Best Manager Ever

Darius Contractor is the Chief Growth Officer at Otter AI. Darius has had a long and impactful career in the startup and tech worlds. Prior to Otter AI, he led engineering, growth and product teams at Vendr, Airtable, Facebook, Dropbox, Bebo and more. He is also an investor and advisor in multiple companies and funds. 

Darius’s direct reports describe him as a master of frameworks and analogies, someone who balances detail orientation with a big-picture vision, and a manager who pushes boundaries with unconventional but memorable approaches.

In this episode, show creator and Fort Light founder Annie Riley sits down with Darius,

and they discuss:

• How to support your team’s career path in a fast-paced, high-growth environment 
• The SEEN framework for career development 
• Designing jobs like dinner plates 
• How frameworks and analogies make concepts more memorable 

If you’re interested in sponsoring an episode of Best Manager Ever, reach out: [email protected]

Join us on Substack

Connect with Darius Contrator

Connect with Annie Riley

Check out Fort Light to level up your leadership skills

Connect with our show’s Producer, Alexis Ramdaou

Nominate your Best Manager Ever for the Podcast

This is a Production of Fort Light and Now it’s Hear

Hosted on Acast. See acast.com/privacy for more information.

Stevie Case is the Chief Revenue Officer at Vanta. Stevie started her career as the world’s first female pro gamer, and then found her way into the tech and startup world through a self-described “winding path”. Prior to Vanta, Stevie had a successful chapter at Twilio, where she started as an individual contributor and then grew to be the VP of Mid-Market Sales.

Stevie’s direct reports consistently describe her as an empowering leader who excels at identifying and nurturing the unique strengths of each individual on her team. They highlight her ability to create an environment where people feel trusted to be themselves, try new things, and take ownership of their work. The most common theme in their feedback is that Stevie makes her team members feel empowered—she is known as a “yes, and…” leader who encourages innovation and supports her team’s ideas, while also setting a high bar for performance and a strong drive to win.

In this episode, show creator and Fort Light founder Annie Riley sits down with Stevie, and they discuss:

• How Stevie has moved between IC and manager roles in her career (and why!) 
• What a manager’s real job is— according to Stevie 
• Why your direct reports are not your “first team” 
• How Stevie vetted Christina as a potential CEO and boss 
• How Stevie’s communication style has evolved as she’s become more senior and Vanta has scaled 
• Why you should prioritize sharing your own story on LinkedIn, even amid a busy startup schedule 

If you’re interested in sponsoring an episode of Best Manager Ever, reach out: [email protected]

Join us on Substack

Connect with Stevie Case

Connect with Annie Riley

Check out Fort Light to level up your leadership skills

Connect with our show’s Producer, Alexis Ramdaou

Nominate your Best Manager Ever for the Podcast

This is a Production of Fort Light and Now it’s Hear

Hosted on Acast. See acast.com/privacy for more information.

Best Manager Ever shares unfiltered leadership lessons and actionable advice from the most successful and beloved leaders in the startup and tech worlds. This season, you'll hear honest, insightful interviews with operators who’ve been nominated by their teams as the best manager they’ve ever worked for. And for the first time, we’re adding interviews with experts who’ve gone deep on the leadership topics that matter most to you.

Each episode is designed to share actionable advice that helps you level up as a leader— almost like a seasoned mentor in your pocket and in your corner. All you have to do is show up and hit play, and we’ll give you something valuable that you can apply in your own work and life. 

Season 3 starts September 10th and new episodes drop every Wednesday. 

Subscribe to make sure you never miss an episode, and join the conversation on Substack. 

If you’re interested in sponsoring an episode of Best Manager Ever, reach out: [email protected]

Join us on Substack 

Connect with Annie Riley

Check out Fort Light to level up your leadership skills

Connect with our show’s Producer, Alexis Ramdaou

Nominate your Best Manager Ever for the Podcast

This is a Production of Fort Light and Now it’s Hear

Hosted on Acast. See acast.com/privacy for more information.

In this solo episode of Best Manager Ever, host Annie Riley of Fort Light takes a moment to reflect on the standout lessons from Season Two.

Annie revisits the powerful insights shared by this season’s guests—from hiring people who challenge you, to seeking out dissenting views, to nurturing both personal and team growth. It’s a chance to pause, look back, and celebrate the wisdom and warmth these leaders brought to the show.

Whether you're a longtime listener or just tuning in, this episode offers a meaningful recap of the themes that shaped Season Two—like independent thinking, purposeful leadership, and finding joy and meaning in the work we do.

Join us on Substack 

Connect with Annie Riley

Check out Fort Light to level up your leadership skills

Connect with our show’s producer Alexis Ramdaou

Nominate your Best Manager Ever for the Podcast

This is a Production of Fort Light and Now it’s Hear

If you’re interested in sponsoring an episode of Best Manager Ever, reach out: [email protected]

Hosted on Acast. See acast.com/privacy for more information.

Sruthi Lanka serves as CFO of Public, an investing platform that allows everyone to invest in stocks, ETFs, crypto, and alternative assets, like fine art and collectibles—all in one place. Prior to Public, she was VP Finance at MoneyLion, a consumer lending platform that listed on NYSE via SPAC in 2021. Her previous career was in investment banking at the Royal Bank of Canada and technology at Goldman Sachs.

Sruthi's direct reports praise her coaching and context-driven leadership approach, maintaining lean teams while investing heavily in tools and automation, fostering a metrics-driven mindset, and the importance of authenticity and personal connection in leadership.

In this episode, show creator and Fort Light founder Annie Riley sits down with Sruthi, and they cover:

• Recruiting 'scary' talent to push the company's boundaries
• How to build cross-functional expertise
• Maintaining a strong understanding of company metrics
• Promoting a culture where lean teams are empowered 
• How to integrate joy into work

Join us on Substack 

Connect with Sruthi Lanka

Connect with Annie Riley

Check out Fort Light to level up your leadership skills

Connect with our show’s producer Alexis Ramdaou

Nominate your Best Manager Ever for the Podcast

This is a Production of Fort Light and Now it’s Hear

Hosted on Acast. See acast.com/privacy for more information.

Asheesh Birla is an Entrepreneur, Angel Investor and Ripple Board Member. Asheesh joined Ripple in 2013 when the team was fewer than ten people. He had a decade-long journey of building Ripple on the product team, and he continues to stay connected to the company as a member of the board. 

Asheesh’s  direct reports admire his passion, strategic vision, and ability to cultivate a positive work culture. They praise his direct communication, commitment to personal development, and knack for making tough situations enjoyable

In this episode, show creator and Fort Light founder Annie Riley sits down with Asheesh, and they cover:

• How to set high standards and expectations while maintaining trust and motivation
• The importance of coaching – for yourself and your team
• Effective strategies to develop and retain talent
• The importance of communicating in a direct and caring way
• Methods to handle difficult situations with positivity

Join us on Substack 

Connect with Asheesh Birla

Connect with Annie Riley

Check out Fort Light to level up your leadership skills

Connect with our show’s producer Alexis Ramdaou

Nominate your Best Manager Ever for the Podcast

This is a Production of Fort Light and Now it’s Hear

Hosted on Acast. See acast.com/privacy for more information.

Lauren Rhode is the VP of Sales at Webflow, and she’s had several interesting chapters to her career. Lauren got her start in public service, working at the Department of Defense. She also played on the national rugby team, and traveled around the world competing for Team USA. She started her tech career in product, before discovering her knack for sales. She has held prior roles at Bablestreet (formerly Vertical Knowledge) and Anaplan.

Lauren's direct reports describe her as a hardworking and empathetic leader. She is known as a “machine”, while also fostering a positive team culture where everyone feels valued and supported.

In this episode, show creator and Fort Light founder Annie Riley sits down with Lauren, and they cover:

• Dealing with leadership transitions in scaling companies 
• How to show up deliberately in virtual interactions
• Empowering teams with optimistic realism
• Managing your time and schedule intentionally as a leader

Join us on Substack 

Connect with Lauren Rhode

Connect with Annie Riley

Check out Fort Light to level up your leadership skills

Connect with our show’s producer Alexis Ramdaou

Nominate your Best Manager Ever for the Podcast

This is a Production of Fort Light and Now it’s Hear

Hosted on Acast. See acast.com/privacy for more information.

Leanna Nazzisi is the Senior Direct of Customer Experience at Victoria Beckham Beauty, a clean beauty, cruelty-free, digital-first makeup and skincare brand. Leanna launched her startup career as a seasonal contractor with Birchbox, where she rose through the ranks to become a senior CX leader as the company scaled. She also had a chapter as a customer success leader during Zendesk’s growth stage. 

Leanna's direct reports praise her for fostering an environment where everyone feels valued and empowered to contribute, highlighting her willingness to embrace change and focus on both personal and professional growth. They describe her as knowledgeable, communicative, in tune with everyday situations, truthful, caring, authentic, and confident.

In this episode, show creator and Fort Light founder Annie Riley sits down with Leanna, and they cover:

• How to manage peers and friends-turned-direct reports 
• Proactively eliciting ideas and really listening 
• Matching the business needs with the strengths and needs of the individuals on the team 
• Creating a culture of transparency, honesty, and clarity 

Join us on Substack 

Connect with Leanna Nazzisi

Connect with Annie Riley

Check out Fort Light to level up your leadership skills

Connect with our show’s producer Alexis Ramdaou

Nominate your Best Manager Ever for the Podcast

This is a Production of Fort Light and Now it’s Hear

Hosted on Acast. See acast.com/privacy for more information.

Amit Shah is the COO of Virta Health, where he’s built the company from ~30 team members to over 800 colleagues working to reverse obesity and diabetes. Amit has 10+ years of experience in building and scaling entrepreneurial and high-growth healthcare organizations, with a focus on delivering financial and operational results while aligning on mission and values.

Amit’s direct reports praise his ability to balance the needs of Virta’s members, business, and staff, describing him as incredibly kind, caring, driven, and a fierce protector of his team. He is celebrated for his passion, structured thinking, dedication to his own growth and development, and continuous improvement in leadership.

In this episode, show creator and Fort Light founder Annie Riley sits down with Amit, and they cover:

• How to build a gratitude practice that supports your team– and yourself
• The importance of emotional awareness and regulation in leadership 
• Energy management habits and practices   
• A process to take charge of feedback, learning, and growth 
• The relationship between execution and strategy in startups 

Join us on Substack 

Connect with Amit Shah 

Connect with Annie Riley

Check out Fort Light to level up your leadership skills

Connect with our show’s producer Alexis Ramdaou

Nominate your Best Manager Ever for the Podcast

This is a Production of Fort Light and Now it’s Hear

Hosted on Acast. See acast.com/privacy for more information.

Liz Ludwig is the co-founder of Takes, a game for sports fans. Liz started out working in Fortune 500 companies, before moving into the startup world. She had a successful career building and scaling marketing functions at Sungevity, OhmConnect, and more. 

Liz’s direct reports describe her as a high-energy manager who builds momentum, trusts her team quickly, empowers them, and balances results with human connection. They appreciate her transparent communication, ability to align teams, and willingness to mentor and support even past their tenure.

In this episode, show creator and Fort Light founder Annie Riley sits down with Liz,

and they cover:

• Approaching the ambiguity of early-stage building as a management advantage 
• The importance of hiring and firing fast – especially at the early stage 
• How to help direct reports find their best role
• Tactics for smooth team transitions 
• Communication tips  

Join us on Substack 

Connect with Liz Ludwig 

Connect with Annie Riley

Check out Fort Light to level up your leadership skills

Connect with our show’s producer Alexis Ramdaou

Nominate your Best Manager Ever for the Podcast

This is a Production of Fort Light and Now it’s Hear

Hosted on Acast. See acast.com/privacy for more information.