Operations Associate
Whippy
Operations Associate
Whippy
AI-powered multi-channel communication platform with automation
Operations Associate (LATAM Remote, Buenos Aires Hybrid Preferred)
Full time | US Eastern hours | $2,000 to $3,000 USD per month total comp, paid monthly
Hi, I'm David, CEO and co-founder of Whippy. I'm hiring an Operations Associate to work directly with me and take over the layer of work that is keeping me from doing the things only a CEO can do.
Why I'm hiring
Whippy is a fast growing bootstrapped, profitable, and the category leader in AI communication for staffing, with over 1,000 customers and new industries opening behind it. We are hiring across sales, marketing, operations, and customer success right now, and the person finding and messaging every one of those candidates is me.
We recruit through my LinkedIn on purpose. A founder's message gets replies at many times the rate of a recruiter's. But running searches, writing outreach, following up, and scheduling interviews is close to twenty hours a week, and that is twenty hours I should be spending with enterprise customers and partners. The same is true of the billing follow ups, account changes, and admin that land in my inbox every evening.
Your job is to take all of that off my plate, run it better than I do, and document it so well that someone else can run it after you. Then you move up to the next thing. I am hiring a Head of Operations in parallel, and you will be the first person on their team. If you are good, you will learn more about how a real business works in a year here than in three years anywhere else, because you will be inside the decisions, not reading about them.
Some things you'll do
The first 90 days are mostly recruiting:
• Build candidate lists in Sales Navigator and Juicebox against the ICPs I give you for each open role
• Message candidates from my LinkedIn account using templates written in my voice, and get good enough at it that I stop editing them
• Handle replies, route interested candidates to a screening call or a Loom, and flag anything you cannot answer
• Keep Ashby current, schedule interviews and reference calls, and chase interviewers for feedback
• Send me a weekly funnel: sent, accepted, replied, screened, hired
By day 90 you add the operations layer:
• Monitor Stripe for failed payments and overdue invoices, chase them to resolution, reconcile checks
• Process upgrades, downgrades, and churn across Stripe, HubSpot, and our internal tools off a checklist you help write
• Keep HubSpot records clean so what a customer signed, uses, and pays always match
• Handle Deel onboarding and offboarding steps, travel and dinner bookings, and the vendor list
Once that runs without reminders, you grow into partner administration, process documentation, and whatever the Head of Operations and I need figured out next. I will not pretend that is the day one job. It is earned by making the operational work disappear. But it is real, and the people who do this well become the operations team.
How we work
Bootstrapped and profitable, so revenue is the strategy. Our customers are East Coast, so we start early. No task is above or beneath anyone here, including me, and I still cold call. We use AI to move fast, but we own our work and verify every fact. Speed over polish. Results over activity. You will always know where you stand with me.
What I'm looking for
• Writing above all. You will be writing as me to VPs at American companies. It has to sound like a sharp person, not a template. This is the number one predictor of success in the role
• Organized to a fault. Nothing you own gets asked about twice
• Comfortable with a daily number. Outreach is a volume game run with care, and you like seeing the funnel move
• Curious, coachable, and low ego. You want feedback and you get better quickly
• Already using AI tools to work faster, and eager to automate your own work
• Judgment. Half this job is defined tasks. The other half is noticing what needs doing before anyone assigns it
• Ideally one to three years as an SDR, recruiting coordinator, or operations associate at a SaaS or tech company selling into the US. If your path is unconventional and you can explain why it makes you good at this, apply anyway
• Fluent written and spoken English, and able to work US Eastern hours
Experience with Stripe, HubSpot, or Ashby is a plus, not a requirement. I can teach tools. I cannot teach ownership.
You'll thrive here if...
• You get energy from a clean inbox and a moving funnel
• You would rather own a small thing completely than touch a big thing lightly
• You want to see how a company actually runs from the inside, and you are willing to do the unglamorous work to get that seat
• You are excited by a job that changes every month
This is not for you if
• You think outreach and billing are beneath you. They are week one, and they are how you earn everything after
• You need detailed instructions for every task
• You are looking for a job description that stays the same
About Whippy
Whippy is a communication, automation, and AI agent platform. You reach customers across calls, texts, and email at scale, with every conversation in one shared inbox. Replies get assigned to a teammate, handled by an AI agent, or carried forward by an automation, and the data flows back into your systems in the format you need. It cuts the repetitive work and frees teams for the human work that drives revenue.
We're industry agnostic, with our biggest wins in staffing, healthcare, and other in person businesses going through digital transformation. We're bootstrapped, profitable, and growing fast, with over 1,000 businesses using Whippy worldwide.
Whippy was founded in 2021 by me and our CTO, Jack Kennedy. Jack is an engineering machine and a marathon runner. I started BloomNation in 2011 after winning $27,205 in a poker tournament, grew it into a platform generating billions in sales for florists, then left to build something bigger with Jack.
Location
Remote across Latin America. Candidates in Buenos Aires who can work hybrid from our WeWork office in Vicente Lopez are strongly preferred, as we are building an in person team there. US Eastern hours required. Full English fluency required.
Compensation
$2,000 to $3,000 USD per month total ( base plus monthly performance bonus) depending on experience and location, with a WeWork membership included for Buenos Aires hires.
Hiring process
You apply and I review it myself
A 30 minute call with me
A short take home: two outreach messages to sample candidate profiles written in my voice, and one billing scenario. You present it to me on a 30 minute call
A 30 minute call with another key Whippy member
Offer made
Whippy is a platform that uses artificial intelligence to handle business communications across phone, chat, and messaging channels. It offers AI Voice & Chat, Messaging, Business Phones, and Workflow Automations to automatically respond to inquiries, screen job applicants, nurture leads, collect reviews, and help generate revenue. How it works: It combines an all-in-one messaging suite with automation. Teams set up rules and AI handles routine tasks, routes conversations, answers common questions, and performs tasks without people having to do them every time. How it’s different from competitors: Unlike systems that require many separate tools, Whippy provides multiple functions in one system, reducing tool switching and setup. It focuses on automating across all channels to help teams work faster and more consistently. Goal: The aim is to help teams engage customers at scale by automating conversations and workflows, improve efficiency, and grow revenue.
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