using digital, omnichannel, and AI-driven approaches. The role sits at the intersection of brand, data, technology, and culture, shaping how high-net-worth travelers discover and engage with Kensington Tours. Key responsibilities Develop strategies for acquisition, conversion, retention, loyalty, and customer lifetime value. Lead a digital-first demand engine, ensuring the majority of revenue and leads originate from online channels. Expand growth beyond paid search by building out lifecycle marketing, paid social, content, partnerships, affiliates, and new platforms. Design growth marketing frameworks that include experimentation, attribution, cohort analysis, and ongoing optimization. Location: Toronto, ON, Canada

We are seeking a visionary and strategic leader to serve as the Chief Executive Officer (CEO) for the British Columbia Forestry Investment Platform. This pivotal role will involve guiding the organization in aligning its strategies with sustainable forestry practices while fostering investment opportunities that contribute to environmental stewardship and economic growth.The ideal candidate will possess extensive experience in executive management, particularly within the forestry or environmental sectors, and will demonstrate a proven track record of driving organizational success at a senior level.

Join a ChallengerAt Equitable Bank, we break the mold of traditional banking by offering innovative solutions tailored for Canadians. Our approach is creative and forward-thinking, as we strive to redefine the future of banking. If you are driven by a passion for innovation and excited about the prospect of transforming the banking landscape, you may have just found your next big opportunity.We are proud to serve over 800,000 customers across Canada through EQ Bank, recognized as Canada’s Challenger Bank™ and backed by over 50 years of excellence in the financial industry. Our wholly-owned subsidiary, Concentra Bank, supports credit unions nationwide that cater to more than six million members. Together, we manage more than $142 billion in assets, dedicated to enriching lives and driving positive change in Canadian banking. Since 2021, our EQ Bank digital platform has been ranked among the top banks in Canada on Forbes World's Best Banks list.The RoleAs the Chief Anti-Money Laundering Officer (CAMLO), you will spearhead the development, implementation, and oversight of EQB’s comprehensive Anti-Money Laundering (AML), Anti-Terrorist Financing (ATF), and Sanctions compliance program. This vital role is designed to protect the bank and its subsidiaries from potential misuse for illicit activities, ensuring adherence to the Proceeds of Crime (Money Laundering) and Terrorist Financing Act (PCMLTFA) and relevant regulations, alongside guidance from the Financial Transactions and Reports Analysis Centre of Canada (FINTRAC).In the context of EQB’s fintech-centric and digital banking operations, you will establish controls that enhance customer convenience and drive innovation while diligently mitigating financial crime risks. Your leadership will be instrumental in maintaining the integrity of the bank's operations and the broader financial ecosystem, effectively managing ML/TF risks and fulfilling regulatory expectations to uphold EQB’s esteemed reputation and compliance standing.

Join medfar as a Chief of Staff and play a pivotal role in shaping our organizational strategy and driving operational excellence. As a key partner to our executive team, you will help streamline processes, enhance communication, and implement initiatives that align with our mission of delivering innovative healthcare solutions.

Role overview Jobgether seeks a Chief of Staff to the Founder, based in Canada. This position works closely with the Founder, playing a key part in advancing strategic projects and supporting daily operations. Key responsibilities Drive progress on major initiatives identified by the Founder Coordinate communication across teams to ensure alignment Support the execution of company goals in line with the broader business strategy Location This role is based in Canada.