Engineering Unblocked

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