Sales Development Rep

The Opportunity

• We're seeking our first Sales Development Representative (SDR) to join our founding team. This isn’t just a job- it’s a chance to help build the front door of Shepherd and define how we engage with startups from their very first interaction.

• You’ll work directly with the founding team to generate pipeline, test messaging, and build outbound and inbound systems that drive customer acquisition. You’ll be on the front lines of the business — speaking with founders, identifying pain points, and creating opportunities for Shepherd to deliver value.

• As an early member of the team, you’ll have meaningful ownership over pipeline generation and play a critical role in shaping our go-to-market engine.

• This is a rare opportunity to help define how a new category — AI-native legal services- reaches and converts customers.

What You'll Do

• 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

What We're Looking For

Required

• 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

Preferred

• 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

Essential Qualities

• Entrepreneurial mindset- You thrive in ambiguity and enjoy building from zero

• Hustle & resilience- You’re energized by outreach, rejection, and continuous improvement

• Curiosity- You want to deeply understand founders and their challenges

• Ownership mentality- You take responsibility for pipeline generation and results

• Coachability- You seek feedback and improve quickly

• Adaptable- You’re comfortable iterating on messaging, tools, and processes in real time

What We Offer

• Competitive compensation: $60,000 – $80,000 base salary + commission (OTE $90,000 – $120,000+)

• 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

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.