“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
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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.
In this episode, we talk about:
- Executive buy-in
- B2B marketing strategy
- Sales and marketing alignment
- Marketing leadership
- Buyer journey optimization
Takeaways
- Simplifying executive communication: Natalie highlights the value of concise communication—focusing on context, desired actions, and outcomes—to drive executive decisions.
- Educating leaders on B2B marketing: Strategies for effectively explaining B2B’s longer buying cycles and different KPIs to D2C-focused executives.
- Balancing sales input strategically: How to leverage sales feedback proactively without becoming an order-taker, using collaborative sessions to prioritize marketing activities.
- Choosing channels wisely: Emphasis on events, ABM, partnerships, and organic over paid channels in highly niche B2B markets.
- Immediate alignment and action: Conducting early-stage workshops to quickly identify friction points and create actionable marketing strategies aligned with sales.
Time chapters
[00:06] Introducing Natalie and her first official head of marketing role
[01:39] Starting from zero: building B2B marketing in a D2C-first company
[03:26] Structuring from chaos: formalizing sales-driven GTM efforts
[04:49] Explaining long sales cycles to short-term thinkers
[05:56] Choosing channels that actually move the needle
[07:03] Leading without precedent: influencing when no one understands B2B
[08:18] Streamlining communication for faster decisions
[09:51] Using audience context to tailor leadership messaging
[11:41] What changes (and doesn’t) in a more mature company
[12:24] Managing expectations in the age of AI speed
[13:49] Running five channels without stretching yourself thin
[15:34] Collaborating with sales to set the right priorities
[16:48] Running a friction workshop to map the buyer journey
[18:42] Turning sales feedback into a strategic roadmap
[19:31] Staying in control without shutting down ideas
[20:25] Picking your two best plays and executing them well
About Rachel
Rachel Weeks is a seasoned marketing leader with over 20 years of experience in high-tech industries, including more than a decade in HR technology. As the former VP of Marketing at MP, she combined her passions for marketing, leadership, and employee engagement. Rachel has collaborated with numerous HR leaders to develop and retain world-class teams, executing successful employee engagement strategies.