Chief of Staff
About The Position
We're seeking a Chief of Staff to join our founding team. This isn’t just a job- it’s a chance to operate at the center of the company and help build Shepherd from the ground up. You’ll work directly with the CEO and founding team across every function- from product and go-to-market to operations and fundraising. This role is about driving clarity, execution, and momentum across the business, ensuring that priorities are translated into action and that nothing critical falls through the cracks. As an early member of the team, you’ll have a unique vantage point across the entire company and play a key role in shaping how Shepherd operates, scales, and makes decisions. This is a rare opportunity to be a force multiplier at a category-defining company building the future of AI-native legal services.
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 decisions
Nice To Haves
- 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
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
Benefits
- Competitive compensation: $145,000 – $160,000 base salary
- Meaningful equity: Early-stage ownership with significant upside
- Full autonomy: Remote work with flexible scheduling
- Direct exposure: Work side-by-side with the CEO and founding team
- Broad scope: Gain experience across all aspects of building a company
- Professional growth: Path to leadership roles across operations, GTM, or product
- Mission-driven work: Help democratize access to high-quality legal services for startups
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What This Job Offers
Job Type
Full-time
Career Level
Entry Level
Education Level
No Education Listed
