Outbound Sales Development Representative

About Us

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.

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