15Five is the AI-powered performance management platform built for business impact. 15Five’s AI-powered all-in-one people management system is easy to use, delivers effortless insights, and enables managers to lead with impact so that companies and their people can thrive. Within the flow of work, HR leaders are empowered with data-driven insights and recommendations while managers are transformed into change-makers, accelerating engagement, performance, and retention. 15Five combines generative AI, custom analytics, and human-centered principles within a complete platform, including 360° performance reviews, engagement surveys, goal tracking, manager coaching and training, and ongoing feedback tools like guided 1-on-1s and check-ins.

A career at 15Five is the chance to have high impact in a fast paced, remote startup environment that operates with focus, urgency, and accountability. Every role and every hire meaningfully impacts our trajectory.

We’re a high-performance, high-purpose team that gives you the chance to Build the Future of Work. We run on High Standards and High Support—holding a high bar for results, ownership, clarity, and disciplined execution, while investing in manager enablement, skill development, and whole-person care. We are committed to a No B.S. environment, meaning we anchor ourselves in truth, course-correct in real time, and expect people to lean into direct conversations. We are focused on ensuring every 15Fiver can Work in the Future and that starts with proactively using AI across all aspects of your role to increase leverage, speed, and impact.

If you're energized by a fast pace, high standards, and high accountability for yourself and others, you'll thrive here and we encourage you to apply.

Key Responsibilities

Strategic Co-Piloting & Deal Strategy (High Focus)
- 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.
Technical Execution & Integration Building (High Focus)
- 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.
Content Creation & Market Intelligence (Medium Focus)
- 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.

Desired Qualifications & Attributes

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.

Tools You'll Use

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