Your ads aren't failing — your benchmarks are

Katherine Riddick has been leading demand gen at OneDigital since the world fell apart in early 2020.

Here’s how she made complicated, long-cycle B2B marketing look easy during a seriously challenging time — and her playbook is more transferable than you might expect. 

Meet the Master

Katherine Riddick
Director, Growth Marketing, OneDigital 

• Claim to fame: Katherine joined OneDigital, a B2B that helps businesses and leaders put together employee benefits packages, in early 2020. She’s been at the front lines of the pandemic, the WFH revolution, and AI disruption. 

Lesson 1: Pipeline progression is the real scorecard. 

“Volume may look like it is down historically for B2B buyers right now, but our pipeline is progressing faster and better than in previous years,” Riddick says. 

AI has shifted the game: It’s more about responding to potential buyers the fastest, and less about simply being found. 

“With the LLMs,” Riddick explains, “they've already got four of your competitors in their list that [buyers are] also going to reach out to. And then it becomes a game of who can get to them the fastest, who can get a quote in front of them, who can engage with them best. It’s really having an impact on how we measure success.”

For instance, “people are remembering us from the first touch of seeing an ad on LinkedIn six months ago,” and that might be driving what looks like organic or direct traffic today.

“We’re running into that inflection moment of taking a step back and stop trying to measure 2026 impact using 2025’s playbook — because it's not the same anymore.”

That's why Riddick is leaning into multi-touch attribution. “Was the ad the first touch point? Did they do additional research six months later? Was organic the last touch, because branded recall is higher?”

When Riddick sits down with leadership, she’s always tying metrics to pipeline progression. “Are we bringing in better quality? Are they moving faster? Are they closing more? What does deal velocity look like? What does the LTV-to-cap look like over time?”

Riddick uses AI to take that data and craft a two- to three-paragraph executive summary tailored specifically to her company’s leadership. For her, that means prompting it to tell a tight story about marketing impact, pipeline progression, and revenue.

Lesson 2: Give your ads time to learn before you pull the plug. 

AI is speeding up marketers’ decision-making faster than the algorithms can keep up with. “It’s tricky, because AI is helping us have better insights faster,” Riddick says. But “[we’re] almost making changes too fast, because the algorithms still need time to learn and find our audience.”

You might think that your ads aren’t performing as well compared to benchmarks from 2024 or 2025. But buyers “need to see our ads eight to 10 times before they’re ready to take an action,” Riddick tells me. 

Your ads aren’t necessarily failing — the market really has changed. Riddick cautions marketers against making cuts “based on what we’ve seen historically, since we're in a very different market this year.”  

Before you kill a campaign, ask yourself: Are you measuring it against benchmarks that no longer apply?

Lesson 3: Your people are your best ad creative. 

Riddick says she’s moving resources away from polished, static ads and redirecting them toward people — specifically OneDigital employees, many of whom are publishing their own social videos.

OneDigital has spent a lot of time “making sure our teams are confident and feel like they have the knowledge and expertise to go out and have conversations with business leaders across many different industries.”

In other words … social ambassadors. 

From there, Riddick says that willing employees are coached on “finding their brand story and crafting their own unique voice,” and given the resources and support they need to “feel more confident posting on social media.”

It starts with leadership. The SVP of marketing is “leaning in and doing these videos more, setting the tone and cadence for the rest of our teams to follow,” Riddick says. “None of us are influencers,” but when leadership goes first, it gives everybody else permission to try.