Account Executive
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Job Description
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.
Responsibilities:
- 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:
- 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:
- 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
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