Senior Staff Operations Manager, Office of the President

Squarespace

. Serve as the President’s right hand and help run, maintain, and continuously evolve the Product, Engineering & Design operating model and cadence .

Posted 9/17/2026full-timeNew York City • California • United StatesSenior💰 $178,500 - $350,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in managing complex cross-functional initiatives, operating models, and strategic decision-making while leveraging AI tools to enhance operational efficiency and communication. Exhibits strong business acumen and the ability to influence stakeholders effectively in a dynamic environment.

Highest-signal resume keywords

Chief Of Staff ExperienceProduct Operations ManagementEnterprise AI Tool ProficiencyCross-Functional Initiative LeadershipStrategic Decision-Making

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Applicant Tracking System Keywords

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Hard Skills

Operating Model ManagementProduct Development Lifecycle KnowledgeFinancial AcumenProcess OptimizationProject Delivery Acceleration

Soft Skills

Exceptional Written CommunicationStrong Executive PresenceFacilitation SkillsConflict ResolutionInfluencing Senior Stakeholders

Tools & Technologies

ChatGPTGeminiClaudeGleanCursor

Industry Keywords

Management ConsultingBusiness OperationsStrategy & OperationsTech CompaniesContinuous Improvement

Tech Stack

Tools & technologies

Switching

About the role

Key responsibilities & impact

Serve as the President’s right hand and help run, maintain, and continuously evolve the Product, Engineering & Design operating model and cadence
Run the President’s operating cadence, including staff meetings, WBRs, MBRs, QBRs, finance and portfolio reviews, priority updates, and annual operating-plan inputs
Synthesize inputs into concise narratives covering priorities, risks, options, tradeoffs, and recommended decisions
Document decisions, assign owners and deadlines, track commitments, and escalate unresolved issues
Identify alignment and execution risks and facilitate resolution across Product, Engineering, Design, Commercial, Customer Operations, Finance, People, and Business Operations
Use AI and advanced tooling to improve decision speed and quality
Measure and improve the operating model, including cadence, governance, templates, roles, and escalation paths
Lead complex, ambiguous, cross-functional strategic initiatives for the President
Support annual strategy, goals, headcount, and budget processes
Represent the President in meetings, events, and discussions
Support two-way access to the President through Town Halls, Roundtables, Office Hours, and written follow-up
Serve as a trusted thought partner to the President and senior leadership team
Report to the VP of Operations

Requirements

What you’ll need

Significant experience in Chief of Staff, Product Operations, Business Operations, Strategy & Operations, or management consulting
Track record of owning an operating model, leadership cadence, or portfolio of complex cross-functional initiatives, preferably in tech companies
Knowledge of the product / software development lifecycle
Demonstrated proficiency with enterprise AI tools such as ChatGPT, Gemini, Claude, Glean, Cursor, or comparable approved tools
Experience integrating AI tools into daily workflows to automate repeatable tasks, optimize processes, improve synthesis, and accelerate project delivery
Exceptional written communication
Strong business and financial acumen
Strong executive presence and facilitation skills
Ability to influence senior stakeholders, build consensus, resolve conflict, and push for decisions without formal authority
High judgment and discretion handling sensitive organizational, people, financial, and strategic information
Comfort operating in ambiguity and switching between strategic and detailed execution
Continuous-improvement mindset
Bias toward action with sound judgment

Benefits

Comp & perks

A choice between medical plans with an option for 100% covered premiums including medical, dental, and vision
Supplemental Life and Disability Insurance plans
Fertility and adoption benefits
Headspace mindfulness app subscription
Global Employee Assistance Program
Retirement benefits with employer match
Flexible paid time off
12 weeks paid parental leave and family care leave
Pretax commuter benefit
Education reimbursement
Employee donation match to community organizations
7 Global Employee Resource Groups (ERGs)
Dog-friendly workplace
Free lunch and snacks
Private rooftop
Hack week twice per year
Option to purchase common stock