[Hiring] Chief of Staff @Workweek

Role Description

We are looking for a highly driven, organized, and strategic Chief of Staff to act as a true thought partner and force multiplier for our CEO. This is a senior, high-impact position where you will dive into messy, cross-functional problems. You will balance strategic planning with hands-on operational execution, drive special projects, and partner directly with the CEO to shape and communicate our product vision.

Core Objectives (Your Mandate)

• Organize Key Initiatives: Bring structure to chaos. You will take our most critical company initiatives, organize them into actionable workstreams, assign clear ownership, and build the operational rhythm to ensure they cross the finish line.
• Translate & Communicate Product Vision: Work closely with the CEO (who leads our product org) to distill complex product roadmaps and visions into clear, tangible communication for both internal teams and external stakeholders.
• Drive Team Alignment & Updates: Act as the central nervous system for company information. You will own internal communications, executive updates, and All-Hands meetings to ensure the entire team knows exactly what we are building, why it matters, and how we are tracking against our goals.

Note: All Workweek employees may work remotely, all work must be done in English and availability to meet during the Central Time Zone workday is required.

What you'll do:

• Special Projects & Growth: Spearhead new vertical launches and new product launches from 0 to 1.
• Key Project Management: Step in to lead high-priority, cross-functional projects when the business needs immediate execution and alignment.
• External Representation: Drive the strategy and creation of Upfronts key external presentations, and support Investor Relations.
• Executive Management:
  • Leadership Team Member: Join our executive team meetings and ensure executive communication is carried through the company.
  • Stakeholder Guidance: Work closely with key stakeholders across the business, providing strategic direction and input where needed to unblock teams and accelerate growth.
• Roadmap & Planning:
  • Strategic Planning & Execution: Translate high-level company goals into actionable milestones (e.g., OKRs, quarterly planning cycles).
  • Operational Rhythm: Run the leadership cadence. Set crisp agendas for executive meetings, capture decisions, assign DRIs (Directly Responsible Individuals), and drive follow-ups to completion.
  • Information Flow: Bridge the communication gap between the CEO and department heads to ensure top-down decisions cascade clearly and bottom-up feedback reaches the executive team.
  • Interim Leadership: Step in as a temporary owner for critical gaps (e.g., HR, Ops, Finance) until a dedicated leader is hired.

Qualifications

• Experience: 7+ years in management consulting, investment banking, venture capital, or a high-growth startup operations/strategy role.
• Product Roadmap Partnership: Ability to work closely with the CEO to translate high-level vision into a tangible, executable product roadmap.
• Internal Comms Mastery: You are an exceptional writer and speaker who can turn messy ideas into crisp, inspiring updates for the whole company.
• Extreme Ownership: You have a "get shit done" mentality. You take low-ego ownership of both high-level strategy and unglamorous process-fixing.
• Exceptional Synthesis: You can turn scattered Slack threads, conflicting opinions, and messy data into concise, one-page decision memos.
• Data Fluency: Comfortable modeling, building lightweight dashboards, and reviewing KPIs to pressure-test business assumptions.

Benefits

• Competitive pay (we don't pay based on location, we assign value to the role).
• Equity in Workweek.
• Remote operations with the ability to work in the time zone of your choice (or work IRL in our Austin, TX office).
• Unlimited PTO with a minimum of 3 days/quarter used.
• 100% health insurance coverage, 75% coverage for dependents, and $150/month towards an HSA (or $150/month health stipend if insurance not used).
• 120 days of parental leave to use within one year of childbirth (available 12 months after your start date and only available every 365 days).
• 401(k) plan with 3.5% company match.
• $500 one-time stipend for any home office needs used after the first 90 days.
• 5-week sabbatical after 4 years on staff.
• 2 volunteering days per year.
• 1x/year in-person team retreat.
• $100/month book stipend.

Note: At Workweek, we’re passionate about building a diverse team. We care deeply about diversity, equality, and inclusion and strive to build a culture where everyone, from any background, feels included, supported, and free to be themselves.

If your experience is this close to what we’re looking for, please consider applying. Experience comes in many forms – skills are transferable, and passion goes a long way. We know that diversity makes for the best problem-solving and creative thinking, which is why we’re dedicated to adding new perspectives to the team and encourage everyone to apply.

*At this time we do not offer visa sponsorship or assistance.