Senior Technical Solutions Consultant – Mid-Market, Enterprise

15Five

. Serve as the Technical Closer and Strategic Co-Pilot for 15Five’s revenue team across Mid-Market and Enterprise segments .

Posted 10/2/2026full-timeRemote • United StatesSenior💰 $147,000 - $165,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in API integrations, HRIS ecosystems, and enterprise procurement processes while effectively communicating with both HR and IT stakeholders. Capable of managing high-stakes demonstrations and providing strategic insights to influence product development.

Highest-signal resume keywords

API IntegrationHRIS Ecosystem ExperienceSalesforce ProficiencySecurity Questionnaire FamiliarityDeal Strategy Development

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

API DevelopmentSFTPSSOData MigrationDemonstration DesignProof of Concept ConfigurationMarket Intelligence AnalysisProduct Roadmap InfluenceDeal Velocity UnderstandingBespoke Workflow Design

Soft Skills

AdaptabilityCommunicationCollaborationStrategic ThinkingProblem Solving

Tools & Technologies

PostmanSalesforceGongSlackLoomVidyardClaudeChatGPTCursorWorkday

Industry Keywords

Mid-MarketEnterpriseHR BuyersIT BuyersGDPRSOC2PIIEnterprise ProcurementSecurity StandardsHRIS

About the role

Key responsibilities & impact

Serve as the Technical Closer and Strategic Co-Pilot for 15Five’s revenue team across Mid-Market and Enterprise segments
Partner with Account Executives throughout sales cycles and elevate deal strategy
Ensure demonstrations are aligned with prospect pain points and challenge inadequate preparation
Manage expectations, navigate workarounds, and remove technical friction to close deals
Conduct high-stakes, segment-specific demonstrations featuring edge cases, bespoke workflows, and global-scale configurations
Design, scope, and build API/SFTP integrations across HRIS ecosystems
Configure bespoke Proofs of Concept and prospect environments
Navigate security questionnaires and enterprise procurement processes
Create micro-demos and annotated sales-enablement assets
Provide market intelligence to Product and influence the roadmap through product-gap and integration-blocker documentation

Requirements

What you’ll need

Desire or experience in building products or API integrations
Demonstrated ability to work with APIs, SFTP, SSO, and data migration
Comfortable using tools like Postman to validate workflows
Understanding of deal velocity and urgency across Mid-Market and Enterprise segments
Ability to speak the language of HR buyers and translate it for IT buyers
Comfortable working in a fast-paced environment and adapting during live demos
Experience or fluency with Workday, ADP, UKG, or similar HRIS ecosystems
Familiarity with security questionnaires and enterprise-grade procurement processes, including GDPR, SOC2, and PII
Experience with Salesforce, Gong, Slack, Loom, Vidyard, Claude, ChatGPT, and Cursor

Benefits

Comp & perks

Medical, dental, and vision insurance with 15Five cost subsidy
Employer-paid short-term disability, long-term disability, and term life insurance
Family planning support with enhanced medical plans and consultation programs
Inclusive Benefits Stipend
Mental health and wellness resources
Flexible Time Off Program
Generous paid leave for new parents
Military leave
Paid Company Holidays
Sabbatical Program
401(k) with 4% matching after 6 months
Remote work
Work with experts in leadership, culture, and personal development
Equity awards
Comprehensive benefit and wellbeing offerings