MOpza Session Spotlight: Reinventing marketing ops with Rippling

Marketing operations is no longer spreadsheets and workflows. It’s a playground for innovation, and Conrad Millen, VP of growth operations at Rippling, is redefining what’s possible. At MOps-Apalooza, Conrad didn’t just present a session; he threw down the gauntlet, showing how Rippling is upending the status quo with bold strategies and cutting-edge technology.

At Rippling, Conrad has rewritten the rules with a custom-built tool powered by Openprise that can send thousands of personalized emails a day and sync them to almost 3,000 sales mailboxes—turning the dream of mass personalization at scale into an everyday reality.

Here’s how Conrad’s game-changing approach is setting new standards in marketing operations.

Mechanized outreach: version 2.0

Conrad kicked off the session with a big splash (and a big photo of himself on the screen). He set the stage by sharing his journey: nearly a decade in marketing operations, now leading a 30-person team at Rippling, a company that he described as the “operating system for your business” from HR to IT and finance.

At last year’s MOpza event, Conrad introduced us to Highly Mechanized Prospecting, Rippling’s cutting-edge solution for scaling one-to-one email campaigns. This year, he revealed how they took it up a notch by incorporating machine learning and artificial intelligence.

What’s changed? A number of things:

What’s different?

1. Corporate culture is data first: Rippling’s engineering-first mentality fuels their ability to innovate. With 700+ engineers in a 3,000-person company, the culture encourages building bespoke solutions rather than buying off-the-shelf tools. Conrad emphasized: “I work for a business that really is a very data-forward company. We use upwards of 10 to 15 different data providers, maybe even more, as we’ve expanded globally. It’s a very embedded part of our culture to look at and analyze data. The entire marketing org knows SQL, they pull their own data, they pull their own dashboards—which is pretty unique to most of the businesses out there—and my team internally is just very data savvy. We have a very heavy buy/build versus buy mentality. This is probably due to the fact that we have 700-800 engineers in a 3,000-person company. So if we can build internally, we’re going to.”
2. People and teams: Conrad’s team includes IT operations, in-house analytics, growth engineering, and data savvy marketers. This blend of skills enables Rippling to move fast and strategically.
3. Processes: Act first, perfect later. Rippling prioritizes rapid testing and learning: “What we learned in this process is, test quickly and optimize before you try and build this whole perfect system that probably isn’t going to give you the results that you expect. Might as well learn quicker and move on to something else.” 
4. Technology: Gone are the days of traditional marketing automation platforms. Rippling ditched Marketo over a year ago and now relies on a tech stack of Snowflake, Salesforce, and homegrown solutions that integrate seamlessly via APIs.

Building the ultimate autonomous prospecting engine

At the heart of Rippling’s marketing strategy (aside from Conrad) is an autonomous engine that combines AI, ML and robust data processes to identify, target, and engage prospects at scale.

Key components of the engine

• Cracking the Dark TAM
  • The “Dark TAM” represents hidden opportunities within the total addressable market. Rippling identifies and engages these prospects through:
  • Aggregating diverse data sources like review sites, hiring signals, and website visits.
  • Centralizing and enriching data to ensure accuracy and usability.
  • Using machine learning models to evaluate data and recommend strategies.
  • Triggering dynamic campaigns based on real-time signals like hiring trends and company news.
  • Centralized data

Rippling aggregates data from 20+ data providers into a single repository, transforming and normalizing it across a single GTM system.

• Lead search waterfall

This custom-built system finds and prioritizes leads using a hierarchy of third-party vendors, ensuring data accuracy and cost efficiency.

• AI-powered personalization

Rippling’s recommendation engine dynamically assigns leads to optimal marketing sequences based on historical performance and real-time indicators.

• Dynamic outreach

Emails are crafted with AI, integrating hyper-relevant details to enhance personalization. For instance, referencing a prospect’s LinkedIn activity or their company’s recent milestones creates a tailored connection. Conrad shared an example:

AI learnings and results

While the AI-driven engine hasn’t delivered a magical 5x conversion boost yet, the early results are promising.

“We’re still learning a lot from it because it’s only been running for a few months. But I would say that the personalization that we had done with third-party vendors that just inserts a few tokens in the message compared to the AI fully written copy was actually pretty comparable.” 

The key takeaway? Personalization works, whether AI-driven or human-crafted. The real value lies in the speed and scale enabled by automation.

Revolutionizing sales with dynamic books of business

Rippling didn’t just stop at marketing. They extended their data-driven approach to sales and introduced dynamic books of business to optimize account assignments and maximize pipeline opportunities.

Highlights of this approach include:

• Intent and event signals: From website visits to funding announcements, Rippling captures dozens of signals to identify in-market accounts.
• Predictive scoring: Machine learning models rank accounts based on fit and intent, enabling SDRs to focus on high-priority targets.
• Dynamic routing: Accounts are reassigned dynamically, ensuring reps always have fresh opportunities without lengthy reassignment cycles.

While this is a relevantly new initiative, “We’ve seen big account-to-opportunity conversions with this new motion,” Conrad said. “So we’re very excited about it.”

Final takeaways

The old way of doing things is over, and it’s now more critical than ever to find fresh, innovative approaches to go-to-market. Conrad closed his session with some actionable advice for marketing ops professionals:

1. Leverage data: Centralize and clean your data. “Garbage in, garbage out” isn’t just a saying—it’s a warning.
2. Test quickly: Don’t overthink it. Learn fast, fail fast, and iterate.
3. Think differently: The traditional B2B SaaS playbook is outdated. Find creative, unconventional ways to go to market.

“There are endless possibilities to build really cool stuff that can actually give you that edge. So ask yourself that critical question and do things differently.” 

From mechanized outreach to dynamic sales motions, Rippling’s approach to marketing ops is a masterclass in innovation. Whether you’re leading a small team or a large enterprise, there’s something here to inspire your next big idea.

Interested in hearing more? Attend our interactive webinar ”Revolutionizing marketing Ops with AI, data, and automation“ with Conrad Millen on January 21, 2025. Register today!

Watch the full session.

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