Senior Enterprise Sales Development Representative - Scout AI

The Skills You'll Have:

Outbound Prospecting Excellence

Complex SaaS Experience: 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: Demonstrated 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 following 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 the opportunities you surface are anchored in genuine business value and clear pain points.

Consultative and Commercial

Strategic Researcher: 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: Able to position AI-driven automation commercially — partnering with marketing and AEs to articulate what it is worth to a business's operational outcomes, not just what it does.

Entrepreneurial Mindset — Non-Negotiable

Comfortable with Ambiguity: There is no established playbook for this motion. You must be eager to help write it.

Territory Ownership: Runs the prospecting territory like its owner. Takes full accountability for goals, activity metrics, and data-driven adjustments without waiting to be directed.

Pace and Urgency: Moves with pace and urgency. The market window is open now. Speed matters.

Resilient & Collaborative by Instinct

High Stamina: Exceptionally resilient, with the mental stamina to maintain momentum, positivity, and continuous performance through high-rejection outreach environments.

Team Multiplying Effect: Collaborative by instinct, thriving in a small founding team environment (your AE, marketing, and leadership) to make the team more than the sum of its parts.

Within 90 Days, You'll:

Certified: Sitetracker and Scout certified — with a working command of how Scout is positioned, where it wins, and how it differs from generic AI tools in an enterprise evaluation.

Strategized: Target account list defined, prioritized, and documented within the agreed ICP for this motion alongside your AE.

Ramped: Initial outbound pipeline established and first discovery conversations underway using a structured, repeatable prospecting rhythm.

Accountable: Demonstrate absolute accountability through clean Salesforce tracking and meticulous activity logging.

Within 180 Days, You'll:

Uncapped Pipeline: Active pipeline consistently meeting and exceeding goals through creative outbound strategies and focused execution.

Trusted Partner: Established yourself as a trusted, strategic partner to your AE and the regional Scout sales team.

Playbook Iteration: Feed continuous insights into the feedback loop regarding market barriers, objection handling, and messaging refinement based on real market evidence.

Within 365 Days, You'll:

Bar-Raising Performance: Become a bar-raising performer, consistently hitting top-quartile pipeline generation performance for the Scout platform.

Playbook Contribution: Material contribution to the formalized Scout GTM playbook — including ICP refinement, sequence optimization, and prospecting strategy that informs how the motion scales beyond the founding team.