Drive Alignment & Accountability
Translate company-level OKRs into clear, measurable workstreams and track progress rigorously.
Facilitate weekly leadership syncs, all-hands meetings, and retrospectives; continuously refine processes for clarity and speed.
Partner with functional leads to surface blockers early and ensure timely delivery of commitments.
Accelerate Cross-Functional Execution
Roll up sleeves to unblock projects—from new revenue experiments and pricing changes to org design and system implementations.
Anticipate risks, propose data-driven mitigations, and ensure initiatives move from “stuck” to “shipped.”
Leverage the CEO & Board Relationships
Prioritize the CEO’s highest-impact initiatives (hiring, strategic partnerships, pricing) and orchestrate follow-through.
Prepare board updates and executive communications that keep stakeholders aligned and informed.
Champion Culture & Communication
Model the company’s high-trust, performance-oriented culture—anchored in psychological safety and inclusion.
Own internal communications, onboarding programs, team off-sites, and leadership-development initiatives that advance belonging and transparency.
Support Talent & Team Development
Partner with hiring managers to design equitable hiring processes that attract and retain women and other under-represented talent.
Monitor team health, craft career ladders, and implement feedback mechanisms that empower every employee to grow.
5–10 years of experience in high-growth startups, strategy consulting, operations, or a prior Chief of Staff role.
Demonstrated record of driving complex business initiatives to completion under tight timelines.
Exceptional written and verbal communication skills; able to distill complexity into crisp action plans.
Fluency with modern workplace tools (e.g., Notion, Trello, Slack, Google Workspace).
Structured thinker who applies systems and metrics to create clarity and accountability.
High agency, sound judgment, and the ability to build trust quickly across diverse teams.
On-site presence in Redwood City at least three days per week (relocation support available).
Mission & Impact – Play a pivotal role in modernizing a $1.3 trillion industry by equipping engineers with faster, smarter design tools.
Comprehensive Health Care – Medical, dental, and vision coverage for employees and dependents.
Retirement Savings – 401(k) plan managed via Guideline.
Professional Growth – Direct mentorship from the CEO, exposure to board-level strategy, and a launchpad toward future GM, COO, or founder roles.
Inclusive Culture – A tight-knit, low-ego team committed to psychological safety, equitable opportunity, and the advancement of women in tech.
Hybrid Flexibility – Three catered in-office lunches each week and the option to work remotely on Tuesdays and Thursdays.
1. Application Review
Submit your application, including your resume and cover letter, through our online portal. Our team will carefully review your qualifications and experiences. We take pride in responding promptly, so if your application aligns with our current opportunities, you’ll hear back from us with next steps. Your journey with Toast begins here, and we’re excited to see what you bring to the table!
2. Vetting Call
If your application is successful, we’ll schedule a vetting call with a member of the Toast team. This 30-45 minute informal conversation is designed for us to get to know you better and assess your skills. Be prepared to discuss your past projects, the challenges you’ve tackled, and the impact you’ve made. This is your chance to shine and show us why you’re a great fit for the roles we offer.
3. Profile Creation
Once you’ve impressed us in the vetting call, we’ll create an unbiased profile that highlights your experience while minimizing common biases. Instead, we focus on your skills, industry experience, and the impact you’ve made. This way, your profile reflects your true potential and accomplishments.
4. Client Submission
After crafting your unbiased profile, we submit it to our trusted clients. We work closely with these clients to ensure they understand the value you bring. Throughout their interview process, we remain by your side, providing support and guidance. Our goal is to help you navigate the hiring process smoothly and confidently, ensuring you have the best chance to secure a role that fits your skills and aspirations.