Toast is hiring a Chief of Staff to the Co-founder & CEO. This role, based from our Brooklyn, NY office approximately 3 days per week, will serve as a critical thought partner and operational extension of the CEO. You will help manage goals, stakeholders, culture, and efficiency to directly support the company's next phase of growth.
What You'll Do
- Be a thought partner on the CEO's annual, quarterly, monthly, and weekly goals, linking them to daily activities via Monday.com.
- Adjust projects and timelines when priorities shift.
- Help craft a rhythm for engaging all key stakeholders and ensure the CEO's schedule allows for meaningful relationship building.
- Stimulate discussion, ask questions, and make decisions on the CEO's behalf to remove bottlenecks across the company.
- Proactively recommend ways to streamline, eliminate manual work, and operationalize recurring activities (e.g., board meeting prep, conference presentations).
- Support the CEO with scheduling and travel management for conferences, off-sites, and board meetings (not to exceed 20% of the role).
What We're Looking For
- Self-starter with strong EQ and the ability to create structure and order from chaos.
- Ability to set clear priorities, stay organized, and keep commitments without oversight.
- Lead with kindness and curiosity, listening to understand and assuming positive intent.
- Exceptional writing skills to draft communications on behalf of the CEO.
- Ability to be direct and succinct, boiling complex information down to the 'so what'.
- Ability to influence without a title, manage up, disagree thoughtfully, and step into conflict.
- Detail-obsessed with discipline and organization to manage two workloads.
Nice to Have
- MBA, a couple of years in management consulting, or a few years helping scale a venture-backed company.
Team & Environment
You'll report directly to Co-founder & CEO (Keith) and join a team of 70+ members. We operate as a remote team with hubs in New York City, Boston, Poland, and Austin.
Work Mode
This is a hybrid role requiring you to work from our Brooklyn, NY office approximately 3 days per week.
We celebrate wins loudly, encourage direct and thoughtful opinions, and believe being great does not require '100-hour work weeks'. We focus on being present and focused, trading quick dopamine hits for fulfilling experiences.
