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Inside the C-Suite
Inside the C-Suite episodes
- What Happens When a Sales Nerd Builds a Startup | EP40
What do red shoes and a sloth mascot have in common? They’re all part of the wild ride that is Mike Stafiej’s leadership style.
In this delightfully unfiltered episode of Inside the C-Suite, Christy Honeycutt sits down with Mike Stafiej, CEO of ERIN - a referral automation platform with serious enterprise muscle and an even stronger personality.
Known as “The Fun CEO” for a reason, Mike shares how he’s
scaled a scrappy team into a global operation, all while keeping culture,accountability, and weird swag front and center. This one’s for the builders,the underdogs, and anyone who’s ever been told to stay in their lane.They dive headfirst into:
- How growing up blue-collar shaped Mike’s unshakable work ethic
- The hard truth about hiring friends - and how to know when to let go
- Why culture isn’t beanbags, it’s accountability
- Lessons from failure, fundraising, and the illusion that more headcount = more growth
- Why leadership means making space for reflection, not just reaction
- Plus: The legendary sloth suit origin story and why branding like you’ve got $10M (even if you’ve got $10K) works
Whether you’re bootstrapping your dream or riding the post-funding rollercoaster, Mike’s story is a masterclass in leading with grit, humility, and a touch of ridiculous.
And if you’re not building something fun… why build it
at all?| Connect with Us |
Learn more about ERIN:
https://erinapp.com/
Follow Mike Stafiej:
LinkedIn - https://www.linkedin.com/in/michaelstafiej/
(The Fun CEO himself – known for sloth-themed branding, pixel-perfect marketing, and leading Aaron with equal parts grit and weirdness)
Follow Inside the C-Suite:
LinkedIn - https://www.linkedin.com/in/cwiseman/
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Want to be on the show or know someone who might?
Contact Form – https://forms.gle/B1fVXPSV6b3x3AsS9
40 min - The Brutal Truth About Scaling a Tech Company: How Giuliana Corbo Took Nearsure to 22 Countries by 32 Years Old
Giuliana Corbo, the CEO of Nearsure, scaled her company to 22 countries by the age of 32, proving that age is just a number when it comes to leading a global business. She shares her no-BS approach to leadership, project management, and building a company culture that thrives under pressure. Along the way, Giuliana reveals the untold challenges of being a young CEO in the tech industry.
In this episode, we look at entrepreneurship, project management, leadership, mentorship, company culture, software development, business growth, and the impact of women in tech. Giuliana's insights uncover the importance of decisive communication, handling emotional challenges, and staying agile while scaling a business rapidly.
Key Takeaways➡️ Nearsure operates in 22 countries solving business problems through technology.
➡️ Most of Nearsure’s clients are in the healthcare space, highlighting a niche focus.
➡️ Effective project management is crucial for successful outsourcing and client satisfaction.
➡️ Giuliana's journey into entrepreneurship began at a young age, driven by a passion for tech.
➡️ Crafting a business plan was an emotionally challenging but necessary step.
➡️ Leadership, for Giuliana, means making tough decisions while prioritizing team well-being.
➡️ Mentorship played a significant role in Giuliana's career development and growth.
➡️ Company culture is a cornerstone of Nearsure's rapid growth and team dynamics.
➡️ Strategic communication within teams helps maintain alignment and efficiency.
➡️ Giuliana’s leadership style has evolved with the company’s expansion and challenges.
➡️ Investing opportunities are being explored as Nearsure scales further.
➡️ The nearshore business model offers a unique advantage in talent accessibility and cost-efficiency.
💬 Hot take or just hype? Are we headed toward a new normal, or is this just workplace chaos rebranded? Drop your thoughts in the comments!
Chapters00:00 — Introduction to Giuliana Corbo and Nearsure
02:55 — Exploring Nearsure's Business Model and Clientele
05:58 — Project Management and Team Dynamics
09:04 — Giuliana's Journey to Entrepreneurship
11:46 — The Challenges of Writing a Business Plan
14:59 — Leadership and Company Growth
18:08 — Mentorship and Personal Development
20:48 — The Reality of Being a CEO
23:52 — Cultural Integrity in Rapid Growth
26:54 — Reflections on Leadership and Future Aspirations
Connect with us here:🔗 Connect with Giuliana Corbo: https://www.linkedin.com/in/giulianacorbo/
🔗 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
31 min - Mastering Global Hiring: Insights from Nicole Sahin of G-P
Nicole Sahin shares her journey from anthropology to entrepreneurship, leading G-P to simplify global employment. She discusses the challenges of compliance, the acceleration of remote work due to COVID-19, and the role of intuition in business decisions. Nicole’s insights on building a global infrastructure and the hurdles faced by female entrepreneurs highlight the intricacies of leading a global company.
In this episode, we look at globalization, remote work, compliance, entrepreneurship, AI, SaaS, hiring, business growth, leadership, and data ownership. Nicole’s experiences and strategies offer valuable lessons for navigating the complexities of global business and building high-performing teams.
Key Takeaways➡️ G-P simplifies hiring across borders.
➡️ The complexity of global compliance is often underestimated.
➡️ COVID-19 has accelerated the acceptance of remote work.
➡️ Entrepreneurship requires strong intuition and adaptability.
➡️ Building a global infrastructure takes time and investment.
➡️ Female entrepreneurs face unique challenges in business.
➡️ High-performing teams are essential for company growth.
➡️ The role of board members is crucial for support and guidance.
➡️ Data ownership is vital for compliance and scalability.
➡️ The evolution of work culture is reshaping hiring practices.
➡️ Intuition can be a powerful tool for business decisions.
➡️ Managing team dynamics requires clear communication and trust.
Chapters
00:00 Introduction to G-P
03:10 The Global Employer of Record Model
05:55 Nicole's Journey to Founding G-P
08:48 The Evolution of Global Hiring
10:45 Navigating Compliance and Legal Risks
12:49 The Impact of COVID-19 on Remote Work
15:40 The Future of Global Employment
20:20 The Journey of a Female Entrepreneur
21:57 Building High-Performing Teams
24:57 Navigating Difficult Conversations
29:01 Managing Team Dynamics
32:31 The Role of Board Members
35:16 Finding Trusted Advisors
💬 What’s your take? Are we headed toward a new normal, or just workplace chaos? Drop your thoughts in the comments!
Connect with us here:🔗 Connect with Nicole Sahin: https://www.linkedin.com/in/nicolesahin/
🔗 Connect with G-P: https://www.globalization-partners.com/
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
40 min - Breaking Barriers: Women, Leadership & The Startup Funding Gap with Caitlin MacGregor
Startup life isn’t for the faint of heart—especially for women entrepreneurs. Caitlin MacGregor, CEO and co-founder of Plum, pulls back the curtain on what it really takes to build a company, secure funding, and challenge gender bias in venture capital. From navigating the complexities of co-founding a business with her husband to finding the right mentors, Caitlin shares the highs, lows, and lessons from her journey.
In this episode, we look at the fundraising hurdles women face, the unique mindset of Canadian entrepreneurs, the evolving role of venture capital in supporting social impact, and how mentorship and executive coaching shape leadership success.
Key Takeaways➡️ Plum helps companies match candidates to roles for better productivity and fulfillment.
➡️ Co-founding a business with a spouse brings unique strengths and challenges.
➡️ Mentorship is a game-changer in leadership growth and career success.
➡️ Women face systemic barriers in raising venture capital compared to men.
➡️ Female investors are often more supportive of women-led businesses.
➡️ Caitlin’s executive coach transformed her approach to leadership at 27.
➡️ Work-life balance is a myth—what matters is setting the right boundaries.
➡️ Canadian entrepreneurs approach risk differently than their U.S. counterparts.
➡️ The startup world is shifting toward a greater focus on social impact.
➡️ Engaging men in women’s leadership conversations is crucial for real change.
➡️ Entrepreneurs shouldn’t rely on luck—everyone has the potential to lead.
➡️ The venture capital landscape is slowly evolving, but there’s still work to do.
Guest and ResourcesCaitlin MacGregor: https://www.linkedin.com/in/caitlinmacgregor
Learn more about Plum here: https://www.plum.io/about
Connect with us here:🔗 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
53 min - Jon Lowe, Chief People Officer at DailyPay, on Workplace Transformation, Career Growth & Influencing the Future of Work
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!
43 min - Lara Abrash on Leadership, Decision-Making, and Career Growth at Deloitte
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
46 min - Revolutionizing Leadership Development with AI with James Cross, Tenor
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 NetworkThe Site | Substack | LinkedIn | Instagram | X | Facebook | TikTok
40 min - Career agility, Joelle Smith, President of First Advantage
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
51 min - Offboarding Done Right: Alumni Networks and Employer Branding with Andrew Hamilton CEO at When
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
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44 min - Jon Shanahan's Journey: How Businessolver Redefined Employee Benefits and Entrepreneurial Success
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
44 min
About Inside the C-Suite
From the publisher's feed
Energy, Influence and Innovation in the C-Suite
Join Christy Honeycutt for an unfiltered look into the minds of influential leaders as they share their untold stories. If you want to know how top leaders manage their energy, expand their influence and transform vision into action, this is for you. Christy and her guests dive deep into the intersection of leadership, impact and innovation, revealing the practices and mindsets that empower them to show up as their most authentic, effective selves.
At its core, Inside the C-Suite is more than just leadership tactics; it’s about the energetic exchange that drives real influence and change. Whether it's navigating chaos, overcoming adversity or building the resilience to lead with clarity, the podcast uncovers the personal and professional journeys of those who are redefining what it means to lead. If you're ready to go beyond the surface and tap into the deeper currents that shape leadership, this podcast is your invitation to listen, learn and lead differently.