Senior Enterprise Sales Development Representative - Scout AI

About the Role

This is a founding role in a new, dedicated Scout sales motion. As a Senior Sales Development Representative, you will be the engine driving outbound pipeline creation during a high-impact period of regional expansion. Scout is Sitetracker's enterprise AI agent platform—it does the work, not just reports on it, and stays grounded in the customer's own operational data, making it credible in enterprise procurement in a way bolted-on AI tools are not.

Your job is to partner with our Scout Account Executive to find organizations that need what Scout does—before they know Sitetracker—and build the initial relationships that bring them in. The initial target is the installed base of field service management and workforce management platforms (ServiceMax, MaintainX, Procore, and adjacent solutions) where vendors lack a credible AI roadmap and customers are actively seeking one. This is a land-grab moment, and you will fuel the pipeline to capitalize on it.

This role operates independently from the core Sitetracker GTM motion by design. You will work alongside a dedicated Scout AE from day one, supported by sales leadership, marketing, and existing SE resources as the motion gains momentum.

Responsibilities

• Collaborate directly with sales leadership and your AE to define and execute the outbound go-to-market and account-based strategy for your territory from scratch—no inherited pipeline, playbook, or blueprint.
• Build the Blueprint: Construct the outreach approach from the ground up, test critical messaging hypotheses, and shape the Scout sales development motion as it scales.
• Drive High-Value Pipeline: Generate high-quality leads through thoughtful, targeted, and persona-driven outreach across phone, email, and social touchpoints.
• Position the Entry Point: Identify and qualify new Scout business in adjacent markets, surfacing opportunities anchored to real business value and positioning Scout as the strategic entry point into the broader Sitetracker platform.
• Maintain a direct, collaborative relationship with your AE and sales leadership, proactively sharing feedback on messaging effectiveness, objections, and necessary pivots in a dynamic, two-way partnership.

Requirements

• Outbound Prospecting Excellence: Proven track record generating high-quality outbound pipeline for complex SaaS solutions, ideally in field service management, workforce management, or adjacent operational software markets.
• Enterprise Navigation: Ability to map enterprise accounts, navigate multi-stakeholder structures, and execute tailored strategies for Tier 1 accounts while scaling outreach for Tier 2/3 accounts.
• Operational Discipline: Highly disciplined approach to building and maintaining a consistent daily rhythm, utilizing time-blocking and meticulous CRM (Salesforce) hygiene to drive pipeline.
• Framework Familiarity: Familiarity with MEDDPICC (or equivalent frameworks) to ensure opportunities are anchored in genuine business value and clear pain points.
• Consultative and Commercial Research: Researches effectively to understand how a target company makes money, where Scout's value proposition intersects with their operational challenges, and who the right stakeholders are.
• Value-Driven Messaging: Ability to position AI-driven automation commercially—articulating its impact on operational outcomes, not just its features.
• Entrepreneurial Mindset:
  • Comfortable with ambiguity; eager to help write the playbook for this motion.
  • Takes full ownership of the prospecting territory, accountable for goals, activity metrics, and data-driven adjustments.
  • Moves with pace and urgency—speed matters in this market window.
• Resilient & Collaborative by Instinct:
  • Exceptionally resilient, maintaining momentum and positivity in high-rejection outreach environments.
  • Collaborative by nature, thriving in a small founding team to amplify collective impact.

Milestones

• Within 90 Days:
  • Sitetracker and Scout certified, with a working command of Scout’s positioning, wins, and differentiation from generic AI tools.
  • Target account list defined, prioritized, and documented within the agreed ICP alongside your AE.
  • Initial outbound pipeline established; first discovery conversations underway using a structured, repeatable prospecting rhythm.
  • Absolute accountability demonstrated through clean Salesforce tracking and meticulous activity logging.
• Within 180 Days:
  • Active pipeline consistently meeting and exceeding goals through creative outbound strategies and focused execution.
  • Established as a trusted, strategic partner to your AE and the regional Scout sales team.
  • Continuous insights fed into the feedback loop regarding market barriers, objection handling, and messaging refinement based on real market evidence.
• Within 365 Days:
  • Bar-raising performer, consistently hitting top-quartile pipeline generation performance for the Scout platform.
  • Material contribution to the formalized Scout GTM playbook, including ICP refinement, sequence optimization, and prospecting strategy that informs scaling beyond the founding team.

Pay

$90K OTE (uncapped commissions) + stock options.