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TitreDateDurée
Season 4 Wrap: What the Best Leaders Do Differently24 juin 202600:21:55

After 50 episodes with some of the top leaders in startups and tech, Annie Riley takes a moment to reflect and share her top five leadership takeaways that surfaced again and again throughout the latest season. 


Annie also reflects on the current moment—from the rapid rise of AI to the growing need for authentic human connection—and why those realities have only strengthened her commitment to building a show that is honest, practical, and deeply human.


Plus, she shares what's next for Best Manager Ever as the team heads into a summer of experimentation, new formats, and fresh ways to support leaders navigating the messy middle of company building.


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Best Manager Ever is a Production of Fort Light and Now It’s Hear

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Rethinking Executive Presence with Scott Lamb17 juin 202600:54:27

The stereotype of the hard-charging executive is hurting performance. Scott Lamb moved to NYC to pursue journalism, but ended up joining Buzzfeed when it was just five people and has been on the startup path ever since. In this episode, Scott sits down with Annie Riley to explore a different model for leadership– one rooted in curiosity, steadiness, psychological safety, and real human connection. They discuss what’s really behind vague feedback about “executive presence”, how management is a learnable craft, and how to have hard conversations that don’t FEEL bad. 


Time Stamps:

00:00 — Why management matters

02:07 — Scott’s leadership style

04:08 — Joining BuzzFeed at five people

06:13 — Management is a skill

08:47 — The problem with “executive presence”

10:02 — Visibility vs. impact

13:21 — Directness over aggression

17:20 — Tough conversations done well

19:42 — Leading through layoffs

22:19 — Avoiding emotional dumping

24:56 — How to fire someone clearly

29:29 — The power of “say more”

37:22 — Listening and accountability

43:04 — Why humor matters at work

48:06 — Reps over perfection


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Best Manager Ever is a Production of Fort Light and Now It’s Hear

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Self-Compassion Break for High Performers10 juin 202600:55:32

The voice pushing you forward is also holding you back, and your inner critic is costing you more than you think. Annie Riley talks with clinical psychologist and self-compassion teacher Dr. Michael Klein to explore the psychology behind ambition, achievement, and the never-ending pursuit of "more." They discuss why success doesn't automatically lead to happiness, how striving and self-criticism can narrow creativity and reduce judgment. And they explore practical self compassion tools to help high-achieving leaders become more resilient, focused, creative, and effective.


Time Stamps:

00:00 – Introduction 

01:00 – Why self-compassion matters for leaders

06:30 – Understanding the threat system

11:15 – The antidote to constant stress

13:00 – The striver's trap

18:00 – Why kindness doesn't kill ambition

20:15 – The self-compassion break

29:00 – Mindfulness, resistance, and suffering

33:00 – Responding instead of reacting

37:00 – Working with your inner critic

41:00 – Bringing compassion into the workplace

43:00 – Building a sustainable practice

49:00 – A better edge than self-criticism


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Speed to Signal with JZ - Laurel CPO03 juin 202600:48:08

JZ has built product teams at Airbnb, Webflow, Dropbox (and now Laurel), and in this episode she shares her honest leadership playbook and lessons learned. JZ covers why conviction is really about speed to signal, how to move fast without creating chaos, and why great leaders should share uncertainty instead of performing conviction. JZ also shares hot takes about 1:1 meetings, asking for help, and scrapping work that isn’t going in the right direction. This conversation between JZ and Annie Riley is packed with practical frameworks for managers and startup operators who want to move faster and build teams that thrive in ambiguity.


TimeStamps:

00:00 — Meet JZ

03:03 — The “fast-moving river” analogy

05:38 — Getting people to jump in

07:22 — Hiring for curiosity and urgency

10:11 — What “speed to signal” means

12:43 — Building through fast feedback

16:16 — The 3 leadership traps

20:41 — Operating at 120%

23:54 — Sharing unfinished work early

27:14 — Open sourcing strategy and workflows

31:34 — Knowing when to stop

34:16 — Graduating out of one-on-ones

36:23 — Asking for help effectively

40:23 — Trust, communication, and speed

43:41 — Ownership, introspection, and time


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This episode is sponsored by Blomma, the AI career coach built to help people grow with more clarity, accountability, and insight over time. Use code MANAGER for a free month and early access: https://www.blomma.com/ 

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How "Temporary Permanent" Drives Progress27 mai 202600:50:41

Don’t let perfectionist fantasies kill progress. Annie Riley sits down with Anna Randall, Director of Enterprise Sales at Curri and former VP of Sales at TigerEye, Autodesk, and PlanGrid, to explore the power of “temporary permanent” thinking. They break down why the best teams prioritize momentum over precision, normalize imperfect solutions, and keep moving when the path changes. Plus: why the traditional “lone wolf” sales mentality is a bad thing, and the best leaders win as a pack.


Time Stamps:

00:00 Meet Anna Randall

02:16 Startup vs enterprise: autonomy, control, and team dynamics

04:38 Grit builds excellence: repetition over talent

06:23 Navigating early-stage chaos in real time

09:52 “Standing on the sun” + embracing uncertainty

10:24 “Temporary permanent”

13:31 The limits of grit:

16:21 The pack mentality: why lone wolves lose

21:07 Connecting team performance to the bigger “why”

23:19 Rethinking one-on-ones: making them actually valuable

27:38 Building trust through human connection

30:22 Saying the hard thing

33:29 Negotiation as trade-offs and “cards”

38:53 Managing expectations

43:35 Choosing the pack over self


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 Ex-Pinterest & Canva Exec: Curiosity As A Muscle 20 mai 202600:47:37

Work is not like school– there are no right answers, and if you’re looking to be “right” then you will always fall behind. Annie Riley sits down with Silvia Oviedo Lopez, Founder & CEO of Blomma AI and former Canva and Pinterest leader, to unpack how the best leaders train curiosity, learn in real time, and see hard questions as a gift.


Time Stamps: 

00:00 — Meet Silvia Oviedo Lopez

03:48 — How to Position Yourself for Growth

05:25 — Be Someone Who Brings Clarity

09:28 — Fast Learning Loops

10:44 — Pattern Matching vs. Fresh Thinking

12:34 — Curiosity Is a Muscle

16:16 — Coaching Without “Right vs. Wrong”

18:18 — Let Go and Keep Moving

27:05 — Scaling as a Leader

33:15 — Building Complementary Teams

36:57 — Leading People Smarter Than You

41:04 — What Are You Hearing From Your Team?

42:33 — Curiosity as a Leadership Superpower

43:16 — Flexibility in a Changing World


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Connect with Silvia Oviedo Lopez

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Unblock Your Team with Powerful Questions 13 mai 202600:52:56

Better questions create better teams. Annie Riley sits down with Maayan Roth, Head of Engineering at Crux Climate, to unpack the skill most managers overlook: asking questions that actually move things forward. Maayan shares how to use curiosity to uncover what’s really going on and guide conversations without controlling them. Plus: the traps new managers fall into, the difference between coaching and interrogating, and the simple question that turns hesitation into action.


TimeStamps:

00:00 – Meet Maayan Roth 

02:53 – Startup leadership: building everything from scratch

05:27 – Why asking better questions is a leadership superpower

06:16 – Open vs. closed questions 

08:28 – The “Socratic trap” and fake curiosity

10:09 – Letting go of having the answer

12:03 – Why leaders should speak last

14:17 – Go-to questions to unblock your team

18:58 – How to know if you’re asking the right questions

23:39 – Common traps: not listening, fake coaching, dead ends

31:23 – When coaching doesn’t work (and switching styles)

32:20 – What coaching actually means as a manager

39:31 – Growth should feel uncomfortable

43:46 – Hard lesson: stop doing everything so your team can step up

47:07 – There’s no “easy mode” in leadership + finding your people


Join us on Substack 

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Connect with Maayan Roth

Nominate Your Best Manager Ever


Best Manager Ever is a Production of Fort Light and Now It’s Hear


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Top CEO Coach On The Difficulty of Empathizing Up06 mai 202600:49:59

Leadership is lonely. Most leaders don’t get enough support or positive feedback. And that includes our own boss too. Annie Riley and top executive coach Ed Batista break down why it’s so hard to empathize up— and how simple shifts like checking in or offering genuine positive feedback can change the dynamic, because sometimes the most powerful move is truly seeing the person behind the role.


Time Stamps:

00:00 Meet Ed Batista

02:36 Why empathizing up is so hard

03:48 The myth of the “invulnerable” leader

05:11 How to actually start empathizing up

06:45 Why your boss isn’t getting enough positive feedback

08:39 Empathizing up vs. managing up

09:56 Empathy does not mean agreement

12:03 What to do when your boss shuts you down

16:34 It’s probably not about you

20:07 Intent vs. impact 

24:50 Leaders as shock absorbers

31:49 Pain is mandatory. Suffering is optional.

33:50 The danger of overvaluing feelings at work

39:07 Is the story you’re telling serving you?

41:52 Leadership is intuition, not a formula


Join us on Substack 

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Connect with Ed Batista

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Best Manager Ever is a Production of Fort Light and Now It’s Hear

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“Smart Rats”: Belief Boosts Performance 29 avr. 202600:52:13

You don’t become a great manager by regurgitating frameworks. Management is a craft and a skillset that gets built over time.  Annie Riley sits down with Maura Church, VP of Product & Engineering at Two Chairs, to talk about how a manager’s mindset impacts team performance. From the “Smart Rats” theory to balancing tough feedback with real belief, Maura breaks down how to coach growth, build confidence, and unlock better results.


TimeStamps:

00:00 — Meet Maura Church

02:54 — Management is a craft, not a side job

04:49 — Why startups can’t afford bad management

07:14 — “No one is coming to save us”

10:09 — The trap of managing by checklist

13:07 — Giving feedback without making it personal

19:06 — “Smart Rats”: belief as a performance levers

25:13 — Turning “non-technical” skills into strengths

38:55 — Clear expectations make feedback easier

41:39 — Psychological safety is built, not assumed

45:10 — Rewriting the rules as your team evolves

47:15 — There’s no one “right” way to manage


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Be Champagne, Not Flat Soda22 avr. 202600:36:36

Building a strong network is a skill. Annie Riley sits down with Whitnie Narcisse, former First Round Capital Partner, to unpack how she has built one of the best networks in Silicon Valley. Whitnie breaks down how to be memorable and build connections that last using her FACE framework (Factual, Authentic, Credible, and Engaging). Plus: why most networking advice falls flat, how to design rooms people want to be in, and the biggest networking mistake most people make. 


Time Stamps:

00:00 – Whitnie's 3 biggest career inflection points

05:50 - How Whitnie got to First Round

06:50 – Agency in networking

09:30 – What actually gets a response

11:30 – Async networking and respecting people’s time

13:30 – Why most networking formats don’t work 

15:30 – Building a high-value community and ecosystem

18:30 – The secret to great events

21:00 – How to create meaningful connections 

23:30 – The FACE framework: how to be memorable 

29:00 – The follow-up gap: why networking really starts after the handshake

31:00 – Generosity, authenticity, and playing the long game


Join us on Substack 

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Get Yourself Some “Boast Bitches”15 avr. 202600:47:18

“Polite silence” is a silent killer on teams. Annie Riley sits down with Dorothy Kilroy, Chief Commercial Officer at Oura Ring and former Airbnb to talk about how to invite productive disagreement while fostering psychological safety and how to give direct feedback without making it personal. Plus: the career-changing power of building your own “Boast Bitches”—a trusted circle that advocates for you and helps you grow.


TimeStamps:

00:38 – Meet Dorothy Kilroy 

03:20 – Storytelling, mission-driven work, and bringing your full self

05:30 – The leadership shift: from having answers to building others

06:44 – Vulnerability at work: not therapy, but a signal of self-awareness

08:48 – Psychological safety + high standards 

11:45 – “I believe in you”: the simplest, most powerful leadership tool

17:59 – Inviting disagreement: how to avoid false harmony on your team

21:54 – High standards without fear

26:00 – Reflection as a system

29:01 – Burnout, recovery, and building sustainable performance

32:40 – Feedback that drives growth

37:00 – “I” vs.“We”: balancing ownership and accountability

38:06 – Get yourself some “Boast Bitches”: building your personal board of directors


Join us on Substack 

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Best Manager Ever is a Production of Fort Light and Now It’s Hear

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Time Kills Follow-Up: Share Context Now08 avr. 202600:47:04

Speed beats perfection every time. Annie Riley dives in with Junan Pang, VP of Customer Success at Intercom, to unpack how he gives direct reports the context they need to act independently. He talks through why most leaders under-share, and how quick, imperfect updates unlock better decisions– without drowning the team in meetings or messages.


Timestamps:

00:00 Meet Junan Pang

01:58 Learning as a mindset

05:28 Taking intentional steps back

08:48 Growth through manager & IC zigzags

14:32 Building authentic, long-term relationships

18:08 Being in the problem

22:32 Fast, imperfect context sharing 

31:35 Learning through osmosis 

37:26 Feedback as a daily practice


Join us on Substack 

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Best Manager Ever is a Production of Fort Light and Now It’s Hear


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Bad Meetings Are Disrespectful01 avr. 202600:49:29

Meetings can be a real problem when they’re not run well or have the wrong people in them. Julia Bernstein, COO at Brightside Health joins Annie Riley to break down how she audits, redesigns, and even “dress rehearses” meetings to make them actually useful. From cutting unnecessary attendees to auditing recurring meetings regularly, Julia shares her no-BS approach to protecting time and driving results.


Timestamps:

00:00 – Meet Julia Bernstein

02:00 – Translating business into people-first leadership

04:50 – Influencing without authority

06:30 – Managing diverse teams 

07:15 – Building career ladders from day one

16:20 – Being involved vs informed

20:50 – The meeting audit: cutting what doesn’t work

24:50 – Designing better meetings 

26:40 – Giving your team real ownership

27:20 – No one will set your boundaries for you

33:15 – Weekly rituals that keep teams aligned, human, and performing


Join us on Substack 

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Best Manager Ever is a Production of Fort Light and Now It’s Hear

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A Manager’s Word Has To Mean Something 25 mars 202600:54:59

What if the secret to great leadership is actually learning to say no? Annie Riley sits down with Gautam Prabhu, VP of Engineering at Scribe AI and longtime startup operator, to unpack his lessons from 25+ years of building teams at PagerDuty, Zendesk, and Opentrons. Gautam talks through why leaders should treat every “yes” as a promise, how winning teams are built through systems (not heroics), why a bad decision is better than no decision at all, and how he builds trust through honesty and accountability.


Time Stamps:


00:00 Meet Gautam Prabhu

02:11 From engineer to accidental manager

05:04 Learning leadership the hard way

08:26 The two kinds of trust

12:03 Why intent matters first

15:42 Competence has to follow

19:18 Why great managers say no

23:57 A bad decision beats no decision

28:41 Startups can’t run on heroes forever

33:22 Building systems that scale

39:48 What great leadership really leaves behind


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Best Manager Ever is a Production of Fort Light and Now It’s Hear



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COO of Headspace: Why You Should Re-Recruit Yourself 18 mars 202600:49:52

What does it take to lead through 15 years of pivots, mergers, layoffs, and massive growth— without losing your people (or your mind!) along the way? Annie Riley sits down with Karan Singh, co-founder of Ginger and COO of Headspace, to unpack why great managers win people over through curiosity and genuine connection, how managers need to learn to ride the “J-curve” of change, and why everyone should re-recruit themselves to their role. 


Timestamps:

00:00 Meet Karan Singh

04:30 Learning to manage on the fly

07:20 Winning people over

09:25 The mindset for surviving startup chaos

12:01 The j-curve of change

14:41 Speed vs. Space: giving teams time to process change

18:32 Healthy departures 

22:24 Creating a “Next Play Plan” 

26:49 Why you should re-recruit yourself

38:52 Rethinking PIPs: What most people get wrong 


Join us on Substack 

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Connect with Karan Singh

Nominate Your Best Manager Ever


Best Manager Ever is a Production of Fort Light and Now It’s Hear

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Welcome to Season 411 mars 202600:01:42

Best Manager Ever shares hard-earned leadership lessons from the very best and most successful managers in startups and tech. But here’s the twist: Every guest is endorsed by their team as the “best manager ever.” We talk to the guest’s direct reports to learn how they *really* lead, and then unpack that feedback live with the guest. 


This season we’re leveling up with world-class experts who have spent their careers studying the science of leadership, including professors, authors, and coaches.


Season 4 kicks off March 18th, with new episodes every Wednesday wherever you get podcasts.


If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.com


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

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Best Manager Ever: Santa24 déc. 202500:13:19

In this special holiday spoof episode of Best Manager Ever,  Annie Riley, host and founder of Fort Light, chats with the one and only Santa Claus!


Known for spreading holiday cheer and managing a diverse team at the North Pole, Santa gives a rare interview about life behind the scenes. His direct reports, including elves and reindeer, praise Santa for his leadership, though they note he's their only manager ever ;) 


We will dive into Santa's leadership style, the secrets behind the naughty and nice lists, and the challenges of maintaining the Christmas spirit all year long. Join us for a fun-filled episode with laughter and insight into the man behind the magic.


Connect with Annie Riley

Connect with our hilarious Santa, Jason Gore

Listen to Jason’s podcast 108.9 The Hawk

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

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Best Manager Ever: Top Takeaways From Season 3 17 déc. 202500:20:24

In this recap episode of Best Manager Ever, host Annie Riley reflects on standout lessons from Season 3.


Annie discusses the six things our top manager guests have in common: high standards, clear communication, strong relationships with peers, a relentless focus on their own growth, a unique view of career management, and a human-first perspective. 


It’s a chance to pause, look back, and notice what makes our guests so exceptional— and then think about how to apply those lessons in your own work. 


Whether you're a longtime listener or just tuning in, this episode offers a meaningful recap of the themes that shaped our season. 

Share your feedback and suggestions from the season in this super quick form, so we can make future episodes even better. 


If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.com


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

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Best Manager Ever: Jared Erondu – Hard Mode Leadership10 déc. 202500:52:09

Jared Erondu is a seasoned design and startup leader, and is currently the Head of Design at early-stage startup Span. Jared spent eight years at Lattice rising from a solo designer pulling all-nighters in the early days, to leading a 50-person design organization and serving as GM across product and GTM as the company scaled. Earlier in his career, he was a design leader at Teespring and Omada Health. Jared is known for his design mentorship and community-building, and is an active advisor and angel investor. 


Jared brings a calm, steady presence, especially during challenging times, always seeing the long view and providing unwavering support. His team appreciates his high standards, attention to detail, and commitment to craft, but also noted that he balances intensity with humor and approachability.


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


  • Why all managers should master selective transparency
  • The right way to communicate destabilizing intel 
  • How to recondition your mindset for “hard mode” leadership
  • How to build a bench of resources to support yourself  
  • The best way to recruit exceptional talent 
  • Why managing your own mindset is the ultimate leadership unlock 


If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.com


Join us on Substack 

Connect with Jared Erondu

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


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Best Manager Ever: Dana Lawson - Conquering Imposter Syndrome and Fostering Team Resilience03 déc. 202500:43:35

Dana Lawson is the CTO of Netlify. She’s been a technologist for decades, and was previously the VP of Engineering at Github and the Director of Engineering at New Relic, Heptio, InVision (acquired by Miro), and more. Dana has a diverse background, and served in the military. 


Dana's direct reports praise her for building confidence, providing autonomy support, for bringing honesty and compassion, and for sponsorship that goes beyond mentorship. 


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


  • How imposter shows up at senior levels– and how to handle it  
  • How to deal with interpersonal conflicts
  • What it takes to be an effective sponsor
  • The importance of embracing change


If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.com


Join us on Substack 

Connect with Dana Lawson

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

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Best Manager Ever: Amit Shah - Building Trust Through Gratitude26 nov. 202500:48:46

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


If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.com


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

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Best Manager Ever: Patrick Reynolds - Creating the Conditions for Success19 nov. 202500:39:44

Patrick Reynolds is the Co-Founder and Head of Product at Office Hours, an expert marketplace. Patrick started his career as a software engineer, before becoming a self-taught product designer and making the leap into product leadership. He has worked at an array of tech companies and startups including Affirm, Sweep, and Adobe. 


Patrick's direct reports praise him for his exceptional thoughtfulness, noting his ability to remember personal details and small, meaningful actions that remove friction and boost morale. They describe him as a natural coach who not only sets high standards but also provides the necessary support and resources to achieve them. 


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


  • The difference between leadership and management  
  • How to prime yourself so it’s easy to spot opportunities to support your team 
  • The difference between a culture that inspires ambition vs. enforces it 
  • How to consume content for maximum ROI 
  • The best way to spot (and stop!) perfectionism 


If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.com


Join us on Substack 

Connect with Patrick Reynolds

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Check out Fort Light to level up your leadership skills

Connect with our show’s Producer, Alexis Ramdaou

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Best Manager Ever: Sophie Ruddock – Showing Up for Your Team During Crisis12 nov. 202500:40:12

Sophie Ruddock brings deep expertise in scaling mission-driven tech companies, and is now the COO at Empathy. Sophie was an early employee at Multiverse, where she grew with the company and ultimately became their global COO leading through rapid growth and market expansion. 


Sophie’s direct reports praise her empowering leadership style, her commitment to their development, and her unwavering advocacy. She hires people for their unique expertise and encourages them to bring their full selves to work, and reminds them of their value even in moments of self-doubt.


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


  • What a “founder mindset” really means for employees 
  • How to earn the right to dissent 
  • How to lead when someone on the team has an unexpected crisis 
  • The mindset shift that enabled Sophie to go from managing 3 to 600+ people 


If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.com


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Best Manager Ever: Behavioral Science as a Leadership Tool 05 nov. 202500:42:02

In this expert episode, Annie Riley sits down with Matt Wallaert, an applied behavioral scientist who made the leap into the tech and startup worlds. Matt is currently the CXO at Oceans, and he’s previously held leadership roles at Clover Health, LendingTree, Microsoft, frog design, and more. 


Matt explains why all leaders should know and use the principles of applied behavioral science– because all startup leaders are in the business of behavior change with our customers, our teams, and ourselves. 


They discuss specific tactics that leaders can use to influence their team’s behavior, including the SIDE framework, promoting and inhibiting pressures, iterative experimentation, and more. Matt explains how applied behavioral science can be the key to unlocking lasting and meaningful behavior change, and to achieving a more empathetic and effective leadership style. 


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Worst Manager Ever: Annie’s Scariest Manager Stories 29 oct. 202500:16:50

​​In this special Halloween episode of Best Manager Ever, host Annie Riley recounts the top worst manager moments of her career. 


Tune in to hear scary manager stories, from tales of micromanagement to vague (and unsettling!) feedback… and even Annie’s own manager missteps. 


There’s value in learning from the best, and ALSO from the worst! You’ll finish this episode feeling less alone, and even with some actionable lessons to help you avoid the same manager mistakes. 


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Best Manager Ever: Amy Jenkins - Context and Connection Before Content 22 oct. 202500:37:22

Amy Yamner Jenkins is the Chief Operating Officer at Meadow, which is an early-stage fintech startup working to transform the financial experience for students and universities. Amy started her career as a classroom teacher, and pivoted into startups by working at NewSchools Venture Fund. Before Meadow, she had a long and successful chapter building Education Elements, and then led the partnerships team at Outschool. 


Amy’s direct reports describe her as an empowering leader, someone who provides useful and constructive feedback, fosters a high-trust environment, and enables team members to grow.


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

and they discuss:


  • Why connection and context should come before content 
  • How to notice and combat bias in hiring 
  • A simple 2x2 framework to exchange feedback with your team 
  • Why you should avoid using common words like “obviously” and “of course” as a leader 


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Best Manager Ever: Adam Fishman - The Right Way to Ask for Feedback15 oct. 202500:45:16

Adam Fishman is a product and growth advisor with 20+ years of experience building and leading startup teams. Adam was on the early team at Lyft, where he served as Head of Growth. He then went on to lead Product & Growth at Patreon and Imperfect Foods, before launching his portfolio career. Adam has been an advisor and fractional leader at ResortPass, Mozilla, HelpScout, Peerspace and more. He is also the creator of FishmanAF newsletter and the host of the Startup Dad podcast. 


Adam’s direct reports praise him for his exceptional support, trust, and empowerment, as is recognized as a catalyst who brings people together across teams, fostering high trust and commitment. His team members appreciate his transparency, proactive communication, and the way he sets clear mutual expectations. 


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


  • How to build trust quickly as a new leader or fractional executive, and why starting from a place of trust matters.
  • How to get more honest feedback from your direct reports
  • The best way to manage defensiveness when receiving feedback– and how Adam learned it the hard way 
  • Predictions for how AI will impact product leadership roles 
  • Why distributing credit and advocating for your team’s growth leads to higher performance and engagement.


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Best Manager Ever: Lauren Gold - The Triple Goal: Learning, Contribution, Fun08 oct. 202500:39:46

Lauren Gold is the Chief Customer Officer at Kustomer, an AI-powered CX platform. Lauren began her tech career at Yahoo before joining the early team at Yext, where she rose from individual contributor to SVP of Enterprise Customer Success. 


Lauren’s direct reports and colleagues describe her as a leader who supports without micromanaging, fosters autonomy, and creates an environment where everyone feels comfortable sharing, learning, and growing. She’s recognized for her attention to detail, data-driven approach, and willingness to jump in and help, while always encouraging her team to take ownership and develop their own skills.


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


  • How to start well in new roles and build trust quickly
  • The art of supporting teams without micromanaging
  • Transitioning from first-line leader to managing managers
  • Spotting and developing leadership talent within your team
  • The importance of over-communication and transparency in leadership
  • Why building relationships and understanding individual motivations matter

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Best Manager Ever: Charlie Coglianese - The Struggle is Real, But So is the Growth01 oct. 202500:48:24

Charlie Coglianese is the Chief Technology Officer at Paloma Learning, a VC-backed edtech startup using AI to improve student learning outcomes. Charlie started his career in finance, before making the leap into startups. He was the Founder & CEO of a startup called Schoolrunner, which was acquired by SchoolMint. Charlie served as the CTO at SchoolMint post-acquisition before returning to early-stage building in his current role


Charlie's direct reports describe him as a leader who invests deeply in the growth of his team. He’s recognized for his ability to spot potential, provide the right level of challenge, and create an environment where people feel trusted to take ownership, try new things, and grow. The most common theme in their feedback is that Charlie empowers his team—he’s known for his intellectual honesty, willingness to jump in alongside his team, and his focus on building trust and clarity.


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


  • How to spot talent through trajectory, instead of outcomes
  • The concept of “productive struggle” and how to balance challenge and support
  • Advice for working with founders and navigating the founder-executive relationship
  • Strategies for retaining top performers and keeping them engaged
  • The importance of clear goals and mission in motivating teams

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Best Manager Ever: Karin Simelaro - Scale Smarter: Building Teams That Thrive at Every Stage24 sept. 202500:40:13

Karin Simelaro is the Chief Revenue Officer at SchoolAI, an AI platform that supports teacher and student success. Previously, Karin served as the Revenue leader at BrainPOP, Pathful, and Seesaw. She was an early employee at Nearpod, where started as the first field sales rep when the company was fewer than 30 people and around $10M ARR, and ultimately grew the business to $100M ARR and a successful exit. 


Karin’s direct reports describe her as open, transparent, energetic, and having high expectations for herself and her team. Her unique blend of skills positions her as a key player in the intersection of education and technology, poised to shape the future of learning.


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

and they discuss:


  • How to evaluate performance amid the uncertainty of early-stage building using the “REKS” framework 
  • The importance of a weekly “coffee and contemplation” 
  • How to act like an owner of the business – whether you’re an IC or C-level 
  • Using AI to prepare and clarify your thoughts


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Best Manager Ever: Darius Contractor - Leading Through Frameworks and Analogies17 sept. 202500:46:01

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 


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Best Manager Ever: Stevie Case - Empowering Leaders by Embracing Authenticity and Trust10 sept. 202500:43:25

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 


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Welcome to Season 3 of Best Manager Ever 03 sept. 202500:02:43

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. 


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Best Manager Ever: Standout Lessons from Season Two25 juin 202500:13:56

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.


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Best Manager Ever: Sruthi Lanka - Hire People That Scare You18 juin 202500:40:11

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


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Best Manager Ever: Asheesh Birla - Embracing Risk and Cultivating Talent11 juin 202500:47:37

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


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Best Manager Ever: Lauren Rhode - Grit, Teamwork & Humility04 juin 202500:42:19

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


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Best Manager Ever: Leanna Nazzisi - From Part-Time to Power Player28 mai 202500:44:08

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 


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Best Manager Ever: Amit Shah - Harnessing Energy, Gratitude & Learning21 mai 202500:47:53

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 


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Best Manager Ever: Liz Ludwig - Leading with Momentum and Empowerment14 mai 202500:44:03

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  


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Best Manager Ever: Luis Duarte - Build Your Own Mold 07 mai 202500:42:56

Luis Duarte is the CEO and co-founder of Amoofy, an AI-guided storytelling platform. Luis has a rich background as a three-time entrepreneur, and a leader in philanthropy and impact investing. 


Luis's direct reports describe him as an amazing listener, who is able to bring a sense of calm to chaos. They praise his willingness to take on short-term challenges for long-term gains and his focus on building trust.


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

and they discuss:


  • Luis’ unique approach to leadership that emphasizes empathy, risk-taking, and redefining success beyond traditional metrics
  • How and when to take on short-term pain for the long-term vision 
  • Values-driven hiring 
  • Living by your own definition of success 
  • How to find roles that are the right fit – or build something where you will be the best fit 


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Best Manager Ever: Carol Mahoney - Human First Leadership30 avr. 202500:43:34

Carol Mahoney is a seasoned Chief People Officer. She’s well known for her work operationalizing the famously beloved company culture at Gainsight. She’s also served as the SVP of People and Culture at Zoosk and SVP of HR at LivingSocial, among others.


Carol's direct reports praise her ability to get things done, while creating a positive culture and showing up as her authentic self. She is recognized for setting high standards and being a strong yet supportive leader, and for adapting to the needs of her team and org. 


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

and they cover:


  • What human first leadership actually means
  • The importance of co-creating mutually beneficial working relationships 
  • Operationalizing values and intentions into a consistent culture
  • Fostering a safe space for concerns and doubts 


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Best Manager Ever: Helen Min - Scaling Impact Through Effective Management23 avr. 202500:44:01

Helen Min is a venture partner at True Ventures, and an investor and advisor to over 50 early-stage enterprise software and fintech companies. Helen has a notable background leading global marketing and communications at companies like AngelList, Plaid, and Quora and was an early marketing leader at Dropbox and Facebook. 


Helen’s direct reports highlight her genuine care for the team, her support for their growth and development, her polished approach to communication, and her ability to involve the team early in strategy and planning. 


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

and they cover:


  • Helen’s background, from joining the early marketing team at Facebook to leading global marketing and comms teams, and now ultimately investing and advising
  • Good vs. bad reasons to want to be a manager 
  • The most rewarding and hardest parts of being a manager 
  • Long-term benefits of authentic relationship-building 
  • When and how to bring the team into project planning 
  • Making the most of 1:1s 
  • Inquiry as an under-utilized manager superpower 
  • Helen’s transition into VC, and how she leverages operating experience as an investor 


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Best Manager Ever: Seif Salama - Mastering Your First Manager Role16 avr. 202500:40:29

Seif Salama is the Senior Director of Product Marketing at Fanatics. Seif previously held marketing roles at Carta, AngelList, Affirm, and more. 


Seif’s direct reports praise his ability to maintain high standards while ensuring the team's morale and his talent for building a diverse and talented team dynamic. They describe him as a leader who, through authenticity and open communication, created an environment where team members felt proud, motivated, and connected.


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


  • Navigating the challenges and surprises of leadership
  • Hiring effectively, including competency-based hiring tactics and when to let go 
  • Setting high standards while fostering a positive team culture


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Best Manager Ever: Hank Taylor - Unconventional Hiring, Learning, and Leading 09 avr. 202500:31:49

Hank Taylor is Head of Marketing at Laravel. Hank has been on the ground floor of Marketing and Rev Ops functions at Vercel, Lambda School, GitLab, Neo Technology, and more. He has also been an advisor and fractional marketing leader at several companies through his company, GrowthSprint. 


Hank’s direct reports describe him as an unconventional leader who cares deeply for his people, encourages creative risks, and invests in his team’s development.


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


  • Set up a strong hiring process 
  • Build trust and set expectations, starting with the hiring process
  • Foster an innovative, high-trust team culture 
  • Break away from conventional methods to take risks and achieve outstanding results  


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Best Manager Ever: Jully Kim - Influencing, Building a Professional Brand, and Communicating Proactively 02 avr. 202500:46:02

Jully Kim is the Senior Director of Technology Excellence at Autodesk and was previously the Senior Director of Engineering Practices at Zendesk. Jully has a track record of excellence in technology enablement and engineering program management. 


Jully’s direct reports describe her as unique, action-oriented, extremely transparent, and deeply caring. 


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


  • How Jully builds a unique and memorable personal brand at work 
  • Tactics for influencing effectively, especially to senior leaders 
  • Proactive communication to promote transparency and trust among the team, especially as it scales 


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Best Manager Ever: Anthony Sottile - Embracing Failures and Celebrating Success26 mars 202500:46:46

Anthony Sottile is the VP of Partner Success at Freewill, a startup that enables free estate planning and has helped individuals commit more than $11B to charity. 


Anthony's direct reports describe him as down-to-earth and accessible, and emphasize his ability to lead through humor and celebration. 


In this episode, Annie Riley sits down with Anthony to discuss his insights on creating a transparent and honest workplace culture, celebrating team successes, and the importance of approachability in leadership. 


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

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Welcome to Season 2 of Best Manager Ever 19 mars 202500:02:35

Best Manager Ever shares the secrets of building and leading winning teams from the most successful and beloved leaders in the startup and tech worlds. All guests have been nominated as the “best manager ever” by their direct reports. Before each interview, we collect feedback and stories from their team about how the guest *actually* shows up as a leader. Each episode unpacks that feedback and explores the guest’s leadership playbook and lessons learned. Our goal is honest, actionable conversations that help you build your own leadership playbook and serve as an expert mentor and friend in your pocket. 


This season, we’ll continue delivering leadership lessons and management advice that you can apply immediately. We’ll go into more specific stories, and chat with leaders from new industries and functions, including Customer Support, People Ops, and Finance.


Season 2 drops March 26th, with new episodes every Wednesday.


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


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

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Best Manager Ever: Amanda Richardson22 janv. 202500:41:01

Amanda Richardson is the CEO of CoderPad, a technical interview and assessment platform. Amanda built her career in Product, and previously led the product teams and played a critical role in scaling the company at HotelTonight and Prezi. 


Amanda has built a reputation as a dynamic and direct leader. Her direct reports describe her as transparent, authentic, and someone who fosters trust and vulnerability within her teams.


In this final episode of season one (!), Annie Riley, Founder of Fort Light sits down with Amanda to dive into her leadership principles, discussing how Amanda builds and monitors team health, the importance of clear expectations, and how to take responsibility as a leader. Amanda emphasizes curiosity, direct communication, and the importance of diving into conflict head-on.  


Connect with Amanda Richardson 

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Check out Fort Light to level up your leadership skills

Connect with our show’s producer Alexis Ramdaou

Looking to create a podcast email our producer Alexis

Nominate your Best Manager Ever for Season 2

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

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Best Manager Ever: Namrata Ganatra15 janv. 202500:49:45

Namrata Ganatra, is the Chief Product and Technology Officer at Pipe. She has a notable career in tech and startups, including roles at Facebook, Coinbase, BloomTech Lambda School, PayPal, and Microsoft. 


Namrata's direct reports praise her for balancing technical expertise with empathetic leadership, and highlight her as a hardworking and inspiring leader with a strong focus on accountability and growth.


In this episode, Annie Riley, founder of Fort Light, sits down with Namrata to discuss her approach to quickly building trust within teams, her unique strategy for managing transitions during chaotic periods, and her method for balancing technical expertise with people management. Namrata also shares insights on fostering innovation and staying ahead of industry trends, providing valuable lessons for both startup leaders and aspiring managers.


Connect with Namrata Ganatra

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 Season 2

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


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