Account Executive

Remote role focused on East Coast mornings (8am ET calling block). Uncapped commission; top performers earn $300K+ annually. Pay is based on production, not tenure. Over the last 90 days, the founder-led sales motion booked nearly $1M in ARR across new customers and expansion.

About Whippy

Whippy is the AI-native platform for business communication, combining AI Voice Agents, AI Recruiting, messaging, VoIP, deep integrations, and a proprietary workflow engine. Customers buy AI that performs the work, not software that assists employees. The platform serves over 1,000 customers, with a strong presence in staffing and HR—where it is the category leader—and expanding into new verticals. Engineering comprises the largest team. Customers like Your Employment Solutions and Staffworks have generated over $1M in measurable value each, supported by public case studies.

Responsibilities

• Own the entire sales cycle: sourcing, discovery, demo, business case, negotiation, close, and post-sale expansion within the account.
• Build pipeline through outbound efforts, referrals, partnerships, conferences, and personal relationships.
• Collaborate directly with the CEO on deals, territory strategy, and scaling the sales organization.
• Work directly with engineering to shape product development based on customer feedback.
• Manage your own time, pipeline, and deal prioritization without reliance on SDRs or managerial oversight.
• Identify and help fix inefficiencies in the sales process.

Expectations

• Demonstrate self-management by deciding where to focus your time and effort.
• Assess deal viability independently and pressure-test your own pipeline.
• Proactively ask for help before deals require rescuing.
• Bring a point of view to discussions with leadership rather than waiting for instructions.

Success Metrics

• First 30 days: Present a target list not provided by the company.
• First 90 days: Run complete sales cycles independently and close your first deals.
• Year one at plan: Close $1M+ in new ARR; top performers can earn $300K+ annually.
• High performers will help shape the team by participating in hiring the next AE.

Qualifications

• Proven track record of closing meaningful B2B software revenue, with a clear explanation of how you created and won deals.
• Experience selling to owners, executives, or operators who sign checks and demand measurable ROI.
• Ability to guide prospects to calculate their own ROI during conversations and secure next steps before ending meetings.
• Preference for proactive outreach (phone calls, in-person meetings) over excessive email follow-ups.
• Experience selling into staffing or HR technology is valuable but not required.

Who This Role Is Not For

• Those who prefer leads to be handed to them or require daily managerial direction.
• Individuals who need fully documented processes before taking action.
• Salespeople who want to sell a single, simple product the same way every day.
• Those unable to consistently work East Coast mornings.

Why Join Now

Whippy is a bootstrapped, profitable company where revenue drives strategy. You’ll join a proven sales motion with active pipeline and direct impact on shaping the organization’s future. The opportunity balances immediate earning potential with the freedom to influence how the sales team scales.