The Engineering Leadership Podcast

Lakshmi Baskaran shares insights on impromptu communication, why it’s important, and a framework for successfully navigating these tricky situations! We also cover team topology and why it’s so important to have the right composition of product-minded vs. technical-minded engineers within any eng team. Lakshmi shares how prioritizing team topology will impact hiring, influence engineering culture, and aid in eng team reorgs / restructures. She also discusses what the future of AI looks like for executive eng leaders & what to consider when adopting AI practices / technologies. And to bring it all together, we dissect how Lakshmi’s Triple-A impromptu communication framework operates in the context of both team topology & AI adoption.

ABOUT LAKSHMI BASKARAN

Lakshmi Baskaran is an accomplished business leader, entrepreneur, and an angel investor with over two decades of experience in the tech industry. She has built and managed high-performing engineering teams for startups, scale-ups, and publicly listed companies across North America, Europe, Australia, and Asia.

She is currently serving as the VP of Engineering at Metadata, a SaaS company that offers a Marketing Operating System to prominent brands and businesses worldwide.

Lakshmi is passionate about coaching and mentoring business leaders and empowering women to pursue careers in technology. With the right support, she firmly believes that any woman can unleash her potential and make a significant impact on the world, rising to the heights of a great leader, entrepreneur, and a board member.

Lakshmi shares her insights on leadership and technology through her writing on Medium and Thrive.

“Imagine you're presenting it to your executive leadership team or to your board. As an engineering leader, you want to spice up that message with how it is interesting to your customers. The framework that I use in scenarios like this is called 'What If And So That' framework. If you're running an email platform, what if you're able to search through millions of emails in a sub millisecond so that your users can have faster search abilities compared to our competitors? Build a dream scenario and tell them how the technology can help them meet their dream scenario.”

- Lakshmi Baskaran   

We’re less than one week away from GLOW 2024 – Jellyfish’s virtual summit for engineering, product, and finance leaders who are looking to deliver greater business impact while building great software and teams. Here’s a preview of what’s in store:

• An inspiring guest keynote by TIME Magazine’s Kid of the Year, Gitanjali Rao
• Strategies for engineering excellence from CTOs at Keller Williams, Genius Sports, and FanDuel
• Jellyfish CEO and Co-Founder Andrew Lau’s keynote on the future of software engineering
• Exciting product roadmap updates from Jellyfish

Register for this May 15 event today at jellyfish.co/glow!

SHOW NOTES:

• Why the topic of effective impromptu communication is important (2:46)
• Dissecting frameworks & tools for impromptu conversations (7:16)
• An example of high-quality impromptu communication with a CEO (11:52)
• Implement the Triple-A framework (14:03)
• The impact of this communication method on peers (16:37)
• Lakshmi’s insights on team topologies & essential aspects of different eng teams (18:26)
• Considerations for eng team composition (20:56)
• How new hires play into assembling and/or reforming early-stage eng teams (23:44)
• Aligning with teams about what they’re looking for in terms of hiring / composition (26:12)
• The impact of product & tech-minded eng leaders on engineering culture (29:19)
• Opportunities to employ impromptu comm skills in the context of team topology (31:42)
• Lakshmi’s observations on AI adoption (33:47)
• Frameworks for effectively communicating about AI considerations (37:11)
• How eng leaders should apply these AI areas into their decision-making (40:40)
• The role of impromptu communication in AI conversations (42:33)
• Rapid fire questions (45:00)

LINKS AND RESOURCES

• Lakshmi’s blog post on identifying product-minded and tech-minded engineers
• The Engineering Executive's Primer: Impactful Technical Leadership - Will Larson shows you ways to obtain your first executive job and quickly ramp up to meet the challenges you may not have encountered in non-executive measuring engineering for both engineers and the CEO, company-scoped headcount planning, communicating successfully across a growing organization, and figuring out what people actually mean when they keep asking for a "technology strategy.”

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

We dissect one of the biggest challenges that eng leaders face in their day-to-day – navigating the balance between going deep in technical work & maintaining a high-level view of business strategy. Oded Kedem, Chief Technology Officer @ BigPanda, shares examples from his experience, covering strategies for prioritizing where to go deep into the technology, bringing technical expertise to the executive team, bridging the gap between marketing & technology, and aligning customer expectations with a product’s actual capabilities. Oded also shares frameworks for prioritization conversations, valuable questions to pose during executive decision-making conversations, and approaches to changing past technical decisions.

ABOUT ODED KEDEM

Oded Kedem, Chief Technology Officer at BigPanda, brings a wealth of experience in software from ground-up development to managing engineering teams and was also the founder of Zerto, a Cloud BC/DR company. Throughout his many years in the industry, Oded has developed a deep understanding of AIOps and the needs of customers. He recognizes that we are just scratching the surface with AI and automation.

“As companies evolve, people change roles and the technology changes, the requirements change. We chose in the past, the product does it in method A. Let's ask, 'Okay, why did we choose A in the first place?' And once in a while, someone from engineering came up and said, 'Yeah, I have a great idea. Let's do B.' And I would always send them, 'Okay, go back to the documentation, because if you thought this through and you think that making these changes is worth our while and the risk and the instability it may bring, let's go, let's do it.'”

- Oded Kedem   

We’re less than one week away from GLOW 2024

Attend GLOW 2024 - Jellyfish’s virtual summit for engineering, product, and finance leaders who are looking to deliver greater business impact while building great software and teams. Here’s a preview of what’s in store:

• An inspiring guest keynote by TIME Magazine’s Kid of the Year, Gitanjali Rao
• Strategies for engineering excellence from CTOs at Keller Williams, Genius Sports, and FanDuel
• Jellyfish CEO and Co-Founder Andrew Lau’s keynote on the future of software engineering
• Exciting product roadmap updates from Jellyfish

Register for this May 15 event today at jellyfish.co/glow!

SHOW NOTES:

• Keeping a high-level view while diving deep into the technology (2:48)
• The story of how Oded first connected to this particular problem (5:03)
• Oded’s process for prioritizing where to go deep into the technology (7:20)
• Prioritization strategies & why it’s sometimes hard to say no to jumping in (9:40)
• How to bring technical expertise / value to the exec team (13:57)
• Best practices for tough conversations regarding org direction & capabilities (17:40)
• Types of questions to ask in executive conversations (19:58)
• Oded’s favorite question to pose (23:33)
• Bridging the gap between marketing & technology (24:26)
• How an eng perspective helps shape a product’s marketing outcome (27:12)
• Frameworks for aligning customer expectations with a product’s capabilities (29:33)
• Approaches to changing past technical decisions as an eng leader (31:21)
• Rapid fire questions (35:25)

LINKS AND RESOURCES

• Talking to Strangers: What We Should Know About the People We Don’t Know - Malcolm Gladwell, host of the podcast Revisionist History and author of the #1 New York Times bestseller Outliers, offers a powerful examination of our interactions with strangers -- and why they often go wrong.

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

Chris Cravens (Former VPE @ Splunk and CIO @ Uber) shares practical tips for applying professional strategies / tech performance tools into our personal lives - to increase intentionality, goal setting, and habit formation in all aspects of our lives. He shares why it’s so easy to dedicate 90% of your time & attention to work while only dedicating 10% to your personal life and reveals from his own experience how he discovered a better work-life balance by applying OKRs, goal setting, postmortems, and deep reflection. We also cover frameworks for identifying feeling-based goals, building habits & accountability within your personal life, combating negative self-talk, and rewiring your brain to focus on the present & not dwell on past failures.

ABOUT CHRIS CRAVENS

Chris Cravens is an industry veteran with a quarter century of successes delivering measurable value for high-growth enterprises in San Francisco and Silicon Valley. An avid change agent and catalyst for transformation, Mr. Cravens has led major global scale-up and transformation efforts for Software Engineering, Information Technology, Security, Facilities teams. As the first CIO at Zynga and Uber, he led critical functions that enabled scale from small startups to major global enterprises in record time. Mr. Cravens led digital transformation at Splunk, scaling revenue from $800M to $2.2BN in three years by reimagining and supercharging Go to Market capabilities with automation and high value software capabilities that drove greater deal size and velocity. Currently, Mr. Cravens provides expert consulting supporting Private Equity and Venture transactions and transformations and is an active Strategic Advisor, Coach, and Investor to startups delivering innovative, disruptive technologies to accelerate digital transformation.

“I would just keep doing things like that because of that philosophy of in the absence of clear leadership, step in, be the one who is responsible and it goes back to that anxiety from childhood. There are people who have much healthier outlooks, and I've just never been wired that way. So I have to kind of question each decision I make as I go to do a new thing or take on more stuff. 'Is this the right thing for me to do right now, or am I making my life harder?'”

- Chris Cravens   

We’re less than one week away from GLOW 2024

Attend GLOW 2024 - Jellyfish’s virtual summit for engineering, product, and finance leaders who are looking to deliver greater business impact while building great software and teams. Here’s a preview of what’s in store:

• An inspiring guest keynote by TIME Magazine’s Kid of the Year, Gitanjali Rao
• Strategies for engineering excellence from CTOs at Keller Williams, Genius Sports, and FanDuel
• Jellyfish CEO and Co-Founder Andrew Lau’s keynote on the future of software engineering
• Exciting product roadmap updates from Jellyfish

Register for this May 15 event today at jellyfish.co/glow!

SHOW NOTES:

• Chris’s experience of his first week @ Uber (2:02)
• Borrowing professional life tools & using them in your personal life (4:53)
• Why it’s easy to give 90% of time to work & only 10% to your personal life (8:26)
• How Chris navigated his own transition (14:34)
• Treat a sabbatical like a job (16:15)
• Adding OKRs to your personal life (19:36)
• Strategies for assessing feeling-oriented goals (22:05)
• Combating negative self-talk & treating yourself like you would a good friend (24:58)
• How Chris’s frameworks have shifted over time when setting personal life goals (27:11)
• Reflection questions to help illuminate where to center your focus (29:35)
• Applying positive self-talk within a work context to your personal life (32:39)
• Incorporate blameless postmortems into a personal context (35:38)
• Strategies for better habit formation (37:00)
• How to overcome feeling a lack of motivation to start a new habit (38:08)
• The significance of having both clarity & accountability (40:56)
• Tips for rewiring the belief that you can accomplish a goal (45:27)
• Rapid fire questions (48:21)

LINKS AND RESOURCES

• Chris’s Guide to Thinking Errors
• The Satanic Verses - novel of Indian-born British writer Salman Rushdie led Ruholla Khomeini, the ayatollah of Iran, to demand his execution and then forced him into hiding.

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

This is a special episode from our show “Engineering Founders” - Jon Perl & Scott Wilson share the origin story of QA Wolf & deconstruct their best practices (and what to avoid) for early-stage cold outreach, how to add value to your cold email communications, and why experimenting with your cold outreach is important to early sales! We also dive in to the story behind QA Wolf’s strategic move to incorporate services into their business strategy & tangible ways to add accountability measures that will help drive growth in the early days of your company. Check out Engineering Founders - https://hubs.la/Q02tq5ym0

ABOUT JON PERL

Jon Perl is the co-founder and CEO of QA Wolf, a startup building the QA solution every engineering leader wishes for. Prior to QA Wolf, Perl led engineering teams in the healthcare and home services space, where he learned firsthand how difficult automated regression testing can be — and how critical it is for teams to have. His interest in software engineering comes from an overarching desire to eliminate boring, repetitive tasks and give people their time back. He has a dog named Finn and enjoys hiking.

"Your goal is simply to book a meeting. You're not trying to close a deal through one email. It's like, 'How can I just get on the phone with somebody?' That's the goal.”

- Jon Perl   

ABOUT SCOTT WILSON

As co-founder and head of growth at QA Wolf, Scott Wilson is trying to upend 20+ years of stagnation in the QA industry. Before this he launched the marketing efforts at Wyze and helped acquire 6 million paying customers. If he’s not working, you might find him backpacking with Frank the dog, or learning a new illusion.

"It's not referencing the weather in Seattle or that you got promoted. Personalization is being contextually relevant to the person. This is how your mind should be thinking. It's like, 'I saw you're a hundred person company with nine engineers on your team and no QA engineers. You're probably going through this and here's a solution for it.'”

- Scott Wilson   

We’re less than one week away from GLOW 2024

Attend GLOW 2024 - Jellyfish’s virtual summit for engineering, product, and finance leaders who are looking to deliver greater business impact while building great software and teams. Here’s a preview of what’s in store:

• An inspiring guest keynote by TIME Magazine’s Kid of the Year, Gitanjali Rao
• Strategies for engineering excellence from CTOs at Keller Williams, Genius Sports, and FanDuel
• Jellyfish CEO and Co-Founder Andrew Lau’s keynote on the future of software engineering
• Exciting product roadmap updates from Jellyfish

Register for this May 15 event today at jellyfish.co/glow!

SHOW NOTES:

• The origin story of QA Wolf & the desire to build an automated QA system (2:08)
• What got Scott excited about joining the QA Wolf founding team (7:14)
• Scott’s experience as the non-technical cofounder on the team (9:13)
• Learn enough to be dangerous & be willing to persist as a founder (10:38)
• The approach of paying people you can learn from & its impact on QA Wolf (14:11)
• Lessons learned about cold emailing & effective strategies to implement (17:12)
• Cold emailing strategies that don’t work (21:00)
• How to add value to email communication & incorporate experimentation (22:24)
• Why they shifted the focus from coding to sales / outreach / identifying solutions (26:23)
• Make accountability mechanisms a key component of early-stage teams (29:09)
• The false signal of free users & expanding product into services (30:45)
• Identifying a gap in the business & being open-minded to new ideas (33:20)
• What the initial testing for QA Wolf’s services approach looked like (35:22)
• Jon & Scott’s perspective on dealing w/ investors in the automated services space (38:31)
• Rapid fire questions (44:01)

LINKS AND RESOURCES

• $100M Offers: How To Make Offers So Good People Feel Stupid Saying No
• How to Hire a Product-Led Sales Leader – at Every Stage

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

Mike Hanley, Chief Security Officer and SVP of Engineering @ GitHub, joins us to discuss how GitHub has successfully combined its engineering & security orgs and shares recommendations for how other orgs can pivot to this model. We cover why it’s so important for eng orgs to collaborate with security early on in the product development cycle and tips for educating your engineers on security best practices. We also discuss how the rise of AI tools / usage is changing how companies need to think about & practice security, why AI is providing opportunities for increased safety & security within product development, and strategies for encouraging your org to adopt AI tooling within engineering, security, and beyond.

ABOUT MIKE HANLEY

Mike Hanley is the Chief Security Officer and SVP of Engineering at GitHub. Prior to GitHub, Mike was the Vice President of Security at Duo Security, where he built and led the security research, development, and operations functions. After Duo’s acquisition by Cisco for $2.35 billion in 2018, Mike led the transformation of Cisco’s cloud security framework and later served as CISO for the company. Mike also spent several years at CERT/CC as a Senior Member of the Technical Staff and security researcher focused on applied R&D programs for the US Department of Defense and the Intelligence Community.

When he’s not talking about security at GitHub, Mike can be found enjoying Ann Arbor, MI with his wife and eight kids.

"The idea that the security team is walled off or separate or not really connected, not just to engineering but the entirety of the business, you really can't have that. If you think about the pace of modern development, things are moving so quickly. It's so driven by software. The idea that you're like, ‘Hey, I got to walk down the hall and check in with somebody from security who has no idea what's going on in my roadmap, who has no idea what my day to day experience is living in engineering...’ That just doesn't work!”

- Mike Hanley   

We’re less than one week away from GLOW 2024

Attend GLOW 2024 - Jellyfish’s virtual summit for engineering, product, and finance leaders who are looking to deliver greater business impact while building great software and teams. Here’s a preview of what’s in store:

• An inspiring guest keynote by TIME Magazine’s Kid of the Year, Gitanjali Rao
• Strategies for engineering excellence from CTOs at Keller Williams, Genius Sports, and FanDuel
• Jellyfish CEO and Co-Founder Andrew Lau’s keynote on the future of software engineering
• Exciting product roadmap updates from Jellyfish

Register for this May 15 event today at jellyfish.co/glow!

SHOW NOTES:

• GitHub’s convergence of the eng & security orgs (2:33)
• Benefits of combining engineering & security org mandates (4:46)
• How the security team is involved with the internal product dev lifecycle (8:05)
• The downsides of engaging your security team as an afterthought (10:46)
• What an early-stage yes/and product conversation looks like (12:48)
• Examples of educating your eng team on security best practices (17:17)
• Expanding two-factor authentication externally (19:29)
• Stewarding security as a responsibility & value (21:59)
• Security & safety implications for orgs using / building AI tools (23:44)
• Why the rise of AI is a great time for eng / security collaboration (27:09)
• How to leverage security best practices using AI tools (29:53)
• Mike’s view that AI will create more opportunities & improve structural tech (32:14)
• Frameworks for getting to “yes” when it comes to adopting AI tooling (35:15)
• AI-powered tools GitHub is using to change workflows outside of eng & security (39:06)
• Considerations pivoting toward combining eng & security functions (40:35)
• Rapid fire questions (42:25)

LINKS AND RESOURCES

• Why Johnny Can’t Encrypt - Alma Whitten And J. D. Tygar’s argument that effective security requires a different usability standard that is not achievable through the user interface techniques commonly found in consumer software.
• The Space Trilogy - C.S. Lewis believed that popular science was the new mythology of his age, and in The Space Trilogy he ransacks the uncharted territory of space and makes that mythology the medium of his spiritual imagination.
• The Works of Peter Drucker

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

In this episode, we are talking about adaptability in engineering orgs, building out impactful management systems, and navigating complex transitions as eng leaders with Cosmin Nicolaescu, CTO @ Brex. He shares how his experience moving from Romania to the United States taught him vital lessons in adaptability that he has applied throughout his eng leadership career. We also discuss how to define what success as a manager looks like, Cosmin’s approach to putting out fires (and deciding which ones to prioritize), why you should restructure your meetings to focus on output vs. review, and how to implement a succession plan.

ABOUT COSMIN NICOLAESCU

Cosmin (@getCos) leads engineering at Brex, building financial technology to accelerate entrepreneurs. Prior to Brex, he was at Stripe, leading financial infrastructure teams, building Stripe Terminal, and establishing engineering teams globally. His career started at Microsoft, launching Azure and Office365.

"How are you actually changing the trajectory of something. If the person wasn't there, would things have come out differently? If the person jumped in on something, did that meaningfully change the trajectory of that particular project? The answer should be yes and I think that is a good proxy for, as a manager, are you actually leading teams, people, projects, initiatives, and moving the company forward or are you just operating the machinery?”

- Cosmin Nicolaescu   

We’re less than one week away from GLOW 2024

Attend GLOW 2024 - Jellyfish’s virtual summit for engineering, product, and finance leaders who are looking to deliver greater business impact while building great software and teams. Here’s a preview of what’s in store:

• An inspiring guest keynote by TIME Magazine’s Kid of the Year, Gitanjali Rao
• Strategies for engineering excellence from CTOs at Keller Williams, Genius Sports, and FanDuel
• Jellyfish CEO and Co-Founder Andrew Lau’s keynote on the future of software engineering
• Exciting product roadmap updates from Jellyfish

Register for this May 15 event today at jellyfish.co/glow!

SHOW NOTES:

• How Cosmin's transition to the U.S. set the foundation for his approach to adaptability (2:40)
• Learn to accept what you can & cannot control as an eng leader (5:00)
• Frameworks for identifying / understanding what execs spend their time on (7:13)
• Navigating the transition from Microsoft to Stripe (9:12)
• Building out a successful & impactful management organization (12:08)
• In-demand qualities of managers during the shift to flatters orgs (15:00)
• Prioritizing which fires to focus on & willingness to delegate (16:39)
• Cosmin’s approach to triaging fires @ Brex (18:31)
• Restructure meetings for output rather than review (21:52)
• Approaches for adapting to the current macroeconomic environment (25:36)
• Roles that contributed to successful distributed hiring (29:09)
• Necessary elements that need to exist for an unconventional transition (31:28)
• Recommendations for developing & executing a succession plan (34:44)
• Rapid fire questions (37:30)

LINKS AND RESOURCES

• Outlive: The Science and Art of Longevity - Wouldn’t you like to live longer? And better? In this operating manual for longevity, Dr. Peter Attia draws on the latest science to deliver innovative nutritional interventions, techniques for optimizing exercise and sleep, and tools for addressing emotional and mental health.
• Zero to One: Notes on Startups, or How to Build the Future - If you want to build a better future, you must believe in secrets. The great secret of our time is that there are still uncharted frontiers to explore and new inventions to create. In Zero to One, legendary entrepreneur and investor Peter Thiel shows how we can find singular ways to create those new things.
• Hit Refresh: The Quest to Rediscover Microsoft's Soul and Imagine a Better Future for Everyone - As told by Microsoft CEO Satya Nadella, Hit Refresh is the story of corporate change and reinvention as well as the story of Nadella’s personal journey, one that is taking place today inside a storied technology company, and one that is coming in all of our lives as intelligent machines become more ambient and more ubiquitous.
• Generations: The Real Differences Between Gen Z, Millennials, Gen X, Boomers, and Silents―and What They Mean for America's Future - Professor of psychology Jean Twenge does a deep dive into a treasure trove of long-running, government-funded surveys and databases to answer these questions. Are we truly defined by major historical events, such as the Great Depression for the Silents and September 11 for Millennials? Or, as Twenge argues, is it the rapid evolution of technology that differentiates the generations?

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

Have you ever wondered what to do in the “third act” of your career & beyond when it comes to opportunities outside traditional eng leadership / operational roles? In this episode, Nidhi Gupta, CEO & Co-Founder @ SheTO, joins us to share her perspectives on identifying new pathways, taking time for self-discovery, and deciding which career opportunity you’re most passionate about. She defines what the “third act” of your career is & explains roles, such as fractional roles, coaching, serving on boards, advising, etc. Plus Nidhi explains how her passion for supporting women in CTO roles led her to found SheTO, how to give yourself permission to explore new paths, and validate your next steps.

ABOUT NIDHI GUPTA

Nidhi (@NidhiGuptaSF) is the CEO and Co-Founder of SheTO, a private community for women and non-binary engineers and engineering leaders. Less than 9% of engineering executive roles are held by women. SheTO is working on changing that.

Prior to founding SheTO, Nidhi was an accomplished engineering and product executive who has built, scaled, and transformed companies. She has extensive expertise in strategy, R&D, business development, and operations. She has led various Marketplaces and SaaS businesses. As an Engineering and Product leader, she is passionate about building and growing thriving operational organizations that deliver world-class products at scale.

Prior to founding SheTO, Nidhi was the Chief Technology & Product Officer at Hired, Upwork and Ning.

"If you had all the free time on the planet and didn't have to worry about anything, what do you think you would do? Every single night I would go to bed and the next morning I woke up more excited solving for this 9% number than I was about my job and that told me that that's really something that I'm more passionate about so literally after I came back from vacation, I went and talked to my CEO and I quit my job.”

- Nidhi Gupta   

We now have 10 local communities of engineering leaders hosting in-person meetups all over the world!

Local communities are led by eng leaders just like you, who wanted to create a place to connect, share insights & tackle critical challenges in the job.

New York City, Boston, Chicago, Seattle, Los Angeles, San Diego, San Francisco, London, Amsterdam, and Toronto in-person events are happening now!

We’re launching local events all the time - get involved at elc.community!

SHOW NOTES:

• Defining “the third act” & exploring career paths beyond operational roles (3:24)
• What it was like for Nidhi to open herself up to new opportunities (6:09)
• How Nidhi’s passions influenced her to start SheTO (8:01)
• Additional consideration for & recommendations to inspire self-discovery (11:21)
• Why it’s important to take a break & pursue additional interests (13:06)
• Things that kept Nidhi honest with herself through the discovery process (14:51)
• Potential pathways to nontraditional eng leader roles (19:04)
• Ruling out particular pathways after the discovery phase (20:47)
• How Nidhi identified her happiness & transitioned into her role with SheTO (23:10)
• Strategies validating your assumptions & the journey of SheTO (25:43)
• SheTO’s pivot during COVID (28:39)
• What it looks like to give yourself permission to explore (31:05)
• Set goalposts & measurements for yourself (34:43)
• Rapid fire questions (35:16)

LINKS AND RESOURCES

• Third Act with Liz Tinkham - Your first act is school, your second act is work, but have you thought about what you’re going to do in your third act? Join host Liz Tinkham, a former Accenture Senior Managing Director, as she talks to guests who are happily “pretired” – using their time, treasure, and talent to pursue their purpose and passion in the third act of their life.
• The Alex Cross series - A crime, mystery, and thriller novel series written by James Patterson. The protagonist of the series is Alex Cross, an African-American Metropolitan Police Department detective and father who counters threats to his family and the city of Washington, D.C.

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

We’re featuring another popular session from ELC Annual 2023 – welcome to “Healthy Tension: GTM & Product/Eng Collaboration at Hundreds of Millions ARR Scale” with Tido Carriero, (Co-Founder @ Koala and Former VPE @ Segment) and Joe Morrissey (General Partner @ a16z & Former CRO @ Segment)! Tido & Joe share stories from the beginning of their partnership at Segment, including their first cross-functional annual planning meeting. They highlight lessons learned from those early days and how others can implement annual planning session frameworks to develop value drivers for their org in order to better serve customers & create products with value. Joe & Tido also cover how to build a healthy, trusting relationship between product & eng when it comes to building / executing a successful GTM strategy.

ABOUT TIDO CARREIRO

Tido is the Co-Founder & CEO of Koala. Prior to Koala, he led the Product & Engineering team at Segment from less than $5M in ARR to their $3.2B acquisition by Twilio.

“I had been at Segment for four years. The big unlock for me and I think what I needed to lean into more in retrospect from a trust perspective was that Joe was really going to be a different kind of go to market partner. We had zoomed way out. We had looked at a multi-year strategy, not just a list of 25 features and ordering them quarter by quarter by quarter.”

- Tido Carriero   

ABOUT JOE MORRISSEY

Joe Morrissey is a general partner on the Growth investing team at Andreessen Horowitz, focused on enterprise technology companies. Prior to joining a16z, Joe was chief revenue officer at Segment, where he scaled revenues to upwards of $200M ARR in advance of the company’s $3.2B acquisition by Twilio. Before Segment, he was was the EMEA vice president and general manager for three open source software companies: Hortonworks, which combined with Cloudera in a $5.2B merger in 2019; MongoDB, which went public in 2017; and MySQL, which was acquired by Sun Microsystems for $1B in 2008. Joe holds a bachelor’s degree in business studies from the University of Limerick, Ireland. He currently serves on the boards of Neon Inc., and Hopsworks AB and lives in Menlo Park with his wife and two kids.

"You've got to go through this tension and I think one of the things that can happen is you avoid the tension, you avoid the conflict, you say yes to things that maybe you're not comfortable with both on the product and on the go to market side then the plan goes wrong, right? So I really think like the tension is the critical thing and that the struggle is the critical thing and that's where the learning is.”

- Joe Morrissey   

We now have 10 local communities of engineering leaders hosting in-person meetups all over the world!

Local communities are led by eng leaders just like you, who wanted to create a place to connect, share insights & tackle critical challenges in the job.

New York City, Boston, Chicago, Seattle, Los Angeles, San Diego, San Francisco, London, Amsterdam, and Toronto in-person events are happening now!

We’re launching local events all the time - get involved at elc.community!

SHOW NOTES:

• Joe’s first impressions of Tido & the beginning of their relationship (2:28)
• The story of their low point & working together on annual planning (5:32)
• What was agreed on in the annual planning session (7:44)
• Focusing on value drivers & building a trusting GTM partnership (10:55)
• Why it’s necessary to embrace tension in order to drive growth (15:01)
• Tido’s lessons learned leading eng product & sales @ Koala (16:05)
• Audience Q&A: Frameworks for narrowing down value drivers (19:00)
• The importance of cross-functional participation in planning sessions (22:21)
• An inside look at the exercise of identifying value drivers (24:02)
• How deep should salespeople go on the product? (26:27)
• How does annual planning change day-to-day operations for the year? (27:56)
• Describing the Lighthouse program (30:10)
• Reorganizing the org to meet the three identified value drivers (32:32)
• Engineering leadership’s involvement during the annual plan (35:24)
• Strategy behind building a platform (38:38)

LINKS AND RESOURCES

• Video version of this episode
• More sessions from ELC Annual

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

We dissect leadership lessons from across vastly different scales of eng orgs – ranging from 13,000-people companies to 10-person start-ups – with Jeremy Burton, CEO @ Observe. He shares how he effectively translated leadership skills from working at large-scale orgs to small, early-stage start-ups & addresses challenges faced when scaling at any point. Jeremy covers start-up strategies for bringing your eng teams closer to your customers & driving innovation at large-scale orgs; characteristics of eng leaders that promote successful scaling; gaining & communicating conviction; driving community engagement & building trust within developer communities; and more.

ABOUT JEREMY BURTON

Jeremy Burton is the chief executive officer of Observe, Inc. Prior to Observe, Jeremy was Executive Vice President, Marketing & Corporate Development of Dell Technologies, and served in various leadership roles at EMC prior to Dell. A 20-year veteran of the IT industry, Jeremy joined EMC from Serena Software, where he was President and CEO. Previous to Serena, he led Symantec’s $2 billion Enterprise Security product line as Group President of Security and Data Management. Jeremy also served as Veritas’ Executive Vice President of Data Management Group and Chief Marketing Officer. Earlier in his career, he spent nearly a decade at Oracle as Senior Vice President of Product and Services Marketing. Jeremy is currently a member of the board of directors at Snowflake, a seat he's held since 2015, and maintains a part-time role on the advisory board at McLaren Group.

"I hear so many times both in startups and bigger companies, 'Oh, we have a sales execution issue.' If your early sales team is not successful, it's never the sales team. It's always the product. Where bigger companies have built new products, they've probably taken it to market too soon and the salespeople will take it to a mature account. It won't be as mature as the other products. The customer will complain and the salespeople will hate it. It'll get a bad name and then it'll get killed. That's the typical mode of operation that I've seen in a large company, which is why you got to keep it a secret until you've got the MVP, then work with a small set of customers and set the right expectation. When you get it right, you've immediately got a distribution channel that you can scale. If you get it wrong, you'll never scale it and you'll just create a whole bunch of problems in your customer base.”

- Jeremy Burton   

We now have 10 local communities of engineering leaders hosting in-person meetups all over the world!

Local communities are led by eng leaders just like you, who wanted to create a place to connect, share insights & tackle critical challenges in the job.

New York City, Boston, Chicago, Seattle, Los Angeles, San Diego, San Francisco, London, Amsterdam, and Toronto in-person events are happening now!

We’re launching local events all the time - get involved at elc.community!

SHOW NOTES:

• Operating at a scale of 13,000 people vs. early stage with 10 (3:13)
• How Jeremy adapted to operating at vastly different scales (6:30)
• Transitioning from a back seat role to the front seat (8:32)
• Approaches to helping folks better operate in ambiguity & face the unknown (11:20)
• Cycles that gave Jeremy more confidence to operate in instability (14:26)
• The romanticization of start-ups & challenges with scaling (18:22)
• Why eng teams should work directly with customers at start-ups (21:14)
• Leveraging leadership at large orgs to bring eng teams closer to customers (24:36)
• Strategies for innovation at large-scale orgs (27:38)
• Dynamics at big companies that incentivize killing new projects (30:38)
• Characters of eng leaders that lead to successful scaling / innovation (32:56)
• Recommendations for gaining conviction & communicating that effectively (34:33)
• Conversation frameworks for creating alignment (37:43)
• How to create influence & community engagement for developers (38:55)
• Gaining trust within your community & exuding authenticity (42:10)
• Rapid fire questions (44:42)

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/