In Part 2 of my conversation with Kai Crayford, founderof a leading Web3 headhunting firm, we dive into the real-world challenges of building and scaling in the fintech, SaaS, and blockchain markets.

If you're a founder, GTM leader, or simply curious abouthow growth occurs in these complex spaces, this one's for you.

We cover:

- The challenges of selling fintech/SaaS to hedge funds,banks, and asset managers

- Why growth in crypto needs a shift from hype tosustainable business models

- How AI is reshaping GTM, business development, andoperational strategy

- The strengths of neurodivergent talent inhigh-performance teams

- What’s really happening in the blockchain space rightnow

- The art of building GTM teams, from founder-led salesto structured scaling

It’s an open, honest, and practical chat. Listen in andlet us know what resonates most.

#Fintech #Crypto #Web3 #GTM #AI #Blockchain#StartupGrowth #Neurodiversity #SalesLeadership #TechTalent

Show note links -

Austin Werner

Digital Clarity

TOKEN2049 DUBAI

In this conversation, Reggie James and Mark Cann explorethe intricacies of LinkedIn data analysis, focusing on the challenges of cold outreach and the effectiveness of messaging strategies.

Mark shares insights from his analysis of nearly 5,000 LinkedIn DMs, revealing key findings regarding message length, timing, and the significance of understanding the recipient's perspective.

They also discuss the innovative tool, Clay - which enhances go-to-market strategies by integrating various APIs for personalized outreach.

Chapters

1. 00:00 - Introduction to LinkedIn DM Analysis
2. 05:25 - Challenges in Cold Outreach
3. 12:19 - Key Findings from the LinkedIn Analysis
4. 17:24 - Exploring Clay: The Go-To-Market Tool

Key takeaways

• Cold outreach is becoming increasingly challenging due toAI advancements.
• Message length significantly impacts response rates;shorter messages often perform better.
• Timing matters; outreach is most effective on Mondays andTuesdays.
• Humor in messages can lead to higher engagement, butresults may vary.
• Understanding the recipient's problems is more effectivethan offering solutions.
• Clay is a powerful tool for marketers, akin to GoogleSheets but more advanced.
• APIs can be integrated into Clay for enhanced dataanalysis and outreach.
• Personalization in messaging is crucial for effectivecommunication.
• Segmenting your audience helps tailor messages todifferent personas.
• DMS should be viewed as conversation starters rather thanplatforms for extended discussions.

Sound Bites

• "Cold email is getting harder."
• "Personalization is key in outreach."
• "Segmenting your audience is crucial."

Links

Growth Warriors - https://www.growthwarriors.co/

Digital Clarity - https://digital-clarity.com/

Reggie James LinkedIn

Mark Cann LinkedIn

A Go-To-Market strategy is a tactical action plan that outlines how a company will present its products or services to the market to achieve a competitive advantage and meet business objectives.

It encompasses various aspects, including product positioning, pricing, distribution channels, and marketing tactics, all tailored to address the needs and preferences of the target audience.

The primary goal is to enhance the overall customer experience by offering superior products or services and creating a clear framework to penetrate a defined market effectively.

Origins of GTM

The concept of a structured approach to market entry has evolved over time. Whilethe exact origin of the term "Go-To-Market" is not distinctlydocumented, the practice of strategizing market entry dates back to the early 20th century, when companies began formalizing sales and distribution processes.

Over the decades, GTM strategies have transformed, adapting to changes in consumer behavior, technological advancements, and competitive dynamics.

These strategies have become more sophisticated in the digital age, integrating data analytics and customer insights to drive decision-making.

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Web: https://digital-clarity.com/

Twitter: https://x.com/reggie_james_

#GoToMarket #GTMStrategy #GTM #B2BMarketing #GrowthStrategy #B2BTech #TechSales #MarketingStratgey

In this episode, Reggie James sits down with Kai Crayford, founder of Austin Werner, a leading headhunting firm in the Web3 and Blockchain space.

They dive into the evolving landscape of recruitment for emerging technologies, the role of marketing in crypto, and the power of community building.

Kai shares insights on product market fit, the challenges of decentralization, and the strategic shifts in marketing for Web3 projects. Plus, they discuss the personal and professional impact of relocating to Dubai and how it shaped new opportunities in the crypto space.

Key Topics:
✅ The unique approach behind Austin Werner’s founding
✅ Why community-driven marketing is essential in Web3
✅ The shift toward product market fit before token launches
✅ How traditional marketing principles still apply in blockchain
✅ The role of decentralization in shaping future business strategies

Tune in for a deep dive into the intersection of tech, marketing, and recruitment in Web3!

🔗 Follow Autin Werner below for more insights into the future of crypto and blockchain.

LinkedIn

Discord

X

Facebook

Instagram

In this conversation, Mark Cann and Reggie James discussthe evolving landscape of B2B Marketing - emphasizing the need for modern strategies that resonate with today's buyers.

They explore the pitfalls of outdated marketing techniques, the importance of content and engagement, and the role of agencies. The discussion also covers the impact of private equity on marketing strategies, the significance of personal branding, and the value of community engagement through in-person events.

The speakers share insights on how companies can prepare for investment and the trends shaping the future of B2B marketing.

Takeaways

• B2B marketing advice is often outdated and siloed.
• Buyers prefer a non-linear, experiential buying process.
• Scale-ups should maintain agility while growing.
• Content needs to be diversified across multiple channels.
• Agencies may push their own specializations rather than tailored strategies.
• Private equity investments require quick results and cultural shifts.
• Personal branding is becoming essential for B2B leaders.
• In-person events for genuine connections and discussions.
• Community engagement is crucial for building trust and relationships.
• Continuous testing of marketing channels is necessary for growth.

Chapters

00:00 Introduction to Digital Strategy and Growth

02:28 Outdated B2B Marketing Techniques

05:55 The Importance of Content and Buyer Engagement

08:49 The Role of Agencies in B2B Marketing

10:30 The Impact of Private Equity on MarketingStrategies

14:47 Navigating Cultural Changes Post-Investment

16:49 Trends in Private Equity Investments

18:38 Preparing for Acquisition or Investment

20:39 The Rise of Personal Branding in B2B

24:45 The Value of In-Person Events

29:55 Community Engagement and Online Platforms

Links

Growth Warriors

Digital Clarity

Perspectives YouTube

Hyypa

Mark Cann - HYPPA

In this conversation, Chip Royce, founder of Flywheel Advisors, discusses the evolving landscape of B2B technology in 2025, emphasizing the need for adaptability in business strategies.

He highlights the importance of revenue operations and the integration of sales and marketing efforts. Chip also addresses the impact of technology, particularly AI, on business processes and the necessity for companies to simplify their go-to-market strategies.

The discussion concludes with insights on the challenges faced by founders in scaling their businesses and the importance of delegation. In this conversation, Chip Royce and Reggie James explore the evolving landscape of sales, particularly focusing on the dynamics of founder-led sales, the challenges faced by introverted founders, and the importance of building communities in B2B.

They discuss how buyer behavior has shifted, emphasizing the control buyers now have in the purchasing process and the necessity for ethical selling practices.

The dialogue highlights strategies for engaging with buyers effectively and the significance of understanding their pain points to provide meaningful solutions.

Key Takeaways

• 2025 will bring significant changes in B2B tech.
• Companies must be prepared to pivot and adapt.
• Revenue operations are essential for business success.
• Go-to-market strategies need to evolve with technology.
• Simplicity is key in business processes.
• AI tools can be misleading if not used wisely.
• Sales and marketing should work in tandem, not in silos.
• Founders must learn to delegate for growth.
• Technology should enhance human judgment, not replace it.
• Understanding customer needs is crucial for success. Founder-led sales can be powerful if channeled correctly.
• Introverted founders can succeed by leveraging their strengths.
• Building communities is essential for B2B success.
• Today's B2B buyers are more guarded and selective.
• Niche marketing is crucial to reach specific audiences.
• Ethical selling is about serving the buyer's needs.
• Understanding buyer pain points is key to effective selling.
• Community engagement can control the narrative in B2B.
• Video content is becoming increasingly important in marketing.
• The landscape of B2B buying is evolving with new generations.

Sound Bites

• "Rev ops is a requirement."
• "We are seduced by technology."
• "You've got to get out your own way."
• "The fix of the deal can be potent."
• "The geek shall inherit the earth."
• "You need to go where people are."
• "Community control the narrative."
• "Buyers are in control in 2025."
• "Integrity in sales is crucial."

------------------------------ Chapters

00:00Introduction to Chip Royce and Flywheel Advisors

03:07Navigating Challenges in B2B Tech in 2025

06:06The Importance of Revenue Operations

09:03Evolving Go-to-Market Strategies

11:58The Role of Technology in Business Strategy

14:46Bridging the Gap Between Sales and Marketing

24:19Navigating Sales Dynamics: The Role of Founders

28:11Introverted Founders: Strategies for Success

29:45Building Communities in B2B

34:59The Evolution of B2B Buyer Behavior

39:45The Importance of Ethical Selling

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#B2B #revenueops #gtm #marketingstrategies #AI, #businessgrowth #ChipRoyce #FlywheelAdvisors #salesstrategies #ReggieJames #DigitalClarity

In this conversation, Reggie James and Susi O'Neil discuss the rapid evolution of AI, discussing its implications for businesses and leadership.

They explore the challenges organizations face in adopting AI technologies, referencing a McKinsey report that highlights leadership failures in AI implementation.

The discussion shifts to the Stargate project and the competitive landscape of AI, particularly focusing on the emergence of DeepSeek as a significant player.

Susi emphasizes the need for a balanced approach to AI adoption, considering both the potential benefits and the risks involved, including issues of regulation and data privacy.

You can contact Susi here:

Substack Newsletter -https://rethinkhypecycle.substack.com/about

LinkedIn -

https://uk.linkedin.com/in/susioneill

BlueSky -

https://bsky.app/profile/susioneill.bsky.social

#SusiONeill #ReggieJames #PerspectivesPodcast #Perspectives #Ai #leadership