15Five

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

15Five • $147K — $165K *
US-AnywhereRemote in United States
Enterprise Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 5-7 years of experience in a technical sales or solutions consulting role
  • Strong understanding of HRIS systems and API integrations
  • Proven ability to manage complex sales cycles and technical requirements
  • Experience in creating tailored product demonstrations for diverse audiences
  • Excellent communication skills with a focus on translating technical concepts for non-technical stakeholders
  • Demonstrated adaptability in fast-paced environments
  • Passion for building and problem-solving in a sales context

Responsibilities

  • Embed in the sales cycle as a proactive revenue partner
  • Hold Account Executives accountable for thorough discovery
  • Manage expectations and navigate workarounds diplomatically
  • Recognize buying signals and execute technical closes
  • Conduct high-stakes, tailored demonstrations for various audience types
  • Build and scope API/SFTP integrations live during sales processes
  • Create sales enablement content to support internal champions

Benefits

  • Medical, dental, and vision coverage with cost subsidies
  • Employer-paid short-term and long-term disability
  • Flexible time off program and generous parental leave
  • 401K with 4% matching after 6 months
  • Access to mental health and wellness resources
  • Remote work flexibility
  • Sabbatical program for long-term employees
Full Job Description
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

Key Responsibilities

1. 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.
2. 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.
3. 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


$147,000 - $165,000 a year

Annual On-Target Earning Pay Range, US Full-Time - Solutions Consultant.

Annual OTE consists of base pay and variable components. This role's Total Rewards package includes participation in equity awards and comprehensive benefit and wellbeing offerings.

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!

About 15Five

Industry
Founded
2011

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