Founding Sales Development Representative

Insightful; New York (NY); Hybrid; USD 60,000 - 140,000; Full time

Job summary

Insightful, a work intelligence platform, seeks an outbound SDR to build qualified pipeline for mid-market and enterprise sales from our New York office. You will operate at the intersection of human judgment and AI, turning AI signals into discovery meetings and real pipeline.

You’ll own messaging and sequences as an early NY SDR, shaping outbound playbooks, and driving efficient targeting with autonomy and accountability. This role offers growth into senior SDR and AE paths.

Qualifications

• Bachelor's degree or equivalent work experience.
• 2+ years in outbound SDR/BDR or sales development in a B2B SaaS company.
• Proven track record of meeting or exceeding pipeline targets through multi-channel outreach.
• Strong phone presence and high-energy during high-volume calling days.
• Ability to personalize outreach at scale without sounding like a template.
• Comfort working with AI tools to move faster in SDR motions.
• Self-directed, execution-oriented mindset with autonomy and ownership of outcomes.
• Experience with mid-market or enterprise outbound motions is highly preferred.

Responsibilities

• Build territory-based pipeline by converting AI-surfaced signals into qualified meetings.
• Execute multi-channel outreach across phone, email, and LinkedIn for target accounts.
• Qualify opportunities with judgment by uncovering goals and buying triggers.
• Leverage AI-driven tooling for research, list-building, and messaging support.
• Engage with key personas across operations, finance, strategy, HR and IT executives.
• Shape the sales playbook by feeding learnings back to marketing to improve messaging and targeting.

Skills

English communication

Outbound SDR/BDR experience

Pipeline & target attainment

Phone presence

Personalized outreach at scale

AI tools usage

Autonomy and self-direction

B2B SaaS/technical background

Education

Bachelor's Degree

Tools

AI tools

Job description

• New York, NY - Hybrid (Remote and In Person)

Job Description

Insightful is a work intelligence platform. We turn precision data analytics into actionable business indicators that drive bottom line results for companies from hyperscalers to the Fortune 500. Our platform is AI-native: we use AI to convert raw work data into the clear, forward-looking intelligence leaders need to rebalance capacity, protect margins, and scale with confidence, all with near-zero hallucination thanks to our activity tracking precision. We sell to modern mid-market and enterprise organizations, and we are building a go-to-market engine to match. This is a chance to join that engine at the ground floor.

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
• Project management in fast‑paced environments

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