Senior Staff Portfolio Operations Manager

Hi there! Thanks for stopping by 👋 Are you actively looking for a new opportunity? Or just checking the market? Well… you might just be in the right place! Lightspeed is seeking a Senior Staff Portfolio Operations Manager to join our Product & Technology Operations team. In this role, you'll help Product & Technology leaders understand portfolio performance, investment priorities, and business outcomes. Using data and business insights, you'll support informed decision-making around priorities, investments, and strategic trade-offs. The role will begin with a six-month assignment leading Product Operations for our Hospitality vertical. During this time, you'll partner with Product & Technology leaders to support roadmap development and execution, manage cross-functional dependencies, and strengthen planning and delivery practices. Following this initial assignment, you'll transition into a permanent, cross-portfolio Business Operations role spanning Hospitality, Retail, and Financial Services. Reporting to the Director of Business Operations, Product & Technology, you'll collaborate closely with Product Operations leads, vertical leaders, Finance, and other cross-functional partners. This is a senior individual contributor role suited to someone who brings experience in software product development, strong business judgment, and the ability to influence senior leaders, challenge assumptions, and drive change without relying on formal authority. Location: Lightspeed is currently seeking candidates based in Canada. Candidates in Canada but residing outside the Eastern Time Zone must be flexible and willing to adjust their working hours as needed to accommodate EST-based collaboration and business requirements. What you'll be doing: - Lead Hospitality Product Operations - Lead Product Operations for Hospitality during the initial six-month assignment, establishing the ways of working needed to support effective product development and delivery. - Partner with Hospitality Product & Technology leaders on roadmap planning and execution, managing priorities, dependencies, and delivery risks. - Establish planning and reporting cadences that provide visibility into progress, emerging issues, and decisions required. - Identify opportunities to improve how teams plan, communicate, and execute against priorities, breaking down silos and strengthening cross-functional collaboration. - Lead special projects and operational improvements aligned with evolving business needs and leadership priorities. - Drive Portfolio Performance & Investment Decisions - Lead portfolio reviews across Hospitality, Retail, and Financial Services, providing visibility into priorities, investments, delivery progress, and business outcomes. - Develop reporting and dashboards to assess investment performance, identify gaps, and highlight areas requiring attention. - Analyze results and root causes to understand performance against expectations and identify opportunities for improvement. - Recommend changes to priorities and investments, helping leaders evaluate trade-offs and determine where to continue, adjust, or deprioritize work. - Partner with Finance, Product Operations, and Product & Technology leaders to challenge assumptions, inform investment decisions, and drive accountability. - Strengthen Cross-Portfolio Planning & Decision Making - Help leaders assess priorities and trade-offs across Hospitality, Retail, and Financial Services, identifying competing demands and opportunities. - Maintain visibility into roadmaps across all three verticals, identifying dependencies, risks, and broader portfolio implications. - Partner with Product Operations leads and vertical leaders to resolve shared challenges, build alignment, and coordinate action. - Establish consistent planning and review processes that support collaboration and timely decision-making. - Prepare leadership recommendations that connect portfolio performance and priorities to broader business objectives, tracking decisions and actions through to completion. - Improve Cross-Portfolio Ways of Working & GTM Alignment - Establish consistent go-to-market handoff processes across Hospitality, Retail, and Financial Services while accommodating each vertical's needs. - Strengthen communication between Product and GTM teams throughout the product lifecycle, ensuring upcoming features, launches, and roadmap changes are clearly communicated. - Create feedback loops that bring market insights, customer feedback, and GTM learnings back to Product teams to inform roadmap planning and prioritization. - Improve visibility into launch readiness, cross-functional dependencies, and ownership to identify and resolve gaps before they impact execution. What you'll need to bring: - Significant experience in SaaS product development, Product Operations, Business Operations, or a related field, with a strong understanding of product development lifecycles, roadmap planning, and execution. - Demonstrated experience managing complex programs or portfolios, including prioritization, resource allocation, cross-functional dependencies, risks, and business outcomes across multiple teams. - Strong analytical and financial acumen, with experience developing portfolio reporting, dashboards, financial models, and investment tracking to support business decisions and evaluate trade-offs. - Proven ability to translate complex data and business performance insights into actionable recommendations that inform strategic priorities, investment decisions, and operational improvements. - Experience partnering with and influencing senior leaders and cross-functional stakeholders, building alignment, challenging assumptions, and driving decisions without relying on formal authority. - Strong business judgment and problem-solving skills, with the ability to independently identify opportunities, anticipate challenges, and drive initiatives forward in ambiguous environments. - Experience improving operational processes, governance, and ways of working within a complex technology organization, balancing strategic priorities with hands-on execution. - Exceptional communication and stakeholder management skills, with the ability to simplify complex concepts, adapt messaging to different audiences, and build trusted relationships across Product, Technology, Finance, and other business functions. - A collaborative and empathetic approach, with the ability to understand different team perspectives, navigate competing priorities, and develop practical solutions that drive meaningful business outcomes. We know that people are more than what’s on their CV. If you’re unsure that you have the right profile for the role... hit the ‘Apply’ button and give it a try! Be a changemaker You’ll enjoy: - A flexible work environment that empowers you to do your best work - A culture that celebrates performance - The chance to make an impact in a team that’s big enough for career growth, but lean enough to make your voice heard - Career-defining opportunities Plus benefits designed to keep you happy, healthy and fulfilled. - Flexible paid time off and remote work policies - Equity options, because this is your company too - Contributions to your pension plan. Your future matters - Training opportunities to grow your skills and career - Health and wellness credit so you feel your best - Time off to volunteer and give back to your community - Interest groups, employee led networks, social committees to sponsored sports teams - Computer purchase program to get your personal Macbook - Enhanced parental leave to support growing families Fuel your growth. Find your people. At Lightspeed, your growth is our priority. We invest in you with continuous learning opportunities, global mobility and benef