Podcast Summary: The Exit Five CMO Podcast

Episode: How to Evolve as a CMO: Navigating New Markets, Personas, and Business Models
Host: Dave Gerhardt
Guest: Kady Srinivasan (CMO, you.com)
Date: August 25, 2025

Overview

Host Dave Gerhardt welcomes Kady Srinivasan, a seasoned marketing executive and current CMO at you.com, for an in-depth discussion on how to successfully evolve as a CMO. They dive into Kady's unique path through various industries and business models—including B2C, gaming, SaaS, and now AI—exploring the universal principles behind her successes, key strategies for aligning with company strategy, driving cross-functional change, building modern marketing teams, and how AI is transforming the CMO role and marketing playbook for 2025 and beyond.

Detailed Breakdown & Key Insights

1. Kady's Career Journey: Reinvention & Learning

• Kady describes herself as a “failed software engineer turned reluctant marketer,” highlighting her transition from engineering to B2C marketing before landing in gaming, tech, SaaS, and AI spaces.
  • (03:25) Quote: “I'm a failed software engineer turned reluctant marketer, and I can talk about why all of those things happened.” – Kady
• Early roles included B2C product marketing for Walmart and games for Ubisoft, Electronic Arts (“my name is on the FIFA mobile app...and Plants vs. Zombies”—05:01).
  • She shares how these diverse experiences forced her to reinvent herself every few years.
• Kady’s moves: Gaming → Dropbox (tech) → Klaviyo (email/SaaS), driving ARR from $150M to $600M, → Lightspeed (public SaaS/Fintech, where she changed ICP and doubled market share) → you.com (AI infrastructure).
• Her approach is adaptive: “Every single year, it's like, oof. This is a whole new era of marketing that I have not been exposed to. So it's been kind of fun.” (03:35)

2. What is you.com? Navigating the AI Landscape

• you.com is an “AI infrastructure company” for building and deploying custom enterprise agents. The company is about four years old.
• Funny story: The domain you.com was originally owned by Marc Benioff and given to the company’s founder (08:00).
• Kady remarks on the dizzying pace of change in the AI infrastructure world—“things are changing crazily every hour it seems like things change.” (06:56)

3. From Public SaaS to Startup AI: The Evolving CMO Role

• Kady left a senior executive role at Lightspeed with intention to try entrepreneurship, but landed at you.com to get more “zero to one” early stage experience (09:32).
• She reveals many CMOs have an entrepreneurial itch and need to be both innovative and highly adaptive—the AI era “requires extremely different economics, different everything growth trajectories compared to SaaS.” (11:24)

4. Universal Principles of Great Marketing Leadership

A. Master the Fundamentals

• Storytelling & Customer Connection:
  • Job 1 for any CMO is “a stronger storytelling about what the company does or connect the product better to customers...understand the job to be done...craft a story and narrative...that connects the product to the market.” (13:29)
  • The “principles are all the same across the board.”
• Demand Creation:
  • Most companies have some balance of inbound, outbound, and partner motions.
  • Marketers must understand how to support each motion differently:
    • Inbound (paid ads, website, SEO, content) vs. Outbound (field sales, sales enablement, market targeting). (13:29–15:33)
• Aligning with Company Strategy:

  • A key up-level from VP to CMO: “A CMO is helping drive the company strategy...so that then you can link the marketing strategy to the corporate strategy.” (16:13)

    Quote: “Take a step back, don't be too involved in the day to day, help the company think about the bigger market. The company strategy overall.” – Kady (17:44)

B. The ICP Pivot at Lightspeed (Case Study)

• Kady details how a deep dive into customer/product fit revealed misalignment:

  • Product features like advanced inventory management appealed to complex, multi-location restaurants (Michelin star, multi-million dollar revenue) rather than small merchants.

  • After identifying this, the go-to-market strategy was rebuilt for this true ICP, aligning marketing, sales, and product roadmaps.

    Quote: “We were trying to sell this really amazing portfolio of features...to people that just need something super quick and dirty. There's a clear misalignment here around who our ICP is.” (20:01)

• She emphasizes that such pivots are company-wide transformations, not just marketing shifts.

  Quote: “When you create and drive an ICP pivot, you have to make sure the sales team is aligned, your customer success is aligned, product teams are aligned. So in essence, you become the quarterback of digital transformation.” (22:18)

C. Letting Go to Lead: Executive Mindset Shifts

• Kady shares practical (and personal) learning about leadership:

  • As teams scale, you must “let go of all of the details,” focus on vision, and embrace cross-functional partnership.

  • Set clear principles and grant autonomy to the team (24:45).

  • Dave relates with a story about moving from “doer” to “coach” as a marketing leader.

    Quote: “You need to know not only how to let go, but also you need to know how to set the right principles and the vision...Then at that point, you need to give people the autonomy to go do it.” (24:45)

• Use data wisely: “The data, absolutely the most critical thing, but it’s also super important to know what data to focus on.” (25:58)

• Kady's team systems:

  • Weekly/Monthly business reviews tracking 10 core metrics
  • Quarterly roadmaps for each workstream
  • Postmortem every quarter
  • Marketing “red threads”—core truths and product themes to stay consistent in messaging (30:00)

5. The Playbook Fallacy: There’s No One-Size-Fits-All

• Both agree: every company is a snowflake, requiring reinvention of the marketing motion, evaluating “what’s working, where’s demand coming from…you can’t just apply a playbook from the past.” (34:02–34:43)

AI & The Future CMO: Transformation in Progress

1. Effects of AI on the Marketing Organization

• Content Velocity & Relevance: AI tools enable fast generation of relevant, targeted content and hyper-personalized market research, if the right prompting and strategy are in place (42:51).
• Work Output: AI can empower tiny teams to “do more with less”—Kady compares the output and velocity of her ten-person team at you.com to that of 180 people previously at Lightspeed (36:50).
  • “This is a highly sensitive topic… I do not believe that AI is destroying jobs...we need higher and higher levels of multi-threaded marketers as we go forward.” (36:52)
  • The role of a marketing leader will evolve to “manager of agents, models, processes...not just humans.” (40:07)
• Creativity & Human Judgment Remain Paramount:
  • “AI is just going to amplify garbage thinking if you let it.” (38:58)
  • “It amplifies your creativity and your intelligence if you do it in the right way.” (41:49)
• The “Multi-Threaded Marketer”: Future marketers will be more “full stack,” able to strategize, prompt, generate, and deploy across channels—hiring roles like “prompt marketer” to build agents and workflows with AI. (39:34, 40:07)

2. The AI Marketing Playbook in Practice

• AI improves content creation, hyper-personalization, market research speed, and experimentation. Kady cautions, however, that good prompting and elbow grease matter more than ever.
  • “You have to put in the effort to come up with the right prompt...the more effort you put into creating the prompt and using it, the better off you are in the long term.” (42:51–45:11)
• The AI SDR Promise: While the market isn't quite there yet, Kady is bullish on the future of AI-powered, hyper-contextual outreach:
  • “If it's email that is very relevant to you in your personal context and that...is very clear in terms of the value proposition...then it does create the hook people are looking for.” (47:02)

3. Organizational Structure for “AI Native” Companies

• At you.com, Kady reorganized her team around outcomes (inbound, outbound, communications) rather than traditional silos, to support velocity and AI-powered shipping.
  • “I've completely changed the way I think about building a marketing organization because it's an AI first company. ...What I'm pushing everyone to do...is to just ship, use AI, ship faster, use as many tools as possible...” (49:36)
• Pressure to ship and scale quickly is echoed by AI founders referencing viral, hyper-growth companies—but Kady and Dave stress the fundamental impact of product-market fit.

Notable Quotes & Moments

• On Career Reinvention
  • “Every single job, every single year, it's like, oof...a whole new era of marketing that I have not been exposed to.” – Kady (03:35)
• On the CMO Job
  • “The difference between maybe a head of marketing or VP of marketing and CMO is...a CMO is helping drive the company strategy.” – Kady (16:13)
• On ICP Alignment
  • “We are trying to sell this really amazing portfolio of features...to people that just need something super quick and dirty. There's a clear misalignment...” – Kady (20:01)
• On Team Leadership
  • “You need to know not only how to let go, but also...how to set the right principles and the vision so people know what you want to get done.” – Kady (24:45)
• On AI’s Role
  • “AI is just going to amplify garbage thinking if you let it.” – Kady (38:58)
  • “Amplifies your creativity and intelligence if you do it in the right way.” – Kady (41:49)
• On the “Multi-Threaded Marketer”
  • “We need higher and higher levels of multi-threaded marketers as we go forward...Future managers may be managers of agents, models, processes—not just humans.” – Kady (40:07)

Timestamps for Key Segments

• Kady’s background & journey: 03:25–06:40
• What is you.com & AI domain story: 06:40–08:51
• Transition from Lightspeed/Public SaaS to AI startup: 09:25–11:24
• Foundational CMO principles & marketing playbook: 13:29–15:33
• Role of strategy & aligning with leadership: 16:13–18:57
• The ICP change at Lightspeed (case study): 20:01–22:26
• Letting go & leadership evolution: 23:24–25:12
• Building team systems/roadmaps/red threads: 25:58–30:39
• No universal playbook & assessing each business: 33:31–34:43
• AI and the new marketing playbook: 35:15–41:49
• AI’s impact on content, SDRs, and productivity: 42:51–48:42
• Structuring an “AI-first” marketing org: 49:36–51:26

Final Thoughts

Kady’s approach to the CMO role is a masterclass in cross-functional strategy, constant learning, and adaptive leadership. Her stories underscore that the fundamentals—storytelling, ICP focus, cross-functional alignment, and a sharp sense of strategy—are what empower marketing leaders to thrive, no matter the business model or how fast technology evolves. For the next generation of marketing leaders, the path involves letting go, thinking holistically, embracing new skills, and leveraging AI not just to “do more faster,” but to enhance the creativity and intelligence of lean, empowered teams.

Call to Action: Kady would love to hear from listeners—find her on LinkedIn and say hello!