{"id":350445,"url":"https://alion.io/job/whippy-account-executive","title":"Account Executive","company":{"id":7340,"name":"Whippy","domain":"whippy.ai","url":"https://alion.io/company/whippy","size_band":"51-200","is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Ashby","truth_index":{"grade":"A","score":91,"open_postings":8,"ghost_share":0,"stale_share":0.375,"repost_share":0,"time_to_fill_p50_days":null,"computed_at":"2026-10-30T05:48:23Z"}},"role":"Sales","role_family":"Sales","seniority":null,"employment_type":"full_time","work_mode":"remote","remote_scope":"stated_countries","remote_scope_basis":"posting_text","remote_working_hours":{"label":"ET","utc_offset_min":-5,"utc_offset_max":-5},"hiring_geo_confidence":"structured","locations":[],"countries":[],"hiring_countries":["US"],"hiring_countries_total":1,"salary":{"min":null,"max":300000,"currency":"USD","period":"year","gross":null,"usd_annual":300000},"salary_estimate":null,"experience_years_min":null,"visa_sponsorship":false,"relocation_package":false,"has_equity":false,"technologies":[{"name":"Voice Agents","optional":false}],"status":"live","first_seen_at":"2026-08-15T15:23:58Z","employer_posted_date":"2026-08-15","last_verified_at":"2026-10-31T02:00:33Z","board_verified":true,"closed_at":null,"days_open":76,"trust":{"level":"ok","repost_count":0,"flags":[],"days_open":74},"description":"Account Executive at Whippy\nRemote (East Coast mornings)\n180-200K OTE (50/50 split), uncapped above quota.\nTop performers will earn $300K+. We pay for production, not tenure.\nOver the last 90 days, our founder led sales motion booked nearly $1M in ARR across new customers and expansion.\nThe opportunity is proven. The sales organization is not finished.\nWe are looking for an exceptional Account Executive who can build their own pipeline, think strategically about their territory and deals, and help us shape the sales organization that comes next. This is not a role where a sales manager tells you what to do every morning. When you see an open lane, we expect you to run with it.\nWhy Whippy\nWhippy is the AI native platform for business communication: AI Voice Agents, AI Recruiting, messaging, VoIP, deep integrations, and our own workflow engine in one system. Our customers do not buy software that helps their employees do the work. They buy AI that does the work.\nOur deepest market today is staffing and HR, where we are the category leader, and new verticals are already opening behind it. We serve more than 1,000 customers, with an engineering team larger than the rest of the company combined. Customers like Your Employment Solutions and Staffworks have each generated more than $1M in measurable value using Whippy, and those are named, public case studies you get to sell with.\nIt is common to land a $50K ARR customer and expand that relationship by another $100K or more over time.\nHow we work\nBootstrapped and profitable, so revenue is the strategy, and your commission comes from customers, not a burn rate.\nLeadership stays close to the pipeline. Our CEO still cold calls, so you'll never be selling in a vacuum.\nAI first in how we sell, not just what we sell. We expect you to use AI to move faster in prospecting, prep, and follow up.\nSpeed over polish. Results over activity.\nThe job\nYou own the entire cycle: sourcing, discovery, demo, business case, negotiation, close, and the expansion inside the account after. You build pipeline through outbound, referrals, partners, conferences, and your own relationships.\nYou work directly with our CEO on deals, territory strategy, and how we scale the sales organization. You work directly with engineering, because customer feedback here does not disappear into a ticketing system. It shapes what gets built next.\nThere are no SDRs filling your calendar, no manager checking your activities, and no rigid playbook. You inherit a product customers want, active pipeline, and proof the motion works. Some people read that as risk. You should read it as freedom.\nRemote role. Our customers run on East Coast time, so your mornings do too. If you can own the 8am ET calling block, we do not care what time zone you sleep in.\n\nWe expect you to operate independently\nYou will have clear revenue expectations, deal qualification criteria, and regular pipeline and deal reviews with the CEO. Within that structure, we expect you to decide where your time is best spent, know which deals are real and which are wasting your time, and pressure test your own pipeline. Ask for help before a deal needs rescuing, and come with a point of view rather than waiting for instructions. If something in our sales process is broken, notice it and help us make it better.\nWhat success looks like\nFirst 30 days: you show us a target list we did not give you.\n\nFirst 90 days: you are running complete cycles independently and closing your first deals.\n\nYear one at plan: $1M+ in new ARR closed. Beat plan, and $300K+ is real math, not a recruiting line.\n\nPerform, and you help pick the next AE and shape the team that follows.\n\nWho succeeds here\nYou have personally closed meaningful B2B software revenue and can explain exactly how you created and won those deals. Your buyer has been the owner, executive, or operator who signs the check and only responds to measurable ROI. You get prospects to calculate their own ROI out loud, you book the next meeting before ending the current one, and you would rather pick up the phone or get on a plane than send a fourth follow up email.\nIf you have sold into staffing or HR technology, that is valuable, because you may already know many of our buyers. It is not a requirement. What matters is that you know how to sell to skeptical, fast moving operators.\nThis is not for you if\nYou want leads handed to you or a manager telling you what to prioritize.\n\nYou need every process documented before taking action.\n\nYou want to sell one simple product the same way every day.\n\nYou cannot consistently work East Coast mornings.\n\nWhy join now\nYou are not joining a company trying to figure out whether customers will buy. They already are. You are also not joining a mature sales organization where every decision has been made. 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