How to Lead an Internal AI Workshop w/ Kirti Dewan, Chief Marketing Officer of Fiddler AI

The Front Lines

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Kirti Dewan.

Chief Marketing Officer · Fiddler AI

Fiddler AI offers an all‑in‑one AI Observability and Security platform for enterprises deploying AI agents, LLMs, and ML models. Its unified environment provides visibility, context, and control across development and production, helping teams monitor model behavior, explain results, and manage risk through real‑time insights. The platform includes the Fiddler Trust Service, which delivers guardrails and moderation controls for gen‑AI and agentic applications in both cloud and VPC environments. Trusted by Fortune 500 organizations, Fiddler enables high‑performance, responsible AI deployment while reducing risk and maximizing ROI.

Guest

Kirti Dewan

Chief Marketing Officer

Company:

Fiddler AI

Location:

San Francisco Bay Area

Funding:

$63.8M Raised

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In this episode of The Marketing Front Lines, we speak with Kirti Dewan, Chief Marketing Officer of Fiddler AI, an enterprise AI observability platform. Kirti navigates one of the most challenging marketing environments in B2B tech history—where buying committees have exploded in size, new AI personas emerge constantly, and competitive dynamics shift every 15 minutes. From implementing quarterly AI workshops that unite marketing and sales teams to experimenting with cutting-edge martech tools, Kirti reveals how lean teams can stay agile in hyper-competitive markets. Her approach emphasizes relentless iteration, strategic experimentation, and maintaining team energy through constant feedback loops—principles that mirror the AI lifecycles her company helps enterprises manage.

Topics Discussed:

Navigating the most competitive B2B tech market in history as an early-stage AI company
Managing expanded buying committees and longer deal cycles in enterprise sales
Building a culture of continuous experimentation and A/B testing across marketing and sales
Implementing quarterly AI workshops to solve team pain points and automate workflows
Evaluating and adopting emerging martech tools (Descript, Restream, N8N, Airtable, Clay)
Operating in constant sales enablement mode as market dynamics shift rapidly
Adapting marketing strategies for buyers overwhelmed by solution proliferation
Preparing the next generation of marketers for an AI-native workplace

Seven takeaways from this conversation.

Actionable for AI marketers

Institute Quarterly Cross-Functional AI Workshops
Fiddler runs workshops every three months with 8-9 participants from marketing and sales. Before each session, team members document pain points, tedious work, and broken processes. The workshop then becomes a collaborative problem-solving session where teams brainstorm tools, workflows, and automation strategies. This structured-yet-fluid format has uncovered solutions like Airtable's template library and sparked ideas for custom MCP servers and N8N workflows.
Embrace Perpetual Sales Enablement as the New Normal
The days of completing a deck, training the team, and moving on are over. Modern B2B marketers must accept operating in a "constant state of sales enablement" where materials require continuous revision as competitive landscapes shift every 15-30 minutes. This requires different energy and mindset—viewing iteration and refinement not as disruption but as standard operating procedure, mirroring the feedback loops in AI systems.
Experiment Relentlessly with Emerging Tools
In crowded markets, competitive advantage comes from testing new martech and sales tech solutions before they become saturated. Kirti's team actively experiments with tools like Descript for content creation, Restream for automated webinar snippets, Infinigrow for marketing analytics and forecasting, and Clay for enrichment. The philosophy: try quickly, measure results, and either scale or kill experiments without fear of failure.
Maintain Market Awareness Through Team-Wide Reading Culture
When competing in rapidly evolving categories, teams cannot afford knowledge gaps. Kirti emphasizes that her team must "have the wherewithal to stay abreast of the market"—constantly reading about ecosystem developments, competitive movements, and adjacent technologies. This collective market intelligence enables faster strategic pivots and more informed experimentation.
Design Workshops for Fluidity Over Structure
While Kirti values structure in most contexts, she deliberately keeps AI workshops loosely structured to encourage creativity, vulnerability, and cross-functional problem-solving. Team members are exploring unfamiliar tools and putting themselves in learning mode, so maintaining a comfortable, natural environment yields better outcomes than rigid agendas. She intervenes only when conversations drift into budget concerns or headcount discussions, refocusing on solving immediate problems.
Recruit for Adjacent Skills, Not Just Domain Experience
As marketing playbooks get rewritten, traditional hiring criteria may limit innovation. Kirti questions whether demand gen hires must have prior demand gen experience or if someone with financial modeling expertise might pioneer new approaches to growth and AI-powered marketing operations. This opens opportunities to bring fresh perspectives from adjacent disciplines into marketing organizations.
Understand That Fundamental Marketing Principles Persist
Despite technological disruption, core tenets remain constant: understand your market to do marketing effectively, know your ICP deeply, and determine what to say, how to say it, and where to meet buyers. The difference lies in execution—programs, tactics, and campaigns must continuously evolve as buyer behaviors and consumption patterns shift with AI adoption.

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