Sales Development Lead

We’re hiring our first Sales Development Lead to own and refine top-of-funnel pipeline at an early-stage B2B startup selling to professional services firms (starting with legal and finance).

This role is about creating real, high-quality sales conversations in a relationship-driven, trust-heavy market. You’ll work closely with the founders and our Founding GTM Lead to refine who we target, how we reach them, and what “qualified pipeline” actually means for Caddi.

This is an SDR role in execution, but a lead role in scope. You’ll be refining and owning our sales development motion—outbound strategy, messaging, qualification, and handoff. If successful, this role is expected to grow into Head of Sales Development, with responsibility for hiring and leading the SDR team.

We’re looking for someone who has spent time earlier in their career doing outbound or SDR-style work and wants to take ownership of improving and scaling a function—not just working a queue.

Success in this role is measured by pipeline quality, learning velocity, and repeatability.
What You’ll Do

- Partner Closely With Sales & Founders

• Work directly with founders and the Founding GTM Lead to generate qualified pipeline
• Own early discovery and qualification conversations
• Ensure clean, high-signal handoffs to AEs
• Translate objections and buyer feedback into better targeting and messaging

- Own Outbound & Pipeline Creation

• Run outbound prospecting
• Research accounts and contacts
• Execute thoughtful, personalized outreach (email, LinkedIn, warm intros)
• Book and qualify discovery conversations
• Confidently disqualify poor-fit leads

- Refine the Sales Development Motion

• Help refine ICPs, personas, and targeting criteria
• Test and iterate on outbound messaging and sequences
• Document what works and turn it into repeatable playbooks
• Create a clear learning loop between sales, founders, and product

- Lay the Foundation for a Scaled SDR Team

• Establish what “good pipeline” looks like for Caddi
• Help define future SDR roles and processes
• Prepare the ground to hire SDR #2 and beyond

• 3–5 years of experience in Sales Development, Business Development, or outbound-focused roles
• Hands-on experience doing outbound prospecting and qualification
• Experience at a Seed or Series A startup, working closely with AEs and founders in an early-stage or fast-growing environment
• Comfort operating in an early, evolving GTM environment and refining existing processes
• Strong written and verbal communication skills
• Thoughtful, professional approach to outbound (not spray-and-pray)
• Bias toward action, testing, and learning
• Familiarity with modern sales development tooling (e.g. Apollo, LinkedIn Sales Navigator, HubSpot, Clay, or similar)

Nice to have:

• Experience selling to professional services (law, finance, consulting, etc.)

• Early sales hire with meaningful ownership and influence
• Clear path to Head of Sales Development
• Competitive base salary ($60,000–$80,000) plus commission tied to performance
• Meaningful early-stage equity
• Medical (platinum PPO), dental, and vision — 100% covered for employees; subsidized dependents
• In-person, fast-paced environment with a technical, ambitious, mission-driven team