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Building AI Fluency, One Uncomfortable Step at a Time with Nikki Jackson

Published

August 18, 2026

AI fluency doesn’t come from waiting until you feel ready. It comes from building, failing in public, and getting comfortable being uncomfortable.

In this episode of Growth Talks, Nikki Jackson, Head of Demand Generation at Gusto, joins host Krystina Rubino to share how she spent the past year making AI fluency a team-wide reality, not just a buzzword. Nikki breaks down the deliberate system behind it: IT and security onboarding, dedicated AI Learning Days, and concrete goals for every team member to leverage AI. She gets candid about the discomfort of learning in public, how she measures the ROI of AI adoption, why she treats AI as a “second brain” for moving faster with data, and what staying authentic looks like in a world flooded with AI-generated noise.

🔑 Key Takeaways

  • Lean into the uncomfortable. Real AI fluency comes from hands-on building and failing in public, not waiting until you feel ready.
  • Structure accelerates adoption. Dedicated AI Learning Days, IT/security onboarding, and concrete AI goals to turn curiosity into consistent, team-wide progress.
  • ROI isn’t as fuzzy as it feels. Time savings and efficiency gains from AI agents can be tracked concretely; don’t let “it’s hard to measure” become the blocker.
  • AI is a second brain, not a replacement. Conversational access to data frees up strategic time and elevates the conversation with analysts instead of eliminating it.
  • Authenticity is the differentiator. As AI content scales, a distinct voice and point of view—especially for women in marketing—become the real competitive edge.

⏰ Timestamps

00:00 Meet Nikki Jackson: Building AI Fluency at Gusto
01:02 How Nikki’s AI Journey Started
03:34 Structuring a Team-Wide AI Rollout
07:24 Clearing IT and Security Hurdles
08:46 AI Learning Days in Action
09:56 Agent-Building OKRs
12:07 Measuring the ROI of AI Fluency
16:10 Building a Prioritization Rubric with AI
19:04 AI as a Second Brain for Data
23:27 The A/B Test: Nikki’s Quick-Fire Round
29:42 Women, AI, and Marketing Leadership
34:57 Staying Authentic Amid AI Slop
39:40 Marketing to Busy SMB Owners
44:44 Brand Storytelling at Gusto
46:16 Creating Demand Before the Search Begins
50:48 Nikki’s Favorite Growth Non-Hack

🔗 Mentioned in this episode

Gusto: https://gusto.com/

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FAQ

What are some practical AI agent use cases for demand generation teams?

Demand generation teams can use AI agents to automate recurring analysis, reporting, and monitoring tasks. Nikki’s team has built an agent that tracks competitors appearing in paid-search auctions, monitors selected keywords, assesses changes in the search landscape, and sends a weekly summary to the team in Slack. Other agents can transform employees’ informal weekly updates into executive-ready impact summaries or help marketers investigate channel performance conversationally. By connecting AI with approved company data, teams can identify performance changes, compare seasonal or year-over-year trends, and spot where prospects may be stalling. These agents reduce manual work while giving marketers more time for strategic thinking.

How should marketing teams measure the ROI of AI training and agent building?

Marketing teams can measure AI ROI by documenting what each agent does, how frequently it is used, and how much manual work it replaces. Time savings are one of the clearest starting points: if an agent saves several hours each week, the team can quantify that capacity and identify the higher-value work it enables. Leaders can also track improvements in process efficiency, access to insights, and the speed of recurring decisions or analyses. Nikki recommends compiling the agents created across the team and assessing their individual and collective impact. This creates a concrete business case for dedicated learning time instead of treating “AI fluency” as an abstract benefit.

How can marketing leaders build AI fluency across an entire team?

Marketing leaders can build AI fluency by giving employees structured time to experiment, learn together, and apply AI to real work. Nikki Jackson recommends leading by example: build something yourself, share what worked and what didn’t, and encourage early adopters to demonstrate their projects. Her team also holds dedicated, meeting-free AI learning sessions, pairs employees in smaller groups, and involves technical partners who can resolve access or security issues. To turn learning into action, each team member receives a goal to build an AI agent every quarter. The key is to make experimentation visible, collaborative, and safe, even when it results in failure.

How can marketers use AI without losing their authentic voice and judgment?

Marketers should use AI to enhance their thinking and execution, not replace their perspective. Nikki recommends beginning with your own ideas and authentic voice, then using AI as an editor, research assistant, or workflow accelerator. For example, she uses it to make executive writing clearer and more concise, including asking it to reduce a draft’s length by 10% to 15%. Human judgment remains essential for evaluating quality, preserving originality, and deciding what represents the brand. As AI makes content easier to produce, distinctive taste and a well-defined point of view become even more valuable. The strongest work combines AI’s efficiency with human creativity, context, and judgment.

How can demand generation teams reach small-business buyers before they are actively searching for a solution?

Demand generation teams can reach future buyers by building awareness well before a purchase becomes urgent. For small-business audiences, Nikki recommends communicating consistent value propositions across multiple channels rather than frequently changing the message or creative identity. Teams should monitor both reach and frequency to ensure prospective customers encounter the brand often enough to remember it. If frequency is too low, narrowing the audience (e.g. such as focusing on selected geographic markets) may make the investment more effective. Authentic customer stories, podcasts, audio, social media, and thoughtful customer experiences can reinforce the message. Over time, these consistent touchpoints build brand recall and encourage word of mouth.

Episode Transcript

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