Operations Associate (LATAM Remote, Buenos Aires Hybrid Preferred)

Why Whippy is Hiring:

Whippy is a fast-growing, bootstrapped, and profitable leader in AI communication for staffing, serving over 1,000 customers across industries. The CEO, David, is hiring an Operations Associate to handle tasks like recruiting outreach, billing follow-ups, and admin work—freeing him to focus on enterprise partnerships.

This role is designed to grow with you: after mastering recruiting and operations, you’ll transition into partner administration, process documentation, and leadership opportunities. The ideal candidate will thrive in a fast-paced, results-driven environment where ownership and autonomy are key.

Key Responsibilities:

The First 90 Days (Recruiting Focus):

• Build candidate lists in Sales Navigator and Juicebox targeting Ideal Customer Profiles (ICPs) provided by the CEO.
• Message candidates from the CEO’s LinkedIn account using customized templates written in his voice—aim to reduce edits over time.
• Handle replies, route interested candidates to screening calls or Loom recordings, and flag unresolved issues.
• Maintain Ashby up-to-date with interview scheduling, reference checks, and feedback tracking.
• Submit a weekly funnel report tracking outreach (sent, accepted, replied, screened, hired).

Beyond 90 Days (Operations Layer):

• Monitor Stripe for failed payments and overdue invoices, resolving issues and reconciling checks.
• Process upgrades, downgrades, and churn across Stripe, HubSpot, and internal tools using checklists you’ll help design.
• Ensure HubSpot records align with customer contracts, usage, and payments.
• Manage Deel onboarding/offboarding, travel bookings, dinners, and vendor lists.

Long-Term Growth:

As operations stabilize, you’ll expand into partner administration, process documentation, and collaborative problem-solving with the Head of Operations and CEO. Success here means making operational tasks disappear through efficiency and ownership.

How We Operate:

Whippy is bootstrapped and profitable, prioritizing revenue growth. Our team operates with:

• Early mornings (East Coast hours).
• No task hierarchy—everyone, including the CEO, handles outreach, billing, and admin.
• AI-driven speed but human verification of every detail.
• Culture of speed over polish and results over activity.
• Transparency: You’ll always know your standing with the CEO.

What We’re Looking For:

• Writing skills: Craft outreach messages in the CEO’s voice—sharp, human, and template-free. This is the #1 predictor of success.
• Organizational excellence: Own tasks without repetition or oversight.
• Volume comfort: Thrives in outreach funnels with daily metrics (e.g., replies, hires).
• Curiosity and coachability: Seeks feedback and adapts quickly.
• Low ego: Values learning over ego.
• AI proficiency: Already uses AI tools to automate work and is eager to expand this.
• Judgment: Proactively identifies tasks before they’re assigned.
• Ideal background: 1–3 years as an SDR, recruiting coordinator, or operations associate in SaaS/tech selling to the US. Unconventional paths welcome if you can explain relevance.
• Fluent English (written/spoken) and US Eastern time availability.
• Plus factors: Experience with Stripe, HubSpot, or Ashby (teachable).

You’ll Excel Here If:

• You’re energized by clean inboxes and moving funnels.
• You prefer owning small tasks completely over lightly touching big ones.
• You want to see how a company runs internally—including the unglamorous work.
• You thrive in a role that changes monthly.

Not a Fit If:

• You view outreach/billing as beneath you—these are week-one tasks that earn future opportunities.
• You need detailed instructions for every task.
• You seek a static job description.

About Whippy:

Whippy is an AI communication and automation platform unifying calls, texts, and emails into a shared inbox. Features include:

• AI agents handling replies or automations.
• Data integration with your systems.
• Reduction of repetitive work to free teams for revenue-driving tasks.

Industry-agnostic with wins in staffing, healthcare, and digital transformation. Bootstrapped, profitable, and scaling rapidly with 1,000+ global customers.

Founded in 2021 by CEO David (former poker pro turned entrepreneur) and CTO Jack Kennedy (engineering powerhouse and marathon runner).