Senior Enterprise Sales Development Representative - Scout AI

Job Description

Job Description

The Opportunity

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 it stays grounded in the customer's own operational data. That makes it credible in an enterprise procurement review in a way that bolted-on AI tools are not.

Your job is to partner with our Scout Account Executive to find the organisations that need what Scout does — before they know Sitetracker — and build the initial relationships that bring them in. The initial target hypothesis is the installed base of field service management and workforce management platforms — ServiceMax, MaintainX, Procore, and adjacent solutions — where vendors have no credible AI roadmap and customers are actively looking for one.

This is a land-grab moment. You will be the person who fuels the pipeline to capitalise on it. This role operates independently from the core Sitetracker GTM motion — deliberately. That separation is structural, not cultural. You will work alongside a dedicated Scout AE from day one, fully supported by sales leadership, marketing, and existing SE resources as the motion builds momentum.

In this role, you will 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. Because this is a founding motion, there is no inherited pipeline, no established playbook, and no blueprint to follow—and that is entirely the point.

• Build the Blueprint: Construct the outreach approach from the ground up, test critical messaging hypotheses, and actively shape what the Scout sales development motion looks like as it scales.

• Drive High-Value Pipeline: Consistently 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.

Throughout this process, you will maintain a direct and collaborative relationship with your AE and sales leadership, proactively feeding back what messaging works, what objections arise, and what needs to pivot within a dynamic, two-way relationship where you are expected to have a view and share it openly.

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.

• 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.

• 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.

• 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.

• 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.

90K OTE (uncapped commissions) + stock options 

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.