In this episode of MustardHub Voices: Behind the Build, Curtis Forbes sits down with Steve Glynn, founder of Experience Milwaukee and self-described Chief Milwaukee Officer, to explore the power of community, connection, and local ecosystems in shaping the future of work.

Drawing from his journey growing up in Milwaukee, building and selling Sprinklr, and dedicating years to connecting entrepreneurs, founders, and business leaders, Steve shares why professional networks can change lives and why cities thrive when people are aligned around a common vision.

The conversation explores what makes strong innovation ecosystems, why talent often goes unrecognized when it doesn't fit traditional career paths, and how communities lose opportunities when entrepreneurs and nontraditional leaders are overlooked. Steve also shares lessons from studying tech hubs across the country, discusses the role of leadership in driving economic growth, and explains why rewarding intelligent failure may be one of the most important shifts organizations can make.

Whether you're a founder, HR leader, business executive, or someone passionate about building stronger workplaces and communities, this episode offers practical insights on leadership, talent, innovation, and the human connections that make lasting impact possible.

Listen now to hear why alignment, community, and a willingness to embrace risk may be the keys to building stronger companies, stronger careers, and stronger cities.



About the Guest

Steve Glynn is the founder of Experience Milwaukee, a media platform focused on the people building Milwaukee’s tech future. Through interviews, articles, and field reporting, he profiles the founders, operators, executives, investors, and community builders shaping where the city is headed, and he helps ambitious people grow their careers, companies, and connections. A founder with an exit, Steve has spent close to two decades cultivating Milwaukee’s tech and creative ecosystem, going back to Spreenkler, the community he built and later sold. More recently, he brought forward Milwaukee’s first Innovation District in Walker’s Point. His work blends storytelling, ecosystem building, and local business insight, and through projects like his City Tech Tour, he studies how other cities grow strong companies and stronger talent so he can bring those lessons home. He also goes by the title Chief Milwaukee Officer, which tells you most of what you need to know about how he feels about his city.

Steve Glynn on Building Communities That Drive Innovation  

In this episode of Mustard Hub Voices Behind the Build, Curtis Forbes sits down with entrepreneur, author, ecosystem strategist, and Startup Economist Paul O'Brien for a wide-ranging conversation on startups, workforce development, public policy, and the future of work.

Drawing on decades of experience in Silicon Valley, Austin, venture ecosystems, and economic development, Paul challenges conventional thinking about entrepreneurship, talent, hiring, and innovation. He argues that many of the systems organizations rely on today - from startup support programs to workforce development initiatives and hiring practices - are solving the wrong problems.

Together, Curtis and Paul explore why startup failure rates remain stubbornly high, why workforce challenges are often problems of optionality rather than talent shortages, and how better infrastructure, data, and workforce intelligence can help organizations make smarter decisions before problems surface.

The conversation also dives into the changing relationship between employers and employees, the evolution of benefits and compensation, the rise of the gig economy, and why predictive workforce intelligence may become one of the most important categories in HR technology over the next decade.



About the Guest

Paul O’Brien is the Managing Director of Startup Economist and the author of Startup Ecosystems, a new book distilled from two decades spent building the infrastructure behind entrepreneurship and venture capital. Based in Austin, Paul advises cities, governments, corporations, and economic development organizations on how venture activity actually gets built: through media, incubators, partnerships, and policy rather than branding and ribbon-cuttings. He’s helped shape Texas into a recognized startup hub and supported programs like Founder Institute and Mass Challenge. His analysis of startups, innovation, economic development, and the future of work reaches a readership of more than 140,000, including people at firms like Google and Sequoia. Much of his attention lives at the intersection of public policy and people: education, entrepreneurship, mental health, and the workforce. He is also the Chief Marketing Officer of MustardHub.

Learn More

 * Startup Economist by Paul O'Brien
 * seobrien.com
 * mustardhub.com

If you enjoyed this episode, subscribe to Mustard Hub Voices Behind the Build for more conversations with the leaders, innovators, and builders shaping the future of work.

Paul O'Brien: Why You're Solving the Wrong Problem 

In this episode of MustardHub Voices: Behind the Build, Curtis Forbes sits down with Sean Dazet, Head of Partnerships at Oyster [https://www.oysterhr.com/?utm_source=chatgpt.com], to explore the future of distributed work, global hiring, and what it really takes to build high-performing remote teams.

Drawing from his experience scaling partnerships at companies like HubSpot [https://www.hubspot.com/?utm_source=chatgpt.com] and leading global growth initiatives at Oyster, Sean shares how modern organizations can unlock talent anywhere in the world while navigating the operational, cultural, and leadership challenges that come with distributed teams.

The conversation explores the realities of employer-of-record (EOR) platforms, why global employment is becoming a strategic advantage, and how companies can scale internationally without building costly legal entities in every country. Sean also explains why communication frameworks, intentional culture-building, and strong leadership habits matter even more in remote-first environments.

Curtis and Sean dive into the difference between remote and truly distributed organizations, the growing importance of follow-through and critical thinking in leadership, and how unclear communication can quietly derail teams. They also discuss how AI is reshaping productivity, hiring, and workforce strategy, while balancing the human side of work, flexibility, and quality of life.

This episode is a must-listen for HR leaders, founders, operators, and anyone thinking seriously about the future of global work, distributed teams, and modern workforce strategy.



About Sean Dazet:

Sean Dazet leads partnerships at Oyster, a global employment platform that helps companies hire and manage talent anywhere in the world. With more than two decades of experience scaling revenue teams across high-growth startups, PE-backed ventures, and global SaaS businesses, Sean has built the partnerships and ecosystems that drive market expansion and competitive advantage. He is known for turning strategy into growth engines, unlocking new revenue streams, and accelerating momentum at every stage of a company’s journey. Sean got his start at HubSpot in the early days of inbound marketing, and has spent the years since working at the intersection of go-to-mark

Sean Dazet on Global Hiring, Remote Work, and Modern Teams  

In this episode of MustardHub Voices: Behind the Build, Curtis Forbes sits down with Sarah Kalogerakis, co-founder of Greatpoint HR, to explore how compensation strategy is being reshaped by real-time data, AI, and the changing expectations of today’s workforce.

Drawing on more than two decades in compensation technology, Sarah shares why traditional salary benchmarking models are no longer enough in a world where jobs, skills, and workforce dynamics are evolving faster than ever. She explains how companies can move beyond reactive compensation decisions and begin using contextual, predictive data to future-proof pay strategies and improve retention.

The conversation dives into the hidden costs of poor compensation planning, why SMBs often underestimate the long-term impact of inconsistent pay practices, and how outdated HR systems continue to hold organizations back. Sarah also discusses the rise of pay transparency, the growing importance of soft skills in compensation leadership, and why AI won’t replace great employees — but will amplify the people who learn how to use it effectively.

Curtis and Sarah also unpack the connection between compensation, engagement, and retention, challenging the idea that culture alone drives employee loyalty. From total rewards strategies to the future of skills-based pay, this episode offers practical insight for HR leaders, founders, and operators trying to build fairer, smarter, and more adaptive workplaces.

Whether you’re leading a growing SMB, managing compensation strategy, or trying to understand how AI will reshape the future of work, this conversation provides a thoughtful look at where workforce strategy is heading next.



About Sarah Kalogerakis:

Sarah is the Co-Founder of Greatpoint HR, a platform redefining compensation with continuous, real-time market signals. With over 20 years in compensation technology, she has built and scaled some of the industry’s most impactful data sets. Her work focuses on challenging outdated HR practices and unlocking the full potential of people data to drive fair, competitive, and more effective workplaces.

The Future of Compensation, AI, and Workforce Strategy with Sarah Kalogerakis 

In this episode of MustardHub Voices: Behind the Build, Curtis Forbes sits down with Kelli Send, Co-Founder and SVP of Financial Planning Services at Francis LLC [https://francisfinancial.com/?utm_source=chatgpt.com], to explore why financial wellness has become one of the most overlooked drivers of employee engagement, retention, and workplace performance.

With more than 35 years of experience in retirement planning and employee financial education, Kelli shares how her early experience inside the traditional brokerage industry revealed a major disconnect: most financial advice was built for wealthy investors, while everyday workers were left to navigate complex financial decisions on their own.

Together, they unpack the hidden impact of financial stress in the workplace, why 401(k) participation alone is not enough, and how employers can better support employees through holistic financial wellness programs. Kelli explains the difference between unbiased financial guidance and conflicted advice, why fiduciary responsibility matters, and how employers can create stronger cultures by helping employees achieve what she calls “work-life money balance.”

The conversation also explores the future of workplace financial wellness, including personalized financial education, AI-powered benefits support, generational differences in money habits, and why small and mid-sized businesses may actually have an advantage when it comes to supporting employees financially.

This episode is a must-watch for HR leaders, founders, benefits professionals, and business operators looking to improve employee well-being, reduce turnover, and build healthier, more productive workplaces through better financial support.





About Kelli Send:

Kelli Send is the Co-Founder and SVP of Financial Planning Services at Francis, where she leads the firm's financial wellness team. With more than 35 years of experience advising plan participants, Kelli oversees curriculum design and delivery as well as Francis's money coaching services. Under her leadership, the financial wellness team has earned more than 20 Eddy Awards for excellence in plan participant education.

Francis was founded on the principle that the American worker deserves holistic investment and money advice without jargon, judgment, or a hidden sales agenda. Kelli and her team work alongside clients, not above them, to help workers achieve what she calls work-life-money balance.

Outside of work, Kelli is a self-described master juggler of career, kids, and household. Her happy place is on top of a mountain with boards on her feet, with Disney World as a close second.

Kelli Send: Why Financial Wellness Is a Workplace Issue  

In this episode of MustardHub Voices: Behind the Build, Curtis Forbes sits down with Steve Boese to break down the future of HR technology, AI in the workplace, and what’s really driving employee experience today.

As a co-founder of H3HR Advisors and host of leading HR podcasts, Steve shares insider insights on how organizations are adopting (and struggling to adopt) new workplace technologies. From AI and automation to payroll and benefits innovation, this conversation uncovers where HR tech is delivering value—and where it’s missing the mark.

They also explore the growing impact of employee burnout, mental health, and workplace well-being, and why these issues are now central to business performance, retention, and culture.

In this episode, you’ll learn:

 * How AI is changing HR and workforce strategy
 * Why many companies fail to adopt HR technology effectively
 * The gap between HR tech innovation and real-world execution
 * How leaders can improve employee engagement and retention
 * Simple ways to gather employee feedback and build trust

Whether you’re an HR leader, founder, or business operator, this episode offers practical insights on navigating HR tech, improving employee experience, and building a more resilient workforce.



About Steve Boese:

Steve Boese is the Co-Founder of H3 HR Advisors, a strategy, research, and advisory firm focused on the global HR and workplace technology market. Through H3 HR Advisors, Steve works with HR technology providers, investors, and enterprise leaders on market positioning, product strategy, thought leadership, and go-to-market execution. He is also the co-host of two of the most recognized long-running podcasts in the HR industry, HR Happy Hour and At Work in America, as well as H3 Live, a video series bringing real-time insight to the HCM community. A respected analyst and commentator on the future of work, Steve has spent years helping the industry cut through noise and build smarter strategies around people and technology.

Steve Boese on AI, HR Technology, and the Future of Work

Most companies think of ACA compliance as a back-office obligation but in reality, it’s a high-stakes, people-impacting system that touches everything from cost control to employee trust.

In this episode of MustardHub Voices: Behind the Build, Curtis Forbes sits down with Todd Hurst, Head of ACA Sales at Equifax Workforce Solutions, to unpack why ACA compliance remains a persistent challenge more than a decade after its introduction and what employers are still getting wrong.

Drawing on over 20 years in healthcare and workforce solutions, Todd breaks down the hidden complexity behind benefits administration, from fluctuating employee hours to the ripple effects of inaccurate data and manual processes. He explains why ACA isn’t just about year-end forms, but a year-round system that requires precision, consistency, and proactive management.

They explore how overwhelmed HR teams - especially in small and mid-sized organizations - struggle to keep up with compliance demands, and how even minor inaccuracies can surface years later in the form of IRS penalties. Todd also shares how data-driven tools are helping organizations move beyond compliance to improve financial efficiency, benefits strategy, and overall employee experience.

The conversation highlights the human side of compliance, emphasizing how benefits offerings, accuracy, and communication directly influence employee perception, retention, and trust. Todd also offers a forward-looking perspective on how AI and automation may reshape compliance workflows, helping teams identify risk faster and operate more efficiently.

This episode is a must-watch for HR leaders, founders, and operators looking to simplify ACA compliance, reduce risk, and turn a traditionally reactive process into a strategic advantage.



About Todd Hurst:

Todd Hurst is Head of ACA Sales at Equifax Workforce Solutions, bringing more than 20 years of experience in the healthcare industry. Over the course of his career, Todd has held roles spanning Benefits Administration, Product Development, Sales, and Project and Account Management. His passion is helping clients save time managing their workforce against ACA regulations, while driving meaningful risk mitigation.

ACA Compliance Made Simple with Todd Hurst: Reducing Risk and Supporting Your Workforce 

Most companies think they have a hiring problem—but what they actually have is a systems problem.

In this episode of MustardHub Voices: Behind the Build, Curtis Forbes sits down with Jeffrey Shapiro, a people and talent executive known for building scalable, human-centered hiring systems, to unpack what’s really driving dysfunction in today’s job market. Drawing on his experience across startups, private equity-backed companies, and global organizations, Jeffrey explains why hiring often feels chaotic—and how most of it is preventable.

They explore why the current market feels “cattywampus,” with layoffs, talent shortages, and misalignment all happening at once, and break down the growing disconnect between applicants, candidates, and employers. Jeffrey shares why poor process design—not lack of talent—is the root cause of many hiring failures, and how simple shifts in structure, accountability, and communication can dramatically improve outcomes.

The conversation also dives into why “culture fit” is the wrong goal, how early attrition is often a failure of onboarding and expectation-setting, and why engagement actually begins at the very first touchpoint—not day one. Jeffrey also offers a grounded perspective on AI in hiring: where it’s adding real value, where it’s introducing risk, and how companies should be thinking about it pragmatically.

This episode is a must-watch for founders, operators, and HR leaders looking to turn hiring from a reactive, inconsistent process into a strategic, repeatable system that drives better outcomes across the entire employee lifecycle.

About Jeff Shapiro:

Jeffrey Shapiro is a People and Talent executive who designs and scales human-centered, data-driven people systems for high-growth startups, private equity-backed companies, and global enterprises. He specializes in turning chaotic hiring and workforce challenges into repeatable, measurable systems that improve quality of hire, accelerate growth, strengthen retention, and elevate the candidate and employee experience. Known for building systems that scale without losing empathy, Jeffrey believes strong people outcomes come from clear design, disciplined execution, and continuous feedback — not shortcuts or performative culture work.

Fixing Hiring Systems with Jeff Shapiro: Scaling Without Losing Empathy

Most companies invest heavily in benefits, but employees still don’t understand or use them.

In this episode of MustardHub Voices: Behind the Build, Curtis Forbes sits down with Spencer Linsley, Head of Partnerships at Bright Benefits, to explore why the gap between benefits strategy and employee experience is, in fact, a communication problem. Drawing on his journey from ski patrol to SaaS partnerships, Spencer shares how empathy and clear messaging shape employees' perception of value.

They discuss why benefits often feel “broken,” even when strong packages are in place, and how a lack of understanding leads to low participation, poor utilization, and missed ROI. Spencer explains why leaders must move beyond treating benefits as a line item and instead see them as part of a broader employee value proposition.

The conversation also covers how culture forms at the team level, why employees underestimate their total rewards, and how better communication can quietly improve trust, retention, and engagement.

This episode is a must-watch for HR leaders, founders, and operators looking to turn benefits into a meaningful driver of culture and performance.



About Spencer:

Spencer Linsley is a seasoned business leader and partnership strategist with deep experience driving growth at the intersection of sales, partnerships, and tech-enabled solutions. Currently leading Partnerships at Brite Benefits, Spencer works at the forefront of modern benefits education — helping brokers, HR teams, and employers better communicate and engage around benefits in ways that are clear, confident, and impactful.

Before joining Brite, Spencer spent several years shaping strategic alliances and revenue growth in the HR tech space, including leadership roles in sales and partnerships at Awardco, where he connected innovative solutions with enterprise customers and ecosystem partners.

His career journey — from sales leadership to partnership development — underscores his belief in building trust, aligning cross-functional teams, and leveraging strategic collaboration to unlock long-term value.

Originally from the Bay Area, Spencer now calls the Salt Lake Valley and Wasatch Front home. He enjoys all things outdoors — skiing, hiking, camping, and spending as much time outside as possible, especially playing and adventuring with his two daughters.

Spencer Linsley on Communication, Empathy, and the Future of Benefits

Most leaders think they know what’s happening inside their organization, but the reality is often very different.

In this episode of MustardHub Voices: Behind the Build, Curtis Forbes sits down with Trish Steed, HR executive, advisor, and co-host of the HR Happy Hour network, to explore how storytelling, transparency, and honest feedback shape better workplaces. With a front-row seat to thousands of conversations across HR, tech, and business leadership, Trish brings a uniquely informed perspective on what’s actually changing and what isn’t.

They discuss why employees often don’t speak up, how leaders misread engagement and retention challenges, and why many organizations ask for feedback but fail to act on it. Trish shares practical insight on building trust through vulnerability, creating space for honest dialogue, and why the biggest culture breakdowns often happen at the manager level.

The conversation also explores the hidden challenges of small and mid-sized businesses, where visibility is limited, and leaders may be closest to the problem but farthest from the truth.

This episode is a must-watch for founders, HR leaders, and operators who want to build more transparent, connected, and resilient teams and turn feedback into meaningful action.

About Trish:

Trish Steed is a seasoned HR executive and strategic advisor with a proven track record of aligning business objectives with transformative people strategies. She counsels HCM vendors on product innovation, go-to-market positioning, and brand storytelling to bridge the gap between HR professionals and technology providers. With deep expertise in market analysis and trend forecasting, Trish has guided companies navigating the evolving landscape of human capital management.

A recognized influencer and analyst in the HR tech space, Trish co-hosts two of the industry’s most influential and long-running podcasts, the HR Happy Hour and At Work in America—alongside Steve Boese. Together, they spotlight the issues shaping the future of work, offering candid conversations with thought leaders, practitioners, and innovators. Trish also co-hosts H3 Live, a dynamic video series that brings fresh perspectives and real-time insights to the HCM community. All of these, along with several other related podcasts, are part of their wider HR Happy Hour Media Network.

What Leaders Miss About Culture, Feedback, and Trust with Trish Steed

Explore what truly creates workplace happiness, builds a better culture, and drives greater engagement for the entire workforce — from the suits in the C-suite to team members on the frontlines. Get real-world insights and practical strategies to recognize, retain, elevate, and empower teams. From engaging interviews with thought leaders in our Voices web series to step-by-step how-tos, MustardHub helps you operationalize great culture and design the workplace of tomorrow... today. MustardHub Voices: Behind The Build addresses these hot topics and more with business leaders, entrepreneurs, HR professionals, consultants, coaches, researchers, and other brilliant minds committed to building, engaging, and elevating culture-driven, high-performing teams.

Fireside Chats: Behind The Build

MustardHub Voices: From the Frontlines takes you inside the businesses where great leadership happens in real time. Hear from owners, operators, and managers who aren’t behind closed doors — they’re right there with their teams, serving customers, solving problems, and setting the tone. From healthcare and childcare to retail, hospitality, home services, and more, our guests share what it really takes to keep people engaged, operations running smoothly, and customers coming back. You’ll walk away with actionable ideas, inspiring stories, and a deeper look at how leaders make an impact where the work and the magic happen.

Curtis Forbes

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