Sr. Director, Strategic Initiatives

Replacement: This position is open due to an existing vacancy to support our evolving business needs. Sr. Director, Strategic Initiatives The Senior Director, Strategic Initiatives Leader is a highly visible, enterprise‑level role responsible for driving strategic rigor, executive decision support, and transformation execution across the Corporates organization. This leader will partner closely with the Segment President and Corporates leadership to shape priorities, evaluate top deals, and deliver board‑level insights that accelerate growth and operational excellence. This role spans the full Corporates value chain, and plays a critical role in enabling effective leadership team (CLT) operating rhythms, decision‑making, and prioritization. Location: hybrid position, need to be based in one of our hub locations (MN, TX or Canada) About the Role : In this opportunity, as Sr. Director, Strategic Initiatives you will: Corporates Strategy: Lead strategic analysis and executive‑level decision support across the Corporates business, identifying growth opportunities, risks, and trade‑offs. Own and facilitate top deal reviews, including financial, strategic, and operational assessments to support executive and board decisions. Partner with Sales, Retention, Customer Success Management, Professional Services, and Solution Consulting leaders to drive aligned, end‑to‑end strategies. Board‑Level & Executive Communications: Develop high‑impact board‑level presentations, executive readouts, and strategic narratives that clearly articulate performance, priorities, and transformation progress. Translate complex data and analysis into concise, actionable insights for senior executives and the Board. Serve as a trusted thought partner to the Segment President and VP of Business Transformation. Transformation & Strategic Initiatives: Design, implement, and own transformation metrics tied to the strategic initiatives, ensuring clarity, consistency, and accountability. Monitor performance against transformation goals, identifying gaps, risks, and corrective actions. Lead executive‑level reporting and cadence reviews on transformation progress and outcomes. Drive Operating Model & Prioritization: Optimize how the executive leadership team operates, including decision frameworks, prioritization, and strategic planning processes to enable efficient decision-making, clear accountability and predictable execution. Establish and optimize business cadences (planning, reviews, prioritization forums) to ensure focus on the highest‑value work and reduce friction, duplication, and low‑value activity. Help define and manage enterprise priorities, ensuring focus on the highest‑value initiatives. Support cross‑functional alignment and execution across GM‑led organizations. Cross‑Functional Leadership: Influence and align senior leaders without direct authority, driving outcomes through partnership and credibility. Collaborate closely with leadership teams and support teams to ensure strategies are aligned and translate into execution. Act as a connector across functions, surfacing dependencies and removing barriers. About You: You're a fit for the role, of Sr. Director, Strategic Initiatives if you have: 12 years of experience in strategy, strategic initiatives, corporate development, consulting, or executive leadership roles. Proven experience supporting senior executive teams, including creation of board‑level materials. Strong background in strategic analysis, financial modeling, and enterprise performance measurement. Demonstrated success leading complex, cross‑functional initiatives in large, matrixed organizations. Experience working across commercial and delivery organizations (Sales, Retention, Onboarding, Professional Services, Solution Consulting). Preferred Experience supporting a Segment President, or equivalent senior executives. Direct involvement in enterprise transformation or operating model redesign initiat ... (truncated, view full listing at source)