Founding GTM / Head of Growth

Shepherd is building the first law firm natively embedded in a startup's business- combining AI agents, contextual intelligence, and dedicated attorneys into a single integrated layer across your company. Agents handle the routine, the repetitive, the data-heavy- everything that scales. Your dedicated attorney handles the strategy, the trust, and the accountability- everything that doesn't. Over time, Shepherd's contextual AI learns each client's business, risk appetite, and deal preferences- enabling proactive legal solutions at fixed, predictable costs and aligning pricing to outcomes, not billable hours.

• We’re seeking a Founding GTM & Head of Growth to build and lead Shepherd’s go-to-market engine from the ground up.

• This role will define how Shepherd reaches and serves startups — developing the strategy, systems, and channels that drive customer acquisition and brand awareness. You’ll work directly with the founding team to design and execute our growth strategy across partnerships, content, community, and outbound.

• This is a rare opportunity to help build the go-to-market foundation for a new category: AI-native legal services for startups.

• Own and execute Shepherd’s go-to-market strategy, including positioning, messaging, and distribution across pre-seed, seed, and Series A startups

• Build and manage the customer acquisition engine across outbound, inbound, partnerships, and community channels — with AI-powered tooling at the core

• Develop scalable systems for lead generation, conversion, and customer onboarding

• Create and manage content and thought leadership across LinkedIn, newsletters, and startup communities

• Build relationships with venture funds, accelerators, startup platforms, and founder communities — and convert those relationships into pipeline

• Design and optimize growth experiments across marketing, sales, and product-led channels

• Implement and manage CRM, marketing automation, and growth analytics infrastructure

• Work closely with the founding team to refine product positioning and pricing strategy

• Help shape Shepherd’s brand narrative in the startup and venture ecosystem

• 7+ years of experience in B2B sales, growth, or go-to-market roles

• Startup ecosystem relationships — warm, active connections with founders, VCs, and accelerator communities that translate to introductions and pipeline on day one

• Player-coach sales experience — proven ability to personally close deals while simultaneously building the team, playbooks, and systems that scale what you prove out

• Proven ability to build and scale customer acquisition channels from zero

• Experience working with or selling into startups, venture-backed companies, or SaaS businesses

• Strong understanding of modern growth strategies, including content, outbound, and partnerships

• Experience with CRM and marketing tools such as HubSpot, Salesforce, or similar

• Excellent communication and storytelling skills

• Experience marketing legal tech, fintech, or B2B SaaS products

• Background in startup ecosystems, venture capital, or founder communities — VC platform roles, EIR, portfolio operator, or active angel investor

• Experience launching early-stage companies or new products

• Strong data-driven approach to growth experimentation and optimization

• Familiarity with AI-driven products or platforms

• Entrepreneurial mindset — You enjoy building systems from zero

• Strategic thinker — You can connect positioning, messaging, and distribution

• Builder mentality — You’re comfortable executing while designing strategy

• Network-driven — You have genuine relationships inside the startup and VC ecosystem, not just a large LinkedIn following

• Mission-aligned — You’re excited to improve how legal services are delivered to startups

• Competitive compensation: $125,000–150,000 base salary

• Meaningful equity: Early-stage equity with significant upside potential

• Direct impact: Define the growth strategy for a new category in legal tech

• Founder collaboration: Work directly with the founding team

• Mission-driven work: Help modern startups access better legal services

We believe ambitious outcomes are possible. We explore unconventional ideas, test them rigorously, and act on the data- learning fast without distraction or comparison.

Mediocrity has consequences. We set the highest standard in our execution, judgement, and how we show up everyday- because excellence compounds.

Speed and urgency are habits that when modeled consistently and scaled through automation, become contagious across the team, the product, and our customers.

Legal work runs on trust, not features. We earn trust by being responsive, transparent, and accountable to our customers- particularly when it’s uncomfortable.

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.