Shortcut

Chief of Staff (to the CEO)

Shortcut$150K — $180K *
US-AnywhereRemote in United States
Consumer Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 7-10+ years in Chief of Staff, product operations, BizOps, or related roles.
  • Experience in building operating systems from scratch.
  • Strong background in product management and metrics analysis.
  • Ability to interface with data directly for strategic insights.
  • Exceptional communication skills and relationship-building capacity.
  • Proven experience managing complex projects independently.
  • Drive for personal growth and self-improvement.

Responsibilities

  • Own and optimize the product operating system for execution success.
  • Leverage data to inform product strategy and growth initiatives.
  • Establish and maintain company metrics and speed improvements with AI.
  • Serve as the CEO's force multiplier in leadership discussions and project prioritization.
  • Create impactful social products that foster global connectivity.

Benefits

  • Opportunity to work directly with the CEO.
  • Experience in a high-growth, founder-led company.
  • Ability to significantly influence company operations and strategy.
  • Support for professional growth and career advancement.
  • Engagement in meaningful product development that connects people.
Full Job Description
The role

The Chief of Staff is one of the most important hires we'll make this year. Our business is at a pivotal point, and our CEO, Paul, is looking for a product-focused operator and strategist to partner with. You'll report directly to Paul, working in lockstep to bring rigor to our operating layers, drive a metrics-driven product strategy, optimize through AI implementation, and own high-impact special projects.

This is not a Chief of Staff role where you watch; you will lead. You'll carry real, delegated authority, designated by Paul and the leadership team. You'll independently own work that shapes how our business operates - strategic product insights, cross-company metrics, EPD health, executive effectiveness, AI enablement, and special projects. Our EA will handle calendaring, event planning, and related tasks so you and Paul can focus exclusively on providing leverage and impact.

This is a rare opportunity to learn how a high-growth, founder-led company actually operates, and shape how it succeeds. If you get your energy from making a company run and you want to found or lead one yourself next, this role will help you get there.

Who you are
  • You are a proven operator. You have 7-10+ years of experience in Chief of Staff, product operations, BizOps, consulting, or other high-accountability operational or strategic roles. You've stood up dashboards, complex roadmaps and operating systems from nothing and weirdly enjoyed it.
  • You think like a product person. You've operated inside a product organization and understand how products get scoped, built, measured, and shipped. You know a complete spec from an incomplete one, and you can tell when a slipping metric is a process vs. product problem. Consumer/social product experience is a big plus.
  • You're quantitative. You get into the data yourself rather than waiting on an analyst. You can pressure-test a metric definition, catch math that doesn't hold up, and build a point of view about which lever actually moves the business. You are truth-seeking when it comes to data and understand its importance.
  • You operate exceptionally at every altitude. You can zoom out to see the strategic picture and zoom in to fix a broken process without losing sight of either. You know when something needs a system and when it just needs one-off handling. You spot inefficiencies, errors, and opportunities immediately through both acute attention to detail and the systems you've put in place to catch them. You bring rigor to everything you touch, without sacrificing speed.
  • You are always up to the challenge. A competitor teardown, a complex model, a prototype, a marketing strategy, a hard question nobody has had time to chase. You don't need a template; you move quickly and deliver a finished product at a high standard. You can't be defined by one functional area; you want to master it all.
  • You have an athlete's mindset. You crave feedback and act on it immediately; growth is non-negotiable. You have thick skin and a find-a-way mentality, and are eager to perform. You move with urgency and confidence, taking great pride in your work and the team's.
  • You are an exceptional communicator. You can accurately represent a leader's voice and vision. You write and speak clearly and concisely, and you know how to surface the right information to the right people in the right format at the right time. Your speed on Slack is unmatched; you are inbox-zero and are obsessed with unblocking the team.
  • You are a trusted partner and teammate. We can't find your ego anywhere. You put the team's success first, and believe that building together is crucial if we want to win. EQ comes naturally to you, allowing you to navigate different personalities with ease and composure as you build durable relationships across the org. You have always been the "go-to" colleague, friend, or family member - trusted to get things done.
  • You think like a future founder. You see beyond the day-to-day. You view this role as a critical proving ground, a rare chance to learn how a running startup actually works at the highest level and across every function, alongside a CEO who's deeply invested in your growth and long-term career.


What you will do
  • Own our product operating system. Paul will provide the vision; you will optimize the system that brings it to life. You will provide the structure and rigor to manage product execution, driving accountability across scope, specs, and PM-owned metrics. This is a critical role in the company, primed for immediate impact.
  • Leverage data as a trusted product strategist. You'll partner with Paul, PMs, and our Head of Data to determine what actually moves the product and our industry.You'll build the quantitative picture of how our products grow, and use it to point the company at the highest-impact work and strategies to get there.
  • Own how Clubhouse measures itself, and make us faster with AI. You will create the source of truth for company metrics, in partnership with functional leaders. You'll build the machine that measures how we move, then find the right ways to move us faster with AI. This will be critical for any future founder and you will develop deep fluency here.
  • Be the CEO's force multiplier. You will embed in the leadership team's meetings, propose agendas, guide discussions, and drive execution across the group. You'll triage roadmaps, escalations, and requests before they reach Paul, keep the company's top priorities moving, and take on the projects that need to be done fast and well by someone he trusts. You will learn Paul's voice and vision, and own the team meeting and roadmap docs that are critical for company alignment.
  • Create something meaningful for the world. Social products allow people to connect in ways that were never before possible. When the telephone was invented, it suddenly allowed people to speak with others across the world. Thanks to FaceTime, grandparents everywhere can now watch their grandchildren grow up. At Clubhouse, you'll be figuring out something entirely new for the world - a positive product that brings people's voices together to help everyone have a life filled with great friendships.


If you are a talented, ambitious operator and think you might be a good fit, we'd love to talk.

About Shortcut

Shortcut is a software company that provides a platform for creating and sharing interactive tutorials. The company's platform allows users to create step-by-step tutorials that can be shared with others. Shortcut was founded in 2020 by Trevor Rogers and is headquartered in San Francisco, California. The company's mission is to make it easy for anyone to create and share tutorials, regardless of their technical expertise. Shortcut's platform is used by individuals and businesses to create tutorials for a variety of purposes, including software training, customer support, and product demos.
Learn more about Shortcut
Size
10 employees
Industry
Founded
2014

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