Marketing’s Role in Training AI (and Teams) with Rachel Weeks.
In this episode of Executive Conversations, Maeva Cifuentes speaks with Rachel Weeks, former VP of Marketing.
Former VP of Marketing
Maeva CifuentesHost, Founder and CEO of Flying Cat
In this episode of Executive Conversations, Maeva Cifuentes speaks with Rachel Weeks, former VP of Marketing. Rachel shares her experience leading B2B SaaS marketing teams and how she’s adapting to the rapid rise of AI across GTM functions. She discusses why AI should be treated like a junior hire, not a plug-and-play solution, and why marketers today are responsible for training not just their teams but also their tools and their execs.
Rachel unpacks how leadership roles are shifting under PE influence, the blurred lines between marketing and sales, and how org structure impacts your ability to lead. She also reflects on how pressure to perform is rising faster than teams can realistically adopt AI, and why marketers need to stay grounded in strategy, not hype.
“You don’t have an AI strategy. You have a business strategy—and AI is just one part of how you execute it.”Rachel Weeks
What leaders can take from Rachel
- 1Simplifying executive communicationNatalie highlights the value of concise communication—focusing on context, desired actions, and outcomes—to drive executive decisions.
- 2Educating leaders on B2B marketingStrategies for effectively explaining B2B’s longer buying cycles and different KPIs to D2C-focused executives.
- 3Balancing sales input strategicallyHow to leverage sales feedback proactively without becoming an order-taker, using collaborative sessions to prioritize marketing activities.
- 4Choosing channels wiselyEmphasis on events, ABM, partnerships, and organic over paid channels in highly niche B2B markets.
- 5Immediate alignment and actionConducting early-stage workshops to quickly identify friction points and create actionable marketing strategies aligned with sales.
