Sales Development Representative (Enterprise)

Insightful • New York, NY

2d • $65,000 - $80,000 • Hybrid

About The Position

Insightful is a Work Intelligence platform that uses organizations’ work data to show how teams work, identify opportunities to improve processes, and determine where to automate. The Sales Development Representative will open doors at enterprise organizations with 1,000 or more employees and book meetings that initiate Insightful’s largest deals. The role engages senior leaders in operations, finance, IT, and business leadership about Workforce Analytics, People Intelligence, and Process Intelligence.

The representative will partner with Strategic or Enterprise Account Executives on named accounts, building deep knowledge of the territory rather than relying on broad cold lists. The position reports to those Account Executives and works closely with Marketing on account-based campaigns. It is based in the New York, NY area, with two days per week in the office.

Requirements

• 1–4 years of experience in sales development, business development, or another quota-carrying outbound role; B2B SaaS experience is preferred.
• A track record of booking meetings against a target, supported by measurable results.
• Comfort initiating conversations with VP- and C-level leaders by phone and in writing.
• Clear, concise writing and the ability to tailor messages to a specific person and problem.
• Curiosity about how large organizations operate and discipline to research before outreach.
• Coachability, including seeking feedback, practicing, and improving quickly.

Nice To Haves

• Experience prospecting into enterprise accounts with 1,000 or more employees and engaging multiple members of buying committees.
• Familiarity with Salesforce, HubSpot, Outreach, Salesloft, and LinkedIn Sales Navigator.
• Practical fluency with AI for research and personalization.
• Interest in workforce analytics, operations, HR technology, or process improvement.
• A bachelor’s degree or equivalent experience.

Responsibilities

• Research target accounts, map buying committees, and identify entry points across operations, finance, IT, and business leadership.
• Conduct multi-threaded outbound outreach to several stakeholders per account by phone, email, LinkedIn, and events, tailoring messages to each person’s priorities.
• Start discovery conversations with VP- and C-level leaders and uncover relevant business problems before positioning the platform.
• Book qualified first meetings and hand them to Account Executives to develop into pipeline.
• Plan and run account-based plays with Account Executives and Marketing, follow up on event and campaign leads, and refine effective approaches.
• Use AI and sales tools to accelerate research and personalization, and review AI-generated output before sending it to prospects.
• Maintain accurate CRM records for contacts, accounts, and activity.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed