The Product Podcast

Rippling GM on Running a $16B+ Company Like a Product at Scale | Anique Drumright | E283

• Product School • Episode 283

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In this episode, Carlos Gonzalez de Villaumbrosia, CEO & Founder at Product School, interviews Anique Drumright, General Manager and VP of Product at Rippling, the workforce management platform valued at $16.8 billion with over $570 million in ARR.

Anique is a product veteran who has shaped high-growth teams at Uber, TripActions, and Loom. Now at Rippling, she helps lead a workforce of over 4,000 employees, including 100 former founders, to maintain the speed and ownership typically lost at scale. In this conversation, Anique breaks down how Rippling successfully operates as a compound startup and why product leaders must evolve into General Managers.

What you’ll learn:

  • How to pivot from managing a backlog to owning a P&L as a GM.
  • The Compound Startup framework for consolidating enterprise categories.
  • How to build high-performing teams by hiring for "founder-level" curiosity.
  • Strategies for proving ROI to enterprise customers to drive platform adoption.

Key takeaways:

  • Go and See: Why leaders must personally investigate customer issues to set the bar for quality.
  • Singular Obsession: How to organize teams to maintain focus and velocity as you scale.
  • Automating ROI: How Rippling uses product efficiency to justify headcount reduction for clients.

Credits:
Host: Carlos Gonzalez de Villaumbrosia
Guest: Anique Drumright

Social Links:

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  • Find out more about Product School here

Anique Drumright | Rippling 00:00:00

Building a great product org ultimately means hiring people to love and own your product the way the founders do. You are hiring for immense amounts of curiosity, leadership, and commitment to execution.

How do you leverage the power of the Rippling platform—from the ability to create workflows to granular groups—while also striving to build the best product experience possible? Groups power everything Rippling does, which makes my specific product better. Unlocking the power of the platform to further differentiate the product is the fun and challenging part of product management.


Introduction

Carlos González | Product School 00:00:59

Hey, this is Carlos, CEO at Product School and your host on The Product Podcast. Today’s guest is Anique Drumright, General Manager and VP of Product at Rippling.

Rippling is an absolute rocket ship in the HR and IT space, currently commanding a massive $16.8 billion valuation and accelerating past $570 million in annual revenue. Rippling maintains its incredible product velocity and AI automation by employing over 100 former founders.

In this conversation, Anique breaks down her playbook for building high-performing product teams based on her experience leading multi-billion dollar products at Uber, Loom, and now Rippling. We cover the GM mindset, the strategy for building compound startups, and the "Go and See" culture. Let’s dive in.

Carlos González | Product School 00:02:00

Hello, everybody. I'm very aware that I am the only thing standing between you and happy hour, so I promise to make this as interactive and fun as possible. It is easy because I have Anique here, who is awesome. Welcome, Anique.

Anique Drumright | Rippling 00:02:15

Hey. No pressure.

Carlos González | Product School 00:02:28

We are doing a live edition of The Product Podcast. I’ve been hosting this for six years—back when nobody cared—and now it’s exciting to do this with a live audience.

You and I go way back. You first contributed to Product School when you were at Uber. Since then, you’ve worked at Uber, TripActions, Loom, and now Rippling.

I have a few stats here about Rippling because they are impressive: raised approximately $8.5 billion, valuation of $16.8 billion, and revenue exceeding $570 million as of early 2025. You also have over 20,000 customers and 4,000 employees globally. But the stat I love most is that there are over 100 former founders working there.

Anique Drumright | Rippling 00:03:40

Some of those stats are even a year later very much out of date. It sounds a little small now! But yes, it is very impressive to see Rippling's growth and scale, and what it is able to do for customers by working across the entirety of their stack.


Main Conversation

Carlos González | Product School 00:04:00

The theme for this conversation is building high-performing product teams. You’ve worked with incredible leaders like Travis Kalanick at Uber and now Parker Conrad at Rippling. As you reverse engineer your experience, what patterns define these high-performing teams?


High-Performing Teams: Uber vs. Rippling

Anique Drumright | Rippling 00:04:30

I was lucky to join Uber as an Individual Contributor (IC); that was my introduction to tech and product. At the time, the company believed in ruthless ownership. We felt we could do anything and were there to change the world. It was impressive to see that even at a scale of 5,000 or 10,000 people, every employee had that willingness to chase down the right customer experience.

At Rippling, I’m over a year into my journey, and it is wildly impressive to watch the company build so many products connected to critical operations in parallel. Parker incubates many parallel ideas and carefully ensures they are completely interoperable from a platform perspective.

Across Uber, TripActions, Loom, and Rippling, the consistency is this: you are hiring people to love and own the product the way the founders do. You are hiring for immense amounts of curiosity, leadership, and a commitment to execution.


Founder Relationships and Trust

Carlos González | Product School 00:06:30

"Commitment to execution" is a critical term. As a founder, I know how hard it is to delegate while still wanting to be in the details. How do you ensure the founder's vision is manifested while maintaining the speed of shipping?

Anique Drumright | Rippling 00:07:07

There are two components. First, you have to love being part of a high-performing team. I played soccer and rugby; I’m a junkie for that environment. That is ultimately what a growth-stage startup is. Founders want to be surrounded by people who earn that trust because they took the immense risk. You are constantly "trying out" for the team to contribute to the mission.

The second piece is curiosity. You have to have a curiosity for their perspective. You won't get it right 100% of the time, but you must own it and correct it quickly. You ultimately want to build the best product for the customer.


Scaling Culture: The "Go and See" Mentality

Carlos González | Product School 00:08:48

You are now over 4,000 employees. There is magic in the early days when everyone is in one room moving at light speed. How do you maintain that hunger and velocity at this scale?

Anique Drumright | Rippling 00:09:46

First, it’s organizational. Can you create teams with singular obsessions? I lead the IT business. I think about it all day, every day. I have dedicated sales, marketing, product, and implementation teams thinking about this singular problem. This allows a large company to deeply own specific work.

Second, Rippling is excellent at making things measurable. We set goals that seem impossible, which forces us to move with velocity and clarity.

Finally, it’s the "Go and See" culture. Parker models this from the top. If there is a customer issue he doesn't understand, he will run it all the way down to the chat logs. He wants to know exactly where the product or implementation had gaps. When your CEO operates that way, it sets the bar for everyone else.


The General Manager (GM) Mindset

Carlos González | Product School 00:12:30

Rippling has a unique structure where products graduate to become business units. You are a GM, not just a VP of Product. What is the difference in how you measure success?

Anique Drumright | Rippling 00:13:00

We did this at Loom as well. It comes down to the best customer experience. If I’m working with someone on implementation for payroll, is that experience as strong as it could be if the implementer specializes in IT?

This logic applies all the way down to support agents. If you want to make a step-change in growth for a specific area, it is more likely to succeed if sales, implementation, and product are working as a single, unified team.

Carlos González | Product School 00:14:23

There might be redundancy when building separate business units. How do you ensure there are shared services and a common goal?

Anique Drumright | Rippling 00:15:00

We are constantly evolving. Matt Plank, our CRO, has done an incredible job supporting the business units while ensuring customers are successful as they expand their Rippling footprint across IT, payroll, and spend.


Platform Strategy: Compound Startups

Carlos González | Product School 00:16:04

Historically, people bought point solutions. Rippling is different—it’s a platform. How do you prove value to expand into other verticals?

Anique Drumright | Rippling 00:16:30

The key insight is that all business operations run off employee data. Every person who joins a company needs a paycheck, a computer, app access, and expense reporting.

Right now, 65% of IT teams use over seven different products. That is a lot of overhead. If you are starting a company, why would you want to talk to 20 different vendors? Because Rippling owns the employee data, we streamline hiring, offboarding, org changes, and everything in between.


Balancing Platform Power vs. Product Quality

Carlos González | Product School 00:17:45

The trade-off with platforms is that sometimes they can’t be the best at everything compared to point solutions. How do you ensure the product quality remains high?

Anique Drumright | Rippling 00:18:10

That is the job of the Product Manager. The assumption that the platform does not enhance the singular product is incorrect.

For example, Rippling invests heavily in "Groups." Because Groups power everything we do, when I build an access management tool, I have one of the most powerful, granular grouping capabilities on the market. That makes my specific product better.

We constantly ask: How do we unlock the power of the platform to differentiate our product? In a traditional product, hiring five people requires creating IT tickets. With Rippling, you just hire them, and the devices and access are provisioned automatically.


Enterprise Sales and ROI

Carlos González | Product School 00:21:07

When you move upmarket to large enterprises, they often have incumbents. How do you penetrate those accounts if they aren't ready to deploy the entire platform?

Anique Drumright | Rippling 00:22:17

You have to listen to the customer. But the core value proposition is efficiency. Rippling’s mission is to free smart people to work on hard problems.

Parker mentioned in a recent interview that when we analyze the size of HR or IT teams at companies using our competitors versus Rippling, the teams using Rippling are roughly half the size. That is the ROI. We automate the admin work so teams can focus on higher-leverage tasks.


Strategic Planning: Big Bets vs. Incremental Wins

Carlos González | Product School 00:24:00

We are in Q4, which is strategy planning season. How do you approach planning?

Anique Drumright | Rippling 00:24:30

I always start with: What are the one or two things that will be a step-change bet? If they work, they change the trajectory of the business.

Then, I layer in the data: feedback from our "Wave Makers" (customer advisory board), sales team, and my own customer calls.

It’s a balance. You need the "big rocks"—the major investments—and the "meaty buckets" of improvements that unblock sales or fix customer pain points. As a leader, I need clarity on the big bets, and every PM on my team needs that same clarity for their specific area.


Rituals and Calendar Management

Carlos González | Product School 00:27:57

I’m a geek for rituals. If I zoomed into your calendar, how do you allocate your time?

Anique Drumright | Rippling 00:28:10

I am very ritualistic. My weeks look the same.

  • Mondays: Thematic meetings focused on the key investment areas and big rocks.
  • Mid-week: Product reviews, marketing reviews, and "Go and See" time.
  • Fridays: Team meetings to bookmark the week.
    The "Go and See" time is vital. Whether it’s listening to sales calls, reading support tickets, or doing competitive research, you must carve out time to understand the reality of the product in the wild. I feel much more present and effective when I do that.


Closing

Carlos González | Product School 00:31:30

One final question on culture. We hear about work-life balance versus the "996" culture. What is required to be part of a high-performing team at Rippling?

Anique Drumright | Rippling 00:31:56

You are choosing to join a high-growth startup and work for Parker Conrad. That should be exciting.

Success requires high levels of ownership. The right people know what that looks like. It’s not necessarily about working specific hours; it’s about owning the outcome entirely.

Carlos González | Product School 00:32:30

Thank you for sharing those insights. It is a pleasure to learn from your experience building great products and teams.

Anique Drumright | Rippling 00:32:40

Thank you so much. It was fun.