The Insight Interviews - Powered by Rewire

Walter Crosby is the CEO of Helix Sales Development, helping growth-minded entrepreneurs build high-performance sales teams and drive repeatable revenue growth with margin integrity. He works with leaders frustrated by underperformance, guiding them toward a performance-based sales culture with transformative results. A University of Michigan alum with a degree from the School of Hard-Won Wisdom, Walter’s sales career spans B2B industries like LED luminaires, financial services, and commercial fire alarm systems. His expertise covers K-12 education, higher ed, contractors, and commercial firms. Known for his love of fine cigars, Walter often reflects in his private lounge and shares insights on sales and cigars as host of the Sales and Cigars podcast.

In this episode, Jason and Walter discuss:

• Align salespeople with company values through a tailored recruitment process
• Prioritize strong communication skills over industry experience in hiring
• Implement a unified "Sifter message" to align sales with marketing strategy
• Ensure effective onboarding and cultivate a self-motivated sales culture
• Insights from hosting a podcast that blends business strategies with cigar appreciation

Key Takeaways: 

• Sales success stems from a commitment to helping customers make informed decisions, emphasizing insightful questioning over traditional pitching.
• A tailored hiring approach prioritizes communication skills and cultural fit, ensuring alignment with target customers rather than focusing solely on industry experience.
• The foundation of a high-performing sales culture lies in effective onboarding, self-motivation, and goal alignment, fostering both individual and organizational growth.
• A salesperson’s values must align with the company’s culture, making the interview process a crucial two-way evaluation rather than a one-sided selection.
• By equipping salespeople with a clear "Sifter message" that integrates sales and marketing strategies, companies can enhance consistency and effectiveness in their sales efforts.

“Salespeople should be helping their customers. We should be helping them make better decisions. We should be helping them think differently about a problem they may have.”

 - Walter Crosby

Connect with Walter Crosby:

Website: https://helixsalesdevelopment.com/ 

LinkedIn: https://www.linkedin.com/in/walterlcrosby/ 

Connect with Steve and Jason:

LinkedIn: Jason or Steve

Website: Rewire, Inc.: Transformed Thinking 

Email: [email protected]

Show notes by: Angelo Paul Tagama

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it. 

Mahesh Guruswamy is a seasoned product development executive with over twenty years of experience in software development and more than a decade of managing teams of varying sizes. He is currently the Chief Technology Officer at Kickstarter and previously led product development teams at Mosaic, Kajabi, and Smartsheet. Inspired by his favorite author, Stephen King, Mahesh began his writing journey with short stories before discovering long-form writing as a powerful way to share insights with product development teams. His essays over the years culminated in his book How to Deliver Bad News and Get Away With It. Passionate about mentorship, Mahesh especially enjoys guiding aspiring people managers and those new to leadership roles.

In this episode, Jason and Mahesh discuss:

• Navigating difficult conversations as leaders through the book How to Deliver Bad News and Get Away With It
• Insights on business innovation, growth, and career risk-taking
• Importance of changing roles every two years for new challenges
• Strategies for delivering honest feedback with emotional intelligence
• Framing problems as collaborative puzzles for effective problem-solving

Key Takeaways: 

• Navigating difficult conversations requires a balance of emotional intelligence and long-term thinking, ensuring feedback is constructive rather than reactive. Leaders who approach tough discussions with empathy create environments where honesty leads to growth.
• A strategic approach to delivering feedback starts with open-ended questions and progressively increases in directness if issues persist, avoiding emotional language while presenting clear solutions.
• Career growth accelerates when individuals embrace calculated risks, change roles every two years for new challenges, and remain open to opportunities rather than instinctively rejecting them.
• Adaptability is essential in navigating career instability, as it demands identifying transferable skills, exploring entrepreneurship, and maintaining persistent networking to pivot effectively when needed.
• True fulfillment extends beyond financial success, emphasizing the importance of mentorship, altruism, and leaving a lasting positive impact on others as the ultimate measures of a meaningful life.

“I actually encourage people to take risks. The way I see it, life is short. If you have a goal in mind and are committed to achieving something, then take the risk. You have to roll the dice.”

 - Mahesh Guruswamy

Connect with Mahesh Guruswamy:

Website: https://www.maheshguruswamy.com/ 

LinkedIn: https://www.linkedin.com/in/maheshguruswamy/ 

Mahesh’s Book: https://www.amazon.com/How-Deliver-Bad-News-Away/dp/B0D7FHTTNN 

Connect with Steve and Jason:

LinkedIn: Jason or Steve

Website: Rewire, Inc.: Transformed Thinking 

Email: [email protected]

Show notes by: Angelo Paul Tagama

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it. 

Corey Morris is an experienced industry speaker, best-selling author, and the owner and leader of VOLTAGE digital marketing agency. His new book, The Digital Marketing Success Plan, was published in July 2024 and details why companies need a documented, objective, and accountable digital marketing plan in today's era of unprecedented change in the digital marketing industry. He provides the context for why having a plan is important, shares real stories, and includes "how-to" content for creating and implementing a plan, leveraging his five-step START Planning process.

In this episode, Jason and Corey discuss:

• Importance of strategic focus and aligning tactics with business outcomes
• Essentials of a defined strategy, articulated goals, and meaningful KPIs
• Explanation of the START framework and its role in digital marketing success
• Impact of AI on SEO, content creation, and audience engagement
• Balancing present strategies with future innovations and emerging technologies

Key Takeaways: 

• A well-defined strategy, clear goals, and meaningful KPIs serve as the foundation for effective marketing, preventing wasted investments and ensuring focused execution.
• The START framework emerges as a structured approach, guiding businesses through a five-step process to define, implement, and measure digital marketing success with precision.
• Rather than fragmented efforts, aligning marketing tactics with overarching business strategy is emphasized as the key to driving meaningful and sustainable results.
• A strategic balance is highlighted—leveraging proven successes while staying open to innovation ensures a future-proof digital marketing approach without sacrificing what already works.
• Optimizing CRM usage and integrating marketing efforts can yield substantial revenue growth, turning well-planned marketing spending into measurable success.

“The thing that doesn’t change is investing in quality content and understanding your audience. If you’ve just been leaning on some personas and your brand, it’s probably time to get deeper.”

- Corey Morris

Connect with Corey Morris:

Websites: https://voltage.digital/ , https://thedmsp.com/ 

LinkedIn: https://www.linkedin.com/in/coreymorris/ 

Corey’s Book: https://www.amazon.com/dp/B0D94Y2R13/ 

Connect with Steve and Jason:

LinkedIn: Jason or Steve

Website: Rewire, Inc.: Transformed Thinking 

Email: [email protected]

Show notes by: Angelo Paul Tagama

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it. 

Be ready to transform the way you think and lead! Let’s uncover the hidden power of mindset as the true driver of leadership excellence and breakthrough growth. Explore why mindset matters more than skillset, how self-care fuels performance, and the science-backed ways to reshape your thinking for success. Discover the power of curiosity in challenging assumptions, the impact of the iceberg model on behavior, and why being precedes doing so in the journey to personal and professional transformation. Let’s dive into the mindset shifts that lead to lasting results!

In this episode, Jason and Steve discuss:

• Mindset as the hidden driver of leadership excellence and growth
• Greater importance of mindset over skillset in personal and professional success
• Iceberg model and the impact of below-the-surface factors on actions and results
• Role of self-care in improving mindset, performance, and goal achievement
• Cultivating curiosity to foster a growth mindset and enable breakthroughs

Key Takeaways: 

• Mindset holds greater weight than skillset in determining both personal and professional success, shaping one's ability to navigate challenges and achieve breakthrough growth.
• Beneath every action and result lies a web of internal drivers—thoughts, emotions, past experiences, and deeply held beliefs—highlighting mindset as the unseen force steering visible outcomes.
• A closer look at mindset reveals three transformative factors: the iceberg model illustrating the power of the unseen, the interplay between being and doing, and the necessity of addressing below-the-line factors to enhance outward performance.
• Self-care emerges as a fundamental pillar of a strong mindset, reinforcing resilience, improving overall performance, and increasing the likelihood of long-term success across different professions.
• The pursuit of curiosity is positioned as a catalyst for growth, with open-ended questions, active listening, and continuous learning serving as essential tools to challenge assumptions and unlock new possibilities.

“If we're always right about everything in our own minds, curiosity becomes virtually impossible. So, curiosity helps me know I'm not always right about everything, and it allows me to listen.”

- Steve Scanlon

Connect with Steve and Jason:

LinkedIn: Jason or Steve

Website: Rewire, Inc.: Transformed Thinking 

Email: [email protected]

Show notes by: Angelo Paul Tagama

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it. 

Jordan Burton brings 17 years of expertise in executive assessment and interview training, helping top VC/PE investors and high-growth startups hire the best of the best. He has trained over 3,000 executives and investors on hiring strategies and interview techniques. As the head of business development at Talgo, he manages relationships with industry leaders like Sequoia Capital, TH Lee, Insight Partners, Twilio, and Scale AI, as well as over 50 venture-backed startups. Previously, he was a Partner at leadership advisory firm ghSMART, a consultant at Bain & Company, and earned his MBA from Harvard Business School.

In this episode, Jason and Jordan discuss:

• Creating a comfortable interview environment to encourage open sharing
• Strategies for young professionals to avoid hiring mistakes
• Approaching candidates with an open and curious mindset for objective evaluations
• Benefits and risks of informal assessment techniques like lunch with employees
• Prioritizing an exceptional candidate experience to attract top talent

Key Takeaways: 

• A mindset of curiosity and openness transforms interviews into genuine conversations, allowing candidates to showcase their true potential without the constraints of premature judgments.
• Evaluating only role-relevant experiences ensures fairness in candidate assessments, making post-interview decisions more objective and data-driven.
• Crafting an exceptional candidate experience—through rapport, coordination, and clear communication—becomes a competitive advantage in attracting top talent.
• The ability to recognize the right talent fit is a skill honed through practice, coaching, and a willingness to hire individuals who may surpass one's own expertise.
• Long-term business success is built on talent development, not just individual competence, emphasizing the need for clear expectations, proactive hiring, and strategic redeployment of struggling employees.

“If you want to differentiate, have an outsized impact, and build an organization that achieves more than anyone expected, view yourself primarily as a talent builder and developer—that’s the job. When I hear the life stories of those who prioritize hiring exceptional talent, developing, coaching, and grooming great people, their careers are spectacular. They realize it’s not about them. They are comfortable hiring people better than themselves, and they are the ones who end up in the most important, high-impact roles.”

 - Jordan Burton

Connect with Jordan Burton:

Website: https://www.talgo.io/ 

LinkedIn: https://www.linkedin.com/in/jordanwburton/ 

Connect with Steve and Jason:

LinkedIn: Jason or Steve

Website: Rewire, Inc.: Transformed Thinking 

Email: [email protected]

Show notes by: Angelo Paul Tagama

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it. 

Stacey Hanke, a leader in influential communication strategies, began her career in voice-over work, where she learned the power of word choice and delivery. With over two decades of research, she realized that true influence isn’t about titles but about building trust and credibility through meaningful connections and communication. Stacey collaborates with Fortune 500 executives, helping them understand their impact from their audience’s perspective, eliminate distractions, and achieve greater success. As a Hall of Fame Speaker, Stacey’s engaging presentations provide practical strategies to overcome modern communication barriers, foster authentic connections, and inspire action.

In this episode, Jason and Stacey discuss:

• Transition from voiceover expert to executive communication coach
• Building client relationships through discipline and work ethic
• Techniques for improving communication and executive presence
• Importance of self-awareness and avoiding multitasking for trust-building
• Role of communication in shaping perceptions and influence

Key Takeaways: 

• Effective communication hinges on connecting with audiences from their perspective, emphasizing the importance of tailoring messages for meaningful impact.
• Discipline and a strong work ethic, cultivated from a young age, are pivotal for fostering enduring client relationships and professional success.
• Leadership influence is enhanced through targeted techniques like videotaping interactions, addressing blind spots, and refining executive presence to shape corporate culture.
• Trust and consistent influence are built through brevity, eye contact, congruent body language, and maintaining a steady presence, whether in virtual or in-person settings.
• Elevating communication skills, personal branding, and influence requires self-awareness, commitment to improvement, and effective leveraging of feedback and resources.

“You can be the smartest person in your industry. You can have the biggest heart to be the kindest to the people in your network. If people don't perceive you that way because of what you're saying and how you're delivering the message, that's what they connect with.”

 - Stacey Hanke

Connect with Stacey Hanke:

Website: https://staceyhankeinc.com/ 

LinkedIn: https://www.linkedin.com/in/staceyhanke 

Facebook: https://www.facebook.com/StaceyHankeInc 

Instagram: https://www.instagram.com/staceyhankeinc/ 

Twitter: https://x.com/staceyhankeinc 

Stacey’s Books: https://staceyhankeinc.com/shop/ 

Connect with Steve and Jason:

LinkedIn: Jason or Steve

Website: Rewire, Inc.: Transformed Thinking 

Email: [email protected]

Show notes by: Angelo Paul Tagama

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it. 

Chad Foster is a motivational keynote speaker, sales/finance leader, and inspirational change agent who works at Red Hat/IBM. He was the first blind executive to graduate from Harvard Business School’s Program for Leadership Development and has been featured with NBC, CBS, Forbes, the Atlanta Journal-Constitution, USA Today, and Chief Executive Magazine.

After losing his eyesight while attending college in his early twenties, Chad started at a top consulting firm and has built a career in the technology industry, directing financial strategies and decisions resulting in more than $45 billion in contracts.

Determination, ambition, and resilience are the key drivers of his incredible journey. The Atlanta Opera has commissioned an opera inspired by his life story and his first book, Blind Ambition: How to Go from Victim to Visionary. Today, Chad speaks to corporate audiences and professional athletes, helping them develop resilience and overcome their own blind spots.

In this episode, Jason and Chad discuss:

• Overcoming blindness to build a billion-dollar tech career
• Power of gratitude in rewiring the brain and finding happiness
• Misconceptions about blindness and fostering patience and comfort
• Role of family support and resilience in facing adversity
• Pursuing ambitious goals through discomfort and incremental growth

Key Takeaways: 

• Gratitude emerges as a powerful tool for rewiring the brain and fostering a deeper appreciation for life's blessings, emphasizing the importance of daily practice.
• Resilience and discipline are highlighted as vital in overcoming hardships, with loved ones playing a pivotal role in providing support and encouragement.
• Embracing discomfort and viewing failure as a stepping stone reflect the transformative potential of continuous growth and incremental progress.
• An ambitious vision is essential, encouraging bold actions even without certainty, while failure is a natural aspect of innovation and exploration.
• The pursuit of purpose is framed as finding meaning through service to others, cultivating empathy, and inspiring intentionality and happiness in their lives.

“So, blindness taught me how to live a happier life. It taught me that success, similarly, is not some sort of destination that we arrive at. It's a way of thinking, it's a way of being. You know, it's not an event. It's a mindset.”

 - Chad Foster

Connect with Chad Foster:

Website: https://chadefoster.com/ | https://chadefoster.com/insightinterviews/ 

LinkedIn: https://www.linkedin.com/in/chadfoster/ 

Facebook: https://www.facebook.com/FindChadEFoster 

Instagram: https://www.instagram.com/FindChadEFoster 

Twitter: https://x.com/ChadEFoster 

Chad’s Book: https://chadefoster.com/book/blind-ambition/

Connect with Steve and Jason:

LinkedIn: Jason or Steve

Website: Rewire, Inc.: Transformed Thinking 

Email: [email protected]

Show notes by: Angelo Paul Tagama

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it. 

Are you prepared to lead through chaos and navigate the challenges of a volatile, uncertain, complex, and ambiguous (VUCA) world? Let’s explore how intentional community, authentic connection, and decisive action can help counter isolation and drive meaningful progress. Discover why coming together, even in the messiest or most uncomfortable moments, is key to thriving amidst uncertainty. Let’s uncover practical strategies to foster collaboration, build resilience, and lead with purpose in turbulent times!

In this episode Jason and Steve discuss:

• Navigating the challenges of a volatile, uncertain, complex, and ambiguous (VUCA) world
• Strategies for finding flow and avoiding chaos amidst turbulence
• Acknowledging reality and naming challenges to address them
• Importance of taking action without seeking perfection
• Role of community and collaboration in countering isolation during adversity

Key Takeaways: 

• The modern world is marked by volatility, uncertainty, complexity, and ambiguity (VUCA), presenting unique challenges in maintaining stability and achieving goals.
• The VUCA concept itself often triggers negative emotions, as understanding its pervasive nature can intensify feelings of turbulence.
• Success in a VUCA environment depends on acknowledging reality and focusing on practical steps toward goal achievement rather than becoming overwhelmed by chaos.
• Decisive actions, naming challenges to confront them, and fostering connections with others are vital strategies for thriving in uncertain times.
• Teams that work together and lean on community support demonstrate how collaboration can counterbalance isolation and strengthen resilience during adversity.

“Whatever your definition of coming together and being in community—whether it’s a regular cadence of communication, a big meeting, gathering people, or even just a simple five-minute phone call—you will tend to do better with that scenario than isolating yourself. Even if it’s embarrassing, messy, or hard to admit, you will always be better in community than in isolation.”

- Jason Abell

Connect with Steve and Jason:

LinkedIn: Jason or Steve

Website: Rewire, Inc.: Transformed Thinking 

Email: [email protected]

Show notes by: Angelo Paul Tagama

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it. 

Leslie Shreve is a workload management and productivity expert, and the Founder and CEO of Productive Day®. Leslie is also the creator of Taskology® The Science of Getting Things Done, an all-encompassing system for managing tasks, time, email, information, and more. For more than 20 years, Leslie has worked with corporate leaders and professionals from more than 30 different industries to show them how to increase efficiency and productivity by 4X, gain 1-2 hours back in their workday, spend up to 50% less time in their email Inbox, and make more powerful progress on projects—WITHOUT giving up all of their personal time to do it.

In this episode, Jason and Leslie discuss:

• Streamlining organization and eliminating wasted time with the Taskology system
• Effective task management strategies for reducing overwhelm and improving focus
• Email management best practices for maintaining a zero inbox and productivity
• Aligning time blocking with prioritized tasks for productive workdays
• Impact of productivity processes and workload management on goal achievement

Key Takeaways: 

• Taskology emerges as a game-changing system that eliminates wasted time by streamlining the organization and protecting calendars through strategic time blocking.
• The importance of aligning time blocking with prioritized tasks is emphasized, advocating flexibility to adapt to changing demands.
• Breaking down large projects into smaller, actionable steps using the "next action" strategy proves to be an effective method for reducing overwhelm and maintaining focus.
• Effective email management, including deciding email usefulness and maintaining a zero inbox, prevents critical tasks from slipping through the cracks and promotes efficiency.
• Productivity is shaped not just by the work itself but by the systems and processes in place, highlighting the vital role of workload management in achieving goals.

“Your workday isn’t just about what you do best—it’s also about how you’re working. If your processes—task management, email management, information management—aren’t running smoothly, they’re like a ball and chain stealing your time and productivity. That’s holding you back from your goals, whether it’s less stress, more sleep, or time with family. Productivity isn’t just in the work—it’s in the how of your day. Let’s fix that and get your time back.”

 - Leslie Shreve

Connect with Leslie Shreve:

Website: https://productiveday.com/ 

LinkedIn: https://www.linkedin.com/in/leslieshreve/ 

Email: [email protected] 

Connect with Steve and Jason:

LinkedIn: Jason or Steve

Website: Rewire, Inc.: Transformed Thinking 

Email: [email protected]

Show notes by: Angelo Paul Tagama

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it. 

Tatyana Mamut is the Founder & CEO of Wayfound.ai, helping companies unlock ROI with AI agents. A transformative Silicon Valley leader since 2001, she has driven innovation through major tech shifts, shaping products at AWS, Salesforce, Nextdoor, Pendo, and IDEO. An award-winning visionary with several technology and design patents, Tatyana also serves on company boards and advises startups and investment funds. She holds a PhD in economic anthropology from UC Berkeley and a BA in economics from Amherst College. A Ukrainian refugee, she now lives in San Francisco with her spouse and daughters.

In this episode, Jason and Tatyana discuss:

• Influence of human culture and behavior on economic realities and AI evolution
• Generative AI systems as evolving non-carbon substrates and their impact on institutions
• Role of responsible leadership in shaping AI-driven technological transformation
• Wayfound’s no-code tooling enabling companies to build and manage AI agents
• Importance of adopting generative AI strategies to meet investor and board expectations

 Key Takeaways: 

• Human culture and behavior significantly shape economic realities and AI's transformative potential, emphasizing the need for leadership that embraces this paradigm.
• The emergence of AI breakthroughs highlights the importance of building responsible platforms and experiences that redefine humanity's evolution and societal structures.
• With billions of AI agents acting as workforce and customers, leaders must rethink traditional business models and design strategies for agent-to-agent interactions.
• Companies like Wayfound are bridging the AI-driven future by enabling businesses to create and manage AI agents while aligning them with organizational values.
• A solid generative AI strategy is essential for maintaining competitiveness and unlocking tangible ROI, driving value beyond operational efficiency in a rapidly evolving landscape.

“ROI isn’t just about short-term operational metrics—it’s about the impact on your stock price if you don’t act. The real cost of not having a solid AI strategy and starting this journey now is a potential hit to your company’s overall value.”

 - Tatyana Mamut

Connect with Tatyana Mamut:

Website: https://www.wayfound.ai/ 

LinkedIn: https://www.linkedin.com/in/tmamut/ 

Connect with Steve and Jason:

LinkedIn: Jason or Steve

Website: Rewire, Inc.: Transformed Thinking 

Email: [email protected]

Show notes by: Angelo Paul Tagama

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.