WTF Did I Just Read? Tech Sales & Marketing Edition

38. Pitch On The Pod + Fortresses of Security in Rapidly Evolving Threat Landscapes

In this episode of WTFDIJR, Chris and Dani are uncovering:
The nuances of effective communication between CISOs, their boards, and vendors. Dani and Chris discuss the importance of understanding the board's expectations and crafting narratives that align with business objectives. The episode also highlights a live pitch session, offering insights into developing technology pitches that resonate with CISOs and their boards.
Key Takeaways:
Understanding the Board's Expectations: CISOs need to understand their board’s preferences and expectations for presentations. This involves knowing the board's composition, their level of technical understanding, and their primary concerns.
Crafting Effective Narratives: When presenting to the board, CISOs should focus on creating narratives that align technology and security initiatives with broader business objectives. The communication should be clear, concise, and devoid of unnecessary technical jargon.
Role of Vendors in Board Presentations: Vendors should assist CISOs by providing key talking points and data that can be independently verified. This support should be concise, relevant, and tailored to the specific context of the board meeting.
Preparation and Research: Preparation is key for CISOs before board meetings. This involves not only understanding the board but also collaborating with internal teams and vendors to gather relevant information and potential solutions.
Importance of Independent Verification: Any data or claims presented to the board should be independently verifiable. This ensures credibility and trustworthiness in the eyes of the board members.
Aligning Tech Initiatives with Business Goals: The core of any presentation to the board should be how technology and security initiatives align with and support the company's broader business goals.
Effective Use of Metrics and Risk Assessment: Presenting clear metrics and a well-defined risk assessment strategy is crucial. This helps the board understand the impact and importance of security measures.
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37. We Have Sent You $0.01 USD. (The MOST Innovative Way To Reach Out.)

In this episode of WTFDIJR, Chris and Dani are uncovering:
Various outreach methods, emphasizing the importance of authenticity and respect in interactions. The episode also touches on the challenges faced by security practitioners in dealing with sales pitches and offers insights into building successful business cases for board meetings.
Key Takeaways:
Effective Sales Outreach: Dani highlights an ideal sales outreach message that was respectful, concise, and not pushy. This contrasts with other less favorable methods, showing the importance of tailored and considerate communication in sales.
Building Relationships with Buyers: Chris discusses the importance of trust and permission in sales interactions. He emphasizes that sales reps should not circumvent the main point of contact in an organization without explicit permission.
Navigating Corporate Budgets and Decision-Making: Dani and Chris explore how sales professionals can help security practitioners build internal business cases for purchasing decisions, including board presentations.
Authenticity in Sales and Marketing: The episode underscores the need for sales reps to be authentic and human in their approach, rather than relying solely on aggressive sales tactics or misleading outreach methods.
Understanding the Buyer's Perspective: Insights are shared on how CISOs and other decision-makers in tech companies think and make purchasing decisions, highlighting the need for sales and marketing professionals to align their strategies accordingly.
Importance of Research and Preparation: The episode reinforces the value of doing thorough research on potential clients and understanding their specific needs and timelines.
The Role of Empathy in Sales: Emphasizing the human element in sales interactions, Chris and Dani suggest that building genuine relationships can be more effective than traditional sales pitches.
Handling Rejection and Persistence in Sales: Dani and Chris discuss how sales professionals should respect boundaries and understand that persistence needs to be balanced with respect for the potential client's time and priorities.
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36. Pardon Me While I Exploit Your Vulnerable Feelings For Clicks

In this episode of WTFDIJR, Chris and Dani are uncovering:
The ethical implications of journalism and content sharing, particularly in the context of the October 7 terrorist attacks in Israel. They delve into the misuse of personal social media posts by a news site, questioning the journalistic ethics of not seeking consent and the potential harm caused by such actions. The episode also touches on the broader issues of misinformation, disinformation, and the responsibilities of media professionals.
Key Takeaways:
Ethics in Journalism and Media: Dani highlight the importance of consent and context when repurposing social media posts for news articles. They both stress that reposting content without permission can lead to misrepresentation and dilution of the original message.
Misinformation and Disinformation: The episode underscores the responsibility of media professionals to verify facts and present information accurately. They emphasize the need to challenge and correct misinformation and disinformation, especially in sensitive situations.
Impact of Emotional Content: Dani shares a personal experience of how her LinkedIn post, expressing deep emotions about the attacks in Israel, was used without her consent in a news article. This misuse of content highlights the fine line between sharing news and exploiting personal sentiments.
Responsibility Towards Audience: Dani and Chris discuss the duty of media outlets to provide timely, accurate, and respectful information to their audiences. They point out that journalism should be based on empathy and understanding of the human aspects of stories.
Personal Impact and Response: Dani expresses her discomfort and the steps she took to address the issue, including contacting the writer and the media outlet. They advocate for open communication and accountability in journalistic practices.
Support and Solidarity: The episode concludes with a call for unity and support for those affected by the terror attacks in Israel. They encourage listeners to stand against terror and support the Israeli community through donations and moral support.
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35. Feel Free To Ignore This Or Tell Us To F*** Off

In this episode of WTFDIJR, Chris and Dani are uncovering:
The challenges of enterprise sales, especially when dealing with internal conflicts and rivalries within client organizations. The episode also touches on the approach and ethics of sales outreach, effective communication strategies, and the importance of empathy and understanding in building client relationships.
Key Takeaways:
Navigating Internal Conflicts in Client Organizations: Chris and Dani uncover unspoken rivalries or conflicts within client organizations.
Sales Outreach and Communication: They suggest the approach to outreach should be respectful and research-driven; avoid using generic messages or irrelevant language. Understand the client's needs and tailor your communication to address those needs effectively. Sales reps should avoid misrepresenting the length of meetings or interactions in outreach efforts.
Utilizing Dungeons & Dragons (D&D) for Business: Chris and Dani reminisce on D&D and how it can be an effective tool for business scenario planning and team building. It allows participants to practice decision-making, problem-solving, and adaptability in a controlled environment. The idea of using D&D in business contexts emphasizes the importance of creativity and thinking outside the box.
Ethics in Sales Practices: They explain that sales professionals should maintain ethical standards and respect the audience's boundaries. Misusing platforms or audience lists for unsolicited outreach is discouraged.
Dealing with Sales Rejection and Persistence: The episode covers how sales reps should learn to recognize when to persist and when to step back in a deal. Understanding the client's buying cycle and respecting their timeline is crucial.
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34. Building A Kickass Relationship Capital Machine with Maria Graham

In this episode of WTFDIJR, Dani and special guest, Maria Graham, are uncovering:
Building genuine relationships, understanding customer needs, and navigating the complex world of tech sales. The episode covers the importance of personal connection in sales, leveraging social media platforms like LinkedIn for engagement, and the effectiveness of in-person interactions at conferences and events.
Key Takeaways:
Building Genuine Relationships: Maria and Dani prioritize forming a human connection before discussing business. Genuine curiosity about clients' needs and challenges leads to better engagement.
Leveraging LinkedIn and Social Media: Maria utilizes LinkedIn's Sales Navigator for targeted outreach. She suggests to engage with prospects' content on LinkedIn to establish recognition before direct outreach. Personalized messaging based on research is more effective than generic in-mails or messages.
Effectiveness of Conferences and Events: Dani and Maria agree networking at conferences and events often leads to more meaningful connections. In-person interactions allow for a better understanding of clients and their needs. The best business conversations often happen in informal settings, like after-hours events.
Understanding Customer Maturity and Needs: Maria and Dani recommend to tailor your approach based on the maturity and specific needs of the customer. Research prospects thoroughly to understand their industry, role, and company challenges. Ask relevant and probing questions to unpack vague responses and understand real pain points.
Navigating Challenges in Sales: They suggest to adapt to the changing landscape of tech sales, especially in a post-pandemic world. Focus on relationship-building rather than aggressive sales tactics. Utilize different communication methods (e.g., text messaging, social media) effectively.
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33. The ”Art” Of Email Marketing Perceptions That Piss Us Off

In this episode of WTFDIJR, Chris and Dani are uncovering:
The personal impact of constant traveling for tech conferences and the role of communities (both physical and digital) in the tech industry. The episode also touches on the challenges of navigating overwhelming workloads and personal life balance, and the importance of choosing the right events and communities for personal and professional growth.
Key Takeaways:
Personal Impact of Travel and Workload: Chris shares his experience with extensive traveling for conferences, highlighting the importance of balancing professional commitments with personal well-being. He emphasizes learning to say no and prioritizing engagements that are truly valuable.
Community Engagement in Tech: Chris and Dani discuss the characteristics of successful tech communities. They note that engagement, a sense of purpose, and the people involved are crucial elements. They stress the importance of contributing to existing communities rather than creating new ones.
Digital Communities: The episode explores the role of digital communities in the tech industry. Chris points out that effective communities are those with meaningful engagement, clear focus, and good management. He expresses a preference for communities that offer diverse viewpoints and challenge assumptions.
Email Marketing and Communication: Dani and Chris discuss the challenges and perceptions around email marketing in the tech industry. They emphasize the need for thoughtful, well-targeted email communication and the distinction between effective marketing communication and inefficient spam.
Learning and Information Gathering: Chris shares his approach to staying informed and learning new things in the tech industry. He relies on LinkedIn, podcasts, and YouTube for diverse and thought-provoking content, emphasizing the value of listening to different viewpoints and engaging with substantial discussions.
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32. Shame On Them. They Wouldn’t Have Gotten Breached With Us.

In this episode of WTFDIJR, Chris and Dani are uncovering:
The recent MGM breach and its implications for cybersecurity sales and marketing strategies. The episode emphasizes the importance of human connection in business interactions and discusses effective ways to approach potential clients, especially in the wake of security incidents.
Key Takeaways:
Empathy in Sales and Marketing: Dani and Chris underscore the importance of empathy in outreach to potential clients during crises. It's vital to prioritize human connection over aggressive sales tactics.
Value of Personal Interaction: The episode highlights the significance of face-to-face interactions and personal connections in establishing trust with clients. This includes understanding and respecting cultural and regional nuances.
Handling Outreach Post-Breach: Dani and Chris discuss appropriate ways to reach out to companies that have experienced a breach. Suggestions include offering practical help like food or coffee, and avoiding using the situation as a direct sales opportunity.
Podcast Invitations and Participation: Chris shares his perspective on accepting podcast invitations, emphasizing the importance of genuine, value-adding discussions over mere marketing opportunities.
Choosing Companies to Collaborate With: When deciding to collaborate with companies, Chris focuses on the people behind the brand, their track record, and whether they genuinely aim to effect change in the industry.
Dealing with Spam and Irrelevant Outreach: The episode touches on the inundation of spam and irrelevant outreach professionals often face, highlighting the need for targeted and thoughtful communication in sales.
Mental Health in the Industry: Chris and Dani briefly addresses the issue of mental health in the tech industry, acknowledging the stress and anxiety that professionals often deal with.
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31. Backstabbing, Disagreeing, and Committing in Organizations

In this episode of WTFDIJR, Chris and Dani are uncovering:
The theme of "disagree and commit," with a focus on how to navigate disagreements in a professional setting. The episode also touches on the challenges of communication and scheduling within the business context, especially in relation to CISOs and vendors.
Key Takeaways:
Disagree and Commit Philosophy: Chris emphasizes the importance of the ability to disagree yet commit to decisions for the greater good of the organization. This approach is vital in instances where consensus is unattainable, and decisions must still be made to move forward.
Strategic Communication: The episode highlights the need for effective communication tailored to the audience, whether it's C-level executives or other colleagues. This involves understanding perspectives, business needs, and conveying messages succinctly.
Scheduling and Follow-ups: Dani and Chris delve into the nuances of following up on warm introductions and scheduling meetings. Tips include providing multiple time options, using calendar links judiciously, and avoiding frequent reminders.
Vendor Relationships and Gifts: They discuss the dos and don'ts of vendor gifts, emphasizing practicality and thoughtfulness over extravagant or irrelevant items. They advise against gifts that lead to excessive marketing follow-ups or those that seem impersonal.
Platform Integration vs. Discrete Solutions: The episode briefly touches on the shift in the industry towards integrated platform solutions rather than discrete security point solutions, acknowledging the need for niche solutions in certain scenarios.
Understanding Seasons and Timings: Chris and Dani recognize the right time to reach out to professionals, especially considering their busy schedules and seasonal variations, is crucial for effective communication and networking.
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Quickly and easily submit an ineffective email, social media post, website landing page, event message, or digital ad to 📧 dani@wtfdidijustread.com. We will provide an alternative and better approach live on the show.

30. We Actually Survived 30 Episodes? Where Do We Go Now?

In this episode of WTFDIJR, Chris and Dani are uncovering:
Various aspects of the show, including past memorable moments, changes in their approach, audience feedback, and potential future directions. They engage in an open dialogue with their community, seeking suggestions for improvement and discussing the impact the show has had on listeners in the cybersecurity sales and marketing sector.
Key Takeaways:
Growth and Evolution: The podcast has evolved from a general discussion platform to a more focused dialogue on improving sales and marketing tactics, particularly in reaching out to CISOs. Dani and Chris note the shift from just highlighting problems to providing constructive solutions and advice.
Community Engagement: They emphasize the value of community feedback in shaping the podcast and discuss how audience participation has been instrumental in driving the content and format of the show.
Impact on Listeners: The podcast has reportedly been used as an onboarding tool for SDRs and sales reps, demonstrating its practical application in the real world.
Future Plans: Chris and Dani discuss the idea of introducing new segments, such as inviting guests to pitch to a CISO live on the show, which could add a practical, interactive element. They also talk about creating more structured formats for episodes, like using a "pain scale" analogy to assess sales outreach methods.
Challenges and Improvements: Dani and Chris acknowledge the need for better planning and possibly more structured preparation for the podcast, alongside expanding the distribution to audio streaming platforms.
Audience Participation: The episode features active participation from the audience, with suggestions ranging from the introduction of a mascot to more focused content on sales and marketing tactics.
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Victim of a crappy marketing or sales message?
Quickly and easily submit an ineffective email, social media post, website landing page, event message, or digital ad to 📧 dani@wtfdidijustread.com. We will provide an alternative and better approach live on the show.

29. Let’s Hit Up Every Single Team Member Inside the Company!

In this episode of WTFDIJR, Chris and Dani are uncovering:
The importance of timing in engaging CISOs, and how vendors can more effectively approach potential clients. They also touch on the structure and cycles of a CISO’s year, giving insights into when and how vendors should interact with them for maximum impact.
Key Takeaways:
Ineffective Sales Tactics: Chris and Dani emphasize the ineffectiveness of sales tactics that involve reaching out to every member of a company, highlighting experiences where this approach led to frustration rather than engagement.
Respecting the CISO's Schedule: Chris details the yearly cycle of a CISO, explaining that there are only specific times in the year when they are open to considering new vendors and solutions. Understanding and respecting this cycle is crucial for successful engagement.
Building Genuine Relationships: Dani and Chris advocate for building genuine, respectful relationships with potential clients, rather than using aggressive or dishonest tactics. They discuss the importance of being honest, providing value, and understanding the client's needs and constraints.
Post-Selection Engagement: Chris talks about the value of post-mortem meetings with vendors who weren’t selected, stressing that these should be opportunities for learning and improvement rather than attempts to renegotiate.
Effective Timing for Vendor Engagement: The best times for vendors to approach CISOs are during their planning phases, typically towards the end of the year and the start of a new one. Engagements outside of these periods are less likely to be successful unless they align with an immediate need or project.
Personal Experiences with Vendors: Chris shares his experiences with vendors like Nuspire and discusses how positive, ongoing relationships with vendors are built on mutual respect, efficient communication, and alignment of roadmaps.
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