Founding Sales Development Representative

Insightful.io, Inc

$100K *
Enterprise Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • Strong English verbal and written communication skills
  • Minimum Bachelor’s Degree or equivalent experience
  • 2+ years in an outbound SDR/BDR or sales development role at a B2B SaaS company
  • Proven track record of achieving pipeline and activity targets
  • Strong phone presence and resilience for high-volume calling
  • Ability to personalize outreach at scale
  • Comfort with AI tools and curiosity about their impact on sales roles
  • Self-directed and execution-oriented with a focus on outcomes

Responsibilities

  • Build territory-based pipeline by converting AI signals into qualified meetings
  • Execute multi-channel outreach through phone, email, and LinkedIn
  • Quickly qualify leads by assessing fit and uncovering goals
  • Utilize AI-driven tools for efficient research and list-building
  • Engage with executives across various functions to build credibility
  • Shape the sales playbook by providing feedback on successful strategies

Benefits

  • Real career path with advancement opportunities from SDR to senior status
  • Work with cutting-edge AI technology to enhance sales processes
  • Opportunity to shape the outbound sales strategy as a founding team member
  • Engage in a collaborative environment dedicated to pipeline building
  • High autonomy in role, promoting personal execution and accountability
Full Job Description
Job Description

We're hiring an Outbound Sales Development Representative to build and own qualified pipeline for our mid-market and enterprise sales team out of our New York office. This is not a traditional, spray-and-pray SDR seat.

You'll work inside an AI-powered outbound system that surfaces high-intent, in-ICP signal -and your job is to turn that signal into qualified meetings and real pipeline. You'll operate at the intersection of human judgment and AI leverage: owning conversations, not just activity. As one of the first SDRs in New York, your messaging, sequences, and field insight will directly shape the outbound playbook we scale from.

Responsibilities:
  • Build territory-based pipeline: Convert AI-surfaced buying signals into qualified meetings for Account Executives to keep a high-quality flow of new opportunities
  • Run multi-channel outreach: Execute personalized sequences across phone, email, and LinkedIn against high-signal mid-market and enterprise accounts
  • Qualify with judgment: Quickly assess fit, uncover goals and buying triggers, and secure discovery meetings with the right decision-makers
  • Use a cutting-edge AI tech stack: Lean on AI-driven tooling for research, list-building, and messaging support so your time is invested in pipeline building work
  • Engage across key personas: Build credibility with leading operations, finance, strategy, HR and IT executives
  • Shape the sales playbook: As a founding rep in the SDR team, feed signal about success back into marketing to drive efficient messaging and targeting

You are a great fit for this role if you have:
  • Excellent English verbal and written communication skills
  • A minimum Bachelor's Degree or equivalent work experience
  • 2+ years of experience in an outbound SDR/BDR or sales development role at a B2B SaaS company
  • A proven track record of meeting or exceeding pipeline and activity targets through cold calls, email, and multi-channel outreach
  • Strong phone presence and the resilience to maintain high energy through a high-volume calling day
  • The ability to personalize outreach at scale without sounding like a template
  • Comfort working alongside AI tools to move faster, and curiosity about how AI is changing the SDR motion
  • A self-directed, execution-oriented mindset - you thrive with autonomy and own outcomes, not just activity
  • A background in SaaS, workforce analytics, or another technical/data product (a plus)
  • Experience with mid-market or enterprise outbound motions and longer, multi-stakeholder cycles (strongly preferred)

Core Skills:
  • Strategic thinking and tactical execution oriented
  • Data storytelling & insight generation
  • Project management in fast-paced environments
  • Continuous-improvement mentality

Compensation:
  • OTE: $100,000 made up of a competitive base plus uncapped variable comp. Base/variable split confirmed in the first conversation
  • A real career path: this is a build-the-engine role with a clear path into senior status on the sales team, first as senior SDR and then in an AE role

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