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About This RoleAI processing…
At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.
All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy .
AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.
Key Responsibilities
- 1Own calendar management and meeting rhythms. Anticipate complex scheduling needs, streamline calendars for maximum impact, and eliminate conflicts before they form for CEO and Head of Engineering.
- 2Partner closely with the Insights & Operations Partner to operationalize meeting cadences and follow through
- 3Embed AI-enabled systems into how Symmetry runs. Use AI to draft, synthesize, and accelerate the work meeting summaries and action-item extraction, inbox triage, first-draft comms and decks, research and briefing prep — then build the repeatable workflows, prompt libraries, and documentation that make the whole leadership team faster. Apply human judgment and Symmetry’s AI policies to everything that ships.
- 4Act as an extension of the leaders you support. Triage inboxes and prioritize responses so clients, employees, and key stakeholders get fast, high-quality answers; represent the CEO with external partners on priorities, timelines, and availability.
- 5Draft executive presentations, company-wide comms, and off-site materials in partnership with the CEO for a range of internal and external audiences.
- 6Lead complex travel and events. Coordinate quarterly travel for the CEO, Head of Engineering, and leadership team, and lead onsite and event planning with cross-org coordination for team off-sites, celebrations, and Symmetry traditions.
- 7Ensure seamless expense and budget processes for key executives including the CEO and Head of Engineering in close coordination with finance partners, and establish new or improve existing administrative systems and processes.
- 8Serves as a trusted thought partner, frames decisions and offers options; Proactively helps leaders and teams identify risks, surface solutions, and shape workflows to prevent issues and adapt to change.
- 9Acts with delegated authority on behalf of leader, making calls on routine decisions and requests.
- 10Serves as a culture carrier and strengthens team identity through your interactions with individuals and teams.
- 11Influences beyond direct leaders across the business, anticipating needs and future risks.
Requirements
- 4+ years supporting VP-level or above executives, including calendaring for multiple executives, complex travel, and event planning — or equivalent relevant experience.
- Demonstrated AI fluency you have built systems around. You can walk us through specific AI workflows you designed, documented, and got others to adopt — not just tools you have tried. You write structured prompts with real context and constraints, you critically review output before it reaches an executive, and you protect sensitive data by default.
- An autonomous, strategic working style. You find ways to add value to the CEO and the leadership team without prompting or significant guidance. You navigate ambiguity, balance tradeoffs in high-stakes projects, and see around corners.
- Influence across leaders and teams. You build trust with executives and cross-functional partners through clarity, follow-through, and discretion, and you mentor others in the craft.
- Outstanding organization and judgment under pressure. Incredibly detail-oriented, able to prioritize competing assignments, and calm when responsibilities shift — with a great deal of common sense and a bias toward "find a way."
- Strong written and spoken communication , plus project management from conception to completion, and complete confidentiality, tact, and discretion on all business matters.
- Culture builder. A strong instinct for bringing people together and collaborating with the workplace experience team.
- Proficiency with Google Suite and AI Tooling : Gmail, Calendar, Drive, Docs, Sheets, Notion, ChatGPT, Gemini, Claude or others
Perks & Benefits
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