In this episode of SheSass Unplugged, I sit down with Carrie Osman, founder and CEO of Cruxy, to explore her journey from early business influences right through to building a company that helps leaders truly understand product value and pricing.

What You’ll Discover

- What Customers Really Value: Why pricing starts with deep understanding of customer behaviour, not spreadsheets or legacy playbooks.

- Leadership Beyond Competence: Why success at senior levels is about influence, empathy, and getting real buy-in, not just being right.

- AI Is Changing the Rules: How faster build cycles and fewer barriers are challenging traditional SaaS valuations and forcing companies to rethink their edge.

What really stood out to me in this conversation is Carrie's combination of intensity and clarity. She doesn’t shy away from the hard truths, whether that’s the reality of building a business, the obsession it requires, or the fact that not everyone will understand or support your journey. But alongside that is a deep commitment to people, to developing talent, and to doing meaningful work that actually creates value.

SheSass Unplugged is produced by Urban Podcasts.

In this episode of SheSass Unplugged, I’m joined by Stephanie Covert, CEO of Macrobond Financial, whose unconventional path from field marketing to the C-suite has shaped her into a builder, transformer, and advocate for women in tech. After years leading global software and analytics teams at Oracle and FICO - long before responsible AI became headline news - Steph now leads Macrobond at a time when financial research is being radically reshaped by AI, automation, and expectations for faster insights.

Steph shares how stepping into roles she wasn’t “qualified” for taught her to lead by asking the right questions, why diversity is a cornerstone of fair and trustworthy AI, and what truly drives commercial excellence in a PE-backed SaaS business.

What You’ll Learn

- Builder’s Leadership: Why saying “yes” to unfamiliar roles creates better leaders and how enabling others beats being the expert in the room.

- AI With Human Purpose: How Macrobond is building agentic research tools that accelerate insight without replacing domain expertise.

- Commercial Excellence in SaaS: What separates good commercial talent from great talent, and how clarity, alignment, and simplicity drive real sales efficiency.

Steph’s journey is a reminder that transformation - whether in leadership, AI, or go-to-market comes from curiosity, courage, and building with purpose.

SheSass Unplugged is produced by Urban Podcasts.

Caroline opens up about her OBE, her Times column drawn from real business struggles, and how motherhood honed her empathy, boosting female partners at Gravita from 10% to 30% without quotas. We also explore fundraising tips for female founders, disrupting traditional industries, and fostering innovative cultures. It’s a candid, inspiring chat about curiosity and connection fuelling progress.

SheSass Unplugged is produced by Urban Podcasts.

Amy shares her path from chief product officer to CEO and now board director, reflecting on her natural leadership spark, navigating challenges, and uplifting other women in the private equity SaaS industry.

What You’ll Learn

- Embrace Leadership Early: How to recognise and nurture your innate leadership skills to seize bold opportunities.

- Balance Responsibilities: Why it’s important to focus on team goals and long-term vision to lead with impact, not ego.

- Pay It Forward: How to mentor and inspire others, especially young women, to pursue leadership roles with confidence.

Amy’s story empowers us to lead with authenticity and purpose, inspiring a ripple effect of change for women in SaaS.

SheSass Unplugged is produced by Urban Podcasts.

Dru also shares the importance of diversity, mentorship, and how to successfully manage a demanding career while maintaining balance in life. Her insights on leadership, risk-taking, and the evolving fintech landscape offer valuable lessons for anyone looking to make bold career moves.

SheSaas Unplugged is produced by Urban Podcasts.

Kendra shares the pivotal moment when she took 10 months off during the pandemic to reset and redefine her career. She shares her unconventional path to CEO in the male-dominated transportation industry and the challenges she faced along the way.

From cultivating a ‘no-asshole’ culture to prioritising inclusivity and diversity, Kendra’s leadership style has reshaped Truckstop’s culture. Her story offers powerful lessons on overcoming setbacks, embracing feedback, and navigating the road to leadership—especially for women in tech and logistics.

SheSaas Unplugged is produced by Urban Podcasts.

She discusses her shift from corporate life to private equity, highlighting her approach to overcoming challenges, building relationships, and empowering CEOs. Resilience, transparency, and collaboration are key to her leadership, especially in high-stakes private equity-backed businesses. 

Dawn also talks about mentorship, self-confidence, and balancing personal ambition with developing others. She shares her charity work, including her involvement in an organisation focused on improving children’s reading skills, showing how leadership goes beyond the boardroom.

SheSaas Unplugged is produced by Urban Podcasts.

Elona recounts her path to becoming CEO, emphasising her background in finance and her early passion for math. She discusses her roles as CFO and CEO and touches on her innovative role as Chief Opportunity Officer at Iris, created to maximise the company's potential.

Elona explores how using numbers can gain business insights and maximise potential. She stresses the importance of making fast, informed decisions, taking risks, and learning from failures.

SheSaas Unplugged is produced and managed by Urban Podcasts.

Drawing from her groundbreaking experience as the former CEO of SUSE, Melissa shares invaluable insights on topics ranging from the impact of AI to her views on Menopause and navigating the challenges of motherhood while advancing in one's career. Through her extraordinary journey, Melissa exemplifies resilience, determination, and a commitment to inspiring the next generation of leaders.

During this empowering discussion, we delve into the intersection of leadership, technology, and personal growth with one of the industry's most visionary leaders.

SheSaas Unplugged is produced and managed by Urban Podcasts.

In this episode, Nicole traces her journey from co-founding Social Chorus to helming Firstup, following its merger with Dynamic Signal in 2021 under the ownership of Sumeru Equity Partners. She reflects on the transformative moments and strategic insights that have shaped her trajectory as a leader in the SaaS ecosystem.

Nicole delves into the intricacies of building a cohesive organisational culture amidst the backdrop of mergers and acquisitions, emphasising the importance of alignment, communication, and shared values. Drawing from her experiences navigating transitions and scaling operations, she offers practical wisdom for fostering resilience and adaptability in turbulent times.

Join Nicole as she explores the nuances of remote leadership and distributed teamwork, leveraging technology to foster connection and collaboration across geographies. She underscores the significance of purpose-driven leadership in galvanizing teams towards collective success, even amidst the challenges of remote work. 

Through candid anecdotes and thought-provoking insights, Nicole invites listeners to reimagine the possibilities of leadership in the digital age, championing authenticity, empathy, and innovation as cornerstones of enduring success. Tune in as we unravel the narrative of transformative leadership with Nicole Alvino, Co-founder & CEO of Firstup.

SheSaas Unplugged is produced and managed by Urban Podcasts.

In this episode, Christina shares her invaluable experiences navigating cultural and strategic shifts while transitioning through tech giants such as Salesforce and Slack. Drawing from her diverse background, she offers insights into the unique challenges and opportunities facing female leaders in the competitive SaaS industry.

Christina shares her approach to nurturing a remote workforce, with the rise of remote work, she emphasises the importance of keeping every team member connected and motivated, no matter where they are, and the importance of balancing life’s demands, conquering self-doubt, and pursuing your passions.

SheSaas Unplugged is produced and managed by Urban Podcasts.