Episodios
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Jenny Xia Spradling is the co-CEO of Freewill, an online software company revolutionizing estate planning and charitable giving. With a background in math competitions, Jenny brings a unique perspective to the intersection of social impact and economic success. Under her leadership, Freewill has helped nearly one million Americans complete their estate planning and committed almost $10 billion to charity. Jenny's commitment to values like courage, joy, kindness, and focus has shaped Freewill's inclusive culture and mission-driven approach.
You’ll hear Lindsay and Jessica discuss:
Early establishment of values is crucial: Defining values early on helps align founders, guide decision-making, and set the tone for company culture, ensuring long-term cohesion.
Public Benefit Corporation designation: Choosing a legal structure that aligns profit with mission can provide clarity, transparency, and protection for purpose-driven companies in decision-making and operations.
Values drive decision-making: Mission, vision, and values act as a litmus test for prioritizing opportunities, ensuring alignment with the company's core beliefs and goals.
Human connection and trust: Building a culture centered on people fosters loyalty, engagement, and a positive customer experience, leading to long-term relationships and brand advocacy.
Inclusivity through hiring practices: Prioritizing diversity, humility, and low ego individuals fosters an inclusive environment, promotes collaboration, and prevents biases in decision-making.
Balancing values: Recognizing the dual nature of values, understanding their edges, and embracing the trade-offs helps navigate complex decisions and maintain integrity in actions.
Math and decision-making: While numbers provide structure and analysis, embracing ambiguity and intuition alongside quantitative data allows for more holistic and nuanced decision-making.
Culture is sticky: Establishing a strong culture early on, emphasizing inclusivity, humility, and feedback, creates a foundation for long-term success and employee retention.
Joy and gratitude: Incorporating moments of celebration, gratitude, and joy in the workplace fosters morale, engagement, and a positive work environment, enhancing overall productivity and satisfaction.
Transparency and clarity: Explicitly defining values, mission, and vision helps guide actions, align stakeholders, and provide a clear framework for decision-making, ensuring consistency and focus.
Resources
Jenny Xia Spradling | LinkedIn | FreeWill -
What happens when the intense focus on solving a specific problem is paired with a clear understanding of what not to do? In this thought-provoking podcast episode, Lindsay Pederson interviews Bill Richter, CEO of Qumulo, about the power of long-term thinking, customer partnerships, and the importance of focus in business. Bill emphasizes the value of creating enduring customer relationships by staying true to the company's mission and not diluting efforts by trying to do everything. The conversation delves into the challenges of maintaining focus, the significance of trust in building a brand, and the necessity of clarity in driving organizational success.
Focus is key: Focusing on solving one specific problem better than anyone else is crucial for startups to stand out and succeed in a competitive market.
Long-term thinking: Prioritizing long-term customer satisfaction over short-term gains builds trust, credibility, and enduring value for the business.
Trust is essential: Building trust with customers through long-term relationships and reliable service leads to positive recommendations and sustainable growth.
Explicitly define what not to do: Clearly outlining what the company will not focus on is as important as defining its main objectives to maintain strategic alignment and avoid distractions.
Customer obsession: Being customer-driven and prioritizing customer needs helps in defining the company's roadmap and ensuring product-market fit.
Clarity is jet fuel: Providing clarity within the organization fuels productivity, engagement, and a sense of purpose among employees, driving overall success.
Balancing customer requests: Balancing customer demands with the company's core mission ensures alignment with the business's long-term goals and values.
Maximizing tool utilization: Focusing on maximizing the use of existing tools rather than acquiring new ones enhances efficiency and productivity within the organization.
Openness as a trait: Valuing openness in others fosters effective communication, collaboration, and a culture of transparency within the team.
Consistency in habits: Maintaining consistent habits, like enjoying a cup of black coffee, can provide stability and routine in a busy workday, enhancing focus and productivity.
Resources
Bill Richter | LinkedIn | Qumulo -
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What does it take for a venture capitalist to build a successful brand strategy that resonates with founders and investors alike? In this episode, host Lindsay Pedersen sits down with Kirby Winfield, the founding general partner at Ascend, to explore the importance of defining and embodying a brand identity in the world of venture capital. Kirby shares insights on the value of authenticity, problem-driven processes, and the power of being intentional in shaping a brand that stands out in a competitive market.
Define Your Brand Early: It's crucial to define your brand early on to establish consistency and clarity, allowing for a compound effect over time.
Focus on Problem-Solving: Prioritize solving the problem over showcasing the product or technology to ensure customer-centricity and value delivery.
Humanize Your Approach: Whether in B2B or B2C, marketing to humans requires understanding human drives and emotions to build a strong brand strategy.
Be Authentic and Consistent: Being authentic and consistent in your brand messaging builds trust with customers and stakeholders over time.
Set Brand Guidelines: Establishing brand guidelines helps in maintaining focus, saving time, and ensuring alignment with your brand values and mission.
Choose Your Brand Values: Identifying and standing for specific brand values early on helps in shaping your brand identity and resonating with your target audience.
Timing Matters: Timing is crucial in defining your brand, with post-Series A being an ideal stage when you have product-market fit and a better understanding of your audience.
Avoid Overthinking: Overthinking brand decisions can lead to wasted resources and potential disillusionment, so it's essential to find the right balance.
Stay True to Yourself: Staying true to yourself and your brand values, even in the face of challenges, helps in maintaining authenticity and building long-term relationships.
Embrace Personal Boundaries: Setting personal boundaries, both professionally and personally, helps in maintaining focus, energy, and consistency in brand messaging.
Resources
Kirby Winfield | LinkedIn | Ascend -
Carole Offredo is the Chief Marketing Officer (CMO) at Dataiku, a leading end-to-end platform for everyday AI. With over eight years of experience in the tech industry, Carole is passionate about democratizing AI and empowering individuals to harness its potential. She has a strong belief in the power of collaboration and transparency, driving her to create impactful marketing strategies that align with Dataiku's vision of making AI accessible to everyone. In this episode, Carole shares why there is power in understanding AI.
Belief in the Vision: Believing in the product and vision you're working for is crucial as it provides meaning and energy to drive you forward.
Team Collaboration: Creating conditions for your team to work together and create memorable moments for customers and prospects is energizing and fosters success.
Democratizing AI: Making AI accessible to everyone empowers individuals to automate tasks, innovate, and create more interesting work, leading to a more efficient and sustainable future.
Truthful Marketing: Telling real customer stories without overselling builds trust and credibility, ensuring marketing efforts are authentic and impactful.
Power of Collective Creation: Harnessing the diversity of thought, background, and experience in a team leads to more vibrant ideas, innovations, and successful outcomes.
Delegation and Empowerment: Delegating tasks in an empowering way allows team members to grow, learn, and contribute to the collective vision, making the organization more scalable and sustainable.
Long-Term Sustainability: Focusing on making people grow as individuals, as a team, and as an organization ensures the business is scalable, sustainable, and creates long-term value.
Kindness as a Trait: Valuing kindness in a person fosters positive relationships, empathy, and a supportive work environment, leading to better collaboration and team dynamics.
Resources
Carole Offredo on LinkedIn | Dataiku -
Adriana Gil Miner, the CMO at Iterable, brings a wealth of experience and passion to the world of marketing. With a background that spans industries like financial services and tech, Adriana's unique perspective on brand building and customer experience shines through in her work. Known for her dedication to creating joyful experiences and building emotional connections between brands and people, Adriana's insights on marketing strategy and the evolving landscape of the tech industry are both enlightening and inspiring.
Brand is more than just a logo or advertising: It is about who you are as a company. Building a brand through every touchpoint helps create emotional connections with customers, leading to loyalty and advocacy.
Invest in Brand Marketing: Investing in brand marketing can increase the efficiency of performance marketing dollars over time. Brand marketing helps build awareness, positioning, and organic interest, making performance marketing more effective in the long run.
Marketing and Business Strategy: Marketing is a strategic function that should be tied to the overall business strategy. Marketing is a variable and unpredictable expense that serves as the engine for growth in a company.
How Brand Evolves: The essence of a brand can evolve and abstract over time, transcending the product itself. A strong brand identity can help a company navigate through different product iterations and market challenges.
Personal Experiences Matter: Personal experiences can deeply impact how we perceive and connect with brands. Emotional connections with brands can be formed through personal experiences, leading to long-lasting loyalty.
Budget for Marketing: Marketing budgets should be allocated strategically, considering a healthy blend of brand and performance marketing. Balancing brand-building activities with performance-driven tactics can lead to more efficient and effective marketing strategies.
How to Approach Branding: The concept of brand transcends industries, with some industries having a more conscious understanding of its value. Different industries may approach brand marketing differently, but the essence of brand building remains universal.
Brands Must Adapt: The evolution of a brand can reflect societal changes and technological advancements. Brands that adapt and evolve with the times can maintain relevance and connection with their audience.
Resources
Adriana Gil Miner on LinkedIn | Iterable -
Elena Donio is a seasoned leader with a wealth of experience in the tech industry. As the former CEO of Axiom and President at Concur, she played pivotal roles in driving growth and innovation. Elena's expertise extends to advising and serving on the boards of companies like Twilio, Benchling, Databricks, Contentful, and PayScale. With a passion for mentoring the next generation of talent, Elena's career has been marked by a commitment to authenticity, leadership, and creating meaningful impact on the next generation.
You'll hear Lindsay and Elena discuss:
Embrace Paradox in Leadership: Managing through paradox is essential for making strategic decisions that balance conflicting priorities, leading to long-term success and growth.
Focus on the How, Not Just the What: A company's way of operating, values, and norms can differentiate it, create a positive work environment, and drive success beyond just the product or service.
Maintain Personal Energy and Well-being: Taking care of yourself physically and mentally, including getting enough sleep and exercise, is vital for sustained high performance and creativity in leadership roles.
Engage Employees Beyond Financial Rewards: During challenging times, leaders must find ways to keep employees connected to the mission, engaged, and excited about their work beyond monetary incentives.
Create Career Opportunities Without Vacancies: Leaders should invent and provide growth opportunities for employees even when traditional career advancements are limited, fostering intellectual and professional development.
Value Creative Thinking and Problem-Solving: Encouraging creativity and challenging individuals with significant problems and opportunities can keep employees motivated and intellectually stimulated, even in stagnant growth periods.
Prioritize Personal Relationships and Relaxation: Spending quality time with loved ones, enjoying leisure activities, and relaxing can recharge leaders, enhance well-being, and improve decision-making.
Resources
Elena Donio on LinkedIn | X(Twitter) -
Barry Padgett, CEO of Amperity, is a seasoned executive with a proven track record in leading innovative companies like Stripe and SAP Concur. His genius lies in driving transformative business strategies and creating new categories in the customer data unification space. Barry's focus on better data, better results exemplifies his commitment to delivering audacious economic value while staying true to a distinctive purpose.
You’ll hear Lindsay and Barry discuss:
Importance of having a North Star: Having a clear guiding principle, like "better data, better results," helps in making trade-offs, prioritizing tasks, and aligning the team towards a common goal.
Building for durability: Companies aiming for long-term success focus on creating enduring customer relationships, employee experiences, and shareholder value, guided by a strong North Star.
Emotional quotient in business: Incorporating emotional elements in products or services, like creating delightful experiences for customers, can enhance brand loyalty and drive long-term success.
Leader-dependent approach: The leader's vision and values play a crucial role in shaping the company's direction, culture, and customer-centric focus, regardless of the industry or vertical.
Balancing short-term and long-term goals: Leaders need to balance short-term demands with a long-term vision to ensure sustainable growth, customer satisfaction, and employee engagement.
Personal preferences and professional choices: Leaders can have personal preferences, like reading nonfiction books, while professionally focusing on customer-centric strategies, durability, and emotional connections.
Utilizing data for customer experiences: Leveraging customer data to create personalized, seamless experiences, like empowering customer service reps with comprehensive customer insights, can drive customer satisfaction and loyalty.
Resources
Barry Padgett on LinkedIn | Amperity -
Elissa Fink, former CMO of Tableau, led the company from its startup phase through its IPO and beyond. With a focus on helping people see and understand data, she emphasized the importance of human connection in marketing. Elissa's expertise extends to advising tech companies and serving on boards for companies like Intellimize, Pantheon Platforms, and Cumulo. Her passion for creativity, collaboration, and brand strategy has made her a respected leader in the industry.
You'll hear Lindsay and Elissa discuss:
Using data and intuition in marketing: Marketers should utilize both data and intuition in decision-making to get a more complete picture and make better decisions.
Focus on people in enterprises: It's crucial to remember that marketing should target people within enterprises, not just the organizations themselves, to appeal to emotions and build relationships.
Brand as a relationship: Branding is about building a relationship between humans and a company, emphasizing trust, credibility, and emotional connections.
Balancing brand and demand: Every demand touch should also be a brand touch, ensuring consistency in messaging and reinforcing the brand promise for more effective marketing.
Inbound leads: Prioritizing inbound leads over outbound campaigns allows for a customer-centric approach, meeting customers on their terms and fostering long-term relationships.
Mission-driven leadership: A clear and simple mission statement, like "helping people see and understand data," serves as a guiding principle for decision-making and aligning actions with the brand promise.
Utilizing persuasion principles: Understanding human behavior and decision-making, as outlined in books like "Influence" by Robert Cialdini, can inform marketing strategies and improve customer engagement.
TV show recommendations: Enjoying TV shows like "Curb Your Enthusiasm" and "Tokyo Vice" can provide entertainment and insights into human behavior and different cultures, offering a break from work.
Personal connections: Building relationships and being open to communication with others, whether in work or personal life, can lead to valuable connections and opportunities for growth.
Continuous learning: Remaining open to new experiences, cultures, and perspectives, like through TV shows or books, can broaden one's understanding and enhance personal and professional development.
Resources
Elissa Fink on LinkedIn | Website -
Frank Mycroft is the CEO of Booster, a company providing energy delivery and logistics solutions for decarbonizing last-mile delivery. With over eight years of experience, Frank has led Booster in its mission to eliminate the need for traditional gas stations and bring mobile energy solutions to the world. When leading his team, he focuses on increasing velocity, raising the bar, and narrowing the focus to drive excellence and innovation. Frank's dedication to sustainability and efficiency has positioned Booster as a leader in the energy delivery industry.
Great leaders excel at saying no to most things, as it is harder but better than always saying yes, allowing for focus and efficiency in decision-making.
Establishing a clear North Star is crucial for leaders to guide their team and organization towards a common purpose, ensuring alignment and direction.
Regularly reminding oneself and the team of the company's mission and values helps maintain focus and motivation, reinforcing the importance of the North Star.
Balancing practical benefits like convenience with aspirational goals like sustainability is essential for creating value and engaging customers on a deeper level.
Building a business off immediate pain points while working towards a visionary goal allows for practical progress and long-term impact, ensuring sustainability.
Finding the balance between functional benefits and emotional aspirations is key to engaging customers and driving business success, catering to both practical and aspirational needs.
Empowering employees to make decisions based on the North Star through clear values, goals, and guiding principles fosters accountability, autonomy, and efficiency in the organization.
Creating artifacts like company values, goals, and guiding principles enables scalable decision-making, asynchronous collaboration, and efficient use of time and resources.
Encouraging a culture of focus, accountability, and excellence by setting high standards, increasing velocity, and narrowing the focus drives productivity, innovation, and success in the organization.
Being open to questions, fostering curiosity, and encouraging open communication with team members and children alike promotes learning, engagement, and meaningful connections in personal and professional relationships.
Resources
Frank Mycroft on LinkedIn | Booster -
Jessica Rolph is the CEO of Lovevery, an early learning platform that offers stage-based information for parents and products for children. With a background in brand strategy and a passion for helping children reach their fullest potential, Jessica leads Lovevery in providing tools for intentional play and connection between parents and children. Her dedication to creating meaningful learning experiences for children during their crucial developmental stages has made her a respected leader in the early childhood education space. Connect with Jessica on LinkedIn at https://www.linkedin.com/in/jessica-rolph-4b86ba/
You’ll hear Lindsay and Jessica discuss:
Balance science and heart. Balancing the science of early childhood development with a big-hearted approach is crucial for creating a brand that resonates with parents and children.
Understand the tensions of parenting. Acknowledging and navigating the tensions of modern parenting, such as screen time and achievement pressures, is essential for both parents and brands like Lovevery.
Growth mindset is for everyone. Embracing a growth mindset as a parent and a leader allows for continuous learning, adaptation, and improvement in both personal and professional roles.
Purpose alignment is key. Aligning personal purpose with the purpose of the company can lead to a fulfilling and all-consuming dedication to the brand's mission and vision.
Pay attention to detail. Paying attention to important nuances, without skimming over them, is vital for maintaining the quality and integrity of a brand's messaging and offerings.
Find the right brand tone. The tone and personality of a brand, like Lovevery, play a crucial role in conveying the right message to parents and creating a positive and engaging experience for families.
Provide the right tools for your audience. Lovevry provides parents with the right tools and information to engage with their children's development can strengthen the parent-child connection and support holistic family growth.
Work-life balance still matters. Balancing the demands of work and family life, like being a CEO and a parent, requires gut instincts and prioritization to ensure both personal and professional success.
Commit to continuous learning. Embracing continuous learning and growth, both as a parent and a brand leader, allows for adaptation to changing circumstances and the ability to evolve with the needs of families.
Resources
Jessica Rolph on LinkedIn | Lovevery -
Xiao Wang is the co-founder and CEO of Boundless Immigration, a technology company that assists immigrants in navigating their immigration journey. With a background at Amazon, Xiao has honed his leadership skills to create a purpose-driven organization. Under his leadership, Boundless has served tens of thousands of immigrants annually, receiving countless positive feedback and testimonials. Xiao's focus on values, culture, and decision-making has led to the development of a successful and impactful company. Connect with Xiao on LinkedIn at https://www.linkedin.com/in/xiaowang1/
You’ll hear Lindsay and Xiao discuss:
Values should have edge and require trade-offs. Setting values that differentiate a company and necessitate trade-offs helps drive decisions and align the organization towards a common goal.
Values evolve with maturity. As a company grows and faces new challenges, revisiting and evolving values is crucial to ensure they continue to guide decision-making effectively.
Build a "black licorice culture." Focusing on attracting individuals who align with the company's unique culture ensures a cohesive team that can thrive in the organization's environment.
Saying no is essential. Prioritizing and saying no to good but not great ideas is necessary to focus resources on what will have the most significant impact on the company's goals.
Deliberate experimentation is key. Conducting experiments with specific learning objectives and actionable outcomes ensures that resources are used effectively and learnings drive meaningful change.
Prioritization before experimentation. Choosing to focus on one key initiative rather than spreading resources thin across multiple experiments leads to more impactful results and clearer learnings.
Specific learning objectives are crucial. Clearly defining what the company aims to learn from each experiment and how that learning will inform future actions is essential for driving progress.
Values should be decision-making filters. Using values and cultural norms as filters for decision-making helps prioritize initiatives that align with the company's core beliefs and goals.
Balance speed and thoroughness. Striking a balance between speed and thoroughness in decision-making is crucial to ensure efficient progress without sacrificing quality or effectiveness.
Clear communication is key. Transparent communication about company values, goals, and expectations helps attract individuals who align with the organization's culture and mission, fostering a cohesive and effective team.
Resources
Xiao Wang on LinkedIn | Boundless Immigration -
Raj De Datta is the CEO and co-founder of Bloomreach, a leading software platform for digital commerce experiences. He is a multiple-time entrepreneur and bestselling author of The Digital Seeker. Raj is known for challenging the status quo and operationalizing company values to drive continuous improvement. With a focus on seeker-centric experiences, he emphasizes the importance of mission-driven leadership in the digital world. A growth mindset characterizes Raj's leadership style, prioritizing energy optimization and a commitment to being a Day Zero leader.
You’ll hear Lindsay and Raj discuss:
Embrace a growth mindset as a leader to stay open-minded and adaptable in the face of new challenges and opportunities, ensuring continuous growth and innovation.
Operationalize company values with specific behaviors to ensure they are not just words on a wall but are actively practiced, creating a strong organizational culture.
Commit to a commitment culture where the level of commitment of teams to various outcomes determines the success of the organization, emphasizing the importance of dedication and alignment.
Differentiate between customer-centricity and seeker-centricity in digital commerce to focus on understanding the deeper needs and motivations of customers, fostering stronger relationships and loyalty.
Harness the power of mission in digital environments to connect with customers on a deeper level beyond transactions, building lasting relationships and brand loyalty.
Prioritize energy optimization by focusing on meaningful tasks and saying no to unnecessary commitments, ensuring personal fulfillment and effectiveness as a leader.
Cultivate a beginner's mindset to approach each day with curiosity and openness, allowing for continuous learning and growth in leadership roles.
Make strategic splurges on items that bring joy and fulfillment, balancing personal rewards with responsible decision-making in financial matters.
Recommend books that offer valuable insights into business strategies and entrepreneurial journeys, expanding knowledge and perspective for personal and professional growth.
Enjoy guilty pleasure TV shows as a form of relaxation and entertainment, balancing work and leisure to maintain a healthy work-life balance.
Resources
Raj De Datta on LinkedIn | Bloomreach -
Tarang Amin is the Chairman and CEO of e.l.f. Beauty, a cosmetics company he took public in 2016. He previously served as CEO of Schiff Nutrition and has over 30 years of experience in the consumer products industry. Under his leadership, e.l.f. has grown into a digital-first cosmetics powerhouse while staying true to its roots of providing prestige quality at accessible price points.
You’ll hear Lindsay and Tarang discuss:
Brand builds economic value by increasing pricing power, enabling premium salaries, driving higher sales per employee, and generating significant goodwill value.
Clearly defining your North Star guides decision-making at all levels. It attracts talent aligned with your purpose and makes it easier to reject opportunities that don't fit your mission.
Seek "healthy conflict" between reflection and action. Thoughtful rituals create space to recharge, but avoid overthinking that leads to paralysis.
Build a diverse team that reflects your consumer base. This fuels innovation, having your finger on the pulse of their needs and desires.
Brands must stay fresh by constantly testing new ideas, platforms, and partnerships. Listen to your community and meet them where they are.
Create a culture of empowerment. Hire those smarter than you for each function then give them ownership to drive results.
As a leader, surround yourself with an executive team that complements your skills and energizes you. Delegate areas of expertise to avoid burnout.
Celebrate failures as learning opportunities while doubling down on what resonates with customers. Stay humble and hungry.
Intentionally carve out time for reflection, travel, passions, and interactions that spark energy. It enables you to show up at your best.
Launch experiments rapidly without overanalyzing. Use consumer signals and engagement to dictate next steps rather than endless planning cycles.
Resources
Tarang Amin on LinkedIn | X (Twitter)
e.l.f. Beauty -
Kristen Hamilton is a seasoned tech founder and CEO. As the co-founder and CEO of Koru, she played a pivotal role until its acquisition in 2019. Currently serving as General Manager with Enjoy the Work, Kristen is dedicated to helping founders evolve into great CEOs. She has over 25 years of experience in building and running companies, and brings a unique blend of expertise and empathy to her advisory role. She has a deep commitment to impact-driven entrepreneurship.
You’ll hear Lindsay and Kristen discuss:
The impact-driven nature of Kristen’s work and the deep connections she forms with entrepreneurs drive her sense of purpose.
The transition from being a CEO to an advisor brought a shift from a constant learning mindset as a founder to realizing the depth of expertise accumulated over years, allowing her to genuinely help others.
Kristen underscores the value of sharing stories, especially the challenges faced during the entrepreneurial journey. Vulnerability and openness create a connection, making the real work possible in the often lonely journey of entrepreneurship.
Your North Star will emerge from a deep understanding of a pressing problem, resonating with both your team and customers.
Ground your mission in practical problem-solving while maintaining an audacious, game-changing vision.
Entrepreneurs must adapt and iterate by understanding how their customers experience pain continually.
Founders face vulnerability, courageously putting their creations out for evaluation. The act of receiving feedback, even if it implies potential flaws, is an essential aspect of leadership. Embracing vulnerability fuels growth and improvement.
A common pitfall is where founders fall in love with their product rather than deeply caring about the problem they are solving. Start with the problem, ensuring a genuine connection to a critical and meaningful issue.
Connecting your personal "why" and company mission becomes a source of courage, endurance, and guidance during the challenging entrepreneurial journey.
Knowing yourself is critical for decision-making, defining priorities, and maintaining a healthy work-life balance.
Kristen introduces the concept of "working theories" as decision-making filters. These are stable viewpoints based on strategy, the North Star, and market analysis. Revisit these theories only when new information challenges existing beliefs.
Resources
Kristen Hamilton on LinkedIn
Enjoy The Work -
Charlie Cole is the CEO of Tribute Technology, a leading provider of software solutions for the funeral industry. His leadership experience includes roles such as CEO of FTD, Chief eCommerce Officer at Samsonite, and Chief Digital Officer at Tumi. He embraces a leadership style rooted in transparency and a commitment to driving positive change. This approach involves blending the best of the past with innovative strategies, ensuring that his teams evolve and thrive in the evolving business landscape.
You’ll hear Lindsay and Charlie discuss:
The key to successful leadership, according to Charlie, is finding the right balance between maintaining elements of the old and introducing new strategies.
Drawing from his experience at FTD, Charlie discusses the complex task of leading a company that recently emerged from bankruptcy, navigating the process of retaining valuable institutional knowledge while implementing necessary changes.
Inherited culture plays a significant role when taking on leadership roles, especially in the context of companies recovering from challenges like bankruptcy.
Charlie's leadership style is rooted in ruthless transparency. He communicates regularly with the team, shares monthly and weekly results, and ensures that everyone is well-informed about the company's direction.
It’s difficult to be transparent when the truth may hurt. However, leaders must be willing to deliver uncomfortable truths that drive positive change.
The challenge of leading change involves identifying individuals willing to adapt quickly and making swift decisions when facing resistance.
In his role at Tribute Technology, Charlie serves three principal constituents: funeral directors, grieving families, and friends and family of the deceased. The company prioritizes customer-centric solutions that benefit all three groups.
Customer centricity in SaaS businesses like Tribute Technology is facilitated by the high lifetime value of customers, allowing for a more long-term and holistic approach.
Certain business models afford more leeway for customer-centric decisions.
Examples from companies like Amazon, Starbucks, and Meta showcase the possibilities of creating new economic value by being customer-centric and taking bold swings.
The best teams have a mix of people with diverse viewpoints and ideas.
Resources
Charlie Cole on LinkedIn
Tribute Technology -
Leigh McMillan is the CEO of Whitepages. She has a diverse professional background that includes roles in politics and Major League Baseball. As the CEO of Whitepages, she has helped to steer the company into the new era of data and technology. Leigh is not only a seasoned executive but also a winemaker and co-owner at Welcome Road Winery in Seattle. She joins Lindsay Pedersen to explore insights into leadership, building a strong company culture, and the challenges of leading a brand with high awareness and trust.
You’ll hear Lindsay and Leigh discuss:
Leigh emphasizes the importance of the diverse and passionate team at Whitepages, highlighting how the company has played the long game in nurturing talent and helping individuals grow their careers.
With over 20 years of history, Whitepages has transitioned from the traditional phone book to a data-centric company. Leigh discusses the challenges of maintaining trust in a brand with high awareness and the need to evolve the business under a changing technological landscape.
Leigh advocates for a non-linear career path, encouraging individuals to explore different roles and take chances to find their strengths and passions.
The core of Whitepages' brand promise lies in balancing changing privacy norms with the necessity of contacting people outside the phone book. Leigh underscores the importance of transparency and trust in handling public information for the greater good.
Whitepages’ commitment to trust and transparency influences day-to-day decisions more than large strategic pursuits.
The dual criteria for decision-making at Whitepages are ensuring it aligns with the brand promise of "data for good" and facilitates the growth and expansion of the team.
Leigh feels a sense of stewardship towards Whitepages' legacy and a responsibility to the team that has trusted and joined her on this journey.
Creating a collaborative environment and taking care of the team fosters a positive work culture.
Leigh’s advice to her younger self would be to have a more relaxed perspective and not perceive everything as a significant stressor.
Resources
Leigh McMillan on LinkedIn
Whitepages -
Clayton Lewis has over three decades of experience launching and scaling early-stage companies. His impressive track record includes leading two companies, Onvia and HouseValues, to public offerings and serving as a general partner at Maveron. He co-founded Arivale in 2014, and served as its CEO. He currently advises CEOs and is a member of the Board of Trustees for Harborview Medical Center. Clayton is recognized for his expertise guiding purpose-driven leaders toward creating audacious economic value while staying true to their purpose.
You’ll hear Lindsay and Clayton discuss:
Clayton’s focus shifted from passion-driven pursuits in his 20s, to prioritizing financial success imid career. Launching Arivale allowed him to reconnect with his passion for health and wellness, marking a transformative stage in his career.
Use joy as a filter to evaluate your daily activities and interactions. This shift allowed Clayton to find balance and fulfillment in both his personal and professional life.
Passion can be both an asset and a liability. While passion fueled Arivale's vision, it also led to challenges, such as losing perspective and overlooking critical business considerations.
Leaders need to balance passion with objectivity to maintain a holistic perspective, especially in assessing product-market fit and strategic direction.
Clayton outlines the practicality of a North Star in guiding day-to-day decisions. He emphasizes the importance of aligning the team with a shared vision, defining success at various intervals, fostering a learning culture, and integrating the North Star into the company's values.
Clayton shares how Arivale brought its North Star to life culturally. This includes storytelling sessions about impactful client experiences, recognizing team members living company values, and creating a culture of continuous learning and improvement.
As an advisor to CEOs, Clayton encourages setting audacious goals, fostering relationships, and maintaining a positive attitude. He emphasizes the role of a North Star in guiding business decisions and aligning teams toward a common purpose.
Clayton uses his North Star as a filter when selecting companies to work with or invest in. He listens for passion, clarity of purpose, and the willingness of entrepreneurs to articulate and refine their goals.
Various terms can be used to describe the guiding purpose, such as mission, vision, values, and brand strategy. Clayton remains flexible with the language, focusing on the essence of a clear and motivating direction.
Sustaining leadership energy involves setting audacious goals, building strong relationships, and maintaining a positive outlook.
Resources
Clayton Lewis on LinkedIn -
Robbie Cape is the co-founder and CEO of Mt. Joy, a mission-driven restaurant aiming to demonstrate that profitability and positive impact can coexist. Having previously served as CEO and co-founder of both 98point6 and Cozy, Robbie has dedicated his career to building mission-driven businesses that transcend traditional boundaries. He envisions a world where restaurants not only serve exceptional food but also prioritize the well-being of the planet, animals, and every participant in the supply chain.
You’ll hear Lindsay and Robbie discuss:
Mt. Joy is a mission-first restaurant committed to proving that a profitable business can simultaneously contribute positively to the planet.
Robbie's journey into regenerative agriculture was sparked by the documentary Kiss the Ground and Michael Pollan's book, The Omnivore's Dilemma.
Regenerative principles can be applied beyond agriculture. From employee well-being to customer experiences, Mt. Joy aims to create a regenerative impact at every stage of the supply chain.
Robbie discusses the inherent challenges in venturing into industries like healthcare and restaurants, where the potential for impact is vast but the obstacles are significant..
The concept of regenerative isn't limited to the environment; it extends to employees, by creating jobs that energize and positively impact workers.
The positive treatment of animals at Mt. Joy has been lauded even by vegetarian and vegan customers, showcasing the broader appeal of regenerative practices.
Regenerative meat tends to be more expensive than industrially produced meat. This necessitates setting higher prices for the products.
Social and environmental change needs to be commercially viable to have exponential impact; this is illustrated by the impact of Tesla in the electric vehicle market.
Mt. Joy adopts transparency as a guiding principle. This extends to employees, which fosters trust and provides them access to information, promoting a culture of openness and honesty.
Transparency guides decision-making within the company, allowing for more informed and ethical choices.
The journey toward regenerative practices is gradual: you need to crawl before you walk and walk before you run, to achieve sustainable growth.
Resources
Robbie Cape on LinkedIn | X(Twitter)
Mt. Joy | Instagram -
As CEO of Assurance IQ, Allison Arzeno is at the forefront of harnessing technology to make a tangible difference in people's lives. Under her leadership, Assurance IQ has focused on its mission to improve and protect personal financial well-being of underserved consumers. She believes that data can be an equalizer in society.
Episode Highlights:
Data science lays the foundation for innovative solutions, by gathering opinions and trends over time. Assurance IQ employs data to pinpoint consumer needs. This approach has enabled them to tailor personalized insurance recommendations, especially for underserved consumers.
Assurance's North Star is centered on promoting personal financial well-being for all.
Assurance's brand strategy is interwoven with their North Star. Both elements work together to help the company achieve its overarching mission. Data is essential to Assurance's brand strategy, influencing major decisions. By aligning these elements, they serve consumers effectively while upholding their core values.
Allison believes that data-driven discussions enhance decision-making processes by introducing objectivity. This allows employees to engage in constructive debates that are grounded in analysis rather than personal biases. This approach is especially empowering for young professionals in tech-intensive roles, as it emphasizes the value of voices backed by evidence, regardless of the seniority of the contributor.
While Assurance advocates for digital solutions, they never overlook the importance of human connection. They understand that certain situations call for a personal touch.
Assurance IQ’s business model seamlessly integrates technology and human interaction, ensuring that consumers are provided with solutions tailored to their unique needs. This balance is achieved through the use of cutting-edge technology, which allows the company to collect and analyze vast amounts of data, and a team of experienced and knowledgeable advisors, who are able to use this data to provide personalized recommendations to consumers.
Operating where profit meets purpose presents its set of hurdles. Assurance grapples with this overlap, especially when data science intersects with consumer requirements. Such challenges require innovative thinking and adaptability.
A data scientist at heart, Allison believes that data helps to demystify discussions and enrich decision-making. She emphasizes the importance of listening and collaborating, especially when additional data can add value to the conversation.
Challenges are inevitable, but a clear and compelling North Star can provide guidance through tumultuous times. Economic goals should not overshadow societal impact.
Resources
Allison Arzeno on LinkedIn
Assurance IQ -
Zack Rosen is the co-founder and CEO of Pantheon Platforms, the leading WebOps platform. With a background in computer science and a passion for innovation, Zack’s North Star is to innovate and protect the open web, ensuring a balance of power and freedom in the digital space. As a purpose-driven leader, Zack emphasizes the importance of autonomy and fulfillment in his career, paralleling the values ingrained in Pantheon's mission.
You’ll hear Lindsay and Zack discuss:
Zack shares the joy and fulfillment from working with a close-knit team on important problems. In the entrepreneurial world, having the autonomy to choose challenges to tackle is crucial for a satisfying career.
Pantheon’s North Star is safeguarding and advancing the open web. Zack explains the significance of the open web—a set of standards that allows for freedom and flexibility in delivering excellent digital experiences without being controlled by a few dominant platforms.
Pantheon empowers digital teams by providing an out-of-the-box workflow that fosters autonomy and velocity.
Pantheon seeks to eliminate friction in the website development process, offering a workflow that is trusted, guaranteed, and conducive to high velocity.
Pantheon unlocks growth for digital teams by providing a well-oiled system that fosters collaboration and confidence.
Zack underscores the importance of value systems in building organizational culture. Values serve as a critical tool for aligning teams and attracting individuals who resonate with the company's mission and principles.
Two of Pantheon’s core values are passion and giving, and they actively embrace individuals who care deeply about their work and engage with a sense of purpose. These values contribute to a vibrant culture, but managing strong opinions within a passionate team can be challenging.
Leaders play a crucial role in embodying and promoting the value system. The goal is to create a culture where values are not just words but are lived and integrated into day-to-day work, interactions, and leadership.
Values, when well-defined and lived, serve as a compass for decision-making and contribute to a vibrant and effective culture.
Lindsay draws parallels between Pantheon's mission to eliminate friction in website development and Zach's work with California YIMBY in removing roadblocks in housing policies. Both endeavors share a common theme of removing unnecessary friction to drive positive outcomes.
Resources
Zack Rosen on LinkedIn | X(Twitter)
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