Freelance Chief Financial Officer

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.

Role Overview JYSK Canada is seeking a Chief Operations Officer based in Longueuil. This senior leader shapes daily operations and long-term growth for the organization. The COO guides teams across the business, focusing on efficiency, process improvement, and a culture that encourages new ideas. What You Will Do Lead operational teams to improve performance and consistency Identify and implement ways to streamline processes Promote a workplace culture that values innovation Support strategic initiatives to drive growth in the retail sector

Join Our Team as an AI Automation Engineer!Aspire Software is on the lookout for a talented AI Automation Engineer to become a crucial part of our dynamic team in Canada! In this exciting role, you will have the opportunity to design, develop, and deploy AI agents that will revolutionize the operational processes of our portfolio companies, as well as create standalone products that deliver value to our customers.Role OverviewThis is not a research position. You will be embedded within Aspire Software, collaborating closely with our portfolio company teams to understand their operational challenges and build AI agents that manage real tasks, including customer service, sales outreach, onboarding, documentation, and more. Your work will directly replace manual workflows and may also lead to the launch of new revenue-generating products for our customers.About Aspire SoftwareAspire Software operates under Valsoft Corporation, a steadfast investor in vertical market software businesses. Our mission is to acquire and manage software companies with a long-term ownership perspective, fostering autonomy, disciplined growth, and the creation of lasting value. We empower vertical market software businesses globally, enabling them to scale sustainably while preserving their entrepreneurial spirit.Why Join Us?The successful candidate can work remotely from anywhere in Canada! Your Daily ResponsibilitiesInternal AI Agent DevelopmentDesign and implement AI agents to streamline operational tasks across Aspire Software and its portfolio companies, covering customer support (tiers 1 and 2), sales development, onboarding automation, marketing workflows, and engineering maintenance.Assess the impact of your work through metrics like hours of labor saved and improved team productivity.Collaborate with portfolio company operators to pinpoint the highest value automation opportunities.External AI Product DevelopmentCreate innovative AI-powered products such as vertical voice agents, AI copilots, workflow automation tools, and AI documentation systems tailored to our vertical markets.Take ownership of the product lifecycle from prototype to launch, including acquiring your first paying customers.Rapid Deployment and IterationQuickly transition from idea to minimum viable product (MVP) to full production.Conduct beta tests with real users, gather feedback, and continuously improve.Work collaboratively across product, engineering, and go-to-market teams.Your QualificationsWhat You Bring to the RoleA proven history of developing products, tools, projects, startups, or side projects that successfully launched.Strong expertise in AI and machine learning concepts, programming languages, and development frameworks relevant to automation.

Join Aspire Software as a Financial Analyst – Remote – Canada!Aspire Software is on the lookout for a skilled Financial Analyst to bolster our expanding Finance team in Canada. We specialize in acquiring, developing, and scaling vertical-market software businesses across the globe. Our operational philosophy is rooted in long-term thinking, empowering local leadership, and upholding high standards of operational and personnel excellence.As a Financial Analyst, you will play an integral role in managing transactional accounting processes, ensuring precision in accounts payable (AP) and accounts receivable (AR), and maintaining comprehensive financial records. This position is vital for the timely processing of invoices, payments, and reconciliations, while also supporting our financial reporting and compliance obligations.Our guiding principle is: 'Be Humble, Stay Hungry!'Key Responsibilities:Accounts Payable Management: Process vendor invoices with precision, manage payment schedules, and resolve any discrepancies.Accounts Receivable Management: Collaborate with the AR team to bridge finance and operations, analyze hardware invoices for COGS, and assist with A/R Aging reports as needed.Bank Reconciliation and Expense Management: Conduct bank reconciliations, ensuring accurate transaction postings, and reconcile credit card expenses and employee reimbursements.General Accounting and Compliance: Maintain accurate records in our ERP system, assist in month-end and year-end closing activities, and ensure compliance with internal controls and accounting standards.

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.

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 Aspire Software as an AI Lead and shape the future of AI-driven solutions!As a part of Valsoft Corporation, Aspire Software is dedicated to acquiring, developing, and enhancing vertical market software companies globally. Our brands enjoy entrepreneurial independence while leveraging shared expertise and collaborative efforts across our international portfolio.Role OverviewThe AI Lead is pivotal in recognizing, constructing, validating, and scaling AI-powered product solutions that deliver tangible results for customers and the business. This hands-on role embodies an AI-first philosophy, working closely with clients to create solutions that evolve through continuous feedback.Core ResponsibilitiesAI-First Product DevelopmentDevelop innovative product solutions utilizing AI as the primary medium.Rapidly prototype and refine ideas to validate concepts early in the process.Leverage AI agents for requirements analysis, design exploration, implementation, and testing.Transition from problem identification to practical solutions without relying on traditional SDLC practices.Customer Engagement & DiscoveryEngage directly with clients to uncover workflows, challenges, and unmet needs.Utilize live demonstrations and working prototypes to stimulate customer discussions.Validate solutions through actual usage rather than assumptions.Build trust by transparently discussing AI behaviors, limitations, and trade-offs.Opportunity Identification & Problem FramingClearly articulate problems before execution.Spot new opportunities for AI-powered solutions and potential revenue streams.Assess ideas based on their impact, feasibility, and learning speed.Use experiments to quickly eliminate less viable ideas.Ownership of OutcomesDefine success in terms of user adoption, retention, operational efficiency, and revenue impact.Prioritize initiatives based on their outcomes rather than feature count.Continuously evaluate if solutions are providing genuine value.Oversee the entire lifecycle from concept to execution.

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.

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.

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.

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.

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.

Human Resources Coordinator – Onsite – MontrealJoin Aspire Software, a dynamic and innovative company, as a Human Resources Coordinator!In this fully onsite role, located in our Montreal office, you will be immersed in an engaging environment that promotes growth and development. We are looking for a proactive and detail-oriented individual who is passionate about building robust HR operations across Canada and the United States. Your contributions will be vital in supporting both employees and leadership, creating compliant, scalable, and employee-focused HR practices.The Human Resources Coordinator will collaborate closely with an HR Business Partner to support a diverse portfolio of software businesses throughout North America.About Aspire Software: Aspire Software operates under Valsoft Corp, managing a global portfolio of software companies that provide essential solutions across various industries. Our commitment to industry best practices enables efficient integration and fosters rapid growth by reinvesting in our portfolio. Our motto is “Be Humble, Stay Hungry!”Key Responsibilities:Act as the primary point of contact for employees, delivering prompt and thoughtful support regarding HR policies and employment queries.Utilize our HR helpdesk system to effectively manage and resolve employee inquiries.Maintain employee records and documentation in BambooHR and related systems, ensuring confidentiality and accuracy.Ensure compliance with US federal, state, and local employment laws as well as Canadian federal and provincial regulations.Assist in the development and maintenance of compliant HR policies, proactively identifying risks and suggesting improvements.Conduct regular audits of employee files and HR processes to ensure alignment with legal and internal requirements.Enhance onboarding processes to ensure a consistent and positive employee experience.Coordinate offboarding processes, including exit interviews, for seamless transitions.Support compensation-related activities including offer letters, promotions, and bonus documentation.Partner with the HR Business Partner to drive various HR initiatives.

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 AuditBoard as a Staff Software Engineer specializing in issues and take your career to the next level! In this pivotal role, you'll be instrumental in developing innovative software solutions that drive efficiency and improvement across our platforms. Collaborate with a talented team of engineers and contribute to our mission of providing the best audit management software in the industry.

The ideal candidate must reside in Canada, specifically within the Eastern or Atlantic time zones.About LiferaftLiferaft creates innovative software solutions that empower organizations to identify, comprehend, and respond to potential risks derived from publicly available data. Our clientele comprises corporate security teams globally, including some of the most prestigious organizations in the world. As a remote-first company, we are dedicated to cultivating a high-performing, values-driven team that operates with clarity, discipline, accountability, and compassion.Recently acquired by the global security leader Securitas, Liferaft has enhanced its capabilities to deliver intelligence-driven security solutions on a larger scale. Together, we provide technology and security solutions that assist organizations in safeguarding their personnel, assets, and operations, thereby making a significant impact in our world.Your Role as the Executive Operations Associate at LiferaftThis is an exceptional entry-level opportunity to work closely with the CEO and Senior Leadership Team (SLT) of a growing SaaS company operating within a global framework. Although our headquarters are situated in Halifax, NS, preference will be given to candidates based in Toronto, ON. The role may entail some travel for quarterly SLT meetings, company events, and conferences, with the possibility of part-time in-office work in the future.You will gain invaluable insights into how a leadership team and business function, encompassing strategy, execution, communication, and decision-making, while playing a vital role in maintaining alignment, organization, and effectiveness within the team.Your responsibilities will include supporting the CEO by alleviating the operational and coordination burdens experienced by the broader leadership team, enabling leaders to concentrate on their priorities while ensuring that essential logistics, communication, and follow-through are managed efficiently.Though this role encompasses administrative duties and core executive assistance tasks, it is tailored for individuals eager to expand their operational responsibilities over time.If you are diligent, highly organized, intellectually curious, and keen to learn how a growth-stage company is managed from within, this position presents an extraordinary opportunity.Core ResponsibilitiesExecutive & Leadership SupportOversee complex calendars, scheduling, and coordination for the CEO and SLTPrepare meeting agendas, document key decisions and action items, and monitor follow-ups from senior leadership discussionsFacilitate internal communications on behalf of leadershipCoordinate travel logistics and scheduling for the CEO and leadership team, including flights, accommodations, and key meetingsLeadership Team Operations & CoordinationAssist the leadership team in communication...

About UsAt Atolio, we are a dynamic, fully remote startup, founded by industry veterans from Splunk and PagerDuty. Our mission is to transform the way enterprises manage and engage with knowledge at work, utilizing cutting-edge AI and machine learning technologies, securely implemented in enterprise settings. We pride ourselves on fostering a flexible, inclusive, and supportive workplace that champions diversity and empowers all team members to excel in their roles. With a collaborative culture, advanced tools, and extensive benefits, Atolio is where innovation and creativity flourish.About the RoleWe are looking for a talented Connector Software Engineer to join our remote engineering team. In this position, you will be responsible for designing, developing, and maintaining connectors that facilitate seamless data integration between Atolio and various external systems. Your contributions will directly improve our platform’s capacity to interface with APIs, databases, and third-party tools, ensuring efficient interoperability and scalability within enterprise environments.

Join our dynamic team at Voldex as a Senior Software Engineer, where you will play a pivotal role in developing innovative software solutions that enhance our products and services. This remote position allows you to work from anywhere in Canada while collaborating with a talented group of professionals dedicated to excellence and innovation.You will be responsible for designing, coding, and testing complex software applications, ensuring high performance and responsiveness to requests from the front-end. Your expertise will contribute to the architecture and design of our software systems, and you will also mentor junior developers, fostering an environment of learning and growth.