Director, Strategic Programs
lwolf
Cambridge, ON
Posted Jun 10, 2026
- Full-time
- Remote
- Strategy
Job description
The Director of Strategic Programs is a strategic operator responsible for driving Lone Wolf's highest-priority cross-functional initiatives and accelerating execution of the company's strategic objectives. This role serves as a force multiplier across the executive team, leading complex programs that span multiple functions and ensuring strategic priorities are translated into measurable business outcomes. Reporting to the SVP, Product & Strategy, the Director of Strategic Programs works closely with executive leadership and senior functional leaders to establish alignment, drive accountability, and maintain execution momentum across distributed teams. This role also leads M&A integration efforts and supports acquisition diligence activities as part of the broader strategic portfolio. This is a highly visible individual contributor role requiring exceptional strategic thinking, operational rigor, business acumen, and relationship-building skills. Success in this position depends on the ability to influence without authority, navigate complexity, and consistently move critical initiatives from concept to execution. ### ESSENTIAL RESPONSIBILITIES & DUTIES: ### Strategic Initiative Leadership Lead the execution of the company's most important cross-functional initiatives and strategic priorities. ### Responsibilities: - Define initiative scope, objectives, success metrics, milestones, governance structures, and decision frameworks. - Partner with executive sponsors and functional leaders to establish clear ownership and accountability across strategic initiatives. - Drive execution across distributed teams while maintaining alignment, transparency, and momentum. - Monitor initiative performance, identify risks and dependencies, and proactively drive issue resolution. - Facilitate cross-functional decision-making and ensure alignment on priorities, timelines, and expected outcomes. - Provide concise, decision-oriented updates to executive leadership on initiative status, risks, and business impact. - Ensure strategic initiatives deliver measurable financial, operational, and customer outcomes. ### Strategy Execution & Value Creation Drive strategic and operational initiatives that improve business performance and create enterprise value. ### Responsibilities: - Lead execution of strategic programs across Product, Technology, Sales, Marketing, Customer Success, Operations, and Finance. - Develop business cases, financial models, implementation plans, and success metrics for strategic initiatives. - Partner with leaders across the organization to evaluate opportunities, prioritize investments, and allocate resources effectively. - Establish KPI frameworks and reporting mechanisms that connect initiative progress to business results. - Apply industry benchmarks, market intelligence, and best practices to identify opportunities for growth and operational improvement. - Translate strategic priorities into executable roadmaps with clear ownership and measurable outcomes. - Drive accountability for achieving targeted financial and operational results. ### Executive Partnership & Strategic Analysis Serve as a trusted advisor and strategic partner to executive leadership. ### Responsibilities: - Act as a key partner to the SVP, Product & Strategy and support executive decision-making on critical business initiatives. - Lead strategic analyses related to market opportunities, competitive positioning, portfolio strategy, operating models, and growth initiatives. - Conduct structured evaluations of build, buy, partner, and investment opportunities. - Prepare executive-level recommendations supported by data, financial analysis, and operational considerations. - Facilitate discussions among senior leaders to align on priorities, tradeoffs, and business decisions. - Bring an external perspective to internal strategic conversations while maintaining a practical understanding of operational realities. ### Program Management Excellence Establish scalable program management disciplines that improve execution quality and organizational effectiveness. ### Responsibilities: - Design and maintain a lightweight program management framework that supports execution without creating unnecessary complexity. - Develop and manage program governance processes, dashboards, milestone tracking, risk logs, and executive reporting. - Ensure strategic initiatives maintain clear ownership, timelines, deliverables, and measurable success criteria. - Drive a culture of accountability, transparency, and execution excellence across the strategic portfolio. - Identify opportunities to improve organizational planning, prioritization, and execution processes. - Standardize successful practices and frameworks that can be applied across future initiatives. ### Mergers, Acquisitions & Integration Management Lead integration planning and execution for acquisitions while supporting strategic diligence activities. ### Responsibilities: - Establish and lead Integration Management Office (IMO) activities for acquisitions. - Coordinate cross-functional integration workstreams across Product, Technology, Finance, HR, Sales, Marketing, Customer Success, and Operations. - Develop and manage Day 1, Day 100, and long-term integration plans. - Track integration milestones, dependencies, risks, and synergy realization efforts. - Support acquisition diligence activities through financial modeling, market analysis, synergy assessment, and integration planning. - Partner with executive leadership to assess acquisition opportunities and associated integration risks. - Translate acquisition assumptions into executable integration plans and measurable value realization programs. ### KEY RESULT AREAS: ### **Strategic Initiative Execution** - Strategic initiatives are clearly chartered, appropriately governed, and consistently delivered on time and within scope. - Business outcomes and success metrics are achieved as planned. ### Strategy & Value Creation - Strategic programs demonstrate measurable impact on revenue growth, operational efficiency, customer outcomes, and profitability. - Leadership maintains clear visibility into initiative performance and value realization. ### Cross-Functional Leadership - Strong relationships exist across departments, enabling effective collaboration and alignment. - Teams work together efficiently to achieve shared business objectives. ### Executive Partnership - Executive leadership views the Director as a trusted advisor who provides sound judgment, actionable recommendations, and reliable execution support. ### Operational Excellence - Program management processes create consistency, accountability, and execution rigor without unnecessary bureaucracy. - Strategic initiatives are managed through clear governance and reporting structures. ### M&A Integration Success - Acquisitions are integrated successfully with minimal disruption to business operations. - Synergy targets and integration milestones are achieved according to plan. - Diligence activities provide leadership with accurate assessments and informed recommendations. ### QUALIFICATIONS & EXPERIENCE: - Bachelor's degree in Business, Finance, Economics, Engineering, Management, or a related field. - 8+ years of experience in strategy, management consulting, business operations, program management, corporate development, private equity portfolio operations, or related fields. - Experience leading complex cross-functional initiatives involving multiple stakeholders and business functions. - Demonstrated ability to influence senior leaders and drive results without direct authority. - Strong analytical, financial modeling, and business case development skills. - Experience building executive-level presentations, recommendations, and decision frameworks. - Exceptional project and program management capabilities. - Strong communication, facilitation, and relationship-building skills. ### Preferred Qualifications - MBA or advanced business degree. - Experience within SaaS, software, technology, or recurring revenue businesses. - Management consulting, corporate strategy, private equity operating partner, or business transformation experience. - Experience supporting mergers and acquisitions, integration management, or corporate development activities. - Familiarity with KPI development, operational performance management, and strategic planning processes.