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.
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.