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Whippy

Account Executive

Whippy

Account Executive selling Whippy’s AI-native business communication platform to B2B customers. Owning full-cycle sales, pipeline generation, strategic deals, and account expansion remotely.

Posted 8/15/2026full-timeRemote • 🇺🇸 United StatesMid-LevelSeniorWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in managing the entire sales cycle, from sourcing to closing, with a focus on building and managing a robust pipeline. Proven ability to engage with executives and deliver measurable ROI through strategic territory management and effective communication.

Highest-signal resume keywords
B2B Software SalesPipeline ManagementTerritory Strategy DevelopmentAccount ExpansionSales Process Improvement

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Sales Cycle ManagementNegotiationBusiness Case DevelopmentROI CalculationDeal Closing
Soft Skills
Self-ManagementIndependent PrioritizationProactive CommunicationRelationship Building
Industry Keywords
Staffing Technology SalesHR Technology SalesOutbound ProspectingCustomer Feedback CommunicationSales Team Development

About the role

Key responsibilities & impact
  • Own the entire sales cycle: sourcing, discovery, demo, business case, negotiation, close, and account expansion
  • Build pipeline through outbound prospecting, referrals, partners, conferences, and personal relationships
  • Develop and manage territory strategy and independently prioritize sales activities
  • Work directly with the CEO on deals and scaling the sales organization
  • Collabor with engineering and communicate customer feedback to influence product development
  • Pressure-test pipeline quality and identify which deals are viable
  • Ask for help proactively when deals need support
  • Identify and help fix broken sales processes
  • Run complete sales cycles independently and close initial deals
  • Close $1M+ in new ARR at plan during the first year
  • Help select future Account Executives and shape the developing sales team

Requirements

What you’ll need
  • Personally closed meaningful B2B software revenue
  • Ability to explain exactly how you created and won deals
  • Experience selling to owners, executives, or operators who require measurable ROI
  • Ability to get prospects to calculate their own ROI
  • Ability to book the next meeting before ending the current one
  • Willingness to use phone calls or in-person meetings rather than repeated follow-up emails
  • Ability to build and manage your own pipeline
  • Ability to think strategically about territory and deals
  • Strong self-management and independent prioritization skills
  • Ability to consistently work East Coast mornings and the 8am ET calling block
  • Staffing or HR technology sales experience is valuable but not required

Benefits

Comp & perks
  • Uncapped commission
  • Top performers can earn $300K+
  • Opportunity to work directly with the CEO on deals, territory strategy, and sales organization development
  • Direct collaboration with engineering, with customer feedback shaping product development
  • Remote work arrangement
  • Freedom to manage your own territory, pipeline, and schedule