The Engineering Leadership Podcast

Craig Martell shares the biggest mistakes leaders of ML teams make, what to do if you have no experience leading an ML team, key skills your ML team needs, plus different models/approaches to building an ML team. You’ll hear the most expensive and time-consuming parts of ML, how to estimate timelines, unique tech debt, and how to manage expectations.“If I had to give one piece of advice about starting AI in your company, one of the first people I would hire is a really great data scientist, even if they can't code. Just so they're the one who's going to start training you and helping you think about, how to gather data, how the modeling is going to work, what you're going to need, whether that feature that you want to build is even modelable in the first place..." - Craig Martell ABOUT CRAIG MARTELLCraig is Head of Lyft Machine Learning. He’s also an adjunct professor of Machine Learning for Northeastern University’s Align program.Prior to joining Lyft, he was Head of Machine Intelligence @ Dropbox, and led a number of AI teams and initiatives at LinkedIn, including the development of the LinkedIn AI Academy. Before LinkedIn, Craig was a tenured computer science professor at the Naval Postgraduate School specializing in natural language processing (NLP). He has a Ph.D. in Computer Science from the University of Pennsylvania and is the co-author of the MIT Press book Great Principles of Computing. RESOURCES(ML training) Galvanize: https://bit.ly/3ckF6Gz(website) Andrew Ng: https://bit.ly/3cgerdU(courses) ML: https://bit.ly/3iNB9gf | AI for Everyone: https://bit.ly/2HeZKwl(course) Fast.AI: https://bit.ly/35SPwMD(book) "Hands-On ML with Scikit" : https://amzn.to/35SbGyh SHOW NOTESAn overview of the machine learning lifecycle (2:49)The most expensive and time-consuming aspect of the machine learning lifecycle (6:07)The key skills of a machine learning team (7:21)How do you build an AI/ML Team and what are the different models? (8:41)What to do If you’re an engineering manager with no AI/ML skills or experience (15:19)How deep does your understanding of AI/ML have to be in order to lead effectively? (18:48)How do you estimate project timelines for AI/ML teams? (19:15)What are the biggest mistakes engineering leaders make managing AI/ML teams? (20:52)How do you manage expectations in an organization that’s in the early days of AI/ML development? (21:33)What are sources of technical debt unique to AI/ML systems? (22:13)How do machine learning teams interface with product teams? (23:55)AI/ML resources for executive engineering leaders (25:44)When’s the right time to invest in AI/ML? (26:10)Can you apply the Pareto Principle (80/20 rule) to AI/ML development? (26:40)Takeaways (28:12) Join our community of software engineering leaders @ https://sfelc.com/

“Giving up control” is about empowering other people to scale yourself, and scale your effectiveness. Maria Latushkin shares with us why you need to give up control as an engineering leader and what holds people back. Plus you’ll learn tons of different ways to influence and manage your performance when it’s dependent on other people’s effectiveness.“You are responsible for the delivery of the team. At the end of the day, nobody really cares like how much YOU work. You can be working around the clock. And it's not how great you are or what you produce. It stops being about you and it starts being about the function that you lead.” - Maria LatushkinABOUT MARIA LATUSHKINMaria is responsible for leading Omada Health’s technology vision and team. Prior to joining Omada Health and moving to the healthcare space, Maria has spent over 15 years in eCommerce, retail, and enterprise SaaS companies ranging from series B startups to large companies, such as Walmart. SHOW NOTESWhy you need to give up control as a senior engineering leader (2:07)What holds people back from giving up control? (9:27)The impact and trade-offs you make when you avoid or resist giving up control (15:31)How to influence and manage your performance now that it’s dependent on your team’s effectiveness (23:49)How to make sure people heard you, so that you know you’re on the same page (29:04)Does the discomfort of “giving up control” happen at every transition to a new leadership level, or is it a one-time thing? (32:44)How to regain “control” and empower your team (39:40)The Impact - how you feel when you give up control (41:25)Takeaways (43:36) ---Join our community of software engineering leaders @ https://sfelc.com/

A dynamic conversation between 4 current and past VPs of Engineering who cover tons of patterns and anti-patterns about being a VPE! You'll hear how leadership is different in large vs. small companies, mental models to determine your greatest leverage, why you DON’T need to act like an owner, how to put trust into practice when you’re transitioning into a new role, and about the imperfect path to become a VPE. SPEAKERS:CATHY POLINKSY CTO @ Stitch FixJERRY KRIKHELI VP of Engineering @ HouzzRICHARD WONG SVP of Engineering @ CourseraERICA LOCKHEIMER VP of Engineering @ Linkedin LearningAnd CLAIRE LEW CEO @ Know Your TeamSHOWNOTESWhat Cathy means by “the best leaders spot patterns, understand problems, then build systems to solve them” (3:55)Jerry’s view on how the practice of leadership is different at large companies vs. small companies (7:30)Erica’s perspective on how the transition to VPE is different than other eng leadership roles and how to put trust into practice (12:27)Why Richard resonates with “act like an owner” and what it actually looks like in practice as VPE (16:40)Cathy’s top 3 priorities as VPE that determine how she spends her time and how to refocus your team (23:50)Richard's mental model to determine where he has the most leverage for impact and why being technical isn't always about writing code (26:16)Jerry's 3 key hiring traits and how to create an environment where you're the first to know when something's wrong (30:10)The imperfect path to become a VPE and Erica’s advice for engineering leaders with an “unconventional” background (34:01)The common struggle to balance being a problem solver and being the bottleneck as a VPE (39:11)How they cope with and manage stress (42:55)Takeaways (45:00)---Join our community of software engineering leaders @ https://sfelc.com/

We were overwhelmed by questions from our event with Doug and Emma! This is a bonus follow up conversation that further digs into measuring productivity through “Waterlining” and Kaplan Meier estimating, hashtags in communication, remote 1:1 best practices, and Doug shows us some of the creative ways he applies Zapier integrations for his personal productivity!"What it does is it forces a debate as to A what's most important and B do we really want that thing below the line waterline? Because what happens sometimes is people are super excited about this thing. And then when you see this rank list of stuff, you're like, Oh, but wait a second. There's like running the business stuff below the water line. We actually have to get that up and staff that..." - Doug Gaff DOUG GAFF - VP of Engineering @ ZapierDoug is the VP of Engineering at Zapier, the software solution that helps your other software work together more effectively. As the leader of an organization with over 100 engineers, he has learned a lot about effective management and leadership. Doug currently resides in the Greater Boston Area. EMMA TANG - Engineering Manager @ StripeEmma is an Engineering Manager in Data Infrastructure at Stripe based in San Francisco. Her team focuses on building distributed computation infrastructure to support Stripe's business. At Stripe, we believe in investing in our remote culture, and have built out the remote engineering hub, and tripled the number of remote engineers in the last year. SHOWNOTESHow to Measure Productivity - Waterlining and Kaplan Meier (2:44)Waterlining as a tool to discuss priorities (9:10)Using hashtags to understand intent and to increase the bandwidth of communication (11:02)Best practices for remote 1:1’s when you don’t see the productivity levels you want (17:37)Tips for onboarding new grads (23:03)Doug’s remote work routine and lifestyle (24:47)Doug’s favorite Zapier integrations to increase productivity (29:21)Takeaways (33:45)---Join our community of software engineering leaders @ https://sfelc.com/

Doug Gaff and Emma Tang discuss high-bandwidth communication, innovation accounting, preventing developer burnout, influencing teams, and communicating priorities. They’ll help you move from frustration and survival in remote work, back to optimized productivity!“Personal stuff is totally in bounds and people just listen. And they don't try to solve a problem for you. And I might be like, I'm red today. I didn't get any sleep. I'm stressed about this thing. I'm not sure I'm going to get it done or this thing's happening personally. I'm worried about a friend who's not well... and it requires a certain level of vulnerability and you've got to have a trust, comfort level, but, that's another thing like as leaders, the best thing you can do is demonstrate this kind of behavior so that other people know it's okay to do it.” - Doug Gaff DOUG GAFF - VP of Engineering @ ZapierDoug is the VP of Engineering at Zapier, the software solution that helps your other software work together more effectively. As the leader of an organization with over 100 engineers, he has learned a lot about effective management and leadership. Doug currently resides in the Greater Boston Area. EMMA TANG - Engineering Manager @ StripeEmma is an Engineering Manager in Data Infrastructure at Stripe based in San Francisco. Her team focuses on building distributed computation infrastructure to support Stripe's business. At Stripe, we believe in investing in our remote culture, and have built out the remote engineering hub, and tripled the number of remote engineers in the last year. SHOWNOTESIdeas for Remote “Offsites” (3:27)How to ensure clear, high-bandwidth communication (5:44)How to make engineers feel connected to the mission and company (9:44)Measuring productivity with “Innovation Accounting” and “Waterlining” (15:03)It's time to trust your people and fix your cultural anti-patterns (21:19)How to prevent developer burnout (25:03)How to influence leadership teams remotely (28:26)How to communicate priorities to multiple groups and teams (33:00)Health metrics to track your team - Happiness surveys, pull requests, and “innovation accounting” (35:11)Takeaways (38:34) ---Join our community of software engineering leaders @ https://sfelc.com/

Martin Casado and Sonal Chokshi explore what makes a great VP of Engineering at startups! You’ll hear how successful VPEs are evaluated, the ideal experience and success criteria. You’ll hear rapid-fire responses covering how to scale yourself, KPIs, the ideal VPE hiring time for startups, and what VPEs should definitely NOT do. MARTIN CASADO, GENERAL PARTNER @ ANDREESSEN HOROWITZHe was previously cofounder and CTOr at Nicira (acquired by VMware for $1.26 billion). At VMware, Martin was SVP & GM of the Networking and Security Business Unit (which he scaled to a $600 million run-rate). Martin’s early career was at Lawrence Livermore National Laboratory working on large-scale simulations for the Department of Defense, networking, and cybersecurity.He holds both a PhD and Masters degree in Computer Science from Stanford University, where he created the software-defined networking (SDN) movement and cofounded Illuminics Systems (acquired by Quova). He’s been awarded both the ACM Grace Murray Hopper award and the NEC C&C award, and he’s an inductee of the Lawrence Livermore Lab’s Entrepreneur’s Hall of Fame. Martin serves on the board of: ActionIQ, Astranis, DeepMap, Imply, Kong, Pindrop Security, RapidAPI, SigOpt, and Yubico.“In my experience over a number of engineering leaders is whether or not they're a good engineer is totally orthogonal to the actual role. And in fact, someone that's deeply passionate about a particular architecture technology or approach can be very damaging because you have a power asymmetry in the team.” - Martin Casado SONAL CHOKSHI, EDITOR IN CHIEF @ ANDREESSEN HOROWITZ AKA "a16z"Sonal built and oversees all of Andreessen Horowitz’s editorial operations, including showrunning and hosting the a16z Podcast, leading production of the a16z Crypto Canon; and more. Prior to a16z Sonal was a Senior Editor at Wired. Prior to that, Sonal was responsible for content and community at Xerox PARC. Before moving back to California from NYC, Sonal was doing graduate work in developmental and cognitive psychology at Columbia University's school of education and worked as a researcher "ethnographer" on NSF grants around teacher professional development and early numeracy. She studied English and Psychology at UCLA. SHOWNOTESHiring misconceptions & Why VPs of Engineering are so valuable (4:21)Ideal experience and success criteria for a Startup VPE (8:45)Does a VPE need to be a good engineer? (10:56)Two key areas VPEs are evaluated (13:01)How to balance product and engineering as a VPE (17:34)The hard issue of managing people (19:54)Why engineering analytics and conscious decisions are important to building great engineering orgs (22:24)Good KPIs and how to scale yourself as a VPE (24:19)When is the right time to become a VPE at a startup? (26:25)What a VPE should NOT do (27:44)What is a CTO’s role and how do you work with them as a VPE? (31:00)Takeaways (32:0) LINKSa16z Podcast

Wade Chambers, CTO & SVP of Engineering at Grand Rounds, shares his extensive leadership experience to redefine success in engineering roles. He dives into how to enhance team potential and the importance of mentorship. Wade discusses methods for overcoming career stagnation, presenting three key areas where growth often gets stuck. He emphasizes the value of self-awareness and principled leadership, urging listeners to apply insights from personal reflections for continuous development and reassessment of their career trajectories.

Wade Chambers, CTO & SVP of Engineering at Grand Rounds, shares his 25+ years of experience in engineering leadership. He discusses 'conscious growth' and the power of neuroplasticity in advancing careers. Wade emphasizes confronting discomfort for self-discovery and effective leadership. He reflects on early managerial failures and the importance of vulnerability in career progression. Listeners will gain insights into aligning personal growth with organizational goals and the role of mentorship and feedback in navigating career challenges.

Andrew Fong shares how to identify, operationalize, and reinforce values in your organization as well as his strategies to scale organizations through values-based decision making and in cultivating values-based environments. You’ll also hear stories about the massive role values had in the outcomes of several large-scale infrastructure projects at Dropbox."If we can operationalize this, the micro decision making on the ground becomes much more powerful and it doesn't force us into a command and control environment." - Andrew Fong ABOUT ANDREW FONGAndrew is the Vice President of Infrastructure at Dropbox. In this role he oversees all infrastructure engineering and operations efforts which are responsible for scaling Dropbox’s infrastructure stack in order to support hundreds of millions of users worldwide. Prior to Dropbox, he was at YouTube, Google, and AOL in various infrastructure capacities SHOWNOTESWhat it means to “operationalize values” and why it matters (2:12)How to operationalize values in OKRs (4:45)How to identify values in your team or organization (8:01)How to reinforce values in your organization in meetings, all-hands, and personally (14:35)How to operationalize values in recruiting (18:52)How operationalized values impact projects: Dropbox’s data center migration story (20:41)Lessons learned from Dropbox’s “Magic Pocket” project (26:09)How to make values endure beyond people in projects with long time horizons: be explicit with your decision making process (29:27)How to operationalize values in small teams and start ups (34:46)How Andrew operationalizes his personal values (40:31)Takeaways (48:11) Join our community of software engineering leaders @ https://sfelc.com/

Organizational change is hard. In part 2, Jean-Denis Greze explores how you can adapt and transform the strengths, capabilities or “spikes” of your organization by intentionally using the strategies of “Isolation”, “Outlets” and “Shocks.” He shares a ton of great real-world examples and case studies to help you apply these strategies in your org."The thing that I think makes over a 10 year period, a really good engineering organization is that at any one moment in time, it has very few spikes, but over a long period of time, it has all the spikes." - Jean-Denis Greze ABOUT JEAN-DENIS GREZEJean-Denis Greze is Head of Engineering at Plaid, the technology company giving developers access to the financial system and the tools to build many of the most influential applications and services of the modern financial era. Companies such as Venmo + Paypal, Coinbase, Robinhood, Acorns, Clarity Money and hundreds more are built on Plaid.Prior to joining Plaid, Jean-Denis was Director of Engineering at Dropbox, where he led the growth, identity, notifications, Paper and payments teams.Prior to Dropbox, Jean-Denis worked in fintech in New York and has CS degrees from Columbia as well as a JD from Harvard Law School. SHOWNOTESHow to mitigate weaknesses in your organization using the strategies of Isolation & Outlets (2:47)How to use “Isolation” in your business units as an org building strategy: examples from Plaid and Xbox (8:44)How to use “Isolation” in recruiting & product strategy: examples of apprenticeships to hire, roles you've never hired for, and incubator programs (12:17)How to use "Outlets" to create different conversations, adopt different values, and set new priorities (16:38)The “Portfolio Theory of Time Allocation” (19:41)How to introduce "Shocks" proactively to change and adapt your organization (28:32)How to intentionally use Acquisitions to “Shock” your organization (33:35)How to intentionally use Reorgs to “Shock” your organization (36:06)The power of peer groups and re-reading (45:19) Join our community of software engineering leaders @ https://sfelc.com/