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
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. We offer amazing benefits that align with our values and culture at 15Five. Your Health & Wellbeing Medical, dental, vision with 15Five cost subsidy Employer paid Short-Term, Long-Term Disability, and Term LifeFamily planning support with enhanced medical plans and consultation programs Inclusive Benefits Stipend Access to mental health and wellness resources Your Life Flexible Time Off Program Generous paid leave for new parents Military leave Paid Company Holidays Sabbatical Program Your Future 401K with 4% Matching after 6 months Your Work Life Remote work Work with experts in leadership, culture, and personal development For more information see: Our Mission, Vision, & Values -https://www.15five.com/about Our People and Culture -https://www.15five.com/about/careers Our Personal & Professional Development Resources -https://www.15five.com/resources/content-library Reading over the role description and feeling like you don’t check every box? That’s okay; if you think you have what it takes but don’t necessarily meet all the criteria, please apply—you could be exactly who we are looking for! 15Five follows equitable hiring practices. Our compensation programs are designed to attract, motivate, and retain talented employees who are highly engaged, high performing, and have an exceptional impact on the business and our customers. The salary range displayed on each job posting reflects the target for new hire salaries for the role across all US locations. Within the range, individual pay is determined by budget allocated for the role and additional factors, including job-related competencies and skills, experience, and relevant education or training. Please note that the compensation details listed in US job postings do not reflect added total compensation including equity or benefits. In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification document form upon hire.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
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