Engineering Unblocked

Lena Reinhard has been a software engineer, a cofounder, and a vice president of engineering, including leadership stints at Travis CI and CircleCI. These days, she’s an engineering leadership coach and consultant. On today’s episode, Rebecca and Lena talk about those experiences, and how they’ve shaped Lena’s perspective of engineering management and managing with metrics. Find the transcript at: https://www.unblocked.fm/episodes/lena-reinhard-introducing-metrics-to-an-engineering-organization Timestamps (00:00) Introductions (00:49) How Lena accidentally got into tech from a finance background (02:33) Lena’s current role as an engineering leadership coach (03:00) What drew Lena into developer tools (05:10) Maintaining situational awareness as a leader of a large engineering organization (06:15) The two purposes of engineering metrics (12:20) How Lena helps engineering organizations drive visibility (17:19) Leading indicators to a visibility problem (21:23) Introducing engineering metrics in a low-trust environment (27:25) How (not) to roll out a metrics program (28:25) The failure mode in running employee engagement surveys (30:37) Lena’s biggest learnings in rolling out metrics programs (36:16) How to get in touch with Lena Where to find Lena • LinkedIn: https://www.linkedin.com/in/lenareinhard/ • Twitter: https://twitter.com/lrnrd Where to find Rebecca • LinkedIn: https://www.linkedin.com/in/rmurphey/ • Twitter: https://twitter.com/rmurphey Links and mentions • Lena's website: https://www.lenareinhard.com/ • What engineering metrics should I use? A guide for engineering managers, directors, and leaders: https://www.lenareinhard.com/articles/what-engineering-metrics-should-i-use-a-guide-for-engineering-managers-directors-and-vps • How to roll out and use engineering metrics successfully: https://www.lenareinhard.com/articles/how-to-introduce-engineering-metrics-successfully

Grant Jenks is a Senior Staff Software Engineer at LinkedIn. In this episode of Engineering Unblocked, Rebecca and Grant discuss how LinkedIn approaches the challenges of keeping its software engineers (and others) happy and productive, and how the Engineering Insights organization informs its work and the work of teams across LinkedIn. Find the transcript at: https://www.unblocked.fm/episodes/grant-jenks-linkedin-like-a-fitbit-for-engineering-teams Timestamps (00:00) Introductions (01:00) Grant’s current role and his career journey (03:51) The origins of the productivity organization at LinkedIn (05:22) From building “tools” to maintaining critical development infrastructure (06:40) Incorporating commodity tools (08:06) Choosing which problems to solve (09:21) How the team’s metrics inform work across LinkedIn (12:05) Using the metrics to help teams set goals (13:30) Choosing the right metrics for the problem (15:32) Unique user problems at scale (18:07) Different problems and different perceptions for different personas (23:09) Working with productivity champions at the team level (23:40) Defining “happiness” and soliciting feedback (28:05) Spotting trends in the sentiment data, and choosing the right cadence (30:26) The product is productivity, and users can do surprising things (34:00) Making change happen at scale (38:33) Using metrics in a productivity emergency Where to find Grant • LinkedIn: https://www.linkedin.com/in/grantjenks/ • Twitter: https://twitter.com/Grant_Jenks Where to find Rebecca • LinkedIn: https://www.linkedin.com/in/rmurphey/ • Twitter: https://twitter.com/rmurphey Links and mentions • LinkedIn: https://www.linkedin.com/ • GitHub Codespaces: https://github.com/features/codespaces • Horizontal initiatives at LinkedIn: https://engineering.linkedin.com/blog/2018/03/scaling-decision-making-across-teams-within-linkedin-engineering • Artifactory: https://jfrog.com/artifactory/

Ben Vinegar has spent the last 8 years at Sentry in a variety of roles, from Software Engineer to VP of Engineering. Today, Rebecca and Ben discuss non-linear careers, engineering career ladders, acquisitions, and more. Find the transcript at: https://www.unblocked.fm/episodes/ben-vinegar-sentry-reflecting-on-ladders-acquisitions-and-personal-trajectory Timestamps (00:00) Introduction (01:26) Third-Party JavaScript and Sentry (02:33) Ben’s journey to VP of Engineering (03:24) Sentry’s growth (05:08) The ladder: differentiating engineering levels (08:45) How Ben became the Co-VP of Engineering (12:42) A new role focused on innovation (16:40) Building an emerging tech team (19:26) Preserving innovation outside the innovation team (21:37) Lessons from acquisitions (26:11) Leading Syntax.fm (28:34) A company within a company (30:36) Non-linear careers Where to find Ben • LinkedIn: https://www.linkedin.com/in/benvinegar/ • Twitter: https://twitter.com/bentlegen Where to find Rebecca • LinkedIn: https://www.linkedin.com/in/rmurphey/ • Twitter: https://twitter.com/rmurphey Links and mentions • Sentry: https://sentry.io/ • Third-Party JavaScript, a book by Ben Vinegar and Anton Kovalyov: https://www.manning.com/books/third-party-javascript • Disqus: https://disqus.com/ • Shape Security (now part of F5): https://www.f5.com/cloud/products/bot-defense • Specto (a Sentry acquisition): https://sentry.io/about/press-releases/sentry-acquires-analytics-firm-specto-to-add-continuous-profiling-to-mobile-application-monitoring/ • Syntax.fm (a recent Sentry acquisition): http://Syntax.fm

David Demaree is a Principal Product Manager at Webflow, where he helps lead the designer experience effort. Before Webflow, David was at Stripe, where he worked on their design system Sail; and at Google, where he worked on Google Fonts and Material Design. In this episode, David and Rebecca discuss the power of platforms to accelerate engineering efforts, and the power of involving a product manager in platforms, even when all of a platform’s users are in-house. Find the transcript at: https://www.unblocked.fm/episodes/david-demaree-webflow-design-systems-and-other-internal-platforms-as-products Timestamps (00:00) Introduction (00:39) Talking about LEGOs (02:20) David’s background (06:32) Material Design (11:01) Selling the investment (14:46) Design systems at Stripe (18:13) Categories of problems that design systems solve (19:55) Selling the long-term, short-term story to leadership (23:07) Speaking the same language as leadership (26:56) Measuring and selling an internal platform (30:55) Secondary effects of platforms (36:04) Platforms as products (42:45) Product for internal platforms vs. external products Where to find David • LinkedIn: https://www.linkedin.com/in/ddemaree/ • Twitter: https://twitter.com/ddemaree Where to find Rebecca • LinkedIn: https://www.linkedin.com/in/rmurphey/ • Twitter: https://twitter.com/rmurphey Links and mentions • Webflow: https://webflow.com/ • Stripe: https://stripe.com/ • Google’s design system, Material Design: https://m3.material.io/ • Adobe Fonts (formerly known as Typekit): https://fonts.adobe.com/ • Microsoft’s design system, Fluent: https://fluent2.microsoft.design/ • The Mythical Man-Month: Essays on Software Engineering: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959

Alex Plugaru is co-founder and CTO at Gorgias, a platform that helps ecommerce businesses provide top-tier customer support. In this episode, Alex talks about the challenges of building a business in an unfamiliar realm, learning from low-risk experiments, and how headcount isn’t an indicator of success. Find the transcript at: https://www.unblocked.fm/episodes/alex-plugaru-gorgias-success-is-more-than-headcount Timestamps (00:00) Introduction (02:04) Origins of Gorgias (03:49) Chrome extension as MVP (06:25) Staying lean when it comes to engineering headcount (10:01) Deciding on growth during COVID (14:25) Mistakes made along the way (18:10) Alex’s role today (22:58) Skip-level meetings (24:11) Alex’s approach to discovering business opportunities Where to find Alex • LinkedIn: https://www.linkedin.com/in/313373/ • Twitter: https://twitter.com/humanfromearth Where to find Rebecca • LinkedIn: https://www.linkedin.com/in/rmurphey/ • Twitter: https://twitter.com/rmurphey Links and mentions • Gorgias: https://www.gorgias.com/ • Scaling Agile at Spotify: https://blog.crisp.se/wp-content/uploads/2012/11/SpotifyScaling.pdf • Team Topologies: https://www.amazon.com/Team-Topologies-Organizing-Business-Technology/dp/1942788819

Niilo Säämänen, CTO of Wolt, talks about lessons learned while scaling an engineering organization in the shadow of Covid. Topics include focusing on the right areas, product management in a 3-way marketplace, principles-driven development, turning big things into reality, customer-centered approach, Wolt's culture, excellence driven by data, recruiting and hiring, growth challenges, ownership and standardization, and Niilo's journey as a CTO.

Heidi is Director of Engineering at Grammarly, leading Grammarly Business, their B2B offering for teams and organizations. In this episode, she shares stories of hypergrowth, the challenges of working on a product that has both business and consumer users, and transitioning a team from startup mode to long-term stability. Find the transcript at: https://www.unblocked.fm/episodes/heidi-williams-grammarly-hypergrowth Timestamps (00:00) Introduction (00:32) Heidi’s journey at Grammarly so far (01:45) Culture at Grammarly (05:43) B2C vs B2B (13:21) Heidi’s short stint in product (14:33) Cross-functional work between engineering, product, and design (16:22) Managing relationships with stakeholders (19:02) The role of an engineering director at Grammarly (20:36) Balancing technical debt with new development (23:18) Centralized vs. decentralized architecture (26:22) The role of platform teams (28:52) Welcoming everyone else to the AI party Where to find Heidi • LinkedIn: https://www.linkedin.com/in/heidiwilliams1/ • Twitter: https://twitter.com/Heidivt73 Where to find Rebecca • LinkedIn: https://www.linkedin.com/in/rmurphey/ • Twitter: https://twitter.com/rmurphey Links and mentions • Grammarly: https://www.grammarly.com/ • Grammarly Business: https://www.grammarly.com/business • Innovator’s Dilemma: https://www.amazon.com/Innovators-Dilemma-Revolutionary-Change-Business/dp/0062060244 • Product for Internal Platforms: https://skamille.medium.com/product-for-internal-platforms-9205c3a08142

Jack Humphrey is an Engineering Director at LinkedIn. In this episode, Rebecca and Jack talk about the transformative impact on engineering velocity he had when they worked together at Indeed. Find the transcript at: https://www.unblocked.fm/episodes/jack-humphrey-linkedin-transforming-delivery-time Timestamps (00:00) Introduction (00:42) Jack’s current role at LinkedIn (01:27) The early days of Jack’s 11-year journey at Indeed (05:09) How Indeed’s developer productivity initiative got its start (12:04) Setting a goal for the productivity initiative (17:08) Managing the engineering teams’ concerns with improving productivity (24:18) Rolling out a productivity project across the entire engineering organization (32:12) Why Jack wouldn’t change anything about the project (33:07) The right time to start working on productivity improvements Where to find Jack • LinkedIn: https://www.linkedin.com/in/leejack/ • Twitter: https://twitter.com/youknowjack Where to find Rebecca • LinkedIn: https://www.linkedin.com/in/rmurphey/ • Twitter: https://twitter.com/rmurphey Links and mentions • LinkedIn: https://www.linkedin.com/ • Indeed: https://indeed.com/ • Measure What Matters: https://www.amazon.com/Measure-What-Matters-Google-Foundation/dp/0525536221

Christian Helvin is an Engineering Director at Tithely. In this episode, Rebecca and Christian chat about his career journey, about being part of an acquisition, transitioning from agency work to software development, and his focus on developer happiness. Find the transcript at: https://www.unblocked.fm/episodes/christian-helvin-tithely-from-engineering-line-manager-to-director Timestamps (00:00) Introduction (00:42) Christian’s journey at Tithely so far (01:39) Being a part of an acquisition (04:22) The difference between running small and large teams (05:32) Leading a geographically distributed team (07:00) Running an agency vs. running a product organization (09:04) Leveling up from a line manager to a director (10:42) Running productive skip-level meetings (13:20) Deciding on which problems to tackle first (15:51) Microservicing (18:30) Measuring the effect of productivity changes (19:52) Introducing cohesion to siloed teams (24:08) Managing expectations from the business (28:39) Growth plans in the current macroeconomic climate Where to find Christian • LinkedIn: https://www.linkedin.com/in/cphelvin/ • Twitter: https://twitter.com/PHPWarrior Where to find Rebecca • LinkedIn: https://www.linkedin.com/in/rmurphey/ • Twitter: https://twitter.com/rmurphey Links and mentions • Tithely: https://get.tithe.ly/ • Breeze: https://www.breezechms.com/ • Holding Skip-Level Meetings: skills you need to build bridges across teams: https://www.amazon.com/Holding-Skip-Level-Meetings-skills-bridges-ebook/dp/B01N6SSN0E/ • American Truck Simulator: https://americantrucksimulator.com/ • Euro Truck Simulator: https://eurotrucksimulator2.com/

In this episode, Rebecca chats with Ainsley Escorce-Jones, Tech Lead for the Developer Infrastructure organization at Stripe. Rebecca and Ainsley talk about the origin stories of the Developer Infrastructure organization and the reasons Stripe invests in that area. Ainsley also shares some of his takeaways from five years focusing on developer productivity at Stripe. Find the transcript at: https://www.unblocked.fm/episodes/ainsley-escorce-jones-stripe-growing-up-devprod Timestamps: (00:00) Introduction (00:54) Ainsley’s journey at Stripe so far (03:38) Learnings from an internship at Facebook (07:55) The origin story of the Developer Productivity org at Stripe (16:31) The right time to start a Developer Productivity organization (22:30) The monorepo vs. polyrepo strategy at Stripe (28:36) Early technology decisions and their effect on engineering work today (30:52) Experimenting with stacked pull requests (34:54) Prioritizing productivity improvement projects (41:59) The value of developer surveys (44:29) Staying in touch with the day-to-day struggles of engineers Where to find Ainsley: • LinkedIn: https://www.linkedin.com/in/ainsej/ Where to find Rebecca: • LinkedIn: https://www.linkedin.com/in/rmurphey/ • Twitter: https://twitter.com/rmurphey Links and mentions • Stripe: https://stripe.com/ • Sorbet: https://sorbet.org/ • Improbable: https://www.improbable.io/ • Sourcegraph: https://about.sourcegraph.com/ • VS Code: https://code.visualstudio.com/ • Livegrep: https://github.com/livegrep/livegrep • Migrating millions of lines of code to TypeScript: https://stripe.com/blog/migrating-to-typescript • rubyfmt: https://github.com/fables-tales/rubyfmt • Stacked pull requests: https://matt-rickard.com/stacked-pull-requests