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Chief of Staff

Job in Burlington, Middlesex County, Massachusetts, 01805, USA
Listing for: Jobtailor
Full Time position
Listed on 2026-07-13
Job specializations:
  • Business
    Corporate Strategy, Business Analyst, Change Management, AI Business & Operations
Salary/Wage Range or Industry Benchmark: 150000 - 210000 USD Yearly USD 150000.00 210000.00 YEAR
Job Description & How to Apply Below

Responsibilities

  • Partner with the CEO and COO as a trusted strategic operator, driving execution on the company’s highest-priority initiatives.
  • Maximise executive leverage by structuring competing demands, prioritising enterprise impact, and ensuring leadership focus on what matters most.
  • Run the Executive Leadership Team (ELT) operating cadence, enabling faster decisions, stronger alignment, and disciplined follow‑through.
  • Build and embed the company’s operating system, including planning cycles, performance reviews, and cross‑functional execution rhythms.
  • Own OKR and performance governance to ensure clear priorities, measurable outcomes, and leadership accountability.
  • Translate enterprise data into clear performance narratives, surfacing value drivers, risks, and opportunities.
  • Lead CEO/COO‑sponsored strategic initiatives and transformation programs with clear milestones, governance, and results.
  • Drive cross‑functional alignment across Product, Engineering, Finance, Operations, and Go‑to‑Market teams to accelerate execution.
  • Prepare and support board‑level and executive communications, ensuring clarity of strategy, performance, and decisions.
  • Operate as a proactive, resilient problem‑solver who anticipates challenges, drives accountability, and delivers measurable business impact.
Requirements
  • Proven experience leading cross‑functional strategic initiatives in SaaS/technology environments.
  • Proven ability to translate ambiguity into structure, defining clear goals, plans, owners, metrics, and executive‑ready updates.
  • Strong analytical and data‑driven mindset, with expertise in KPI storytelling and using insights to drive decisions.
  • Exceptional executive communication and influence skills, able to align senior stakeholders and navigate complex, matrixed environments.
  • High judgment, discretion, and integrity, with experience handling sensitive information and complex organizational dynamics.
  • Resilient, results‑oriented operator with a bias to action, capable of thriving in fast‑moving, high‑priority, high‑impact environments.
Hard Skills
  • OKR governance
  • KPI storytelling
  • Data analysis
  • Performance reviews
  • Cross‑functional execution
  • Strategic initiatives
  • Transformation programs
  • Performance narratives
  • Enterprise data analysis
  • Measurable outcomes
Soft Skills
  • Executive communication
  • Influence skills
  • Problem‑solving
  • Resilience
  • Results‑oriented
  • High judgment
  • Discretion
  • Integrity
  • Organizational dynamics
  • Stakeholder alignment
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