Tracy Lee talks with industry veteran Grant Ingersoll about his insights and experiences as a Fractional CTO, shedding light on the patterns and anti-patterns he encounters while working with various engineering teams. As a Fractional CTO, Grant's role involves tackling challenging situations, bridging transitions, and ensuring that technical decisions align with a company's long-term vision. His rich experiences and observations offer valuable lessons for both aspiring CTOs and businesses seeking to optimize their software development processes.
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Get Inside the Mind of a Fractional CTO: The Untold Secrets of Tech Leadership!
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“We were seen as amplifiers, not collaborators,” Ashley Willis, Sr. Director of Developer Relations at GitHub, on How DevRel has Changed, Open Source, and Holding Space as a Leader
Ashley Willis has seen Developer Relations evolve from being on the sidelines of the tech team to having a seat at the strategy table. In her ten years in the space, she’s done more than give great conference talks or build community—she’s helped shape what the DevRel role looks like for software providers. Now as the Senior Director of Developer Relations at GitHub, Ashley is focused on building spaces where developers feel heard, seen, and supported. > “A decade ago, we were seen as amplifiers, not collaborators,” she says. “Now we’re influencing product roadmaps and shaping developer experience end to end.” DevRel Has Changed For Ashley, the biggest shift hasn’t been the work itself—but how it’s understood. > “The work is still outward-facing, but it’s backed by real strategic weight,” she explains. “We’re showing up in research calls and incident reviews, not just keynotes.” That shift matters, but it’s not the finish line. Ashley is still pushing for change when it comes to burnout, representation, and sustainable metrics that go beyond conference ROI. > “We’re no longer fighting to be taken seriously. That’s a win. But there’s more work to do.” Talking Less as a Leader When we asked what the best advice Ashley ever received, she shared an early lesson she received from a mentor: “Your presence should create safety, not pressure.” > “It reframed how I saw my role,” she says. “Not as the one with answers, but the one who holds the space.” Ashley knows what it’s like to be in rooms where it’s hard to speak up. She leads with that memory in mind, and by listening more than talking, normalizing breaks, and creating environments where others can lead too. > “Leadership is emotional labor. It’s not about being in control. It’s about making it safe for others to lead, too.” Scaling More Than Just Tech Having worked inside high-growth companies, Ashley knows firsthand: scaling tech is one thing. Scaling trust is another. > “Tech will break. Roadmaps will shift. But if there’s trust between product and engineering, between company and community—you can adapt.” And she’s learned not to fall for premature optimization. Scale what you have. Don’t over-design for problems you don’t have yet. Free Open Source Isn’t Free There’s one myth Ashley is eager to debunk: that open source is “free.” > “Open source isn’t free labor. It’s labor that’s freely given,” she says. “And it includes more than just code. There’s documentation, moderation, mentoring, emotional care. None of it is effortless.” Open source runs on human energy. And when we treat contributors like an infinite resource, we risk burning them out, and breaking the ecosystem we all rely on. > “We talk a lot about open source as the foundation of innovation. But we rarely talk about sustaining the people who maintain that foundation.” Burnout is Not Admirable Early in her career, Ashley wore burnout like a badge of honor. She doesn’t anymore. > “Burnout doesn’t prove commitment,” she says. “It just dulls your spark.” Now, she treats rest as productive. And she’s learned that clarity is kindness—especially when giving feedback. > “I thought being liked was the same as being kind. It’s not. Kindness is honesty with empathy.” The Most Underrated GitHub Feature? Ashley’s pick: personal instructions in GitHub Copilot. Most users don’t realize they can shape how Copilot writes, like its tone, assumptions, and context awareness. Her own instructions are specific: empathetic, plainspoken, technical without being condescending. For Ashley, that helps reduce cognitive load and makes the tool feel more human. > “Most people skip over this setting. But it’s one of the best ways to make Copilot more useful—and more humane.” Connect with Ashley Willis She has been building better systems for over a decade. Whether it’s shaping Copilot UX, creating safer teams, or speaking truth about the labor behind open source, she’s doing the quiet work that drives sustainable change. Follow Ashley on BlueSky to learn more about her work, her maker projects, and the small things that keep her grounded in a fast-moving industry. Sticker Illustration by Jacob Ashley....
Apr 18, 2025
3 mins
“ChatGPT knows me pretty well… but it drew me as a white man with a man bun.” – Angie Jones on AI Bias, DevRel, and Block’s new open source AI agent “goose”
Angie Jones is a veteran innovator, educator, and inventor with over twenty years of industry experience and twenty-seven digital technology patents both domestically and internationally. As the VP of Developer Relations at Block, she facilitates developer training and enablement, delivering tools for developer users and open source contributors. However, her educational work doesn’t end with her day job. She is also a contributor to multiple books examining the intersection of technology and career, including *DevOps: Implementing Cultural Change*, and *97 Things Every Java Programmer Should Know*, and is an active speaker in the global developer conference circuit. With the release of Block’s new open source AI agent “goose”, Angie drives conversations around AI’s role in developer productivity, ethical practices, and the application of intelligent tooling. We had the chance to talk with her about the evolution of DevRel, what makes a great leader, emergent data governance practices, women who are crushing it right now in the industry, and more: Developer Advocacy is Mainstream A decade ago, Developer Relations (DevRel) wasn’t the established field it is today. It was often called Developer Evangelism, and fewer companies saw the value in having engineers speak directly to other engineers. > “Developer Relations was more of a niche space. It’s become much more mainstream these days with pretty much every developer-focused company realizing that the best way to reach developers is with their peers.” That shift has opened up more opportunities for engineers who enjoy teaching, community-building, and breaking down complex technical concepts. But because DevRel straddles multiple functions, its place within an organization remains up for debate—should it sit within Engineering, Product, Marketing, or even its own department? There’s no single answer, but its cross-functional nature makes it a crucial bridge between technical teams and the developers they serve. Leadership Is Not an Extension of Engineering Excellence Most engineers assume that excelling as an IC is enough to prepare them for leadership, but Angie warns that this is a common misconception. She’s seen firsthand how technical skills don’t always equate to strong leadership abilities—we’ve all worked under leaders who made us wonder *how they got there*. When she was promoted into leadership, Angie was determined not to become one of those leaders: > “This required humility. Acknowledging that while I was an expert in one area, I was a novice in another.” Instead of assuming leadership would come naturally, she took a deliberate approach to learning—taking courses, reading books, and working with executive coaches to build leadership skills the right way. Goose: An Open Source AI Assistant That Works for You At Block, Angie is working on a tool called goose, an open-source AI agent that runs locally on your machine. Unlike many AI assistants that are locked into specific platforms, goose is designed to be fully customizable: > “You can use your LLM of choice and integrate it with any API through the Model Context Protocol (MCP).” That flexibility means goose can be tailored to fit developers’ workflows. Angie gives an example of what this looks like in action: > “Goose, take this Figma file and build out all of the components for it. Check them into a new GitHub repo called @org/design-components and send a message to the #design channel in Slack informing them of the changes.” And just like that, it’s done— no manual intervention required. The Future of Data Governance As AI adoption accelerates, data governance has become a top priority for companies. Strong governance requires clear policies, security measures, and accountability. Angie points out that organizations are already making moves in this space: > “Cisco recently launched a product called AI Defense to help organizations enhance their data governance frameworks and ensure that AI deployments align with established data policies and compliance requirements.” According to Angie, in the next five years, we can expect more structured frameworks around AI data usage, especially as businesses navigate privacy concerns and regulatory compliance. Bias in AI Career Tools: Helping or Hurting? AI-powered resume screeners and promotion predictors are becoming more common in hiring, but are they helping or hurting underrepresented groups? Angie’s own experience with AI bias was eye-opening: > “I use ChatGPT every day. It knows me pretty well. I asked it to draw a picture of what it thinks my current life looks like, and it drew me as a white male (with a man bun).” When she called it out, the AI responded: > “No, I don’t picture you that way at all, but it sounds like the illustration might’ve leaned into the tech stereotype aesthetic a little too much.” This illustrates a bigger problem— AI often reflects human biases at scale. However, there are emerging solutions, such as identity masking, which removes names, race, and gender markers so that only skills are evaluated. > “In scenarios like this, minorities are given a fairer shot.” It’s a step toward a more equitable hiring process, but it also surfaces the need for constant vigilance in AI development to prevent harmful biases. Women at the Forefront of AI Innovation While AI is reshaping nearly every industry, women are playing a leading role in its development. Angie highlights several technologists: > “I’m so proud to see women are already at the forefront of AI innovation. I see amazing women leading AI research, training, and development such as Mira Murati, Timnit Gebru, Joelle Pineau, Meredith Whittaker, and even Block’s own VP of Data & AI, Jackie Brosamer.” These women are influencing not just the technical advancements in AI but also the ethical considerations that come with it. Connect with Angie Angie Jones is an undeniable pillar of the online JavaScript community, and it isn’t hard to connect with her! You can find Angie on X (Twitter), Linkedin, or on her personal site (where you can also access her free Linkedin Courses). Learn more about goose by Block. Sticker Illustration by Jacob Ashley...
Mar 13, 2025
4 mins
“Music and code have a lot in common,” freeCodeCamp’s Jessica Wilkins on what the tech community is doing right to onboard new software engineers
Before she was a software developer at freeCodeCamp, Jessica Wilkins was a classically trained clarinetist performing across the country. Her days were filled with rehearsals, concerts, and teaching, and she hadn’t considered a tech career until the world changed in 2020. > “When the pandemic hit, most of my gigs were canceled,” she says. “I suddenly had time on my hands and an idea for a site I wanted to build.” That site, a tribute to Black musicians in classical and jazz music, turned into much more than a personal project. It opened the door to a whole new career where her creative instincts and curiosity could thrive just as much as they had in music. Now at freeCodeCamp, Jessica maintains and develops the very JavaScript curriculum that has helped her and millions of developers around the world. We spoke with Jessica about her advice for JavaScript learners, why musicians make great developers, and how inclusive communities are helping more women thrive in tech. Jessica’s Top 3 JavaScript Skill Picks for 2025 If you ask Jessica what it takes to succeed as a JavaScript developer in 2025, she won’t point you straight to the newest library or trend. Instead, she lists three skills that sound simple, but take real time to build: > “Learning how to ask questions and research when you get stuck. Learning how to read error messages. And having a strong foundation in the fundamentals” She says those skills don’t come from shortcuts or shiny tools. They come from building. > “Start with small projects and keep building,” she says. “Books like You Don’t Know JS help you understand the theory, but experience comes from writing and shipping code. You learn a lot by doing.” And don’t forget the people around you. > “Meetups and conferences are amazing,” she adds. “You’ll pick up things faster, get feedback, and make friends who are learning alongside you.” Why So Many Musicians End Up in Tech A musical past like Jessica’s isn’t unheard of in the JavaScript industry. In fact, she’s noticed a surprising number of musicians making the leap into software. > “I think it’s because music and code have a lot in common,” she says. “They both require creativity, pattern recognition, problem-solving… and you can really get into flow when you’re deep in either one.” That crossover between artistry and logic feels like home to people who’ve lived in both worlds. What the Tech Community Is Getting Right Jessica has seen both the challenges and the wins when it comes to supporting women in tech. > “There’s still a lot of toxicity in some corners,” she says. “But the communities that are doing it right—like Women Who Code, Women in Tech, and Virtual Coffee—create safe, supportive spaces to grow and share experiences.” She believes those spaces aren’t just helpful, but they’re essential. > “Having a network makes a huge difference, especially early in your career.” What’s Next for Jessica Wilkins? With a catalog of published articles, open-source projects under her belt, and a growing audience of devs following her journey, Jessica is just getting started. She’s still writing. Still mentoring. Still building. And still proving that creativity doesn’t stop at the orchestra pit—it just finds a new stage. Follow Jessica Wilkins on X and Linkedin to keep up with her work in tech, her musical roots, and whatever she’s building next. Sticker illustration by Jacob Ashley....
Apr 25, 2025
3 mins
Increasing development velocity with Cursor
If you’re a developer, you’ve probably heard of Cursor by now and have either tried it out or are just curious to learn more about it. Cursor is a fork of VSCode with a ton of powerful AI/LLM-powered features added on. For around $20/month, I think it’s the best value in the AI coding space. Tech giants like Shopify and smaller companies like This Dot Labs have purchased Cursor subscriptions for their developers with the goal of increased productivity. I have been using Cursor heavily for a few months now and am excited to share how it’s impacted me personally. In this post, we will cover some of the basic features, use cases, and I’ll share some tips and tricks I’ve learned along the way. If you love coding and building like me, I hope this post will help you unleash some of the superpowers Cursor’s AI coding features make possible. Let’s jump right in! Cursor 101 The core tools of the Cursor tool belt are Autocomplete, Ask, and Agent. Feature: Autocomplete The first thing that got me hooked was Autocomplete. It just worked so much better than the tools I had used previously, like GitHub Copilot. It was quicker and smarter, and I could immediately notice the amount of keystrokes that it was saving me. This feature is great because it doesn’t really require any work or skilled prompting from the user. There are a couple of tricks for getting a little bit more out of it that I will share later, but for now, just enjoy the ride! Feature: Ask If you’ve interacted with AI/LLMs before, like ChatGPT - this is what the Ask feature is. It’s just a chat feature you can easily provide context to from your code base and choose which Model to chat with. This feature is best suited for just asking more general questions that you might have queried Google or Stack Overflow for in the past. It’s also good for planning how to implement a feature you’re working on. After chatting or planning, you can switch directly to Agent mode to pick up and take action on something you were cooking up in Ask mode. Here’s an example of planning a simple tic-tac-toe game implementation using the Ask feature: Feature: Agent Agent mode lets the AI model take the wheel and write code, make edits, or take other similar actions on your code base. The goal is that you can write prompts and give instructions, and the Agent can generate the code and build features or even entire applications for you. With great power comes great responsibility. Agents are a feature where the more you put into them, the more you get out. The more skilled you become in using them by providing better prompts and including the right context, you will continue to get better results. The AI doesn’t always get it right, but the fact that the models and the users are both getting better is exciting. Throughout this post, I will share the best use cases, tips, and tricks I have found using Cursor Agent. Here’s an example using the Agent to execute the implementation details of the tic-tac-toe game we planned using Ask: Core Concept: Context After understanding the features and the basics of prompting, context is the most important thing for getting the best results out of Cursor. In Cursor and in general, whenever you’re prompting a chat or an agent, you want to make sure that it has all the relevant information that it needs to provide an answer or result. Cursor, by default, always has some context of your code. It indexes your code base and usually keeps the open buffer in the context window at the very least. At the top left of the Ask or Agent panel, there is an @ button, and next to that are badges for all the current items that have been explicitly added to the context for the current session. The @ button has a dropdown that allows you to add files, folders, web links, past chats, git commits, and more to the context. Before you prompt, always make sure you add the relevant content it needs as context so that it has everything it needs to provide the best response. Settings and Rules Cursor has its own settings page, which you can access through Cursor → Settings → Cursor Settings. This is where you log in to your account, manage various features, and enable or disable models. In the General section, there is an option for Privacy Mode. This is one setting in particular I recommend enabling. Aside from that, just explore around and see what’s available. Models The model you use is just as important as your prompt and the context that you provide. Models are the underlying AI/LLM used to process your input. The most well-known is GPT-4o, the default model for ChatGPT. There are a lot of different models available, and Cursor provides access to most of them out of the box. Model pricing A lot of the most common models, like GPT-4o or Sonnet 3.5/3.7, are included in your Cursor subscription. Some models like o1 and Sonnet 3.7 MAX are considered premium models, and you will be billed for usage for these. Be sure to pay attention to which models you are using so you don’t get any surprise bills. Choosing a Model Some models are better suited for certain tasks than others. You can configure which models are enabled in the Cursor Settings. If you are planning out a big feature or trying to solve some complex logic issue, you may want to use one of the thinking models, like o1, o3-mini, or Deep Seek R1. For most coding tasks and as a good default, I recommend using Sonnet 3.5 or 3.7. The great thing about Cursor is that you have the options available right in your editor. The most important piece of advice that I can give in this post is to keep trying things out and experimenting. Try out different models for different tasks, get a feel for it, and find what works for you. Use cases Agents and LLM models are still far from perfect. That being said, there are already a lot of tasks they are very good at. The more effective you are with these tools, the more you will be able to get done in a shorter amount of time. Generating test cases Have some code that you would like unit tested? Cursor is very good at generating test cases and assertions for your code. The fewer barriers there are to testing a piece of code, the better the result you will get. So, try your best to write code that is easily testable! If testing the code requires some mocks or other pieces to work, do your best to provide it the context and instructions it needs before writing the tests. Always review the test cases! There could be errors or test cases that don’t make sense. Most of the time, it will get you pretty close to where you want to be. Here’s an example of using the Agent mode to install packages for testing and generate unit tests for the tic-tac-toe game logic: Generating documentation This is another thing we know AI models are good at - summarizing large chunks of information. Make sure it has the context of whatever you want to document. This one, in particular, is really great because historically, keeping documentation up to date is a rare and challenging practice. Here’s an example of using the Agent mode to generate documentation for the tic-tac-toe game: Code review There are a lot of up-and-coming tools outside of Cursor that can handle this. For example, GitHub now has Copilot integrated in pull requests for code reviews. It’s never a bad idea to have whatever change set you’re looking to commit reviewed and inspected before pushing it up to the remote, though. You can provide your unstaged changes or even specific commits as context to a Cursor Ask or Agent prompt. Getting up to speed in a new code base Being able to query a codebase with the power of LLM’s is truly fantastic. It can be a great help to get up to speed in a large new codebase quickly. Some example prompts: > Please provide an overview of this project and how to get started developing with it > I need to make some changes to the way that notifications are grouped in the UI, please provide a detailed analysis and pseudo code outlining how the grouping algorithm works If you have a question about the code base, ask Cursor! Refactoring Refactoring code in a code base is a much quicker process in Cursor. You can execute refactors depending on their scope in a couple of distinct ways. For refactors that don’t span a lot of files or are less complex, you can probably get away with just using the autocomplete. For example, if you make a change to something in a file and there are several instances of the same pattern following, the autocomplete will quickly pick up on this and help you tab through the changes. If you switch to another file, this information will still be in context and can be continued most of the time. For larger refactors spanning several files, using the Agent feature will most likely be the quickest way to get it done. Add all the files you plan to make changes to the Agent tab’s context window. Provide specific instructions and/or a basic example of how to execute the refactor. Let the Agent work, if it doesn’t get it exactly right initially, you can always give it corrections in a follow-up prompt. Generating new code/features This is the big promise of AI agents and the one with the most room for mixed results. My main recommendation here is to keep experimenting. Keep learning to prompt more effectively, compare results from different models, and pay attention to the results you get from each use case. I personally get the best results building new features in small, focused chunks of work. It can also be helpful to have a dialog with the Ask feature first to plan out the feature's details that the Agent can follow up on and implement. If there are existing patterns in your codebase for accomplishing certain things, provide this information in your prompts and make sure to add the relevant code to the context. For example, if you’re adding a new form to the web page and you have other similar forms that handle validation and making back-end calls in the same way, Cursor can base the code for the new feature on this. Example prompt: Generate a form for creating a new post, follow similar patterns from the create user profile form, and look to the post schema for the fields that should be included. Remember that you can always follow up with additional prompts if you aren’t quite happy with the results of the first.. If the results are close but need to be adjusted in some way, let the agent know in the next prompt. You may find that for some things, it just doesn’t do well yet. Mentally note these things and try to get to a place where you can intuit when to reach for the Agent feature or just write some of the code the old-fashioned way. Tips and tricks The more you use Cursor, the more you will find little ways to get more out of it. Here are some of the tips and patterns that I find particularly useful in my day-to-day work. Generating UI with screenshots You can attach images to your prompts that the models can understand using computer vision. To the left of the send button, there is a little button to attach an image from your computer. This functionality is incredibly useful for generating UI code, whether you are giving it an example UI as a reference for generating new UI in your application or providing a screenshot of existing UI in your application and prompting it to change details in reference to the image. Cursor Rules Cursor Rules allow you to add additional information that the LLM models might need to provide the best possible experience in your codebase. You can create global rules as well as project-specific ones. An example use case is if your project has some updated dependency with newer APIs than the one on which the LLM has been trained. I ran into this when adding Tailwind v4 to a project; the models are always generating code based on Tailwind v3 or earlier. Here’s how we can add a rules file to handle this use case: ` If you want to see some more examples, check out the awesome-cursorrules repository. Summary Learn to use Cursor and similar tools to enhance your development process. It may not give you actual superpowers, but it may feel like it. All the features and tools we’ve covered in this post come together to provide an amazing experience for developing all types of software and applications....
Apr 18, 2025
11 mins
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