Flip
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TITLE: Account Executive (Healthcare OR Retail)
REPORTING TO: Chief Customer Officer
LOCATION: Marina del Rey, CA OR Brooklyn, NY (Onsite Monday - Friday)
Who Is Flip?
Ever call your favorite eCommerce brand or healthcare provider, and have a crazy good Voice AI answer? That’s Flip. Hundreds of brands from Under Armour and Tory Burch in retail to Experity and Fast Pace Health in healthcare trust Flip to have millions of phone calls with their customers every month.
We’ve built our company on the idea that the best way to grow is to have a reference list as long as our customer list, and a constant belief that the team is the best thing we’ve built. Both are true today and increasingly so every day.
Many on our team would tell you this is their favorite place they’ve ever worked, and the hardest they’ve ever worked. It’s ideal for people who want to go all-in, do the work, ride the roller coaster, and have a great Flippin time doing it. We’re a small and mighty team of 50 today with offices in NYC, LA, and the UK.
The Tech Behind the Revolution
Flip doesn’t just “answer phones.” We embed directly into a company’s tech stack to personalize every interaction and resolve complex issues in seconds.
- In Retail, we power high-volume, brand-sensitive customer interactions—protecting voice, driving conversions, and elevating CX at scale.
- In Healthcare, we deliver HIPAA-compliant, clinically reliable AI that manages patient communication, scheduling, and inquiries with precision and empathy.
Our AI evolves through millions of real-world conversations—delivering human-level empathy, operational efficiency, and outcomes that legacy systems simply can’t match.
The Role: Join the AI Rocketship
We just secured our Series raise. The engines are primed. The launchpad is clear. We’re not hiring traditional “Account Executives.” We’re hiring mercenaries of CX. Reporting directly to our Chief Customer Officer, you’ll help lead a GTM expansion designed to dismantle outdated systems across the Retail or Healthcare business sectors. If you want your career tied to a high-velocity AI transformation, this is your seat.
Core Responsibilities - Across the board for all our Account Executives
- Hunt Without Mercy: Drive net-new revenue across MM and Enterprise accounts ($50K–$250K+ deals and beyond)
- Earn the Keys to the Kingdom: Build trust with senior stakeholders and earn the right to own mission-critical customer interactions
- Bridge the Gap to Greatness: Partner closely with Product, Engineering, and Customer Success to shape the platform through real customer insight
- Burn the Playbook: Move fast, challenge legacy processes, and help build a world-class GTM engine
Vertical Focus: Where You’ll Specialize - Retail OR Healthcare
- Retail (Ecommerce & Consumer Brands):
- Target elite retail and ecommerce brands
- Protect and enhance brand voice and customer experience at scale
- Navigate orgs where CX is deeply tied to revenue, loyalty, and conversion
- Build relationships with CX, Digital, and Ecommerce leaders
- Position Flip as a competitive advantage in a crowded, high-expectation market
What makes Retail unique: Speed, volume, and brand sensitivity. You’re selling into environments where every interaction impacts revenue and perception instantly.
- Healthcare (Urgent Cares & Healthcare Providers):
- Target leading healthcare systems and provider groups
- Replace legacy communication systems with AI-driven patient engagement
- Navigate complex buying groups with compliance, IT, and clinical stakeholders
- Build trust in HIPAA-compliant, mission-critical workflows
- Position Flip as infrastructure—not a tool—for modern patient communication
What makes Healthcare unique: Trust, compliance, and precision. You’re selling into environments where every interaction impacts patients and operational integrity.
Who You Are: You’re not just an AE—you’re a force of nature.
We are a team of owner-operators. We’re in-office—NYC, LA, and the UK—because we believe high-stakes innovation happens when we’re in the trenches together. If you’re a reverse-hacker who sees obstacles as puzzles to break—and you operate with uncompromising integrity in your work—you’ll fit right in.
- A Natural-Born Closer: You don’t hit quota—you destroy it
- Product Obsessed: You sell solutions, retail or provider wins, not features
- Customer-First: You deeply understand stakeholder pain and use it to build trust fast
- Startup Warrior: You thrive in chaos, move fast, and outwork the market
- Experience in startup tech sales (B2B SaaS, AI/ML, cloud, etc.) preferred
- Proven success in complex, multi-threaded sales cycles (ideally $500K+ ACV)
More About Us
- We're international, spanning the US, UK, and Canada
- We’ve raised +$30M to date including our recent $20M Series A - backed by Ridge, Next Coast, ScOp, Bullpen Capital, Data Point and Forum Ventures, as well as founders & executives from Amazon Alexa, Ada, Attentive, and Simon Data
- Comprehensive healthcare and unlimited vacation, including a mandatory half week for everyone over July 4, and a full week off at the end of the year
- In office 5 days/week
#FlippinLegend
Final compensation may vary based on location, experience, and qualifications. This role is also eligible for bonus and/or commission as well as equity, in accordance with company policy, and subject to board approval.
Our customers span the globe, and so do our offices. Flip is committed to providing equal employment opportunities for all employees, applicants, and covered individuals regardless of protected characteristics. We want our company to be as diverse and inclusive as our customers.
Ready to apply?
Apply to Flip
TITLE: Account Executive (Healthcare OR Retail)
REPORTING TO: Chief Customer Officer
LOCATION: Marina del Rey, CA OR Brooklyn, NY (Onsite Monday - Friday)
Who Is Flip?
Ever call your favorite eCommerce brand or healthcare provider, and have a crazy good Voice AI answer? That’s Flip. Hundreds of brands from Under Armour and Tory Burch in retail to Experity and Fast Pace Health in healthcare trust Flip to have millions of phone calls with their customers every month.
We’ve built our company on the idea that the best way to grow is to have a reference list as long as our customer list, and a constant belief that the team is the best thing we’ve built. Both are true today and increasingly so every day.
Many on our team would tell you this is their favorite place they’ve ever worked, and the hardest they’ve ever worked. It’s ideal for people who want to go all-in, do the work, ride the roller coaster, and have a great Flippin time doing it. We’re a small and mighty team of 50 today with offices in NYC, LA, and the UK.
The Tech Behind the Revolution
Flip doesn’t just “answer phones.” We embed directly into a company’s tech stack to personalize every interaction and resolve complex issues in seconds.
- In Retail, we power high-volume, brand-sensitive customer interactions—protecting voice, driving conversions, and elevating CX at scale.
- In Healthcare, we deliver HIPAA-compliant, clinically reliable AI that manages patient communication, scheduling, and inquiries with precision and empathy.
Our AI evolves through millions of real-world conversations—delivering human-level empathy, operational efficiency, and outcomes that legacy systems simply can’t match.
The Role: Join the AI Rocketship
We just secured our Series raise. The engines are primed. The launchpad is clear. We’re not hiring traditional “Account Executives.” We’re hiring mercenaries of CX. Reporting directly to our Chief Customer Officer, you’ll help lead a GTM expansion designed to dismantle outdated systems across the Retail or Healthcare business sectors. If you want your career tied to a high-velocity AI transformation, this is your seat.
Core Responsibilities - Across the board for all our Account Executives
- Hunt Without Mercy: Drive net-new revenue across MM and Enterprise accounts ($50K–$250K+ deals and beyond)
- Earn the Keys to the Kingdom: Build trust with senior stakeholders and earn the right to own mission-critical customer interactions
- Bridge the Gap to Greatness: Partner closely with Product, Engineering, and Customer Success to shape the platform through real customer insight
- Burn the Playbook: Move fast, challenge legacy processes, and help build a world-class GTM engine
Vertical Focus: Where You’ll Specialize - Retail OR Healthcare
- Retail (Ecommerce & Consumer Brands):
- Target elite retail and ecommerce brands
- Protect and enhance brand voice and customer experience at scale
- Navigate orgs where CX is deeply tied to revenue, loyalty, and conversion
- Build relationships with CX, Digital, and Ecommerce leaders
- Position Flip as a competitive advantage in a crowded, high-expectation market
What makes Retail unique: Speed, volume, and brand sensitivity. You’re selling into environments where every interaction impacts revenue and perception instantly.
- Healthcare (Urgent Cares & Healthcare Providers):
- Target leading healthcare systems and provider groups
- Replace legacy communication systems with AI-driven patient engagement
- Navigate complex buying groups with compliance, IT, and clinical stakeholders
- Build trust in HIPAA-compliant, mission-critical workflows
- Position Flip as infrastructure—not a tool—for modern patient communication
What makes Healthcare unique: Trust, compliance, and precision. You’re selling into environments where every interaction impacts patients and operational integrity.
Who You Are: You’re not just an AE—you’re a force of nature.
We are a team of owner-operators. We’re in-office—NYC, LA, and the UK—because we believe high-stakes innovation happens when we’re in the trenches together. If you’re a reverse-hacker who sees obstacles as puzzles to break—and you operate with uncompromising integrity in your work—you’ll fit right in.
- A Natural-Born Closer: You don’t hit quota—you destroy it
- Product Obsessed: You sell solutions, retail or provider wins, not features
- Customer-First: You deeply understand stakeholder pain and use it to build trust fast
- Startup Warrior: You thrive in chaos, move fast, and outwork the market
- Experience in startup tech sales (B2B SaaS, AI/ML, cloud, etc.) preferred
- Proven success in complex, multi-threaded sales cycles (ideally $500K+ ACV)
More About Us
- We're international, spanning the US, UK, and Canada
- We’ve raised +$30M to date including our recent $20M Series A - backed by Ridge, Next Coast, ScOp, Bullpen Capital, Data Point and Forum Ventures, as well as founders & executives from Amazon Alexa, Ada, Attentive, and Simon Data
- Comprehensive healthcare and unlimited vacation, including a mandatory half week for everyone over July 4, and a full week off at the end of the year
- In office 5 days/week
#FlippinLegend
Final compensation may vary based on location, experience, and qualifications. This role is also eligible for bonus and/or commission as well as equity, in accordance with company policy, and subject to board approval.
Our customers span the globe, and so do our offices. Flip is committed to providing equal employment opportunities for all employees, applicants, and covered individuals regardless of protected characteristics. We want our company to be as diverse and inclusive as our customers.
Ready to apply?
Apply to Flip
TITLE: Director of Revenue Operations
REPORTING TO: CoFounder/CRO
LOCATION: Marina del Rey, CA (Onsite Monday - Friday)
Who The Flip Is Flip?
Ever call your favorite eCommerce brand or healthcare provider, and have a crazy good Voice AI answer? That’s Flip. Hundreds of brands from Under Armour and Tory Burch in retail to Experity and Fast Pace Health in healthcare trust Flip to have millions of phone calls with their customers every month.
We’ve built our company on the idea that the best way to grow is to have a reference list as long as our customer list, and a constant belief that the team is the best thing we’ve built. Both are true today and increasingly so every day.
Many on our team would tell you this is their favorite place they’ve ever worked, and the hardest they’ve ever worked. It’s ideal for people who want to go all-in, do the work, ride the roller coaster, and have a great Flippin time doing it. We’re a small and mighty team of 50 today with offices in NYC, LA, and the UK.
What You’ll Do
Flip has scaled quickly by being scrappy, pragmatic, and execution-focused. Our GTM and revenue systems were built to help us move fast and get to where we are today. Now, we’re ready for the next chapter.
We’re looking for a Director of Revenue Operations who enjoys rolling up their sleeves, operating autonomously, and taking something that works and making it truly scalable.
This role is for someone who doesn’t wait for a roadmap. You’ll proactively design, evolve, and operate the systems that power our GTM engine—often before the organization realizes a change is needed.
Your job is to make revenue mechanics feel invisible to the rest of the company by anticipating issues, eliminating friction, and turning GTM data and analytics into a tailwind rather than a headwind.
Current GTM Stack
Our current stack reflects a scrappy, build-what-we-need approach and is used end-to-end — from lead intake through billing and revenue reporting:
- HubSpot (current CRM / GTM system of record)
- Matillion
- Omni
- SQL-based analytics and transformations
This stack is not sacred, and you’ll have full latitude to evolve or rethink it over time. That said, you should be comfortable operating in this type of environment on day one. If working close to systems like this — understanding how data flows from lead to deal to billing — isn’t something you enjoy or feel confident doing, this is probably not the right role.
Your Core Responsibilities
- Own the end-to-end revenue operating system: Lead → Deal → Contract → Billing → Reporting
- Act as the autonomous owner of GTM mechanics across Sales and Customer Success
- Own the GTM system of record (currently HubSpot), with permission and expectation to challenge, evolve, or replace tools as needed
- Ensure contracts and sold line items translate cleanly into billable revenue
- Partner with Finance to deliver clean, system-driven invoicing and revenue visibility
- Own forecasting inputs, pipeline hygiene, and GTM data integrity
- Partner with Data to turn GTM analytics into a tailwind for day-to-day decision-making
- Identify friction before it becomes a blocker—and fix it decisively
- Take what’s been built to date and level it up for the next phase of growth
Who You Are
- You enjoy getting your hands dirty and improving imperfect systems
- You operate comfortably with high autonomy and minimal direction
- You think ahead of the team and are rarely surprised
- You take pride in solving problems before they surface
- You’re technically fluent and curious, even if you’re not an engineer
- You’re comfortable reasoning about data flows, transformations, and system dependencies
- You care more about outcomes than tools
What You Bring
- 3–6 years experience in Revenue Operations, GTM Operations, or similar roles, with meaningful ownership of systems and processes
- Experience helping scale revenue systems in a fast-growing B2B SaaS environment
- Strong understanding of CRM systems, billing mechanics, and forecasting
- Comfort working close to the data using SQL and modern analytics tooling
- Ability to partner deeply with Finance and Data without needing translation
- Low-ego, high-ownership collaboration style
- Comfort balancing hands-on execution with long-term system design
More About Us
- We're international, spanning the US, UK, and Canada
- We’ve raised +$30M to date including our recent $20M Series A - backed by Ridge, Next Coast, ScOp, Bullpen Capital, Data Point and Forum Ventures, as well as founders & executives from Amazon Alexa, Ada, Attentive, and Simon Data
- Comprehensive healthcare and unlimited vacation, including a mandatory half week for everyone over July 4, and a full week off at the end of the year
- In office 5 days/week
#FlippinLegend
Final compensation may vary based on location, experience, and qualifications. This role is also eligible for bonus and/or commission as well as equity, in accordance with company policy, and subject to board approval.
Our customers span the globe, and so do our offices. Flip is committed to providing equal employment opportunities for all employees, applicants, and covered individuals regardless of protected characteristics. We want our company to be as diverse and inclusive as our customers.
Ready to apply?
Apply to Flip