Chief of Staff at Shepherd | CA, US | Rezi

Chief of Staff at Shepherd

Chief of Staff

Shepherd · CA, US

1 weeks ago

Chief of Staff

Shepherd · CA, US

11 days ago
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About the Role

This role offers the opportunity to operate at the center of a founding team, helping to build a company from the ground up. You will work directly with the CEO and founding team across all functions, driving clarity, execution, and momentum. As an early member, you will shape how the company operates, scales, and makes decisions, contributing to the future of AI-native legal services.

Responsibilities

  • Act as a strategic partner to the CEO, helping drive priorities, decision-making, and execution
  • Own and manage key cross-functional initiatives across product, GTM, operations, and hiring
  • Build and implement operating rhythms (weekly exec meetings, OKRs, KPI tracking, investor updates)
  • Drive alignment across teams and ensure clear communication of priorities and goals
  • Identify gaps, bottlenecks, and opportunities across the business — and take action to solve them
  • Support fundraising efforts, including investor outreach, materials, and follow-ups
  • Analyze key metrics and performance data to inform strategy and decision-making
  • Help design and improve internal processes, systems, and workflows
  • Step into high-priority projects as needed (0→1 execution across any function)
  • Help recruit, onboard, and scale the team

Requirements

  • 4–8+ years of experience in operations, strategy, consulting, investment banking, or startup roles
  • Strong analytical and problem-solving skills
  • Proven ability to manage complex, cross-functional projects
  • Excellent communication and stakeholder management skills
  • High level of organization and attention to detail
  • Experience working closely with senior leadership or founders
  • Ability to operate independently and execute in ambiguous environments
  • Experience at an early-stage or high-growth startup
  • Background in SaaS, fintech, legal tech, or professional services
  • Experience with fundraising, investor relations, or board materials
  • Familiarity with tools like Notion, HubSpot, Google Workspace, and analytics platforms
  • Interest in AI, startups, and the future of professional services
  • Operator mindset- You turn strategy into execution and get things done
  • Force multiplier- You make the CEO and team more effective
  • Owner mentality- You take responsibility for outcomes, not just tasks
  • Structured thinker- You bring clarity and organization to ambiguity
  • Highly adaptable- You’re comfortable jumping across functions and priorities
  • Low ego, high impact- You do what’s needed, no matter the task

Skills

  • Analytical skills
  • Problem-solving skills
  • Project management
  • Communication skills
  • Stakeholder management
  • Organization
  • Attention to detail
  • Independent execution
  • Ambiguity navigation
  • Fundraising support
  • Data analysis
  • Process improvement
  • Workflow design
  • Recruiting
  • Onboarding
  • Team scaling
  • Notion
  • HubSpot
  • Google Workspace
  • Analytics platforms

Location

  • Remote

Work Type

  • Remote
  • Full-time

Experience Level

  • 4-8+ years

Salary/Compensations

  • $145,000 – $160,000 base salary

Benefits

  • Competitive compensation
  • Meaningful equity
  • Full autonomy
  • Remote work with flexible scheduling
  • Direct exposure to CEO and founding team
  • Broad scope of experience
  • Professional growth opportunities
  • Mission-driven work

About the Company

  • We are building the future of AI-native legal services.
  • Our core values are: BE BOLD & TAKE INTELLIGENT RISKS, DEMAND EXCELLENCE, EXECUTE RELENTLESSLY, EARN TRUST THROUGH ACTION, BE A GOOD PERSON.

Equal Opportunity

  • We are an equal opportunity employer and are committed to building a diverse and inclusive workplace. We do not discriminate on the basis of race, color, religion, gender, gender identity or expression, sexual orientation, national origin, age, disability, veteran status, or any other legally protected characteristic.