Director, Chief of Staff Job at SimpliSafe (Boston)

Job Description

The DIRECTOR, CHIEF OF STAFF & ENTERPRISE OPERATIONS serves as the PRIMARY STRATEGIC AND OPERATIONAL PARTNER to the Chief Information and Global Supply Chain Officer (CIO/GSC). This role owns the OPERATING SYSTEM for the CIO/GSC organization—how priorities are set, how execution is governed, how performance (including financial performance) is monitored, and how risks are surfaced and resolved. Sitting at the intersection of strategy, operations, financial stewardship, and executive communication, this leader translates executive intent into enterprise-level clarity and ensures that technology and global operations execute as a coherent system. This is a senior enterprise leadership role designed to scale executive impact, improve decision quality, and bring order to complexity.

Job Responsibility

Serve as a trusted advisor and thought partner to the CIO/GSC Officer, sharpening strategic options, clarifying tradeoffs, and accelerating decision-making
Amplify executive effectiveness by protecting focus on the highest-impact priorities and removing organizational friction
Represent the CIO/GSC Officer in key forums, escalating only decisions requiring direct executive judgment
Own and evolve the enterprise operating cadence for the CIO/GSC organization, including annual strategic planning, quarterly planning and prioritization, monthly operating and financial performance reviews, leadership forums, escalation paths, and decision-making mechanisms
Design and maintain an integrated performance management system spanning Enterprise Systems, Information Security, Manufacturing & Supply Chain, Quality, and Logistics
Surface execution, risk, and financial signals early and ensure corrective actions are clearly owned and driven to resolution
Act as a performance truth-teller, creating transparency and accountability when execution drifts
Partner with senior leaders to define strategy and set priorities based on value creation, risk exposure, and opportunity size
Drive alignment across domains with differing incentives, timelines, and constraints—ensuring the organization operates as a single system
Force clarity and tradeoffs when priorities conflict and ensure enterprise decisions are executed consistently
Serve as a financial integrator for the CIO/GSC organization, ensuring execution and strategy are grounded in financial reality
Partner closely with FP&A and Finance to interpret financial performance, derive meaningful metrics, and translate financial data into operational insight
Support leadership teams in annual and quarterly planning by connecting operational plans to financial outcomes and ensuring assumptions are explicit and testable
Monitor financial performance across the CIO/GSC portfolio and sense early when initiatives or plans are drifting off course financially
Work with functional leaders to diagnose financial variance, evaluate corrective options, and re-chart course when plans are not delivering expected results
Develop executive-ready financial narratives integrating financial, operational, and risk perspectives
Step into ambiguous, undefined, or at-risk initiatives at the direction of the CIO/GSC Officer to diagnose root causes, establish clarity of scope, outcomes, and decision rights, impose structure, cadence, and accountability
Stabilize execution by aligning stakeholders, resolving blockers, and restoring momentum
Deliberately transition ownership to an appropriate long-term leader or function once clarity and execution discipline are established
Leave behind stronger systems, clearer ownership, and durable outcomes
Serve as the principal architect of CIO/GSC executive narratives, translating strategy, execution, risk, and financial performance into clear, compelling communication
Prepare materials for the CEO, executive leadership team, and Board as required
Ensure leadership decisions cascade into actionable, well-understood guidance across the organization

Requirements

10+ years in Chief of Staff, Strategy & Operations, Enterprise Operations, or similar senior hybrid leadership roles
Demonstrated success operating at or alongside VP/C-suite leaders in complex, multi-domain organizations
Proven experience designing and running annual, quarterly, and monthly enterprise operating cadences
Track record of stepping into ambiguity or execution risk and leaving behind clarity, structure, and ownership
Experience partnering closely with Finance and FP&A in planning, performance monitoring, and course correction
Enterprise-minded operator who can influence senior leaders without relying on formal authority
Strong judgment, discretion, and comfort surfacing uncomfortable truths early
Financially fluent and operationally grounded, able to interpret financial signals and implications without owning the numbers
Pragmatic, structured, and execution-oriented with a strong systems mindset
Consultative style with clear boundary management

Nice to have

Have designed and run an enterprise operating cadence across annual, quarterly, and monthly horizons
Have parachuted into ambiguous or failing initiatives, stabilized them, and transitioned ownership successfully
Are trusted by executives to interpret performance and financial signals before problems become visible
Have partnered deeply with FP&A to translate financial data into operational insight
Can move fluidly between strategy, execution, and executive communication
Leave organizations stronger and clearer than you found them

What we offer

A mission- and values-driven culture and a safe, inclusive environment where you can build, grow and thrive
A comprehensive total rewards package that supports your wellness and provides security for SimpliSafers and their families
Free SimpliSafe system and professional monitoring for your home
Employee Resource Groups (ERGs) that bring people together, give opportunities to network, mentor and develop, and advocate for change
Participation in our annual bonus program, equity, and other forms of compensation, in addition to a full range of medical, retirement, and lifestyle benefits

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