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Remote, Oregon, United States
Remote only
In this role, you will serve as the Technical Closer and Strategic Co-Pilot for 15Five’s revenue team, covering both Mid-Market and Enterprise segments. You are not a "demo jockey"; you are a revenue partner and a solution builder. Working alongside Account Executives (AEs), you will secure the "Tech Win" by validating complex requirements, navigating global HRIS integrations, and translating high-level HR philosophy into technical reality for organizations ranging from mid-sized disruptors to large-scale enterprises.
We are looking for an ambitious, high-grit professional who has a passion for building—whether that’s mapping out a complex API integration or shaping the "vibe" and functionality of a new product feature.
Reports to: VP, Revenue and Emerging AI
Proactive Partnership: Embed yourself in the sales cycle as a revenue partner. Adapt to various sales styles and actively elevate deal strategy on every call, from quick-moving mid-market deals to long-cycle enterprise evaluations.
Prep Authority: Hold AEs accountable for deep discovery. You have the authority to "push back on prep" to ensure every demonstration is strategically aligned with the prospect's pain points.
The "Cleanup" & Reality Checks: Skillfully manage expectations if a prospect has been over-promised. Diplomatically navigate workarounds that solve the core pain point without stalling the deal.
Closing: Recognize buying signals and execute the "Technical Close" by confidently removing any lingering technical friction.
Segment-Specific Demonstrations: Conduct high-stakes demos tailored to the audience—from agile Mid-Market teams to complex Enterprise committees. Showcase edge cases, bespoke workflows, and "art of the possible" configurations that address global scale.
Integration Architecture & Construction: Serve as the authority on the HRIS ecosystem (Workday, UKG, ADP, etc.). You don't just talk about data flows; you enjoy building and scoping API/SFTP integrations live to remove technical friction for IT stakeholders.
Product Prototyping: Act as a "builder" within the sales process. Configure bespoke Proof of Concepts (POCs) and environments that reflect the specific culture and "vibe" of a prospect’s organization, regardless of size.
Security & Compliance: Confidently navigate security questionnaires (GDPR, SOC2, PII) and enterprise-grade procurement processes without needing constant support from InfoSec.
Sales Enablement: Create "micro-demos" (Loom/Vidyard) and annotated assets to arm internal champions with the tools to sell 15Five when you aren’t in the room.
Voice of the Market: Act as a bridge between Sales and Product. Influence the roadmap by documenting product gaps, integration blockers, and "vibe" shifts in the market to ensure our product stays ahead of the curve.
The "Builder" Mindset: A genuine desire or experience in building products or API integrations. You enjoy the "how it works" as much as the "how it sells."
Integration Fluency: Demonstrated ability to work with APIs, SFTP, SSO, and data migration. You should be comfortable using tools like Postman to validate workflows.
Sales Grit & Ambition: We value "hunger" over years of experience. You should view yourself as part of a sales engine, understanding deal velocity and urgency across different market segments.
HR Domain Empathy: Ability to speak the language of HR buyers (calibration, competency matrices, flight risk) and translate it for IT buyers.
Adaptability: Comfortable in a fast-paced environment where you may need to "call an audible" during a live demo or build a custom environment late in the day to keep a deal moving.
Technical/Building: Postman (API testing), HRIS Ecosystem (Workday, ADP, UKG, etc.), Demo Automation Tools (Postman)
Communication: Slack, Loom, Vidyard.
Sales/CRM: Salesforce, Gong
AI: Claude, ChatGPT, Cursor, etc
