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Leadership Fails & Flexible Work Wins: A Story You Need to Hear with Gillian Brookes - ep. 101

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Content provided by Rick Haney and Kaleem Clarkson, Rick Haney, and Kaleem Clarkson. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Rick Haney and Kaleem Clarkson, Rick Haney, and Kaleem Clarkson or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://ppacc.player.fm/legal.

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In the latest episode of our NSFRW series, Gillian Brookes—New Zealand’s leading flexible work specialist and author of Flexperts—joins us for a candid, laugh-out-loud conversation about workplace chaos, executive misfires, and the surprising power of honest dialogue.
From a “hot-mess” holiday leadership meeting to a high-stakes workshop that goes hilariously off-track, Gillian shares the story of an overworked leadership team and a brutally honest chief exec that led to some awkward moments and surprising lessons. Along the way, Gillian opens up about her mission to help organizations thrive with flexible work practices, how to navigate uncomfortable workplace dynamics, and why reframing challenges is the secret to successful leadership.
Packed with both humor and wisdom, this episode is a perfect blend of entertainment and insights. Grab a coffee and tune in for a story you won’t forget—and a few lessons you can actually use!

Learn more about Gillian:

More about us:

  continue reading

108 episodes

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Manage episode 463699010 series 2990470
Content provided by Rick Haney and Kaleem Clarkson, Rick Haney, and Kaleem Clarkson. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Rick Haney and Kaleem Clarkson, Rick Haney, and Kaleem Clarkson or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://ppacc.player.fm/legal.

Send us a text

In the latest episode of our NSFRW series, Gillian Brookes—New Zealand’s leading flexible work specialist and author of Flexperts—joins us for a candid, laugh-out-loud conversation about workplace chaos, executive misfires, and the surprising power of honest dialogue.
From a “hot-mess” holiday leadership meeting to a high-stakes workshop that goes hilariously off-track, Gillian shares the story of an overworked leadership team and a brutally honest chief exec that led to some awkward moments and surprising lessons. Along the way, Gillian opens up about her mission to help organizations thrive with flexible work practices, how to navigate uncomfortable workplace dynamics, and why reframing challenges is the secret to successful leadership.
Packed with both humor and wisdom, this episode is a perfect blend of entertainment and insights. Grab a coffee and tune in for a story you won’t forget—and a few lessons you can actually use!

Learn more about Gillian:

More about us:

  continue reading

108 episodes

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Send us a text Join us for a new episode featuring Suman Siva, the CEO of Marco Experiences , as he shares his inspiring journey from consultant to entrepreneur in the dynamic world of experience design with Kaleem Clarkson and guest co-host Jeff Frick! With a robust background that includes his tenure at Bain & Company and significant investment experience with SoftBank , Suman’s unique blend of consulting, investing, and passion for consumer experiences has shaped his approach to building meaningful connections in the workplace. We dive deep into Suman's transition to entrepreneurship, sparked by his early experiences with startups like Scoop Technologies. His enthusiasm for technology and direct-to-consumer ventures set the stage for the creation of Marco, a platform dedicated to organizing retreats and offsites that foster genuine employee connections. Initially launched as a consumer-focused experience marketplace, Marco had to pivot to virtual events as businesses sought ways to connect remote teams during the COVID-19 pandemic. As restrictions were lifted, Marco shifted back to in-person events, where Suman emphasized the importance of creating opportunities for employee connection. With 80% of companies now operating in a hybrid model, he believes that intentional in-person interactions are crucial for building trust and camaraderie among remote teams. The significance of intentionality in designing impactful offsite experiences does not go under the table! Drawing from research conducted by industry experts like Brian Elliott and insights from the Future Forum, Suman shares with us how brief quarterly in-person interactions can significantly enhance productivity and employee engagement. As remote work continues to shape workplace dynamics, the ongoing challenges of loneliness and collaboration faced by remote employees stay present: 60% of remote workers experience connection issues! Discover more about the vital role of experience design in enhancing employee connection, the concept of a "social connection strategy," and building community within organizations. Suman's insights challenge traditional notions of workplace relationships, advocating for a community-centered approach that promotes respect and collaboration while acknowledging the diverse tapestry of individuals within the workforce. Tune in to gain valuable perspectives on how to foster genuine connections in today’s remote and hybrid work environment and learn how thoughtful experience design can transform your organization's culture and performance. Whether you're a leader seeking to enhance your team's dynamics or an employee striving for deeper connections at work, it’s time to put on your headphones and equip yourself with the insights and strategies needed to thrive in the modern workplace! Learn more about Suman: Suman’s LinkedIn: https://www.linkedin.com/in/suman-siva-64b0712b/ Marco Experiences’ Webpage: https://www.marcoexperiences.com/ More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text In our latest episode, guided by Kaleem Clarkson and guest co-host Josh Morse , we dive deep into the fascinating path of Joshua Parkinson, founder of Post Planner , a SaaS platform revolutionizing social media management. From street performer to philosopher to tech entrepreneur, Joshua’s journey embodies adaptability, creativity, and resilience. This conversation explores his unconventional path, philosophies on work and leadership, and strategies for building a thriving remote-first business in the digital age. Joshua’s story begins with a degree in philosophy, which continues to shape his worldview. These academic interests fueled his creativity during a transformative period living in Europe, where he supported himself by rapping on the streets. This phase, filled with spontaneity and cultural immersion, also brought personal growth and love—it was during this time that he met his French wife. Flash-forward to 2009 , when Joshua embarked on his entrepreneurial journey with the inception of Post Planner . Inspired by the rise of social media platforms like Facebook, he identified a gap in the market for scheduling tools tailored to marketers. What began as a suite of Facebook apps quickly evolved into a flagship product, now serving businesses across eight social platforms, with Facebook remaining a core focus. A significant part of Post Planner’s success lies in Joshua’s ability to forge meaningful partnerships. Early on, he collaborated with Slav, a Bulgarian developer who built the platform’s first version. This partnership not only provided technical expertise but also demonstrated the value of leveraging global talent. Today, Post Planner’s development team remains based in Bulgaria, a testament to the enduring impact of this early collaboration. Post Planner’s innovative approach to work centers on asynchronous communication, offering a refreshing alternative to traditional, meeting-heavy environments. By minimizing interruptions and embracing tools like Slack, the fully remote team maintains a strong focus on output while preserving work-life balance. This model eliminates time zone conflicts—like late-night calls for overseas colleagues—and replaces micromanagement with trust and autonomy. Joshua, as the company’s founder, champions this method, driven by his distaste for inefficient synchronous workflows. While acknowledging initial concerns about team cohesion, he highlights how written communication fosters thoughtful contributions and builds a culture of autonomy. Employees are free to balance personal and professional priorities without rigid oversight, fostering loyalty and engagement. For startups, he argues, this flexible model reduces costs, unlocks global talent, and drives efficiency—key advantages in today’s remote-first world. Discover how Joshua’s philosophical roots and global experiences shaped his approach to entrepreneurship. Hear insights into Post Planner’s innovative asynchronous work model and learn how he leverages global talent to build a culture of trust and autonomy. Tune in to hear how Joshua’s journey can inspire your own path and transform your approach to work and leadership! 🔥 Get a Post Planner Promo Code ! CODE: REMOTELY25 🚨 This coupon will get you 25% off the signup fee on any of their plans! 🔥 Learn more about Joshua: Joshua’s LinkedIn: https://www.linkedin.com/in/joshuaparkinson More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text In this episode, our host Kaleem Clarkson, joined by guest co-host Laurel Farrer , dives into the compelling journey of entrepreneur Bo Abrams, co-founder of Kommu , a revolutionary home-sharing platform. Bo's evolution—from a spirited youth navigating diverse environments to an innovative leader tackling inefficiencies in the home-sharing industry—is both impressive and full of insightful turns. Bo’s unique upbringing as part of a nationally ranked basketball team alongside hip-hop legend Master P exposed him to diverse experiences from a young age. These experiences helped build his confidence, adaptability, and knack for navigating challenges—a foundation that has served him well in his entrepreneurial pursuits. This drive undoubtedly motivated him to earn an MBA from UCLA’s Anderson School of Business , all while continuing to pursue his musical endeavors! Bo’s professional journey began in finance, where he took an entry-level position at a hedge fund, likening the experience to starting in the mailroom. Although the job involved humbling tasks like fetching coffee, it introduced him to ambitious colleagues who inspired his career aspirations. Realizing that the hedge fund path wasn’t his true calling, Bo pivoted to operations roles in startups, including a stint at Steelhouse (now Mountain) . The inspiration for Kommu struck during a trip to Whitefish, Montana, when Bo encountered the inefficiencies and high costs of home-sharing platforms like Airbnb. He wondered why homeowners couldn’t monetize their properties as easily as car owners using platforms like Turo. This lightbulb moment led to the creation of Kommu—a social marketplace designed to offer young people trusted, affordable home-sharing options while fostering a sense of community. Bo envisioned Kommu as a disruptor in the space, providing a more equitable and user-friendly alternative to traditional rental platforms. Bo’s partnership with co-founder Gus marked another milestone in Kommu’s journey. The two met at UCLA, and their shared vision for transforming the home-sharing market solidified their collaboration. However, the road to success wasn’t without sacrifices. Bo candidly shared how his laser focus on career and academic goals led to personal challenges, including the end of a significant relationship. Despite these setbacks, he found strength in his achievements and the unwavering support of family and friends. Take a moment to delve deeper into Kommu’s ethos and mission with Laurel and Kaleem’s sharp and delightful guidance! Bo’s experiences and journey are a testament to the transformative power of resilience, adaptability, and innovation. From a trumpet-playing teenager in Beverly Hills to the co-founder of a disruptive startup, his story underscores the importance of perseverance in overcoming obstacles. Learn more about navigating the startup world, cultivating a growth mindset, and balancing ambition with personal sacrifices! Bo’s story—filled with relatable anecdotes and actionable takeaways—serves as a beacon of inspiration for aspiring entrepreneurs and remote professionals alike. Learn more about Bo: Bo’s LinkedIn: https://www.linkedin.com/in/bo-abrams/ Kommu’s Webpage: https://www.gokommu.com/ More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text New week, new episode! This time, Rick and Kaleem sit down with Francis Saele, a thought leader in workplace real estate and technology and Managing Principal at Mortevita , for an in-depth conversation about the evolving role of office spaces, especially in the context of remote and hybrid work, and the broader shifts occurring in the commercial real estate sector. Francis takes us through his professional journey, including building a startup in the commercial real estate industry that was later acquired by CBRE . His expertise in real estate has shaped his views on workplace transformation, particularly with the rise of remote and hybrid work. According to Francis, the role of the office has fundamentally shifted in recent years—and it certainly has! The shift toward distributed work is undeniable. Many organizations have adopted hybrid models, enabling employees to work remotely part-time. As a result, businesses no longer need as much office space, and many workers can perform tasks remotely, eliminating the need for daily office commutes. Landlords, however, are facing significant challenges as the demand for traditional office space declines. At the same time, companies are struggling to optimize their office use. The future of office spaces may not lie in legacy downtown buildings but in decentralized hubs located closer to where employees live. This concept, known as " central living districts ," integrates office spaces into communities, making them more accessible and convenient for workers. With reduced demand for traditional office spaces, repurposing older buildings for alternative uses is becoming an intriguing possibility . Potential options range from residential spaces to niche industries like vertical farming, though conversion processes can be complex. Cities are increasingly focusing on transforming downtown areas with walkability, green spaces, and mixed-use developments—ideas that could reshape the future of office real estate. As the landscape of office spaces continues to evolve with the rise of remote work and a growing emphasis on employee-centric environments, we dive into the potential for repurposing office buildings and the role of technology in reshaping the future of work . Grab your coffee and notebook, and join us as Francis Saele takes us through these exciting changes and shares the mission behind Mortevita —an integrator specializing in consulting for the new knowledge workplace, corporate real estate, and emerging workplace technologies. Thank you for joining us, Francis! Learn more about Francis: Francis’s LinkedIn: https://www.linkedin.com/in/fran-saele/ More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text Get ready for a delightful blend of laughter and insights in this Not Safe for Remote Work ( NSFRW ) episode! We’re joined by Anna Burgess Yang , a freelance fintech writer, content marketing expert, and remote work pioneer ( ABY Creative ) who’s been thriving in the remote world since 2006. Anna takes us on an incredible journey, from being one of the only remote employees at her company to becoming a seasoned veteran long before working from home became the norm. Along the way, she shares some unforgettable stories—like her grueling eight-hour road trips to maintain her marriage as a newlywed and when a coworker got locked out of the house by a mischievous child. And who could forget the epic company meeting interrupted by potty training chaos? But it’s not all laughs. Anna also reflects on the evolving culture of remote work, the challenges of proving herself in a pre-remote era, and the strategies she used to build a successful career entirely from home. Whether you're a remote work pro or just curious about how the landscape has changed, this episode delivers the perfect mix of humor, wisdom, and inspiration. Don’t miss it! Learn more about Anna: Anna’s LinkedIn: https://www.linkedin.com/in/annabyang/ ABY Creative’s webpage: https://annabyang.com/ More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text We are excited to present a fascinating new episode to kick off the year strong with some remote wisdom . This time, we sat down with Tony Jamous, CEO and co-founder of Oyster —a pioneering global employment platform. Joining our host Kaleem Clarkson for this insightful conversation is guest co-host, Jeff Frick . Together, they explore Tony's purpose-driven journey and how it shapes his approach to entrepreneurship, sustainable leadership, and remote work culture. Tony’s entrepreneurial story began with the founding of Nexmo , a communications platform whose rapid growth eventually led to its acquisition first by Vonage and then by Ericsson for $6.5 billion. This experience, while financially rewarding, led Tony to reassess his priorities after seeing the toll intense work demands were taking on his health and well-being. This period of introspection inspired him to take a sabbatical and rethink his career goals. Determined to pursue a more meaningful path, Tony envisioned a platform that would enable economic freedom and allow individuals to access global employment while staying in their home communities. This vision led to the founding of Oyster, now valued at $1 billion and dedicated to providing cross-border employment solutions that empower individuals and benefit local economies. A key aspect of Oyster’s mission is its focus on hiring talent from emerging markets, with 40% of its team now hailing from these regions—a significant increase from 30% just two years ago. This strategy goes beyond simply filling roles; it embodies a commitment to measurable social impact. By allowing companies to hire globally, Oyster directly invests in these economies through salaries and taxes, bolstering local development. What values does Tony consider essential? At Oyster, diversity and inclusion are foundational, with operations spanning over 80 countries and a workforce representing more than 100 nationalities, achieving gender balance across top management and the board. Tony also dives into the topic of compensation within remote teams, highlighting Oyster’s three-zone pay system, designed to promote fair wages and reduce global income disparities. His insights reveal a profound commitment to sustainable leadership, inclusivity, and a progressive workplace culture. Through Oyster, he is championing a new model of employment that transcends borders and fosters global equality. To top it off, Tony shares his philosophy of 'sustainable leadership‘, a concept that has become foundational to his approach to building and leading teams. Unlike traditional models focused solely on servant leadership or relentless growth, sustainable leadership prioritizes leaders’ well-being, enabling them to support their teams better. Inspired by the “oxygen mask” analogy, Tony emphasizes the need for leaders to care for themselves first to lead effectively. This approach promotes empathy-based management, which is especially relevant in today’s evolving remote work environment. Tony’s mission is to democratize job opportunities worldwide and create a new employment model that drives social impact, especially in emerging economies. His dedication to building a more equitable global workforce and his principles of sustainable leadership make this episode a valuable roadmap for leaders seeking to align business success with positive social contributions. Start this year strong: put on your headphones and get your remote-work inspiration! Learn more about Tony: More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text In the latest episode of our NSFRW series, Gillian Brookes —New Zealand’s leading flexible work specialist and author of Flexperts —joins us for a candid, laugh-out-loud conversation about workplace chaos, executive misfires, and the surprising power of honest dialogue. From a “hot-mess” holiday leadership meeting to a high-stakes workshop that goes hilariously off-track, Gillian shares the story of an overworked leadership team and a brutally honest chief exec that led to some awkward moments and surprising lessons. Along the way, Gillian opens up about her mission to help organizations thrive with flexible work practices, how to navigate uncomfortable workplace dynamics, and why reframing challenges is the secret to successful leadership. Packed with both humor and wisdom, this episode is a perfect blend of entertainment and insights. Grab a coffee and tune in for a story you won’t forget—and a few lessons you can actually use! Learn more about Gillian: Gillian’s LinkedIn: https://www.linkedin.com/in/gillian-brookes-88928aa2/ Gillian’s webpage: https://www.gillianbrookes.co.nz/ More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text We’ve Reached 100 Episodes! Isn’t That Amazing? In the 100th episode of Remotely One , co-hosts Kaleem Clarkson and Rick Haney celebrate this significant milestone —a journey that began three years ago—by reflecting on their incredible growth and the valuable lessons they've learned along the way! This landmark episode perfectly captures the podcast’s core mission: to bring remote work closer to listeners by sharing authentic stories from industry leaders, researchers, and everyday professionals who humanize this evolving work model. Filled with laughter, heartfelt gratitude, and memorable anecdotes, Kaleem and Rick reflect on how far they’ve come, look forward to an exciting future, and proudly announce their recent recognition as Podcasters of the Year by Crossover , the world’s largest recruiter of full-time remote jobs—highlighting the significant impact Remotely One has had in shaping conversations around remote work. Have you checked out some of the incredible insights shared on Remotely One ? If you’re wondering where to start, the duo reflects on some of their most impactful interviews. One standout guest was Jack Nilles , who coined the term "telework" in 1967. A former rocket engineer on the Apollo mission, Nilles questioned why traffic congestion couldn’t be solved if humans could be sent to the moon! Another powerful discussion was with Brian Elliott , former executive at Slack’s Future Forum. Elliott emphasized that "time matters more than place," a perspective supported by research showing a 39% productivity boost when employees have flexible schedules. Still learning about the advantages of remote work? Tune into the episode with Dr. Nick Bloom , a leading researcher on remote work. His data-driven analysis debunked widespread myths and highlighted the productivity advantages of flexible work models. Curious about pay equity in remote work? Dive into their conversation with Job van der Voort , founder of Remote.com , who raised an impressive $500 million in funding. Insights from Dr. Kelly Monahan of Upwork’s Research Institute and from Sasha Connor , a pioneer in remote leadership at Clorox, further enriched the podcast! Looking for more unfiltered stories? Check out the fan-favorite segment, "Not Safe for Remote Work" , where frontline workers share their most hilarious and inspiring remote work experiences. One unforgettable story came from Becky Jones , who delivered a high-stakes pitch to an executive board from a café—only for a nearby child to smear frosting on her face mid-call. Then there’s Kristen Bass , whose story could rival a thriller. Jamie Jackson , co-host of the Humorous Resources podcast, also left a lasting impression with relatable stories about managing remote work while parenting. We proudly celebrate our achievements—from meaningful interviews with top industry voices to fostering one of the largest remote work communities, now boasting over 3,500 Slack members and 5,000 email subscribers . With deep gratitude, we thank our listeners and guests for making this journey possible! Kaleem and Rick are more committed than ever to sharing authentic stories and fresh insights as they continue to explore the evolving landscape of remote work. Here’s to the next 100 episodes! More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text In this engaging podcast, Shelly Morales, founder and CEO of Morales HR , takes us on an inspiring journey—from her early days working at her family’s hot dog stand, “Sandy’s Happy Hot Dogs,” in the Bay Area to holding influential HR leadership roles in top tech companies and ultimately establishing her own HR consulting firm. Shelly shares how grit and determination fueled her path from a receptionist manually tracking resumes to impactful HR leadership positions at companies like LinkedIn, Quantenna, Atlassian, and Cadence Design Systems. Reflecting on her growth from an HR generalist to a strategic business partner, she discusses how her dedication to connecting people with meaningful work, improving employee experiences, and advocating for flexible employment practices has shaped her career. A pivotal chapter of her career was at Atlassian, where she saw firsthand the power of technology in building connectivity and engagement within remote teams. Atlassian’s early commitment to remote work, long before the COVID-19 pandemic, highlighted the essential role of tools like Confluence, Slack, and the now-retired HipChat in fostering team cohesion and a strong company culture across continents and time zones. These tools not only allowed dispersed teams to stay connected in real time but also encouraged personal storytelling that bridged physical distances. The onset of the pandemic accelerated the acceptance of remote work and highlighted how blending work and personal life could enhance productivity and work satisfaction, shifting companies’ focus from rigid office hours to outcome-based performance and helping establish a more human-centered work culture. Through Morales HR, Shelly aims to create a supportive network for professionals seeking roles that align with today’s flexible and dynamic work environments—from remote and fractional engagements to gig work opportunities. Her firm connects members across industries and roles, from CHROs and CFOs to customer support, without relying on traditional job postings. Kindness is at the heart of Morales HR’s intake process, where prospective members engage in a personal interview to ensure alignment with the company’s values. Shelly firmly believes that kindness and inclusivity are essential yet often overlooked qualities for creating a supportive workplace. By working with companies that value these principles, Morales HR builds relationships that uphold professionalism and empathy, benefiting both employees and employers. Shelly also highlights Morales HR’s role in the expanding gig economy, a trend she has championed for years. While not all early predictions around the gig economy and digital currency came to fruition, Shelly notes that the demand for flexible, project-based roles has steadily grown. Shelly Morales’s story is one of resilience and transformation. Her career represents the evolution of HR from administrative support to a people-centered, strategic practice that embraces flexibility, kindness, and the power of technology. Her mission is clear: to build connections between employees and employers that prioritize human connection, work-life balance, and mutual respect, setting a foundation for a thriving future in HR. Learn more about Shelly: Shelly’s LinkedIn: https://www.linkedin.com/in/shellymorales/ MoralesHR’s webpage: https://moraleshr.com/ More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text In this episode of the Remotely One podcast , co-hosts Rick Haney and Kaleem Clarkson sit down with Chicago-based entrepreneur Sam Rosen, co-founder of Deskpass, to explore his unconventional path to success and the future of coworking and flexible workspaces. Sam’s journey, full of twists and surprises, exemplifies resilience, innovation, and a sharp instinct for recognizing the shifting needs of the modern workforce. Sam’s career didn’t follow a traditional route. His unique backstory as a "three-time college dropout" is a label he proudly embraces. Rather than viewing it as a setback, Sam sees it as an essential part of his identity as an entrepreneur. His success story proves that a college degree is not the only path to achievement—what really matters is passion, resilience, and adaptability. Sam’s first major business venture was One Design Company , a digital design agency he founded from his spare bedroom in 2005. At a time when businesses were just beginning to navigate the digital space, Sam found himself in a unique position—acting as a translator between generations familiar with the internet and those who were not. In 2008, Sam’s entrepreneurial instincts led him to co-found Chicago’s first coworking space, The Coop . At the time, the coworking movement was still in its infancy, with only about 300 spaces globally. His inspiration for The Coop came during a visit to Brooklyn, where he struggled to find reliable internet while working remotely from his girlfriend’s cramped apartment. After an unsuccessful attempt to work from a local café, Sam discovered coworking through a space called "The Change You Want to See." He was immediately drawn to the community-driven atmosphere and knew he wanted to bring this model back to Chicago. As Sam’s career evolved, so did his business interests. By 2010, he had developed proprietary software to manage The Coop’s operations, including billing and scheduling. This software became the foundation for his next company, DeskTime , which he eventually sold. However, DeskTime was just a precursor to what would become his most successful venture to date: Deskpass . Deskpass, the platform Sam currently helms, is designed to meet the growing demand for flexible workspaces. Remote and hybrid teams can use Deskpass to find coworking spaces across the globe, giving them the flexibility to work from various locations. Unlike traditional coworking companies like WeWork, which tie members to specific locations, Deskpass operates as a marketplace, offering a wide variety of workspaces without owning any real estate. Today, Deskpass plays a pivotal role in the evolving landscape of remote work. The platform not only connects users with coworking spaces but also provides businesses with a way to offer remote and hybrid work options to their employees. Sam’s story is a testament to the power of innovation, resilience, and the ability to forge one’s own path. His ventures—from One Design Company to Deskpass—highlight his forward-thinking approach to business and his deep understanding of the evolving needs of today’s workforce. As the world of work continues to shift, Sam remains at the forefront of the coworking and flexible workspace revolution, offering solutions that cater to both companies and individuals! Learn more about Sam: Sam’s LinkedIn: More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text In this engaging episode of Remotely One, co-hosts Rick Haney and Kaleem Clarkson sit down with the multi-talented Kendall Wallace, Founder and Lead Facilitator at Executive Offsites, to discuss her transformative career, her approach to building strong team connections, and her insights into customer and user experience. With a career spanning leadership roles in customer experience, user experience (UX), and remote team facilitation, Kendall brings a wealth of knowledge to the conversation. Hailing from Richmond, Virginia, and a proud University of Virginia graduate, Kendall began her professional journey in sales before transitioning into the tech world. Her first significant role came at Park Jockey , a startup where she eventually rose to become the Global Head of Customer Experience . It was in this role that she realized the power of user experience in creating more intuitive and efficient digital platforms. One of the key takeaways from Kendall's journey is her passion for building meaningful team connections, especially in the context of remote work. As the founder of Executive Offsites, Kendall designs and leads in-person retreats aimed at fostering communication, trust, and collaboration among distributed teams. Her retreats emphasize the importance of blending work-related goals with opportunities for personal connection, helping remote teams build stronger relationships and tackle the challenges of maintaining trust and communication. A highlight of this conversation is the in-depth look into Kendall’s transition from customer experience to UX, a move driven by her role at Park Jockey. As the head of customer support, she noticed recurring issues that could be solved through better UX design. By identifying patterns in customer inquiries, she saw how user-friendly digital experiences could prevent problems from arising in the first place. Kendall shares her confidence that remote work is here to stay and reveals why in-person retreats are set to play a pivotal role in shaping the future of distributed teams. She dives into how these offsites can build trust and connection, emphasizing the need for personalized approaches rather than one-size-fits-all solutions. Expect valuable insights on designing meaningful team experiences that truly impact dynamics! Her passion for fostering meaningful relationships in both personal and professional spaces shines throughout the episode. Kendall’s mix of vulnerability, leadership wisdom, and enthusiasm makes this a must-listen for anyone navigating remote work or looking to strengthen team dynamics. Whether you’re leading a remote team or simply navigating workplace challenges, Kendall’s story offers valuable lessons on growth, self-awareness, and the power of human connection. With her holistic approach to team-building, Kendall provides a roadmap for creating stronger, more resilient teams in an increasingly remote world. Learn more about Kendall: Kendall’s LinkedIn: https://www.linkedin.com/in/kendall-wallace/ Executive Offsites: https://executiveoffsites.com/ More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text Join hosts Rick Haney and Kaleem Clarkson for a lively and insightful chat with Iwo Szapar, the CEO and co-founder of Remote How . Together, they dive into a conversation brimming with humor, camaraderie, and deep insights into the ever-evolving future of work. Iwo, a trailblazer in remote work advocacy and an expert in AI integration takes us on a journey from his hometown of Gdynia, Poland, to becoming a global thought leader. With a resume boasting over 3,000 companies—including heavyweights like Walmart, Microsoft, and ING Bank—Szapar has been at the forefront of helping businesses navigate the complexities of remote and hybrid work. Iwo reflects on his international adventures, which began with a work opportunity in Austin, Texas, and blossomed into a nomadic lifestyle that has seen him living in 15 countries across Asia, Europe, and beyond. His travels, driven by a passion for experiencing diverse cultures and broadening his perspective, have deeply influenced his approach to remote work. From the vibrant streets of Vietnam to the serene landscapes of Colombia, he has witnessed firsthand the global shift toward remote work, a trend that surged during the COVID-19 pandemic. The spark that ignited Remote How in 2017—a time when remote work was still gaining traction—was fueled by the growing demand among millennials for work flexibility and the challenges companies faced in attracting talent. Remote How was born with a clear mission: to empower individuals and organizations to fully embrace the freedom that remote work offers. As one of the early adopters of the digital nomad lifestyle, Iwo shares his insights into the unique challenges and rewards of this way of life. He also traces the remarkable evolution of Remote How and its significant impact on the remote work landscape. From its inception with the Remote Future Summit—the largest virtual conference on remote work at the time—to the launch of the Remote How Academy, the world’s first certification program for remote workers, Iwo has been committed to equipping individuals and companies with the skills and knowledge necessary to excel in a distributed work environment. Now the Remote Work rocket continues to soar and the intersection of AI and remote work becomes increasingly inevitable. For Iwo, AI is set to reshape industries, emphasizing that AI should be seen as a tool for empowerment rather than a threat. But despite being a visionary, Iwo remains grounded in the reality of uncertainties surrounding the future of work, particularly with the rapid advancement of AI. Traditional career paths, like software engineering, which were once considered secure, are now being challenged by the rise of AI. This must-listen episode is perfect for anyone interested in the evolving landscape of remote work, the challenges of organizational change, and the transformative potential of AI. Szapar’s unique insights and experiences offer valuable guidance for navigating these complex and rapidly changing environments. Whether you’re a remote work enthusiast, a digital nomad, or simply curious about the future of work, this episode is packed with knowledge and inspiration to help you embrace the future with confidence and creativity. Learn more about Iwo: Iwo’s LinkedIn: https://www.linkedin.com/in/iwoszapar/ Remote How: https://www.remote-how.com/ Remote-First Institute: More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text In this lively episode of the Remotely One podcast, hosts Rick Haney and Kaleem Clarkson chat with Sacha Connor, founder of Virtual Work Insider and a seasoned expert in remote work . Get ready for some valuable insights as Sacha takes us through her professional journey, marked by her pioneering role in remote work long before it became mainstream. Her story, deeply influenced by her Philadelphia roots, is one of resilience, innovation, and a commitment to redefining work in a distributed environment. Sacha's career took off in brand marketing after she graduated from Lehigh University. She worked at various advertising agencies, including the prestigious Goodby Silverstein & Partners in San Francisco. But her desire to get closer to the products she was marketing led her to The Clorox Company in Oakland, California, where she managed iconic brands like Hidden Valley Ranch, Kingsford Charcoal, and Brita Water Filters ! A pivotal moment came when Sacha decided to relocate to Philadelphia after the birth of her first child. Not wanting to leave her role at Clorox, she boldly asked to work remotely from the opposite coast—a groundbreaking idea in 2010, long before remote work was widely accepted. Clorox agreed but with significant caveats. However, despite these limitations, Sacha embraced the challenge and became one of the early pioneers of remote work, navigating the steep learning curve during a time when the tools and technologies we now take for granted were still in their infancy. As Sacha's remote work experiment at Clorox evolved, she effectively led distributed hybrid teams. Initially, the company viewed her remote work arrangement as a temporary experiment with strict boundaries. Still, Sacha's success eventually paved the way for a broader acceptance of remote work within the company. Turning 40 became another turning point in Sacha's life. Contemplating the next stage of her career, she decided to establish Virtual Work Insider. Virtual Work Insider offers training programs aimed at developing virtual leadership skills and equipping leaders with the tools they need to manage hybrid, remote, or geographically distributed teams. They also assist organizations in developing "team working agreements" or "team charters," which are foundational documents that clearly define how teams will operate in a distributed work environment. These agreements cover aspects like meeting times, communication norms, and how to accommodate team members in different time zones, helping to overcome some of the challenges that come with flexible work arrangements. Sacha’s experiences and insights provide a valuable perspective on the ongoing evolution of work in a post-pandemic world. As companies continue to navigate the complexities of hybrid work, clear communication, effective coordination, and strong leadership skills are becoming more critical than ever. Through Virtual Work Insider, Sacha is helping shape the future of work by providing the tools and training necessary for teams to thrive, no matter where they are located! Learn more about Sacha: Sacha on LinkedIn: https://www.linkedin.com/in/sachaconnor/ Learn more about Virtual Work Insider’s training programs and speaking engagements: https://virtualworkinsider.com/ More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text In our latest episode, Rick and Kaleem chat with the brilliant Adam Horne, co-founder of Open Org , for a captivating discussion you won’t want to miss. Dive into Adam's remarkable journey, the complexities of today's workplace culture, and the inspiring mission behind Open Org. Adam, who also was co-founder and Chief People Officer at Scout , has helped over 60 companies hire around 1,500 people. Named a LinkedIn Top Voice in HR communications, his insights are invaluable, especially given his introverted nature and preference for a quiet life outside of work. This intriguing mix of public professional persona and private nature sets the stage for an in-depth exploration of his professional philosophy. Adam stirred up a buzz with his recent LinkedIn post likening company culture to processed food, coining the term "ultra-processed culture." He explains how companies often present glossy facades to lure talent, much like processed foods use flashy packaging to entice buyers. This conversation highlights the importance of genuine transparency in company culture. Adam believes open communication and realistic expectations are key. Companies that share handbooks and maintain detailed knowledge bases tend to retain employees better and foster a healthier work environment! The trio discusses the impact of remote work on company culture. Adam notes that remote companies must excel in communication and transparency, as they can't rely on physical proximity to manage their teams effectively. When it comes to communicating work culture effectively, Adam stresses the importance of honesty and transparency. He suggests that companies provide a balanced view of their work environment, highlighting both positives and challenges. Drawing on insights from Brian Adams, an expert in employer branding, Adam underscores the value of clear and honest messaging about what it's really like to work at a company. This balanced perspective allows candidates to make informed decisions and ensures a better fit between employer and employee. Adam's insights reflect a profound understanding of evolving workplace dynamics, emphasizing the crucial role of transparency from employers and the necessity for job seekers to be diligent in their research. His focus on clear communication and resource accessibility aligns perfectly with Open Org's mission to support HR and people-focused professionals worldwide. Adam’s advice serves as a comprehensive guide for both job seekers and employers navigating the complexities of modern work environments. Whether you're looking to understand workplace culture better or improve it, especially in the era of remote work, this conversation is a must-listen! Learn more about Adam: Adam’s LinkedIn: https://www.linkedin.com/in/adam-open-org/ Open Org Webpage: https://open-org.notion.site/Apply-for-Open-Org-Community-Membership-db23d711b708434ca3f4b906065ecd4e More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
Send us a text Welcome again to Remotely One’s Not Safe For Remote Work, where employees at all levels share their most outrageous moments while working remotely! In this episode, we chat with Kristin Bass, CEO of AbstractOps , a company that eliminates the stress, uncertainty, and financial risk of state compliance. From Kernersville, North Carolina, now living in Auburn, Alabama, Kristin shares her wild journey from fintech to startups and her rapid rise to CEO. Hear about her adventures managing payroll tax compliance and scaling back-office operations. Tune in for hilarious stories involving her loyal Labs, Duke and Dixie, a shotgun scare that'll leave you laughing out loud, and a memorable sales call interrupted by some unexpected behavior. Don’t miss this fun and unforgettable episode with the charming and resilient Kristin Bass! Learn more about Kristin: Kristin’s LinkedIn: https://www.linkedin.com/in/kristinlbass/ AbstractOps webpage: https://abstractops.com/ More about us: Remotely One’s LinkedIn: https://www.linkedin.com/company/remotelyone Remotely One’s Webpage: https://www.remotelyone.com/…
 
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