Sr. Technical Solutions Consultant (Mid-Market & Enterprise)

15Five

12d•$147,000 - $165,000•Remote

About The Position

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. 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

Requirements

The "Builder" Mindset: A genuine desire or experience in building products or API integrations.
Integration Fluency: Demonstrated ability to work with APIs, SFTP, SSO, and data migration.
Comfortable using tools like Postman to validate workflows.
Sales Grit & Ambition: "Hunger" over years of experience.
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 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.

Nice To Haves

Enjoy the "how it works" as much as the "how it sells."
Experience with AI tools like Claude, ChatGPT, Cursor, etc.

Responsibilities

Serve as the Technical Closer and Strategic Co-Pilot for 15Five’s revenue team, covering both Mid-Market and Enterprise segments.
Secure the "Tech Win" by validating complex requirements, navigating global HRIS integrations, and translating high-level HR philosophy into technical reality.
Embed yourself in the sales cycle as a revenue partner, adapting to various sales styles and elevating deal strategy.
Hold AEs accountable for deep discovery and ensure demonstrations are strategically aligned with prospect pain points.
Manage expectations and diplomatically navigate workarounds to solve core pain points without stalling the deal.
Recognize buying signals and execute the "Technical Close" by confidently removing any lingering technical friction.
Conduct high-stakes demos tailored to the audience, showcasing edge cases, bespoke workflows, and "art of the possible" configurations.
Serve as the authority on the HRIS ecosystem (Workday, UKG, ADP, etc.) and build/scope API/SFTP integrations live.
Configure bespoke Proof of Concepts (POCs) and environments that reflect the specific culture and "vibe" of a prospect’s organization.
Confidently navigate security questionnaires (GDPR, SOC2, PII) and enterprise-grade procurement processes.
Create "micro-demos" (Loom/Vidyard) and annotated assets to arm internal champions.
Act as a bridge between Sales and Product, documenting product gaps, integration blockers, and "vibe" shifts in the market to influence the roadmap.