Chief of Staff

The Opportunity 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. What You'll Do 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 What We're Looking For Required 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 Preferred 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 Essential Qualities 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 What We Offer 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 Our Core Values Be Bold & Take Intelligent Risks We believe ambitious outcomes are possible. We explore unconventional ideas, test them rigorously, and act on the data- learning fast without distraction or comparison. Demand Excellence Mediocrity has consequences. We set the highest standard in our execution, judgement, and how we show up everyday- because excellence compounds. Execute Relentlessly Speed and urgency are habits that when modeled consistently and scaled through automation, become contagious across the team, the product, and our customers. Earn Trust Through Action Legal work runs on trust, not features. We earn trust by being responsive, transparent, and accountable to our customers- particularly when it’s uncomfortable. Be a Good Person We pair high standards with empathy and ambition with humanity. Respect and integrity are NOT separate from winning- they are how we win. 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.