Head of Operations; Remote

Position: Head of Operations (Remote)
Location: Montreal

TAG Software Group, a Valsoft operating group, is seeking an exceptional leader to join a growing portfolio of software businesses as a Director of Operations! About TAG Software Group TAG Software Group is a team of experienced investors and operators dedicated to acquiring, enhancing, and growing mission-critical software companies serving SMB, enterprise, and public sector customers. Founded as part of Valsoft Corporation, TAG provides a permanent home for software companies we don’t buy to sell.

Our focus is on long-term partnerships that protect your legacy, employees, and customers. Our in-house team delivers an efficient, transparent, and seller-friendly process, ensuring speed and certainty of close. Once part of TAG, your company gains access to proven best practices, dedicated value-creation resources, and the extended ecosystem of our sister companies, including proprietary in-house technology such as Val Pay and Sadie AI helping your business reach the next level.

Investment Approach Unlike private equity and venture capital firms, we are Entrepreneurs who Buy, Enhance and Grow Software Businesses. we don’t sell businesses. We form a strategic alliance with existing management teams. We recognize the dedication and perseverance required to create a firm and place a premium on customers’ and workers’ well-being over short-term goals. Culture TAG Software Group is more than just a place to work;
We mean it when we say people are our greatest assets, so investing in them is our number one priority. We create an environment where our employees feel first-day-on-the-job excitement day after day, building a culture of high performers and collaboration. Position Description As Director of Operations, you will work closely with portfolio company leadership teams during periods of transition and growth to assess how businesses operate today, align on priorities, and drive execution across the areas that matter most.

You will help translate strategic objectives into practical operating actions, ensuring continuity in the near term and stronger operating foundations over time. As part of TAG’s portfolio model, this role may support more than one business at a time, adjusting depth of involvement based on company needs, stage, and priorities. What You Will Do Portfolio Operations & Execution
• Partner closely with CEOs and functional leaders to improve operational execution across the business
• Assess operational and financial performance to identify gaps, risks, and improvement opportunities
• Define priorities and drive execution across initiatives that improve scalability, efficiency, and results
• Balance involvement across multiple portfolio companies as needed, adjusting focus based on business priorities and transition stage Transition & Operating Alignment
• Support businesses as they align to shared expectations, systems, and operating rhythms
• Ensure continuity through early transition periods while progressing toward more scalable operating models
• Work with leadership teams to clarify roles, decision rights, and ownership during periods of change Operational Improvement & Scaling
• Strengthen core operating capabilities, including:
• Financial visibility, forecasting, and cost control
• Operating cadence, KPI tracking, and management rhythms
• Revenue operations, delivery effectiveness, and customer experience
• Help businesses evolve from informal or founder-led processes into repeatable, scalable ways of working Performance Management
• Establish and refine performance metrics aligned to business objectives
• Monitor results, identify deviations early, and work with teams to course-correct
• Reinforce accountability through clear targets, regular review, and disciplined execution Business Assessment & Planning
• Evaluate organizational structure, leadership capacity, and operational maturity
• Identify dependencies, constraints, and execution risks that could impede progress
• Translate assessments into practical operating plans with clear sequencing and ownership Operating Playbooks & Knowledge Transfer
• Develop and refine practical operating playbooks based on hands-on…