Episodes

  • Jon Lowe, Chief People Officer at DailyPay, on Workplace Transformation, Career Growth & Influencing the Future of Work

    Jon Lowe, Chief People Officer at DailyPay, on Workplace Transformation, Career Growth & Influencing the Future of Work
    Feb 17 2025
    HR isn’t what it used to be, and neither are career paths. In this episode, we sit down with Jon Lowe, Chief People Officer at DailyPay to explore the evolution of HR, the importance of self-awareness in career choices, and why adaptability is the key to success. From home improvement projects that went hilariously wrong to lessons learned in the workplace, we discuss how grit, intentionality, and accountability shape personal and professional growth. In this episode, we look at earned wage access, HR transformation, professional development, and career pivots—breaking down the unpredictable nature of the job market and how to find the right workplace fit. Whether you’re in HR, exploring new career opportunities, or just trying to navigate life’s unexpected turns, this conversation is packed with insights and laughs. Key Takeaways: ➡️ Home improvement projects can spark unexpected (and hilarious) neighbor disputes. ➡️ The role of HR is evolving—fast. ➡️ Self-awareness is critical in shaping career paths. ➡️ No two days in HR look the same. ➡️ Personal growth often comes from career pivots. ➡️ Humor makes even the toughest career lessons more bearable. ➡️ Workplace dynamics are changing, and adaptability is key. ➡️ Career paths are rarely linear—embrace the pivots. ➡️ HR titles and responsibilities are often misunderstood. ➡️ Family expectations can heavily influence career choices. ➡️ There’s a lack of real resources for career guidance. ➡️ Most people don’t end up working in their college major. ➡️ Finding work you enjoy is more important than chasing a title. ➡️ Grit and adaptability determine long-term success. ➡️ Building something meaningful beats maintaining the status quo. ➡️ Intentional career choices lead to better opportunities. ➡️ Self-reflection is essential for personal and professional growth. ➡️ Accountability is the backbone of career development. ➡️ The job market is always changing—flexibility is a must. Chapters 00:00 Building Projects and Neighborly Relations 05:01 Introduction to DailyPay and HR Evolution 10:00 The Changing Landscape of HR 12:50 Jon Lowe's Journey: From High School to Career 20:00 Self-Awareness and Career Choices 20:32 Navigating Career Choices and Education 23:00 The Journey from College to Career 29:01 Finding the Right Fit in the Workplace 35:12 Building a Career in Tech and Beyond 41:11 The Importance of Grit and Adaptability 46:52 Intentionality in Career Growth Connect with us here: 🔗 Connect with Jon Lowe: https://www.linkedin.com/in/lowejon/ 🔗 Connect with William Tincup: https://www.linkedin.com/in/tincup/ 🔗 Connect with Ryan Leary: https://www.linkedin.com/in/ryanleary/ Connect with WRKdefined on your favorite social network: 🔗 Site: http://www.wrkdefined.com 🎥 TikTok: https://www.tiktok.com/@wrkdefined 💼 LinkedIn: https://www.linkedin.com/company/wrkdefined 📘 Facebook: https://www.facebook.com/WRKdefined/ 🐦 Twitter (X): https://twitter.com/WRKdefined 📩 Substack: https://wrkdefined.substack.com 🔥 What’s your take? Is career success more about luck or grit? Drop your thoughts in the comments! Learn more about your ad choices. Visit megaphone.fm/adchoices
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    43 mins
  • Lara Abrash on Leadership, Decision-Making, and Career Growth at Deloitte

    Lara Abrash on Leadership, Decision-Making, and Career Growth at Deloitte
    Feb 10 2025
    Lara Abrash didn’t just climb the corporate ladder—she redefined the ascent. As Chair of Deloitte’s US firm, she leads one of the most influential professional services organizations in the world. But leadership isn’t just about strategy and governance; it’s about listening, making tough decisions, and preparing the next generation for success. In this episode, we dive into Lara’s career journey, the lessons that shaped her leadership style, and the pivotal role mentorship played along the way. She shares why listening is an active skill, why calculated risks drive innovation, and how personal fulfillment should be at the core of career decisions. From navigating the complexities of corporate governance to the evolution of mentorship in a fast-changing business world, Lara offers an unfiltered look at what it takes to lead at the highest level. Key Takeaways Lara Abrash is the Chair of Deloitte’s US firm, overseeing governance, risk management, and long-term strategy. Effective decision-making hinges on understanding trade-offs and seeking diverse perspectives. Leadership isn’t about just managing—it’s about vision, impact, and preparing the next generation. Listening is a skill that requires active engagement, not just hearing. Corporate culture thrives when leaders embrace calculated risks and innovation. Personal experiences shape leadership styles—Lara’s mother was a key influence on her career aspirations. Deloitte fosters an apprenticeship mentality, emphasizing mentorship and continuous learning. Career fulfillment should be a guiding principle in professional decision-making. The ability to pivot and stay curious is crucial in today’s leadership landscape. The distinction between management and leadership requires a mindset shift from execution to strategy. Trusted leadership is essential for navigating uncertainty and change. Stewardship isn’t optional—leaders must actively prepare the next generation for success. Chapters 00:00 Who is Lara Abrash and Deloitte 02:52 The Role of the Chair at Deloitte 05:59 Navigating Decision-Making in a Complex Environment 09:00 The Importance of Listening as a Leader 11:58 Personal Influences and Early Aspirations 15:00 Career Journey and Growth at Deloitte 18:58 Navigating Corporate Culture and Personal Growth 21:10 The Importance of Fulfillment in Career Choices 22:48 Understanding the Art of Accounting 25:37 The Role of Leadership vs. Management 28:06 Transitioning from Manager to Leader 35:07 The Evolution of Mentorship 38:47 Key Ideas for Aspiring Leaders 42:04 Stewardship and Future Leadership Connect with WRKdefined on your favorite social network 🔗 Site: http://www.wrkdefined.com 🎥 TikTok: https://www.tiktok.com/@wrkdefined 💼 LinkedIn: https://www.linkedin.com/company/wrkdefined 📘 Facebook: https://www.facebook.com/WRKdefined/ 🐦 Twitter (X): https://twitter.com/WRKdefined 📩 Substack: https://wrkdefined.substack.com/ 🔥 Share your brand across the WRKdefined Podcast Network: https://wrkdefined.com/work Learn more about your ad choices. Visit megaphone.fm/adchoices
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    46 mins
  • Revolutionizing Leadership Development with AI with James Cross, Tenor

    Revolutionizing Leadership Development with AI with James Cross, Tenor
    Feb 3 2025
    James Cross’s career has been anything but linear. A musician turned teacher turned tech entrepreneur, he’s spent years figuring out how to make learning more engaging, scalable, and effective. Along the way, he’s explored how AI can transform leadership development, making personalized coaching accessible to the next generation of managers. Here's a quick breakdown: https://www.tiktok.com/@wrkdefined/video/7465459318578482462 In this episode, we look at football, e-learning, AI, leadership development, skills training, music education, technology, corporate training, personal journey, innovation, education, video technology, startups, corporate culture, business strategy, and employee engagement. James breaks down how startups can stay focused, why video is reshaping education, and the real-world challenges of scaling AI-powered learning solutions. Key Takeaways AI is reshaping the e-learning and leadership development landscape. James Cross’s journey spans music, teaching, and tech entrepreneurship. The Liverpool vs. Everton rivalry is deeply woven into family traditions. Personalized coaching is critical for making managers more effective. Startups must focus on a clear audience to survive and thrive. Skills training often struggles with real-world application in corporate settings. Video technology has revolutionized engagement in education. Strong team culture is essential for scaling leadership development. Classical music and AI share a common thread—experimentation. Strategic hiring can make or break a company’s success. AI-driven leadership tools can accelerate the growth of emerging leaders. Adaptability and execution separate good ideas from actual impact. Connect with James here: https://www.linkedin.com/in/jamesrcross/ Connect with William Tincup LinkedIn: https://www.linkedin.com/in/tincup/ Connect with Ryan Leary LinkedIn: https://www.linkedin.com/in/ryanleary/ Connect with WRKdefined on Your Favorite Social Network The Site | Substack | LinkedIn | Instagram | X | Facebook | TikTok Learn more about your ad choices. Visit megaphone.fm/adchoices
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    42 mins
  • Career agility, Joelle Smith, President of First Advantage

    Career agility, Joelle Smith, President of First Advantage
    Jan 19 2025
    Career agility isn’t just a buzzword—it’s the backbone of success. In this episode, Joelle Smith, President of First Advantage, dives into her journey from marine science to tech leadership. She reveals how learning agility, integrity, and hustle have fueled her path, offering insights on sales, mentorship, and thriving in male-dominated industries. In this episode, we look at podcast, career development, learning agility, college experience, sales, integrity, hustle, Joelle Smith, First Advantage, technology, diversity, mentorship, decision-making, leadership, business strategy, team culture, women in business, networking. Key Takeaways Agility is critical for navigating modern career paths. Hustle and ambition can open doors where experience might not. College builds a foundation of discipline and work ethic. Sales experience provides financial independence and business insight. Mentorship is a proactive journey—seek diverse guidance. Vulnerability in leadership builds trust and strong networks. Decision-making agility is key—pivot when needed. Team culture thrives on shared pace and ambition. Diversity in mentorship accelerates career growth. Passion and honesty are essential for lasting success. Networking builds bridges to unexpected opportunities. Progress trumps perfection in fast-paced industries. William Tincup LinkedIn: https://www.linkedin.com/in/tincup/ Ryan Leary LinkedIn: https://www.linkedin.com/in/ryanleary/ Connect with WRKdefined on your favorite social network: The Site | Substack | LinkedIn | Instagram | X | Facebook | TikTok Share your brand across the WRKdefined Podcast Network Learn more about your ad choices. Visit megaphone.fm/adchoices
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    51 mins
  • Offboarding Done Right: Alumni Networks and Employer Branding with Andrew Hamilton CEO at When

    Offboarding Done Right: Alumni Networks and Employer Branding with Andrew Hamilton CEO at When
    Dec 9 2024
    Offboarding isn’t just a goodbye—it’s a strategy. Andy Hamilton dives into why this often-overlooked process can make or break employer branding. We explore how When is redefining offboarding to foster strong alumni networks, improve team dynamics, and boost long-term organizational growth. In this episode, we look at offboarding, employee experience, employer branding, alumni network, career transitions, team dynamics, leadership, and startup challenges in the tech industry. From building transparent teams to balancing salesmanship with technical skills, Andy shares actionable insights that bridge the gap between career growth and business success. Key Takeaways: Offboarding is a critical yet neglected part of the employee lifecycle. A positive offboarding process strengthens alumni networks and enhances employer branding. Younger employees value respectful transitions and share their experiences widely. Financial costs of poor offboarding practices can hurt long-term growth. Leadership must assign a dedicated owner to the offboarding process. Transparency and communication are essential to team dynamics and retention. Founders need to align technical skills with sales credibility for startup success. Startups benefit from hiring committed engineers and fostering supportive cultures. Career growth in tech requires balancing coding skills and architectural insights. Co-founders should prioritize alignment and clear communication to navigate challenges. Transitioning business models can open up new revenue streams. Entrepreneurs must adapt to market changes and remain flexible to pivot. Chapters 00:00 Philadelphia Roots and Real Estate Ventures 05:57 The Importance of Offboarding in Employee Lifecycle 11:56 The Financial Implications of Offboarding 17:54 Navigating Career Moves with Intent 23:18 Navigating Career Growth in Tech 30:03 Salesmanship vs. Technical Reality 37:41 Transitioning to Short-Term Rentals with Apartments Jet 44:19 Building and Leading Effective Teams Connect with Andrew Hamilton is the Co-Founder and CEO of When, an AI-powered offboarding platform and severance solution. https://www.linkedin.com/in/hamiltonac8/ William Tincup LinkedIn: https://www.linkedin.com/in/tincup/ Ryan Leary LinkedIn: https://www.linkedin.com/in/ryanleary/ Connect with WRKdefined on your favorite social network: The Site | Substack | LinkedIn | Instagram | X | Facebook | TikTok Share your brand across the WRKdefined Podcast Network Learn more about your ad choices. Visit megaphone.fm/adchoices
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    45 mins
  • Jon Shanahan's Journey: How Businessolver Redefined Employee Benefits and Entrepreneurial Success

    Jon Shanahan's Journey: How Businessolver Redefined Employee Benefits and Entrepreneurial Success
    Nov 19 2024
    Jon Shanahan, CEO of Businessolver, shares the intricate journey of transforming employee benefits enrollment through technology. We dive into the challenges of annual enrollment, team building, and the psychology behind decision-making. Jon’s insights cover everything from mentorship to personal sacrifices, offering a roadmap for leadership and innovation. In this episode, we look at Businessolver, employee benefits, annual enrollment, entrepreneurship, insurance industry, technology, team building, community, challenges, personal growth, organizational psychology, decision-making, leadership, company growth, mentorship, sacrifices, employee benefits, and culture. Key Takeaways Businessolver redefines employee benefits enrollment with cutting-edge technology. Annual enrollment requires innovation to simplify complex processes for employees. Success in entrepreneurship hinges on teamwork, mentorship, and adaptability. Leaders must embrace trust and delegation to scale businesses effectively. Personal sacrifices are part of navigating growth in entrepreneurship. Technology and culture play pivotal roles in modern employee benefits management. Chapters 00:00 Who is Jon Shanahan and businessolver 03:04 The Evolution of Employee Benefits Enrollment 05:54 The Journey of Entrepreneurship 09:10 Navigating Challenges in the Insurance Industry 12:00 Building a Team and Finding Success 14:53 The Importance of Community and Timing 18:00 Personal Reflections and Future Aspirations 19:10 Understanding People and Organizational Psychology 21:31 The Evolution of Decision Making in Growing Companies 25:00 The Balance of Control and Trust in Leadership 28:32 Navigating Growth and Technological Advancements 32:11 The Importance of Mentorship and Career Growth 37:26 Sacrifices and Trade-offs in Entrepreneurship Connect with Jon Shanahan, CEO and Co-Founder at businessolver: https://www.linkedin.com/in/jon-shanahan/ William Tincup LinkedIn: https://www.linkedin.com/in/tincup/ Ryan Leary LinkedIn: https://www.linkedin.com/in/ryanleary/ Connect with WRKdefined on your favorite social network The Site | Substack | LinkedIn | Instagram | X | Facebook | TikTok Share your brand across the WRKdefined Podcast Network Learn more about your ad choices. Visit megaphone.fm/adchoices
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    45 mins
  • Navigating Stock Options: Challenges and Strategies for Employees with Scott Chou, Co-Founder ESO

    Navigating Stock Options: Challenges and Strategies for Employees with Scott Chou, Co-Founder ESO
    Nov 11 2024
    Scott Chou unpacks the ESO Fund's role in addressing the stock options dilemma for employees in venture-backed startups. We explore the hurdles in stock options, vesting schedules, and the big disconnect in employee expectations. Scott emphasizes the power of financial education, sharing insights on tax implications, company valuation, and how recruiters can better guide candidates through these tough conversations. In this episode we look at ESO Fund, venture capital, stock options, employee negotiations, recruiters, vesting schedules, tax implications, startup compensation, company valuation, employee compensation, liquidity, investment strategies, tax implications, recruiter education, employee options, customer success stories. Key Takeaways Stock Options Untapped: Over half of stock options granted are never exercised due to tax and financial challenges, highlighting a missed opportunity for many employees. Understanding Vesting Schedules: Vesting typically follows a one-year cliff model, and employees need to stay long enough to realize full benefits. Tax Implications Matter: The tax impact on stock options can be significant, affecting an employee's decision to exercise their options and the financial outcomes. Role of Recruiters in Stock Options: Recruiters are crucial in educating employees on stock options, helping them make informed decisions during negotiations. Liquidity Events Unlock Value: Stock options only hold tangible value once a liquidity event, like an IPO or acquisition, occurs, making timing critical. Confusion Over Stock vs. Options: Many employees mistake stock options for actual ownership, which can lead to unrealistic expectations about wealth accumulation. Impact of Company Valuation: As a company’s worth multiplies, employees may see their options increase in potential value—if they understand when to exercise. Perverse Incentives Exist: Companies may create unintended consequences in compensation structures, influencing when and if employees exercise options. Education is Key: Financial and tax education empowers employees to maximize their benefits from stock options and navigate complex decisions confidently. Chapters 00:00 Introduction to the ESO Fund and Venture Capital 02:00 Understanding Stock Options and Their Challenges 05:57 The Disconnect in Employee Negotiations 10:02 The Role of Recruiters and Direct Marketing 11:55 Stock Options on the Balance Sheet 15:01 Vesting Schedules and Their Implications 16:59 Negotiating Salary and Options 18:08 Understanding Company Valuation and Employee Compensation 21:21 Liquidity and Investment Strategies 24:50 Tax Implications and Employee Education 29:27 Recruiter Education and Employee Options 32:52 Customer Success Stories and Quick Turnarounds Connect with Scott Chou and ESO Fund here: https://www.linkedin.com/in/soonervc/ https://www.esofund.com/ William Tincup LinkedIn: https://www.linkedin.com/in/tincup/ Ryan Leary LinkedIn: https://www.linkedin.com/in/ryanleary/ Connect with WRKdefined on your favorite social network The Site | Substack | LinkedIn | Instagram | X | Facebook | TikTok Share your brand across the WRKdefined Podcast Network Learn more about your ad choices. Visit megaphone.fm/adchoices
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    40 mins
  • Jason Lee: Entrepreneur, Architect of On-Demand Pay, and the Visionary Behind Two Major Exits

    Jason Lee: Entrepreneur, Architect of On-Demand Pay, and the Visionary Behind Two Major Exits
    Nov 4 2024
    Jason Lee’s entrepreneurial journey has reshaped the on-demand pay industry. After founding and successfully exiting both DailyPay and Salt Labs, he's now leading Chime Enterprise with the same innovative spirit. His insights into scaling businesses, pioneering financial wellness, and transforming employee pay access continue to drive industry change. In this episode we look at entrepreneurship, financial wellness, on-demand pay, HR technology, venture capital, startup journey, business strategy, banking innovation, leadership, decision-making, financial solutions, market dynamics, and trust. Key Takeaways: Jason Lee pioneered the on-demand pay industry with successful exits from DailyPay and Salt Labs. As Chief at Chime Enterprise, he’s leading the charge on innovative financial wellness solutions. Jason’s entrepreneurial journey highlights the value of creating businesses that drive real-world impact. Scaling and exiting companies with a purpose is central to Jason’s approach to entrepreneurship. He emphasizes the role of accessible pay in supporting employee financial security and well-being. Building trust with investors and clients has been key to Jason’s success across multiple ventures. Jason shares valuable insights on navigating market dynamics and adapting to changing industry needs. With Chime Enterprise, Jason is positioned to lead the next wave of financial wellness and HR tech innovation. Chapters 00:00 Who is Jason Lee, pioneer of the on-demand pay industry, DailyPay, Salt Labs, and Chime 06:14 Jason's Entrepreneurial Background 11:54 The Concept of On-Demand Pay 18:05 Building Financial Solutions for Everyday Americans 23:53 The Genesis of an Idea 30:18 Building Trust in Entrepreneurship 36:41 Navigating Market Dynamics 42:05 The Reality of Decision-Making Connect with Jason Lee here: https://www.linkedin.com/in/jasonleem2/ William Tincup LinkedIn: https://www.linkedin.com/in/tincup/ Ryan Leary LinkedIn: https://www.linkedin.com/in/ryanleary/ Connect with WRKdefined on your favorite social network The Site | Substack | LinkedIn | Instagram | X | Facebook | TikTok Share your brand across the WRKdefined Podcast Network Learn more about your ad choices. Visit megaphone.fm/adchoices
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    47 mins