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About the Role
We are seeking our first Sales Development Representative (SDR) to join our founding team. This role offers the opportunity to build the front door of Shepherd, define customer engagement, and generate pipeline by testing messaging and building outbound/inbound systems. You will be on the front lines, speaking with founders, identifying pain points, and creating opportunities for Shepherd to deliver value. As an early team member, you will have meaningful ownership over pipeline generation and play a critical role in shaping our go-to-market engine. This is a chance to define how AI-native legal services reach and convert customers.
Responsibilities
- Generate qualified pipeline through outbound (email, LinkedIn, cold calling) and inbound lead follow-up
- Research and identify high-potential startup prospects (pre-seed through Series B)
- Craft personalized outreach that clearly communicates Shepherd’s value proposition
- Qualify leads through discovery conversations and schedule meetings for Account Executives / founders
- Maintain and manage CRM (HubSpot or similar), ensuring accurate tracking of outreach and pipeline
- Test and iterate on messaging, sequences, and targeting to improve conversion rates
- Collaborate with marketing and growth on campaigns, content, and lead generation strategies
- Build relationships with founders and operators early in their journey
- Provide feedback from the market to help refine positioning, product, and GTM strategy
- Help build scalable outbound systems and playbooks from scratch
Requirements
- 1–3+ years of experience in SDR/BDR, sales, or customer-facing roles (or strong demonstrated interest in sales)
- Excellent written and verbal communication skills
- High level of organization and attention to detail
- Strong work ethic and willingness to do high-volume, high-quality outreach
- Comfort using sales tools (e.g., HubSpot, LinkedIn Sales Navigator, Apollo, etc.)
- Ability to learn quickly and adapt messaging based on feedback
- Experience selling or prospecting into startups
- Familiarity with SaaS, legal tech, fintech, or B2B services
- Experience with outbound sequencing and experimentation
- Interest in AI, startups, and early-stage company building
- Entrepreneurial mindset: Thrive in ambiguity and enjoy building from zero
- Hustle & resilience: Energized by outreach, rejection, and continuous improvement
- Curiosity: Desire to deeply understand founders and their challenges
- Ownership mentality: Take responsibility for pipeline generation and results
- Coachability: Seek feedback and improve quickly
- Adaptable: Comfortable iterating on messaging, tools, and processes in real time
Skills
- Sales Development
- Pipeline Generation
- Outbound Sales
- Inbound Lead Follow-up
- Cold Calling
- Email Outreach
- LinkedIn Outreach
- Prospect Research
- Value Proposition Communication
- Lead Qualification
- Discovery Calls
- CRM Management (HubSpot)
- Messaging Testing
- Sequence Optimization
- Targeting Improvement
- Marketing Collaboration
- Growth Strategy
- Relationship Building
- Market Feedback Analysis
- GTM Strategy Refinement
- Outbound System Building
- Sales Tools Proficiency (HubSpot, LinkedIn Sales Navigator, Apollo)
- Communication Skills
- Organization
- Attention to Detail
- Work Ethic
- Adaptability
Experience Level
- 1-3+ years
Salary/Compensations
- $60,000 – $80,000 base salary + commission (OTE $90,000 – $120,000+)
Benefits
- Meaningful equity: Early-stage ownership with significant upside
- Direct impact: Build and shape Shepherd’s outbound and inbound engine from day one
- Career growth: Clear path to Account Executive or broader GTM roles as the company scales
- Hands-on learning: Work directly with founders and gain exposure to full-cycle sales
- Mission-driven work: Help democratize access to high-quality legal services for startups
About the Company
- 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.
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.