Technical Project Manager

About the role

The organization accelerates the growth of vertically focused B2B SaaS companies through acquisition and long-term tactical and financial guidance. It partners with founders to scale their businesses, increase year-over-year revenue and efficiency, and help every company reach its full potential by building on existing strengths. The team consists of experienced operators and subject-matter experts who share a passion for software and building enduring businesses.

Responsibilities

• Lead end-to-end planning and execution for strategic technology projects, including platform consolidation, Secure Retail-to-Solutions migration, database modernization, unified reporting, reliability improvements, integrations, and AI-enabled initiatives.
• Translate approved business priorities and product roadmaps into clear project charters, workstreams, milestones, dependencies, resource plans, delivery forecasts, and measurable acceptance criteria.
• Establish and maintain integrated project plans across Engineering, Product, Architecture, Data, Quality, Infrastructure, Customer Success, Support, Sales, and external partners.
• Facilitate project kickoffs, planning sessions, weekly execution reviews, risk and dependency reviews, decision forums, retrospectives, and executive status updates.
• Track scope, schedule, capacity, budget, risks, assumptions, issues, decisions, and changes; drive timely resolution and escalate with context, options, impact, and a recommendation.
• Create transparent reporting for planned-versus-delivered work, milestone health, delivery confidence, resource constraints, quality, release readiness, and business outcomes.
• Coordinate release and migration readiness across technical and customer-facing teams, including validation, cutover, rollback, communications, training, support preparedness, and post-launch stabilization.
• Partner with Product Managers and Engineering leaders to maintain clear priorities, healthy backlogs, realistic commitments, and alignment between customer needs, architecture requirements, and delivery capacity.
• Improve the technology delivery operating model, including standards for project intake, prioritization, status reporting, dependency management, RAID logs, decision records, and lessons learned.
• Administer and improve project-management workflows in tools such as Asana, Jira, or similar platforms while keeping reporting useful and avoiding unnecessary process overhead.
• Manage vendor and contractor deliverables when assigned, including statements of work, milestones, invoices, risks, performance, and expected return on investment.
• Build trusted relationships across teams, resolve ambiguity, and ensure stakeholders understand decisions, owners, next steps, and delivery tradeoffs.

Competencies

• Delivery Leadership: Creates structure and momentum for complex initiatives involving multiple products, teams, and business functions.
• Technical Fluency: Understands software development, cloud platforms, databases, APIs, integrations, testing, releases, and production operations well enough to manage dependencies and risk.
• Planning and Forecasting: Builds credible plans from incomplete information and continuously improves forecasts as evidence changes.
• Risk and Decision Management: Identifies threats early, clarifies tradeoffs, and drives timely decisions with accountable owners.
• Executive Communication: Presents concise, evidence-based status, risks, financial implications, and decisions without obscuring problems.
• Facilitation and Influence: Aligns stakeholders across organizational boundaries and moves work forward without relying on formal authority.
• Customer and Business Focus: Connects technology delivery to customer impact, operational readiness, revenue, retention, and strategic outcomes.
• Continuous Improvement: Uses delivery data and retrospectives to improve predictability, quality, speed, and team effectiveness.

Requirements

• Bachelor’s degree in Computer Science, Engineering, Information Systems, Business, Project Management, or a related field, or equivalent practical experience.
• 7+ years of experience managing technology projects or programs, including complex initiatives spanning multiple engineering and business teams.
• Demonstrated success delivering SaaS software, platform, data, cloud, integration, infrastructure, or migration projects through the full lifecycle.
• Strong working knowledge of Agile and hybrid delivery approaches, software development lifecycles, release management, and production-readiness practices.
• Experience building integrated project plans and managing scope, schedule, dependencies, resources, risks, budgets, vendors, and organizational change.
• Proficiency with project and work-management tools such as Asana, Jira, Azure DevOps, Smartsheet, or similar platforms.
• Ability to define meaningful delivery metrics and communicate status, risks, decisions, and forecasts to both technical teams and senior executives.
• Excellent facilitation, organization, written communication, stakeholder management, and conflict-resolution skills.

Preferred Qualifications

• Experience managing technology integration or consolidation following acquisitions or across a multi-product SaaS portfolio.
• Experience leading customer migrations, cloud modernization, database migrations, data-platform implementations, or enterprise reporting initiatives.
• Familiarity with retail, point-of-sale, inventory, e-commerce, donation, or thrift/resale software environments.
• Experience coordinating distributed teams, contractors, vendors, and stakeholders across time zones.
• Experience using dashboards and engineering metrics for capacity, flow, predictability, quality, reliability, and planned-versus-delivered analysis.
• Working knowledge of information security, data privacy, business continuity, and operational readiness.
• PMP, PgMP, PMI-ACP, Scrum, SAFe, or comparable project/program-management certification is a plus.
• Experience coordinating AI or data-intensive initiatives is a plus.

Benefits

• Health and Wellness: Comprehensive health coverage beginning on the first day of employment.
• Retirement Savings:
  • 401K Plan (US): 1:1 match on the first 3% of contributions and 0.5:1 on the next 2%. Contribute 5% to receive a 4% match. Pre-tax and Roth options available. Eligibility begins the first of the month after 90 days; immediately vested.
  • RRSP (CAN): 1:1 match on the first 3% of contributions and 0.5:1 on the next 2%. Contribute 5% to receive a 4% match. Pre-tax and Roth options available. Eligibility begins the first of the month after 90 days; immediately vested.
• Paid Time Off: Uncapped flexible PTO to balance work and personal life.
• Parental Leave: 12 weeks paid leave for all employees.
• Remote Work Support: $75 USD / $140 CAD monthly stipend for phone and internet if working remotely.
• Holidays: Extensive holiday schedule to recharge and spend time with loved ones.