Director Strategic Initiatives

Dayforce

1d•CA$140,600 - CA$251,100

About The Position

The Director, Strategic Initiatives is a senior leader within Dayforce’s Global Enterprise Transformation team, responsible for owning and driving a portfolio of enterprise-wide strategic initiatives — including mergers and acquisitions integration and separation, enterprise transformation programs, and the operational execution of Dayforce’s Long Range Plan (LRP) goals. Guided by the strategic direction set by senior leadership, the Director translates complex, ambiguous business initiatives into structured, executable plans that deliver measurable outcomes aligned to LRP priorities. This role emphasizes execution, analytical rigor, and hands-on leadership. It is a coach-player role: the Director sets direction and coaches a small team while personally building models, drafting executive materials, and driving critical workstreams across cross-functional teams, executive sponsors, and the Board.

Requirements

8 years of professional experience, with at least 3 years leading large-scale strategic initiatives, enterprise transformation, or M&A integration and separation programs at an enterprise level.
Proven ability to convert complex, multi-workstream business initiatives into clear, actionable plans — and to hold cross-functional teams accountable to delivery.
Experience operationalizing Long Range Plans (LRPs) or multi-year strategic roadmaps — connecting financial and operational targets to executable workstreams, milestones, and governance.
Deep experience designing and managing KPI frameworks, performance scorecards, and program health dashboards.
Strong analytical rigor — comfortable working in the numbers, pressure-testing assumptions, and independently validating results before they reach executives or the Board.
Coach-player orientation — equally comfortable setting strategy, coaching a small team, and personally building the model, deck, or plan when the moment calls for it.
Strong executive presence with experience presenting to and influencing C-suite and senior leadership stakeholders.
Experience building and leading Integration Management Offices (IMOs) or Program Management Offices (PMOs) in an M&A context.
Proficiency in English is required for this position as this role will regularly interact with English-speaking stakeholders, co-workers, managers and/or clients across the world.

Nice To Haves

Industry experience in technology, SaaS, or HCM is strongly preferred; prior exposure to high-growth enterprise software environments is a meaningful advantage.
Execution Excellence — Translates complex, ambiguous initiatives into structured plans and disciplined delivery.
Analytical Rigor — Applies data and pressure-tested assumptions to validate results before they reach executives or the Board.
Coach-Player Leadership — Sets direction and coaches a small team while personally driving critical workstreams.
Cross-Functional Influence — Builds alignment across matrixed, global teams and influences senior stakeholders without direct authority.
Program Governance — Strong command of RAID logs, dependency mapping, milestone tracking, and change management integration.
Executive Communication — Distills complex program detail into crisp, leadership-ready narratives for C-suite and Board audiences.
Ambiguity Navigation — Builds structure where none exists and creates momentum early.

Responsibilities

Own a portfolio of enterprise strategic initiatives end-to-end, including global M&A integration and separation programs — from deal close through full integration or clean separation.
Drive transformation initiatives across Dayforce — partnering with functional and business leaders to design, mobilize, and deliver programs that modernize the operating model, scale the business, and unlock productivity.
Translate Dayforce’s Long Range Plan into sequenced initiatives, milestones, and measurable outcomes, tracking progress against revenue, margin, and operational targets.
Establish and manage KPI frameworks and performance dashboards that provide real-time visibility into program health and business outcomes.
Lead teams across HR, Finance, Technology, Legal, Operations, and Commercial to deliver integrated outcomes on time and within scope.
Design and facilitate governance structures — steering committees, integration management offices (IMOs), and workstream cadences — and drive consistent leadership alignment on status, risks, and decisions required.
Identify, escalate, and resolve risks and issues that threaten program delivery or business continuity.
Build and embed repeatable playbooks, toolkits, and methodologies across M&A, transformation, and LRP execution to accelerate future initiatives.
Partner with executive leadership to shape integration and transformation strategy, define the target operating model for newly acquired or separated entities, and align LRP-linked initiatives to enterprise priorities.
Develop and present concise, executive-ready communications and program dashboards that make complex information accessible and actionable for C-suite and Board audiences.