The Unexpected Path to VP of Marketing: A Conversation with Russell Reams

Join us for a captivating conversation with Russell Reams, Vice President of Marketing and Client Services at Calligraphy. Russell shares his unique journey from early roles at Nabisco and UPS to leading marketing strategy, emphasizing that "marketing is the thread of everything I do".12

Russell dives deep into his lifelong passion for curiosity, learning, and the intersection of psychology and data science. Discover how his extensive academic background—including a doctorate in marketing and data science—fuels his data-driven approach to marketing strategy, which he simplifies as: "Follow the data".34567

Learn about: How Russell uses data and insights to help customers strategically grow and "future-proof" their business (by understanding the operating environment and innovation).

His experience launching the U.S.-based healthcare segment at UPS, operating under the tagline, "It's a patient, not a package". Why human psychology adapts to technology but remains a reliable constant for marketers.

Russell's perspective on the massive investment in AI and its current and future impact on the job market, data analytics, and the marketing industry. The surprisingly "low-tech" strategy (thought leadership and public speaking) that is currently driving the most success for Calligraphy. Russell’s advice for staying "future-proof" through lifelong learning, sharpening soft skills, and building a strong network.

Don't miss Russell's thoughts on the power of curiosity, the value of being the least smart person in the room, and his take on the future of business in the age of accelerating technology. Chapters

Learn more about Keaton Olson: https://www.linkedin.com/in/keatonolson/ Learn more about Russell Reams: https://www.linkedin.com/in/russellreams/

0:00 Future-Proofing Your Business

0:47 The Career Thread: From Nabisco and UPS to Calligraphy

1:29 Curiosity, Psychology, and Marketing

1:55 Working at UPS: Patients, Not Packages

3:20 Why Russell Pursued Academic Degrees

6:48 The Lifelong Learning Mindset

8:01 The "Smartest Person in the Room" Adage

10:07 Psychology in the Age of Accelerating Technology

13:49 AI in the Classroom and the Psychology of Efficiency

16:02 Efficiency and Strategy at Calligraphy

19:37 Oil Painting and Professional Juggling

21:56 Favorite B2B Marketing Strategy: Follow the Data

23:48 Outcome-Driven Nonprofits

27:48 Where AI is Headed and the Problem of "Work Slop"

33:07 Leveraging AI Safely for a Competitive Advantage

37:48 The Best Strategy Working Now: Low-Tech Thought Leadership

41:58 How to Personally Stay Future-Proof

From UN internships to HubSpot’s IPO to running a modern events + content agency. Nick Sal unpacks how he shifted from politics to social entrepreneurship, became an early HubSpot Academy leader, helped scale through INBOUND and partner ecosystems, and now builds high-impact webinars, field events, and customer storytelling programs.

We cover sales math (why “1 in 6” closes), offers that convert (audits and graders), culture at scale, and how AI accelerates B2B marketing without losing the human spark.

You’ll learn → How to productize “assessments” to turn interest into pipeline → What changed inside HubSpot from ~300 to 1,300 employees and IPO → The partnership motion: software + services “better together” → Sales tactics that shorten time to yes → Practical AI stack for decks, prompts, agents, and post-event content

Guest: Nick Sal, founder of Next Level Inbound; former HubSpot Academy leader Host: Keaton Olson

• Website: https://nextlevelnbound.com

• YouTube Channel: https://youtube.com/@visiontovibe-nsi

• All Links: https://linktr.ee/nicksal

• Gamma (AI deck builder): https://gamma.app

• MetaPrompt (Dharmesh Shah’s prompt optimizer): https://github.com/dharmesh/metaprompt

• Agent.ai (AI agent builder by Dharmesh Shah): https://agent.ai

• Riverside (remote recording studio): https://riverside.fm

• HubSpot Academy: https://academy.hubspot.com

• INBOUND Conference: https://www.inbound.com

• Website Grader: https://website.grader.com

• Drift / Salesloft Lineage: https://www.linkedin.com/in/keatonolson/

00:00 – Intro 00:30 – Nick’s path: PR intern → HubSpot Academy 01:19 – UN and State Assembly internships → entrepreneurship 03:30 – Discovering HubSpot and “idea whose time has come” 05:15 – Inside early HubSpot and Academy’s one-to-many model 06:22 – Paramify and HubSpot use 07:24 – What it felt like at ~300 employees 10:01 – Keaton’s Paramify startup story 11:38 – Why in-person years still matter in a remote world 15:14 – Scaling to ~1,300 and the IPO mechanics 18:01 – Negative churn, rebuilds & culture as a product 20:54 – Culture durability and founders’ role 24:42 – Going solo: skills, sales resilience & law of large numbers 29:41 – Content as sales ammo and social proof 34:13 – Sales math: why “1 in 6” closes & how to get to six 35:53 – Offers that convert: graders, audits & assessments 39:53 – Closing tactics: ask directly, bring in SMEs, start small 42:45 – Low-risk paid diagnostics to kick off 45:27 – How AI changed B2B marketing workflows 49:16 – Templates, research, invites & event ops with AI 55:00 – “Underground” tools: Gamma, MetaPrompt, Agents 1:01:16 – Agent.ai & HubSpot’s free-tool playbook 1:01:33 – Staying future-proof in the age of AI 1:07:49 – Wrap and where to find Nick

In this conversation, Yi, co-founder of Besimple AI, shares his journey from product management at Meta to founding his own AI company. He discusses the challenges and insights gained from his experience in the AI landscape, the importance of human elements in technology, and the evolving nature of workplace dynamics due to AI. Yi emphasizes the significance of building strong teams and relationships in entrepreneurship, as well as the need for continuous learning to stay relevant in a rapidly changing world.

Chapters: 00:00 Introduction to Yi and Her Journey 02:37 Understanding Be Simple AI 05:26 The Pain Points of Product Management 08:15 B2B Marketing Strategies for AI Companies 10:55 Adapting Marketing Strategies in a Changing AI Landscape 13:38 The Future of AI and Its Impact on Work 16:34 Favorite AI Tools and Their Applications 21:40 Exploring AI Tools and Their Applications 24:35 The Human Element in Automation 27:17 The Challenges of Achieving AGI 29:52 Building Relationships in a Digital Age 31:27 Lessons from Startup Failures 34:05 The Importance of Team in Startups 38:53 Advice for Aspiring Founders 39:33 Staying Future-Proof in a Changing World

Learn more about Yi: / yzhong94

Learn more about Besimple AI: https://besimple.com/

Learn more about Keaton: / keatonolson Learn more about Syntray: syntray.com

In this conversation, Tamerlan, co-founder and CEO of Armenta AI, shares his journey from being a commercial manager to leading an AI company focused on engineering compliance. He discusses the importance of compliance in the engineering sector, the expansion of his company beyond Kazakhstan, and the future of AI in government. Tamerlan emphasizes the role of AI in automating workflows and enhancing job creativity rather than replacing jobs. He also shares insights on effective sales strategies in government contracts, the significance of building relationships, and offers valuable advice for aspiring founders.

Learn more about Armenta AI: https://armeta.ai/ Learn more about Temirlan: https://www.linkedin.com/in/temirlan-rakhmetzhanov/ Learn more about Keaton: https://www.linkedin.com/in/keatonolson/

Chapters

00:00 From Commercial Manager to AI Innovator 02:53 Understanding Armenta AI's Mission 05:45 Navigating Compliance in Engineering 08:39 Expanding Horizons: Future Markets for Armenta AI 11:55 The Future of AI in Governance 14:39 AI's Role in Job Transformation 17:47 Essential AI Tools for Founders 20:49 Building Relationships in Government Sales 23:39 Marketing Strategies for Government Contracts 26:22 Advice for Aspiring Founders 29:29 Staying Future-Proof in a Rapidly Changing Landscape

In this conversation, Vincent Roberts shares his journey from a sales executive to the head of growth at US Digital Partners. He discusses the evolution of marketing strategies in the age of AI, emphasizing the importance of human connection in B2B relationships. Vincent highlights various AI tools that are transforming sales and marketing, and he reflects on the future of AI and its implications for businesses. The conversation also touches on the significance of trade shows and conferences in a digital world, as well as the value of soft skills in an increasingly automated landscape.

Learn more about Vincent: https://www.linkedin.com/in/vincent-roberts-194955112/ US Digital Partners: https://www.usdigitalpartners.com/ Vincent's favorite favorite AI tools: https://www.rb2b.com/ https://www.surfe.com

Chapters: 00:00 Introduction to Vincent Roberts and His Podcast Journey 03:39 Vincent's Career Path and Transition to US Digital Partners 08:09 Understanding US Digital Partners and Its Services 12:27 B2B Marketing Strategies and the Impact of AI 16:59 The Role of Content and Thought Leadership in Marketing 21:33 The Future of Podcasts in Marketing and Relationship Building 24:14 Human Interaction in a Digital World 27:16 The Role of Conferences and Trade Shows 30:33 Under-the-Radar AI Tools for Business 35:22 The Importance of Soft Skills in the AI Era 39:29 I am Future Proof Intro Concept-copy.mp4

She scaled Wix globally. Then jumped to cyber. Here’s the playbook.

I sat down with Diana Rabba, VP Marketing at AccessiWay (ex-Wix, Exein), to unpack:

• How to scale growth across 20+ markets without losing authenticity

• Brand + community as the B2B cheat code for pipeline

• Why AI isn’t magic, but a multiplier for senior talent

• What it really takes to stay “future proof” in marketing

Chapters

00:00 Diana's Journey in Marketing 02:52 Transitioning to Cybersecurity Marketing 06:07 B2B Marketing Strategies in Cybersecurity 08:57 The Impact of AI on Marketing 11:59 Favorite AI Tools for Marketing 15:07 Future of AI in Marketing 18:04 The Role of Humans in AI-Driven Marketing 20:56 Building Trust in B2B Marketing 23:58 Advice for Aspiring Marketers 27:00 Staying Future-Proof in Marketing

In this conversation, Eric Campos shares his journey into freelance marketing with a focus on cybersecurity and B2B SaaS. He discusses the challenges and rewards of helping businesses navigate the complex cybersecurity landscape, the importance of understanding niche markets like GRC, and how he leverages AI tools to enhance his content creation process. Eric emphasizes the need for authenticity and authority in marketing, and he reflects on the future of AI in the industry, advocating for a balanced approach that combines foundational skills with technological advancements. In this conversation, Keaton Olson and Eric Campos discuss the evolving landscape of marketing in the age of AI. They explore the importance of adaptability, empathy, and soft skills in a world increasingly dominated by technology. Eric emphasizes the need for marketers to stay informed about industry trends and to leverage content strategies that foster engagement and drive sales. The discussion also highlights the significance of continuous learning and the value of networking on platforms like LinkedIn and Reddit.

Learn more about Eric here: https://www.linkedin.com/in/eric-campos-875b0545/

Learn more about Keaton here: https://www.linkedin.com/in/keatonolson/

00:00 Introduction to Freelancing and Cybersecurity Marketing 02:28 The Appeal of B2B SaaS Marketing 05:19 Navigating the Cybersecurity Landscape 08:57 Learning Niche Markets: The GRC Experience 12:34 The Role of AI in Content Creation 17:47 Future of AI in Marketing and Content Creation 31:07 Navigating AI in Marketing 37:24 Essential Skills for New Marketers 46:08 Content Strategies and Engagement 52:05 Continuous Learning and Resources

The “Dead Internet” theory is no longer a theory. It’s happening.

I sat down with Sky Yang, founder of Imagine AI, for the first episode of my new podcast, "I Am Future Proof."

His take? As AI creates more and more content, our digital world is becoming a sea of generic noise.

So how do you stand out when everyone has the same tools?

You double down on being human.

Here’s what we covered:

☑ Authenticity is your new moat. When everyone sounds like a robot, a genuine, human voice becomes the ultimate competitive advantage. People are tired of corporate jargon; they trust real personality.

In-person matters more than ever. As the internet gets noisier, trade shows and face-to-face meetings become even more critical. Sky sees this in SF, and we see it at Paramify. Real connections close deals.

The most future-proof skill isn't technical. It’s an interpersonal connection. Your ability to build trust and communicate one-on-one is the one thing AI can't replicate.

We also talked about the single best piece of advice for any founder (The Mom Test) and the under-the-radar AI tools he uses daily.

Learn more about ImagineAI here: https://imagineai.me/ Learn more about Sky Yang: https://www.linkedin.com/in/skyyang/

The Mom Test clip i was talking about: • Exploring Joshua Baron's Transition to a R... at 47:30

Timestamps: 00:00 – Meet Sky Yang: CEO & Co-Founder of Imagine AI 00:40 – The “Aura Farming” LinkedIn Hook 01:08 – From Surfboards to AI Startups: The Founder Journey 03:39 – Why Personal Branding is the Future of Marketing 04:27 – Building a High-Fidelity Digital Persona 06:22 – The Vision: Your AI Twin Running Your LinkedIn 08:29 – Where AI is Headed in the Next 5 Years 11:32 – The “Dead Internet” Theory & Digital Twins 13:01 – Will In-Person Events Become More Valuable? 15:10 – Trade Show Hacks: How to Stand Out & Get Leads 17:22 – Imagine AI’s Event Strategy & ICP Targeting 18:39 – Sky’s Favorite Under-the-Radar AI Tool 21:43 – The Most Future-Proof Skill in an AI World 24:18 – Why Authenticity Beats Corporate Jargon 25:34 – Best Advice for B2B SaaS Founders 27:40 – The “Mom Test” & Avoiding Fluff Feedback 30:16 – Book & Essay Recommendations for Founders 32:14 – Sky’s Go-To AI Tools for Daily Work 35:33 – Fighting Content Burnout with AI 36:22 – AI Hype vs. What’s Actually Working 40:14 – How Sky Plans to Stay Future-Proof 42:19 – Dream Big, Set Goals, Go After Them