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 Run small experiments, unlearn out-of-date tactics, and stay anchored to clear business outcomes.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