[Hiring] Senior Staff Operations Manager @Squarespace

Role Description

We are looking for a Chief of Staff–style operator to serve as the President’s right hand and help run, maintain, and continuously evolve the Product, Engineering & Design operating model and cadence. This role will turn strategy into a durable execution system.

• Own the connective tissue across the President’s leadership cadence.
• Prepare the right inputs, create clarity on decisions and tradeoffs, ensure commitments are followed through, surface risks early, and improve the operating model as the organization changes.
• Work across Product, Engineering, Design, Commercial, Finance, People, and Business Operations, partnering with senior leaders who do not report to you.
• Influence through judgment, trust, and clarity.
• Use approved enterprise AI tools to automate repeatable operating work, synthesize information across functions, improve leadership preparation, surface risks and dependencies, and accelerate strategic-initiative delivery.

Qualifications

• Significant experience in Chief of Staff, Product Operations, Business Operations, Strategy & Operations, or management consulting.
• A 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.
• Exceptional written communication skills.
• Strong business and financial acumen.
• Strong executive presence and facilitation skills.
• Demonstrated ability to influence senior stakeholders.
• High judgment and discretion when handling sensitive information.
• Comfort operating in ambiguity and switching between strategic altitude and detailed execution.
• A continuous-improvement mindset.
• A bias toward action.

Requirements

• Run the President's operating cadence.
• Drive decision quality.
• Improve execution velocity.
• Evolve the operating model.
• Lead high-priority strategic initiatives.
• Represent the President and build transparency.
• Serve as a trusted thought partner to the President and senior leadership team.

Benefits

• 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.
• US Cash Compensation Range: $178,500 - $350,000 USD.