Engineering Unblocked

Colleen Tartow, Field CTO and Head of Strategy at VAST Data, shares her experience from years in data engineering leadership roles. In this episode, Rebecca and Colleen talk about how “data” has evolved over the years, how AI is turning everything we know about data upside down, and how a PhD in Astrophysics got her started on this path. Find the transcript at: https://www.unblocked.fm/episodes/colleen-tartow-vast/ Timestamps (0:00) Introductions (0:44) Colleen’s background (3:01) About VAST’s approach (7:18) Unique challenges of data engineering (10:56) Setting reasonable expectations (13:34) The importance of process (16:29) The future of data engineering (21:00) What Colleen misses about engineering (22:39) How to set goals for a data organization (25:58) Colleen’s perspective on people in business (29:58) Colleen’s unusual path to data Follow Colleen on LinkedIn: https://www.linkedin.com/in/colleen-tartow-phd/ Follow Rebecca on LinkedIn: https://www.linkedin.com/in/rmurphey/ Links and mentions • VAST Data: https://www.vastdata.com/

Andrea Corey is a VP of Engineering for platform engineering at Homebase. In today’s episode, Rebecca and Andrea talk about Andrea’s experience in working at scaleups, the lessons she’s learned, the pitfalls she’s trained herself to avoid, and some of the biggest problems leaders need to solve as their organization grows. Find the transcript at: https://www.unblocked.fm/episodes/andrea-corey-homebase/ Timestamps (0:00) Introductions (0:46) Andrea’s background (4:37) Unlocking potential among teams (7:02) About Homebase’s team strategy (11:26) Tips to make ideas a reality (15:20) How Andrea manages multiple teams (18:11) Countering hero culture (21:44) Incident handling (25:19) Setting goals around incidents (27:23) Avoiding past mistakes (33:45) When to federate vs. centralize (37:01) Who Andrea wants to be Follow Andrea on LinkedIn: https://www.linkedin.com/in/andreacorey/ Follow Rebecca on LinkedIn: https://www.linkedin.com/in/rmurphey/ Links and mentions • Homebase: https://joinhomebase.com/ • FreshBooks: https://www.freshbooks.com/ • Eloqua: https://www.oracle.com/cx/marketing/automation/

Liz Hustedt is a Senior Engineering Manager at ActBlue, an American political action committee and fundraising platform established serving left-leaning and Democratic nonprofits and politicians. In today’s episode, Rebecca and Liz talk about how Liz’s early experience as an ICU nurse shaped her leadership skills and style, and about managing change in a way that’s empathetic to where the organization is at the moment. Find the transcript at: https://www.unblocked.fm/episodes/liz-hustedt-actblue Timestamps (00:00) Introductions (00:50) Liz’s background (04:00) About ActBlue and Liz’s experience there (08:55) Understanding team health (12:35) Building trust (15:15) Roadmap planning (20:07) How Liz and her team are evaluated (21:21) About outcome-driven goals (26:26) Tips to transition towards outcome-driven goals (28:59) Skills needed in management (34:34) Managing through change (40:50) Milestones and who Liz wants to be Follow Liz on LinkedIn: https://www.linkedin.com/in/lizhustedt/ Follow Rebecca on LinkedIn: https://www.linkedin.com/in/rmurphey/ Links and mentions • ActBlue: https://secure.actblue.com/

Scott Bonneau is the EVP of Product and Operations at Karat, the end-to-end solution for technical hiring. Before Karat, Scott has worked in various engineering and HR roles at Google and Indeed. In today’s episode, Rebecca and Scott discuss Scott’s career at the intersection of technology and people, how leaders can win the trust of a team that they’ve inherited, and how the tech industry has changed over the past 30 years. Find the transcript at: https://www.unblocked.fm/episodes/scott-bonneau-karat Timestamps (00:00) Introductions (02:18) Scott’s journey to his current role (07:10) About Karat (11:05) The role of EVP Product & Operations at Karat (15:43) How to keep everyone close to the ultimate company goal (22:15) Navigating low-trust environments (27:15) What has changed in tech industry during Scott’s career (30:40) How AI is going to change in the tech industry — especially for junior engineers (35:35) What is changing with regards to the hire-ability of developers (38:01) Where you can find Scott play music Follow Scott on LinkedIn: https://www.linkedin.com/in/bonneau/ Follow Rebecca on LinkedIn: https://www.linkedin.com/in/rmurphey/ Links and mentions • Karat: https://karat.com/ • Indeed: https://www.indeed.com/ • The Five Dysfunctions of a Team: https://www.tablegroup.com/product/dysfunctions/

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 is the CTO of Wolt, a subsidiary of DoorDash. In this episode, he talks to Swarmia founder and CEO Otto Hilska about lessons learned while rapidly scaling an engineering organization. Timestamps (0:23) Niilo’s background (03:49) Where to focus first (06:02) Product management in a 3-way marketplace (07:36) Principles-driven development (09:18) Turning “big things” into reality (12:26) Choosing the right work (15:18) Staying close to the customer (17:26) The culture at Wolt (21:17) A high bar for excellence, driven by data (24:11) Recruiting and hiring (32:43) Growth & Growing Pains (41:30) Ownership and standardization (47:11) Niilo’s journey Find the transcript: ⁠https://unblocked.fm/episodes/niilo-säämänen-cto-scaling-wolt Where to find Niilo https://www.linkedin.com/in/niilosaamanen Where to find Otto https://www.linkedin.com/in/hilskahttps://twitter.com/mutru Where to find Rebecca https://www.linkedin.com/in/rmurpheyhttps://twitter.com/rmurphey Links and mentions https://wolt.com/enhttps://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884https://www.amazon.com/stores/Marty-Cagan/author/B00J21JTNMhttps://rework.withgoogle.com/print/guides/5721312655835136/

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