Shift & Thrive: CEO Insights on Driving Change

What changes when a COO becomes CEO? In this episode of Shift & Thrive, Natalie Nathanson sits down with Monique McDonough, CEO of WorkTango, to explore the unexpected lessons of stepping into the top seat, the emotional realities of leadership, and what it really takes to guide organizations through change. With more than two decades of experience across consulting, technology, and employee e...

Go-to-market is no longer a function, a plan, or a quarterly initiative; it’s a living, evolving operating system. In this episode of Shift & Thrive, Natalie sits down with Sangram Vajre, one of the most influential voices in modern B2B go-to-market strategy, to unpack what GTM really means in today’s market and why CEOs must take ownership of it. Drawing from his experience as a co-founder of...

Are you leading your business like a hero or an architect? We’re re-airing this powerful conversation between Natalie Nathanson and Bill Flynn, a seasoned growth advisor and business strategist with over 30 years of experience leading startups, driving company turnarounds, and coaching executives. Bill shares timeless lessons on what it really takes to lead through complexity, empower teams, and c...

In this special solo episode of Shift & Thrive, Natalie steps back from the usual interview format to reflect on the year, what it taught leaders, what themes surfaced repeatedly, and what’s ahead. The episode invites listeners to slow down during the holiday season and consider the lessons they want to carry forward into the new year. A Look Back: Lessons That Shaped This Year Openness is the...

What does real growth look like when leaders reinvent themselves, rebuild systems, and rediscover purpose? This special Shift & Thrive compilation brings together unforgettable stories and lessons from some of the year’s most thoughtful leaders. Listen to our guests share insights about transforming AI’s evolution into human-like teammates and the profound clarity that comes from surviving a l...

What happens when leaders discover that most barriers to transformation come from within their own systems rather than the people inside them? In this episode of Shift & Thrive, Natalie sits down with transformation strategist Marcia Daszko, whose work with CEOs, boards, and executive teams has shaped transformations across industries from Fortune 50 corporations to school districts and privat...

Why do some leaders thrive in ambiguity, and how can you build that same capability across your organization? In this episode, Natalie sits down with Elizabeth Harz, CEO of Veriato, to explore what it really takes to lead through continuous transformation. Elizabeth’s career has spanned enterprise technology, digital media, gaming, edtech, and now insider-risk management and behavioral intelligenc...

What does it really take to build and evolve a go-to-market engine that drives sustainable growth in today’s environment? This week, we’re re-airing one of our most popular conversations from the Shift & Thrive Go-To-Market Miniseries: a deep dive with Scott Brown, Partner and Head of Platform & Go-To-Market at Cervin Ventures. It’s packed with practical insights for leaders rethinking how...

What does it take to balance innovation with reality when AI moves faster than your market? In this episode of Shift & Thrive, Natalie Nathanson sits down with Yossi Carmon, CEO of Accelario, to unpack what it really means to lead through transformation in the age of AI. Drawing on his early startup lessons and his experience leading tech companies, Yossi explores how founders and CEOs can sta...

How can marketing leaders build go-to-market engines that evolve with today’s fast-changing buyer behaviors, while using AI intentionally, not accidentally, to drive meaningful transformation? In this episode of Shift & Thrive, Natalie sits down with Sajag Chikarsal, GTM Leader, advisor, and ex-Celona, Google, and Zscaler. His career spans every stage of company growth, from being the first ma...

What does it take to build a go-to-market motion that actually works today? In this special compilation of Shift & Thrive, host Natalie Nathanson brings together insights from CEOs, founders, and marketing leaders who’ve learned that growth starts and ends with one thing: the customer. As markets evolve and AI-generated content floods every channel, connecting with buyers requires a deeper, mo...

What does it take to lead a company through transformation while keeping people motivated, curious, and focused on the future? In this episode of Shift & Thrive, Natalie sits down with Matt Waxman, Chief Product Officer at Arctera, a data management company reimagining how enterprises handle compliance, resilience, and lifecycle governance. From making people “comfortably uncomfortable” to cre...

What can entrepreneurs learn from bootstrapping a startup, leading with empathy, and embracing the mindset of “Why not?” even when the odds are slim? In this episode, Natalie Nathanson sits down with serial entrepreneur Sanjay Manandhar, whose journey from Nepal to Massachusetts is filled with resilience, creativity, and servant leadership. Sanjay shares how bootstrapping shaped his approach to bu...

How can CEOs adapt their go-to-market strategy when the old playbooks no longer deliver results? In this episode of Shift & Thrive, Natalie Nathanson sits down with Stephen Ochs, Head of Marketing at Selector, to explore how startups can build smarter go-to-market engines in today’s market. Stephen shares his experience leading marketing and biz dev teams in SaaS companies from Series A throug...

How can executives harness AI without losing sight of strong business foundations? In this episode of Shift & Thrive, Natalie welcomes back Adi Klevit, Founder and CEO of Business Success Consulting Group. With more than 25 years of experience, Adi has been at the forefront of helping organizations build scalable systems and adapt to transformative technologies. She shares how process document...

What does it take to disrupt an industry dominated by giants like Salesforce and HubSpot? In this episode of Shift & Thrive, Natalie sits down with Adam Honig, founder and CEO of Spiro, to talk about his journey from building one of the largest Salesforce consulting firms to launching an AI-powered CRM that redefines how companies engage with customers. Adam shares how focusing on the manufact...

What does it take to lead massive business transformations in automation and robotics? On this episode of Shift & Thrive, Natalie sits down with Craig Ulrich, CEO of Acieta and a veteran leader in industrial automation with more than 30 years of experience. From scaling warehouse automation from a few million to $80M in revenue to guiding major transformations at companies like Amazon and Gene...

How can leaders drive company transformation without losing their team’s trust and energy? In this episode of Shift & Thrive, Natalie Nathanson talks with Leslie Poston, a seasoned go-to-market strategist and leadership advisor. Leslie shares how she led Austin Data Labs’ transformation from a small, multi-industry SaaS company into a high-growth leader in food and agriculture, culminating in...

How can leaders balance automation and AI with the irreplaceable human elements of sales, culture, and leadership? In this episode, Natalie Nathanson sits down with Tameem Hourani, founder and CEO of RapDev, to explore his journey from a technologist to leading a rapidly growing tech services firm. Tameem opens up about the challenges of shifting from an engineering mindset to scaling a sales-driv...

What does it take to turn a market gap into a thriving business? In this episode of Shift & Thrive, Natalie Nathanson sits down with Haseeb Budhani, co-founder and CEO of Rafay Systems, to explore how he’s navigated multiple startups, scaled innovative technology, and adapted to the evolving demands of AI and Kubernetes infrastructure. From his early entrepreneurial lessons to building high-im...

How can leaders shift from being the hero who fixes problems to the architect who builds teams that thrive on their own? In this episode of Shift & Thrive, growth advisor and business strategist Bill Flynn joins host Natalie Nathanson to share hard-won lessons from decades of leadership experience. From embracing frameworks like EOS to turning around struggling companies and guiding CEOs throu...

How can businesses stay competitive in an AI-driven world? In this episode of Shift & Thrive, Cheryl Jordan-Aguilera joins host Natalie Nathanson to share lessons from her 25-year career in sales and strategy, highlighting the power of collaboration, cultural fit, and consultative selling. She reflects on building scalable growth at GutCheck, navigating M&A challenges, and leading at Offic...

What’s the real reason most companies invest in cybersecurity, and why is it too late? In this episode of Shift & Thrive, host Natalie Nathanson sits down with Corey White, veteran cybersecurity leader and CEO of Cyvatar.ai. With nearly 30 years of experience, including time spent on the front lines of major breaches, Corey shares what leaders get wrong about cybersecurity, why compliance isn’...

In this episode of Shift & Thrive, Natalie Nathanson interviews Pete Jones, founder and CEO of Grypp, about the unexpected moment that led to a complete business pivot, from in-person sales tech to a visual-first platform transforming the contact center industry. Pete shares the story behind Grypp’s evolution, including how a single conversation exposed the inefficiencies in traditional call c...

Is your go-to-market strategy built for today’s challenges? In this episode of Shift & Thrive, Natalie sits down with Jacki Leahy, founder of Activate the Magic, for a deep dive into all things Revenue Operations (RevOps). We explore how RevOps can serve as the backbone of a modern go-to-market strategy, especially as traditional outbound tactics lose effectiveness and AI raises the bar for pe...