Overview
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 Qualifications
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
#J-18808-Ljbffr
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 Qualifications
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
#J-18808-Ljbffr