What if the fastest way to grow your career isn’t a straight climb but a series of smart, sideways moves that sharpen your empathy and judgment? In this episode, I had the pleasure of sitting down with Catherine Wong, COO and CPO at Entrata, to unpack how she scales products and people by shaping cultures where every voice is invited, and the best ideas surface early. From engineering during the dot-com downturn to leading global teams through acquisitions and hypergrowth, Catherine shares the habits that turn uncertainty into momentum: practice your voice, ask for real feedback, and reward behaviors that build trust.

We go deep on how product and operations intersect when you’re building an operating system for real estate. Catherine explains why diverse perspectives improve outcomes and how leaders can intentionally signal what matters by recognizing thoughtful execution, not just loud opinions. Her take on the future of work is refreshingly actionable: AI changes the “how,” not the “why.” Whether you specialize or stay broad, treat curiosity like a muscle. Run small experiments, unlearn out-of-date tactics, and stay anchored to clear business outcomes.

You’ll hear practical frameworks for deciding under ambiguity. widen inputs, seek data, welcome dissent, and iterate with agility. Catherine also breaks down visibility tactics for women who are competent but overlooked: volunteer for updates, lead slices of complex projects, and request precise post-meeting feedback. Her story of integrating a UK acquisition while battling imposter syndrome reveals a simple truth: courage plus clarity compounds into trust, scope, and impact.

If you care about culture design, product leadership, AI fluency, and building a resilient career in tech, this conversation is a blueprint you can use today. Follow along, share it with a friend who needs a nudge, and subscribe to get more candid, practical conversations. Loved this one? Leave a review and tell us the bold step you’re taking next.

Resources:
Catherine Wong on LinkedIn
Entrata

What if the fastest way to grow your career is to reinvent how you work before the market forces you to? In this episode, I had the pleasure of sitting down with Caitlin Clark-Zigmond, a two-time entrepreneur and former CMO for Intel’s global software and SaaS portfolio, to map the leap from hands-on operator to AI-powered brand builder, and why clear value translation beats clever slogans every time.

Caitlin takes us from scaling a catering business to shipping Comcast Digital Voice, to leading massive B2B portfolios at Verizon and Intel. We dig into how Intel Tiber emerged to make software visible inside a hardware giant, uniting trust and security, AI and ML, edge and cloud, performance optimization, and developer workflows under a narrative customers could navigate. The result: sharper messaging, analyst clarity, and real pipeline acceleration. If your portfolio feels like a maze, her brand framework shows you how to draw a clean map.

Then we get practical with AI go-to-market. Forget tool-chasing—start with painful use cases, build on clean, connected data, and let AI amplify what already moves the needle. Caitlin explains why a CDP or an MCP layer unlocks CRM, marketing automation, analytics, billing, and customer success, enabling them to communicate effectively with each other. We cover intent data for account prioritization, conversation intelligence for coaching, predictive scoring for pipeline, and agents that handle repetitive data pulls and weekly reporting so teams can focus on thinking, not tab-hopping.

For leaders and modern marketers, the upskilling path is clear: achieve 30% fluency in core AI concepts, measurement, and understanding how your stack—HubSpot, Salesforce, GA, CDPs, and chat systems —actually works. You don’t need to code; you need to understand revenue mechanics. We also share Caitlin’s strategic networking system—the 5–5–5 method—that turns coffee chats into an operating system for your career, with value-first follow-ups that work even for introverts.

We conclude with candid insights on the value of progress over perfection, investing in relationships before you need them, and redefining success in terms of client transformation, sustainable growth, and work-life integration. Subscribe, share with a friend, and tell us: what’s the scary move you’re finally ready to make?

Resources:

• Website: www.clarkgp.com
• LinkedIn: https://www.linkedin.com/in/caitlinclarkzigmond
• Upcoming LILive GTM Event: https://www.linkedin.com/events/2026gtmrealitycheck-makemisalig7393722093324107776/
• Monthly Blog: https://gtmmaven.substack.com/p/why-the-c-suite-must-work-together

AI only works at scale when the shiny demo meets the gritty realities of deployment, security, and change management. In episode #146 of the 2B Bolder Podcast, I had the pleasure of sitting down with Monica Livingston, AI Platform Lead for the Americas at Red Hat and a former Intel leader, to unpack how open source accelerates real outcomes, and why the “plumbing” behind enterprise AI matters more than most roadmaps admit. Monica shares a clear view of what platforms must do in production: version control, monitoring, governance, policy, and cost discipline, all while staying flexible enough to avoid stack lock-in.

We get candid about the two biggest misconceptions leaders hold: AI isn’t a black box you plug in once, and the most complex variable is people, not models. Monica explains how to align teams through transparency, psychological safety, and clear KPIs so pilots survive the leap to operations. She also offers practical advice for new managers under pressure, from building trust to making recognition routine, and reflects on mentors who pushed her to trade constant breadth for deep expertise that compounds.

For anyone mapping a career in AI, this conversation covers real paths forward, including accessible learning, hands-on projects, and emerging roles that are reshaping the field. We discuss early STEM exposure as a lever for agency, guidance for young women entering the tech field, and the value of calculated risk anchored in personal values such as family and health. Monica also shares her perspective on how to stand out in crowded applicant pools, the power of referrals, and why transformation often occurs on your own time before it becomes a job title.

If this resonates, follow and share with a colleague who’s building AI for the real world. Subscribe for more conversations at the intersection of open technology, human leadership, and careers with purpose, and leave a quick review to help others find the show.

Hi Mary here, through my conversations with women leaders, I’ve learned just how urgent the need is for AI strategies that actually make sense. It’s not about adopting tools just to keep up; it’s about building a smart foundation. That’s exactly what Beyondsoft is doing. To learn more visit
https://www.youtube.com/playlist?list=PL-yCsEeZbsl6ivoZoS9YW1quYxbQr1Teo

Curiosity is a gift—but it only turns into momentum when it’s tied to impact. Host of the 2B Bolder Podcast, Mary Killelea, sits down with Carol Wilder, a strategic operator who helped launch the Alexa Skills Kit at Amazon, led generative AI partnerships at Dell, and now advises companies and municipalities on pragmatic AI adoption. Carol shares how aligning questions to concrete outcomes reshaped her career—and how that same shift can turn AI from a buzzword into a lever that reduces cycle time, improves resource utilization, and frees people to do higher‑order work.

We trace her pivotal moments: choosing the right team under pressure to ship Alexa skills, learning to communicate with crisp, results‑first clarity, and reinventing after hard feedback by defining what to stand for. Carol explains why so many AI programs stall, starting with tools rather than business goals, and outlines a simple framework: pick the outcome, fix process debt, unify data, then layer intelligence. She also challenges the cost of mass layoffs, noting how creative friction, hallway collisions, and institutional memory are often the real engines of innovation.

For women building careers in AI and product management, Carol offers direct, useful guidance: use automation to mute the noise, make impact legible, and build fundamentals in programming and model thinking through credible paths like Coursera and DeepLearning.AI. We explore mentorship as a multiplier, customer‑centricity as adopting a client’s aspirations as your own, and the underrated power of showing up prepared, questions ready, network engaged, and confidence primed.

If this conversation helps you refocus on outcomes and sharpen your AI strategy, share it with a friend, subscribe for more candid career playbooks, and leave a quick review to help others find the show.

Resources:
Carol Wilder on LinkedIn
Company websites: productmuseai.ca & www.atomic47.co

Hi Mary here, through my conversations with women leaders, I’ve learned just how urgent the need is for AI strategies that actually make sense. It’s not about adopting tools just to keep up; it’s about building a smart foundation. That’s exactly what Beyondsoft is doing. To learn more visit
https://www.youtube.com/playlist?list=PL-yCsEeZbsl6ivoZoS9YW1quYxbQr1Teo

What if the fastest way forward wasn’t pushing harder, but tuning in sharper? On episode #144 of the 2B Bolder podcast, I had the chance to sit down with Karina Marie Diaz, a trusted and sought-after leadership coach who explores how high-performing founders, CEOs, and senior executives create meaningful change by turning down the static and turning up their own signal. Karina’s journey from internationally published photographer to sought-after executive coach brings a rare blend of creativity, empathy, and strategic rigor to the conversation, proof that bold transitions can be both brave and practical.

Karina breaks down her coaching philosophy as a true collaboration grounded in presence and deep curiosity. Instead of prescribing fixes, she helps clients hear their own station more clearly, unlocking decisions that bring more ease without losing ambition. We dig into vertical leadership development, the Energy Leadership Index, and the mindset shifts that move leaders from overdrive to aligned performance. Her stories, from global weddings on the Nile to boardroom breakthroughs, illustrate how seeing people clearly can change how they see themselves.

You’ll learn specific strategies for navigating career pivots: how to listen for what lights you up, find the hidden map in your curiosities, and build a circle that reinforces creation over doubt. Karina shares her “Olympic-level emotional thought cardio” for designing habits backward from the future you want, plus a simple but powerful invitation: if you feel the itch to evolve, lean into it. The result is a blueprint for leadership that is clear, human, and sustainable.

If this conversation sparks something, consider that a sign. Then share the episode with a friend who’s ready for growth, subscribe for more candid career insights, and leave a quick review so others can find the show. Your next small step might be the one that changes your map.

Resources:
Karina Marie Diaz on LinkedIn

Hi Mary here, through my conversations with women leaders, I’ve learned just how urgent the need is for AI strategies that actually make sense. It’s not about adopting tools just to keep up; it’s about building a smart foundation. That’s exactly what Beyondsoft is doing. To learn more visit
https://www.youtube.com/playlist?list=PL-yCsEeZbsl6ivoZoS9YW1quYxbQr1Teo

What happens when the career you’ve chased for years stops fitting the life you’re building? We sit down with attorney and founder Miriam Airington-Fisher to explore how she transformed a courtroom-centered path into a thriving, family-first immigration practice—without abandoning ambition or impact.

Miriam traces her journey from legal aid and criminal defense to launching a firm as a new single mom. She breaks down the scrappy early days, the power of a 90-day startup plan, and the mindset shift from perceived job security to true entrepreneurial control. We dive into the boundary playbook she now lives by, no email on her phone, firm hours aligned to school pick-up, and a stacked team schedule that keeps clients supported while protecting deep work. If you’ve ever felt tethered to pings after dark, her approach will feel like oxygen.

We also unpack the business engine behind a sustainable law firm: choosing a scalable practice area, building an org chart that blends attorney judgment with strong staff workflows, and fixing fragile margins by treating profit as a discipline. Miriam shares how a women-led immigration mastermind and a trusted CFO turned chaos into clarity, why retained earnings matter, and how daily revenue visibility guides calm decisions. Along the way, we talk personal brand, Lawyer Like A Mother, how authenticity attracts the right clients, and why creators shouldn’t fear a few stray critics.

You’ll leave with actionable steps to start a firm faster, set cleaner boundaries, and scale without sacrificing family life. If you’re a woman in law or any demanding field, this conversation offers a clear path from overwhelm to ownership—proof that a values-driven practice can be both client-friendly and founder-friendly.

Enjoy the story, then subscribe, share with a friend who needs it, and leave a review to tell us the boundary you’re setting this week.

Resources:
LinkedIn lawyer-like-a-mother
Instagram: @lawyerlikeamother
momsalawyer.com (Company)
airingtonlaw.com (Company)

Hi Mary here, through my conversations with women leaders, I’ve learned just how urgent the need is for AI strategies that actually make sense. It’s not about adopting tools just to keep up; it’s about building a smart foundation. That’s exactly what Beyondsoft is doing. To learn more visit
https://www.youtube.com/playlist?list=PL-yCsEeZbsl6ivoZoS9YW1quYxbQr1Teo

Want a real look at how breakthrough tech actually gets built and shipped? I had the pleasure of sitting down with Samira Naraghi, Chief Business Officer at Enovix, who has held previous roles at AWS, Meta, Qualcomm, and other notable companies, to unpack a career defined by tackling challenging problems, making significant pivots, and achieving results that speak louder than titles. From growing up in post-war Iran, where power outages made technology feel magical, to leading global go-to-market strategies and launching industry-defining products, Samira shows how adaptability, curiosity, and grit compound into leadership.

We trace the through line across semiconductors, cloud, and next-gen batteries: translating deep technology into real business impact. Samira breaks down why go-to-market must start on day one, how co-building with early customers derisks product-market fit, and what it takes to prioritize nascent bets like AR when constraints around power, space, and manufacturability are unforgiving. She shares the unglamorous truth of innovation, fighting physics, supply chains, and disbelief, while still hitting commitments through decisive execution and a culture built for pressure.

For women in tech navigating ceilings and seeking visibility, the guidance is clear and actionable. Choose the messy, high-impact work others avoid. Build trust by delivering under pressure. Communicate with clarity, drop the hedging, and be overprepared. We also explore becoming future-ready with AI: learn the fundamentals, speak the language, and use the tools to amplify your work. Mentorship, peer networks, and “quiet boldness” round out a candid playbook for career growth that doesn’t wait for permission.

I hope this conversation gives you the nudge to take the harder path intentionally, and if so, share it with a friend who needs the encouragement. Subscribe for more honest, tactical stories from leaders building the future, and leave a review to tell us the bold move you’re making next.

Hi Mary here, through my conversations with women leaders, I’ve learned just how urgent the need is for AI strategies that actually make sense. It’s not about adopting tools just to keep up; it’s about building a smart foundation. That’s exactly what Beyondsoft is doing. To learn more visit
https://www.youtube.com/playlist?list=PL-yCsEeZbsl6ivoZoS9YW1quYxbQr1Teo

What if the straightest line to a bigger career is choosing the uncomfortable zones? On episode #141, I had the pleasure of sitting down with Tracy Nolan, Fortune 100 executive, transformation leader, and champion of women in leadership, to unpack the choices and mindsets that turned discomfort into momentum. From retail floors to the front lines of telecom, from global negotiations to a mission-driven role in healthcare, Tracy shows how to trust your instincts, claim your seat, and bring others with you.

We dig into the moment a sponsor pushed her into a stretch role and why that single act of belief changed her trajectory. Tracy breaks down the difference between mentorship and sponsorship (and how to be a great mentee), shares a simple mental model for speaking up in intimidating rooms, and explains how demanding goals can coexist with deep empathy and active listening. Her stories, like giving a CEO-ready plan just ten days into a new job, reveal how confidence is built: not by waiting to be “A+ ready,” but by acting, learning, and iterating.

Tracy also opens up about why healthcare fits her purpose, the women-first culture she’s found at Humana, and the platform she’s building, Lift as They Climb, to make sponsorship among women the norm, not the exception. We talk board pathways, continuous learning, and the skill set that will outlast every tool in an AI-driven economy: leading people through change with clarity, process, and heart.

If boldness has been on your list, consider this your nudge. Listen, and share this with a friend who needs a push. Additionally, if possible, please leave a review of the show. This will help us grow and increase our visibility on the streaming channels.

Resources:
LinkedIn: https://www.linkedin.com/in/tracyenolan/
Website: www.tracynolan.com

Hi Mary here, through my conversations with women leaders, I’ve learned just how urgent the need is for AI strategies that actually make sense. It’s not about adopting tools just to keep up; it’s about building a smart foundation. That’s exactly what Beyondsoft is doing. To learn more visit
https://www.youtube.com/playlist?list=PL-yCsEeZbsl6ivoZoS9YW1quYxbQr1Teo