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