Sunny Side Up Podcast

About Sunny Side Up Podcast

The Prompt is a podcast about the questions shaping the future before anyone agrees on the answers. Hosted by Rachel Truair, the show brings together operators, creators, analysts, academics, and unconventional thinkers for candid conversations that start with a simple prompt and spiral from there. Before the playbooks exist and consensus forms, The Prompt explores the ideas, tensions, and hot takes shaping what comes next in AI, work, brands, business, and human relevance.

Publisher

By Demandbase

Category

business

Language

en

Explicit

No

First episode

5 Apr 2018

Latest episode

29 Oct 2026

Latest episodes

2 of 597 episodes have a transcript.

1. 

   29 Oct 2026

   > Are founders becoming the last trusted institution? — Sydney Sloan

   A founder’s story is often a company’s first brand. It is easier to build, easier to believe and easier to trust than anything the company says about itself. Sydney Sloan joins Rachel Truair to ask what that means for the company, and for the founder, when the two become hard to tell apart. She explains why a company brand takes longer to earn trust than a personal one, why the pressure on founders has changed as expectations for growth speed up, and why a logo can feel less like a design choice than a piece of someone’s identity. They also get into how founders and the people around them work together: what good founders see that others miss, why co-founders and leadership teams matter, how to give a new idea a fair hearing without letting it derail the plan, and what a marketing leader should ask a founder before taking the job. The conversation ultimately asks who a company is really built around, and what happens to trust when the answer is one person. Quotes “It’s almost like renaming a child.” (on why a founder resists a rebrand) “For startup founders, their brand is almost more important than the company brand in the beginning.” “I think it’s just harder to build a trusting brand for the company than it is a personal brand.” From the conversation Why Sydney believes a founder’s personal brand can matter more than the company’s in the early days, how a founder story tied to the company’s purpose builds trust, and why that trust is earned in the founder’s own voice on social channels. Why a company brand is harder to build than a personal one, and what erodes trust along the way: inconsistency, too little investment in brand and turnover in marketing leadership. She points to Gong and Snowflake as brands that stayed consistent. How the pressure on founders has changed, from building a $100 million company in ten years to being expected to do it in two, and why Sydney starts with empathy but still argues founders should give their people psychological safety and a clear way of working. Why the people starting companies are getting younger, what experience adds that speed and ambition don’t, and why choosing investors and board members becomes a personal decision for a founder. What good founders see that others can’t: staying close to the problem and the customer, often as the company’s top salesperson, and why the best of them surround themselves with co-founders and leaders who balance their strengths. How Sydney helps a leadership team handle a founder’s next big idea: document the options, size them, choose together and write down what the company is choosing not to do. Her rule of thumb is three priorities, because more than that makes it harder to hit any of them, and the CEO still has the final call. What Sydney would tell a marketing leader working for a founder: ask how they think about marketing before taking the job, bring the customer’s voice into creative decisions, and take the founder along on any rebrand, because for many founders the brand is personal. About the guest Sydney Sloan is a four-time CMO, board member, and advisor who has led marketing at Salesloft, Drata, G2, and Alfresco.. Before that, she spent 17 years at Adobe across its enterprise and developer product lines. Today she's co-founder of the B2B CMO Project with Jon Miller, CMO Advisor at G2, Executive-in-Residence at Scale Venture Partners, and an LP at Stage 2 Capital, advising over 50 B2B founders and marketing leaders on go-to-market strategy, brand and demand, and building for the AI era. Connect with Sydney (https://www.linkedin.com/in/sydsloan/). Resources: The Growth Framework Model (https://www.scalevp.com/resources/growth-prioritization-matrix)

2. 

   8 Oct 2026

   > Is earning AI's trust just horse training with better software? — Mark Drosos, Conductor

   Horses don’t trust you because you tell them to. They learn from consistency, predictability and what you do over time. Mark Drosos, SVP of Channel Sales & Alliances at Conductor, joins Rachel Truair to explore why that idea has surprising implications for how brands show up in AI. As answer engines increasingly interpret, recommend and eventually select brands, simply creating more content or chasing citations will not be enough. They discuss why the best brand may still lose if AI does not see the right signals at the right moment, how “agent selectability” changes the role of content across the buying journey, and why brands may need to start thinking of AI agents as another audience, or even another member of the buying group. The conversation ultimately asks what happens when brands are no longer trying to earn credibility only from people, but from the machines increasingly helping people decide what to believe, what to buy and eventually what to do. Quotes “I want to own the consensus, not the source.” “Today, it only knows what you tell it to know. And not every consumer knows what to tell it.” “This selectability and this area of being mentioned and cited won’t be enough. You’re gonna have to be authentic about what you do eventually.” What we cover ● Why Mark sees an unexpected parallel between earning a horse’s trust and earning credibility with AI: both depend on consistency, predictability and repeated signals over time. ● Why AEO may follow the same evolution social media did, moving from trying to game a new channel toward genuinely earning the right to participate in the conversation. ● How Mark compares AI discovery to a horse-show flat class, where even the best horse can lose if the judge does not see it at the right moment, and why brands need the right message for different personas, topics and stages of the buying journey. ● What Mark means by “agent selectability,” and why the next challenge is not simply getting cited by AI but helping an agent understand the customer well enough to choose the right product for that person. ● Why AI recommendations still lack some of the verification signals consumers have learned to expect from reviews, influencers and other sources of third-party credibility, and why Mark believes authenticity will become increasingly important. ● Why Mark thinks companies should start treating the AI agent as a distinct audience, rethink how their content maps to personas and buying journeys, and prepare for a future where people increasingly ask and get rather than search and click. About Mark Drosos Mark established himself as a pioneer in human-generated data partnerships well before AI and Big Data dominated industry discussions. He currently leads global partnerships at Conductor, a leader in AI Search and Content Creation. He launched Lodestone, a platform leveraging AI and data to enhance fan engagement for sports franchises and media organizations. While at Bazaarvoice, he led the creation of syndicating premium user-generated content, powering Agentic Shopping Engines with authentic images, videos, and consumer reviews. Prior to Bazaarvoice, at Khoros, he managed the shift toward early chatbots and agents by overseeing the partnership and acquisition of Flow.ai. When Mark is not focused on AI partner ecosystems, his weekends are dedicated to being a horse show dad to his daughter and serving as the versatile "extra guy" for his wife's equestrian enterprise. From hauling horses to repairing well pumps, fences, trailers, and tractors, his hands-on approach to the “dirty jobs” at the barn has led his friends to jokingly call him the Mike Rowe of AI. LinkedIn: https://www.linkedin.com/in/markdrosos/ (https://www.linkedin.com/in/markdrosos/)

3. 

   24 Sept 2026

   > If AI does the entry-level work, who becomes the next expert? — Elizabeth Maxson, Contentful

   AI can make people productive before it makes them experienced. That creates a new problem for leaders: if junior employees stop doing the work that once taught judgment, where will the next generation of experts come from? Elizabeth Maxson, CMO of Contentful, joins Rachel Truair to explore what her team calls “judgment debt”—the long-term cost of automating away the experiences people use to build instinct, context and expertise. They discuss why Elizabeth still requires humans to write the brief, why knowing when AI is wrong may become more valuable than knowing how to use it, and why she believes leaders need a “human on the hook,” not simply a human in the loop. The conversation ultimately asks whether businesses can capture AI’s efficiency without accidentally dismantling the apprenticeship system that creates their future leaders. Quotes “You have to build judgment by actually doing the work and having lived experiences.” “I want to shift ‘human in the loop’ to ‘human on the hook,’ because if something does not work, who’s accountable? We are.” “Do you have enough expertise to know when it’s wrong? And if you don’t, do you at least have enough expertise to ask the question to figure it out?” From the conversation Why automating entry-level work could create a long-term shortage of judgment, skills and institutional knowledge, even if nothing appears broken today. How Elizabeth separates work AI should accelerate, such as analyzing large data sets and creating a “crappy first draft,” from the strategy, curiosity and accountability she believes should remain human. Why Contentful still requires humans to build detailed briefs, and why Elizabeth believes some organizations may need to “go slow to go fast” instead of treating speed as the objective. What “judgment debt” looks like when people rely on AI before they have enough experience to recognize when its answers are wrong, and why mentorship and human relationships still matter. How hiring may change when candidates use AI to produce excellent work: Elizabeth argues leaders should test the thinking, response to feedback and decision-making behind the output rather than simply banning the technology. About the guest Elizabeth Maxson is the Chief Marketing Officer of Contentful, a content management platform trusted by more than 4,200 companies around the world. Elizabeth brings nearly two decades of integrated marketing leadership to the role and is focused on driving marketing strategies that leverage AI and personalization to help brands deliver personalized and scalable content to their audiences. Prior to Contentful, Elizabeth served as the Chief Marketing Officer at Tableau, a Salesforce company, where she led go-to-market strategy and drove end-to-end marketing initiatives. In addition to her role at Tableau, Elizabeth has also served as the Head of Marketing at Quip, another Salesforce acquisition, as well as spearheaded Strategic Technology Partnerships marketing, launching critical relationships with industry giants such as AWS, Google Cloud, Alibaba, Apple, and many others. She carries a BAA in Facility Management and Marketing from Central Michigan University.LinkedIn: https://www.linkedin.com/in/emaxson/ (https://www.linkedin.com/in/emaxson/)

Inside a recent episode

Ep. 542 | Branding for sales success: Likeability, podcasts & B2B growth

Published 17 Jun 2025 · Transcript excerpt

[…] And somebody that's not legit, you're not going to, you're not going to damage your reputation by bringing someone on that could potentially do your customers harm or do your audience wrong. So number one, there's already a trust between me and you. We've already had a conversation off air. […]

Who has been a guest on Sunny Side Up Podcast

Names identified in recent episode analyses. Showing up to five guests.

• Dan Rosenberg
• Yas Dalkilic
• Yasemin Dalkilic
• Michael Miller
• Katie Skene

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

5 ratings

Spotify

4.9 / 5

30 ratings

Podcast Authority Score: 58 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

95

Social presence

0

YouTube

0

Engagement

51

Questions about Sunny Side Up Podcast