Jason Blessing

Transforming Childcare in Seattle: Success Stories from 3 SI In this video, we explore the significant impact of 3 SI in Seattle over the past decade. Discover how strategic initiatives have led to over $150 million in funding for early learning services in underserved neighborhoods, addressing crucial childcare access issues. #ChildcareAccess #SeattleSuccess #EarlyLearning #3SIImpact #CommunitySupport #EducationFunding #AccessDeserts #LocalInitiatives #ChildCareReform #KingCounty

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 🌟 Exciting Announcement 🌟 Upflex is honored to be a part of MatterMore Bringing Work Back to Life: Redefining Leadership in the Age of AI on November 14th at the New York Times Building as a key sponsor, alongside brilliant leaders who are shaping the future of work, AI, and culture design. In a time of rapid tech innovation, alongside challenges in well-being and connection, this event brings together founders, investors, and change-makers dedicated to creating more resilient, trust-based, and human-centered workplaces. Together, we’ll explore essential questions, such as:  How can leaders prioritize well-being and collective thriving?  What skills are essential for leadership in a world reshaped by AI?  How do we build systems that support trust, resilience, and collaboration at scale? Join us for an evening of deep discussion and connection with inspiring thinkers, including Elizabeth J. Sandler (futurist + workplace transformation), Anthony Onesto (Gen Z + HR innovation), Fabiola Cazares (early-stage growth + FoW investor) - hosted by MatterMore Coo+Co-Founder Matt Shenker Why Attend? This gathering is more than a conversation – it's a call to action to rethink leadership for a tech-driven future. Whether you’re a founder, executive, or investor, this is an opportunity to:  Connect with like-minded visionaries dedicated to transformative change  Discover how to lead with purpose and adapt in a world where tech reshapes our identities and workplaces  Gain actionable insights for designing work environments where people can truly thrive When: November 14th, 6:30 PM - 9:00 PM  Registration required:  https://lu.ma/3vqynbi7 I look forward to seeing you there as we collectively chart a path toward a future of work that brings life back into the workplace.

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Great article on leadership in uncertain times by Alissa Finerman, published by The Wharton School. Key takeaways: - Share your vision and the "why" - Communicate and Listen - Maintain a focus on People, People, People Alissa, your advice is spot-on! I have always agreed on your philosophy on leadership. Thank you for interviewing and including me in your article. Quick piece that highlights how to lead with purpose and compassion to drive high engagement and results. Worth a read! #culturedrivensales #leadership

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🌟 Join Crane’s Exclusive CXO Advisory Board! 🌟 What Scott doesn’t mention below is that the “Fill in the Blank” survey is the path for enterprise tech executives to apply for a spot on Crane’s CXO Advisory Board, where your expertise will directly influence and shape the future of technology startups. To be considered, simply complete our “Fill in the Blank” survey. #CXOAdvisory #EnterpriseTech #TechLeadership #Innovation #CraneVenturePartners #FillInTheBlank #TechFounders

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When scaling a business, establishing a strong operating rhythm is essential for creating and maintaining alignment across the organization. In today’s episode of the “Founder & CEO” podcast, I join Michael Viscuso to dive into the key elements of building an effective operating rhythm. We also reflect on our experiences at Carbon Black, sharing insights on what worked, what didn’t, and what we might approach differently if we had the chance to do it all over again. https://lnkd.in/g2fw7v9g

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Earlier this week, I brought my fully remote, distributed team together in Napa for a two-day offsite, where I intentionally stepped away from the typical planning and strategy sessions. Instead, I created space for us to simply connect.🙌 The days were mostly unstructured—a welcome break from the daily grind. We shared great meals, stories, and laughter—lots of it.🤣 Here’s what I walked away with: ✅ Immense gratitude for each person I work with. ✅ Confidence that those two days were time well spent. I truly believe that the supportive, psychologically safe environment we’ve built as a team is a direct result of the time we’ve dedicated to getting to know each other, understanding one another better, and prioritizing playfulness and fun. Too often, leaders underestimate the value of this type of connection, dismissing it as "fluff" or making minimal efforts, treating it as an afterthought. But for me, it’s the foundation of a thriving, cohesive team.❤️ Each smiling face in this photo is a big part of why my career is such a fulfilling and positive force in my life.🙏 #leadership #innovation #mentalhealth #peoplefirst #remote #remotework #wfh #humanresources

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Elated to be speaking at the Chief Clubhouse in New York tomorrow! Calling all #NYC-based Chiefs! Tomorrow, I have the pleasure of joining Osnat (Os) Benari for a relevant leadership discussion about how we lead, adapt and thrive through resiliency. With this session, we aim to create a real and honest dialogue around this topic and underscore actionable steps on navigating oneself, your team and organizations through the rapidly changing business landscape. We’d be thrilled to have you join us and hope to see you there!! #Chief #LeadershipInsights #CareerInsights #CareerJourney

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Happy Friday, everyone! 🌟 As we wrap up another week of hard work and collaboration, I'm reminded of the power of strong teams and resilient leadership. In my book, "When Grit Is Not Enough," I delve into the essential role of teamwork and effective leadership in overcoming challenges and achieving success. Here's to the strength of teamwork and the promise of a bright future ahead! #FridayFeeling #Teamwork #Leadership #WhenGritIsNotEnough 📚

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To scale your business successfully, it is important to learn from great leaders who were able to take a company beyond the startup phase through team empowerment. Noel Goggin is a great example of this, and CSQMag writes that he focused on talking to his customers to determine their needs. By being connected to his consumer base, he was able to come up with great solutions to their needs and build trust that he wouldn't have otherwise had. #Scaling #Growth #Leadership

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Calling all PE companies who understand that strong and effective leadership helps portfolio companies achieve their value creation goals. #privateequity #leadership #leadershipassessment #leadershipcoaching #leadershipdevelopment

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Great insight on the latest talent trends across the startup ecosystem. Thanks for including us in this report Atli Thorkelsson Josh Machiz!

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Alternate title: "Cultural Magic with Amy Mosher" The pendulum sways between employers' and employees' wants and perceived needs, and the #employeeexperience hangs in the balance -- and Amy and I dug into it. Amy just so happens to be isolved's chief people officer, and she joined me for the inaugural episode of "Small Talk Window," Open Window Strategies' podcast at WRKdefined. Hat tips are in order for Christine Allen, Hannah Stephenson, Amberly D. and, of course, William Tincup and Ryan Leary. You guys all help make the #worldofwork go 'round. #HR #HCM #employerculture

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Great news! Markel has joined AI Ready RVA as a corporate member. Many thanks to Markel CIO Morris Taylor, AI Ready RVA board member Ida Pierce, steering committee member Jonathan Bowman, and the rest of the AI Ready RVA team for bringing this together. Markel’s commitment to leveraging AI underscores their forward-thinking approach to innovation and operational excellence. By embracing AI technology, Markel enhances decision-making, optimizes processes, and uncovers new opportunities across their extensive portfolio. As a corporate member of AI Ready RVA, they bring valuable expertise in risk management and analytics, contributing significantly to the development of AI-driven solutions that benefit not only their organization, a leader in niche insurance and investment solutions with an emphasis on long-term growth, financial strength, and a unique corporate culture — but also the broader Richmond community. Their involvement reinforces the importance of collaborative efforts in shaping a future where AI empowers businesses and communities alike. As we gear up for a plethora of programming facilitated through our themed cohort groups in 2025, we invite your organization to join in on the discussion as a leader in improving AI literacy in the greater Richmond region. Reach out here in a DM and I'd be happy to share more about our mission, vision and ways to contribute to the cause.

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What if the key to the perfect executive isn’t in their past titles but in their potential to grow with your company? At Bolster, we look beyond conventional criteria, instead prioritizing growth potential and cultural alignment to unearth candidates who drive transformative results. Revamp your executive search process:  🔍 Identify skills and vision: Seek innovative, strategic thinkers who excel at problem-solving  🌟 Prioritize culture fit: Ensure candidates align with your company’s values  💡 Consider future potential: Choose individuals eager to grow with your business, not just repeat past successes Ready to transform your executive search? 👉 https://bit.ly/3SPcrjD #ExecutiveSearch #Leadership #HR #TalentAcquisition #CareerGrowth #BusinessTransformation #Bolster

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Hope to see you in Santa Monica this week for TECH WEEK by a16z! DM if you'd like to schedule a 1:1 to ask questions about scaling your business, journeying through M&A, or how you can empower your industry with a strategy that works. 🚀 🚀 🚀 #techweekla #techweek #tech #saas #founder #founders #startup #startups #investors #YC #VC #PE

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In our fast-paced business environment, one element that often gets overlooked is the power of effective board packs. A recent study by Board Intelligence and NACD highlighted that while great board packs can significantly enhance board conversations and decisions, a staggering 59% of directors express concerns about the effectiveness of the materials they receive. We have room for improvement. #BoardEffectiveness #CorporateGovernance #BusinessSuccess

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From Art History to HR Powerhouse: Ara Tucker's Journey to becoming an incredible storyteller and the Chief People Officer at Flatiron Health: Did you know that Ara Tucker once studied art history at Princeton and served as a corporate lawyer? 🤯 Tune into the latest episode of the Built by People podcast to hear her incredible story and gain valuable insights on: ✴ Work-life balance vs. finding happiness: Learn how to prioritize what truly matters. ✴ Overcoming burnout: Discover practical strategies to recharge and thrive. ✴ Building a personal brand: Stand out from the crowd and share your unique story. ✴ Introverts in leadership: Embrace your strengths and lead with confidence. And much more! Whether you're an HR professional or aspiring leader, this episode is a must-listen. 🎧 Find the episode in the comments 👇

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When Brian Chesky founded Airbnb he had essentially ZERO business experience. How has he successfully led the company for the last 16 years? Answer: With relentless #CURIOSITY driving continuous #LEARNING and #GROWTH. Chesky’s journey stands out as a compelling example of accelerated leadership growth. Leigh Gallagher's The Airbnb Story captures the early stages of his success (through 2016). But thereafter Chesky’s leadership has continued to evolve through some VERY challenging times. Here are a few lessons: Lesson 1: Embrace the Lifelong Learner Mindset One of Chesky’s greatest strengths is his commitment to continuous learning. As Reid Hoffman once said, “Brian is always in student mode, constantly asking questions and seeking advice.” This mindset has allowed him to adapt quickly and lead Airbnb through times of growth and crisis. For founder CEOs, the “I’m still learning” approach is invaluable. None of us start with all the answers, but those willing to constantly learn, refine, and evolve are the ones who succeed in the long run. It’s this humility that has enabled Chesky to build a multibillion-dollar company from scratch. Lesson 2: Leading with Empathy in Crisis Strengthens Trust During the COVID-19 pandemic, Airbnb faced an existential threat. Chesky made the difficult decision to lay off 25% of the workforce—but his approach was a masterclass in empathetic leadership. In a message to employees (https://lnkd.in/gBZ9ZtHV), Chesky clearly explained the reasons behind the layoffs, outlined how the company would support affected employees, and took personal responsibility for the decision. The impact of Chesky’s approach was tangible: not only did Airbnb retain its top talent, but the company saw a productivity boost from those who remained. Many employees reported that Chesky’s transparent and compassionate communication deepened their loyalty to the company and renewed their sense of purpose. As Airbnb scaled back up, it became clear that this decision set the stage for its successful IPO later that year. Lesson 3: Build a Culture of Curiosity and Growth Chesky didn’t just apply this growth mindset to himself—he built a company culture that values curiosity, creativity, and continuous learning. Airbnb employees are encouraged to challenge the status quo and pursue new ideas, which has been instrumental in the company’s ability to pivot and innovate during times of uncertainty. For founders, this is a reminder that culture starts at the top. By fostering an environment where learning and exploration are core values, you give your team the tools to solve problems creatively and navigate uncertainty with confidence. Brian Chesky’s journey offers invaluable lessons for #CEOs. His story teaches us that it’s not about having all the answers—it’s about staying curious and continually learning. How are you LEARNING and GROWING in your LEADERSHIP? #Leadership #ScaleUp #CEOCoach

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