Operations Associate (LATAM)

Responsibilities

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