401 Best ups Jobs in Chicago, Illinois (October 2025) - page 2

Ashby

Senior Product Engineer - Americas

7 days ago

Chicago

Job Description:\n\nHi 👋🏾 I’m Abhik, Ashby's Co-Founder and VP of Engineering. We’re looking for a versatile, persistent product engineer who’s not afraid to set up reusable building blocks across the stack and advocate for the time and space to do so. At Ashby, all our engineers ship features end-to-end at a high pace. Example is the best leadership. We’ll give you the room to do your best work, and you'll be our guide! If that speaks to you, read on. What Ashby gives you in return is the best of both early and growth-stage environments. The agency and no-nonsense of a seed startup: you write product specs, make product and design decisions, and build in an almost-no-meeting culture. While also the product-market fit and scale of a growth-stage startup: tens of thousands of daily users who depend on your software and eagerly await your next feature. We have notable customers like Notion, Linear, Shopify, and Snowflake. Our growth and retention metrics are best-in-class among our peers: we have tens of millions in ARR, growing >100% year over year, very low churn, and many years of runway. We’ll share more details once we meet. You’ve probably seen this role posted before, and it’s because we’re always expanding the team (we’re on track to double this year). We’re bubbling with ideas on how to support Talent Acquisition through software, and we’ve started the journey of building products beyond Talent Acquisition. We read every application and aim to respond to yours within 3-4 days (often sooner). About the Role and How We Work Our engineering culture strives to recreate the environments where we did our best work as ICs – where we had the ownership and agency to impact our users with creative and innovative software. I started my career building software for artists in the Visual Effects industry. It was a formative experience for me as a software engineer because success relied on my ability to be a product manager and designer. I talked to artists to understand their needs. I came up with ideas. I did industry research, designed interfaces, and prototyped ideas. I watched artists use what I built and decided what to tackle in the next iteration. No daily stand-ups, no t-shirt sizing, no planning meetings. I studied computer science to solve problems, not tickets, and this felt exactly like that. I not only felt creative and fulfilled but the agency and ownership we were given as engineers powered an incredible amount of innovation. Innovation came differently (or not at all) at technology startups beyond the seed stage, often through an engineer’s force of will and ability to push back against culture (rather than any encouragement from it). Engineering was narrowed to implementation and delivery, partly due to the influence of other departments and partly due to the influx of "Agile" processes like sprint planning. In those companies, I felt like a JIRA jockey. At Ashby, we’re building an environment that is optimistic about what engineers can own and achieve. An environment that embraces innovative engineers, and, frankly, often stays out of their way. As a Product Engineer, you’ll take ownership over a large portion of one of our products and own projects end-to-end (wearing hats traditionally worn by product and design). You’ll research competitors, write product specs, make wireframes, and more. To ground it with examples, product engineers at Ashby have: Designed and built automated interview scheduling. This feature automates scheduling by calculating possible times from a pool of interviewers and other constraints, and then presenting these times to the candidate for selection via our responsive web app. This solves the “Calendar Tetris” problem I talk about in "What We're Building." Built a generalized declarative filter architecture that allows users to create complex filters for any record with a consistent UI and compile it to SQL in our backend. Many user-facing features use it. Specced, designed, and implemented a feature that allows users to complete signing offers entirely within Ashby. This project involved talking to customers to understand their requirements, deciding what technologies to use, building a prototype, and working with other team members to integrate the final implementation into additional features. What We’re Building As engineers, we are used to tooling that makes us better at what we do. When we started Ashby, we saw the opposite with Talent Acquisition software. Recruiting teams were leveling up how they did their work, but instead of software meeting this new standard, it held them back. Scheduling a final round is an excellent example. Recruiting teams wanted to schedule candidates faster, track interviewer preparation and quality, and do it with half the headcount. A recruiter needed to manually collect availability from the candidate, identify qualified interviewers, perform “Calendar Tetris” to find who is available to interview the candidate, schedule on the earliest date possible, and make any last-minute adjustments as availability changed. They must do this while considering the interview load on each individual and whether interviewers need to be trained and shadowing others. 🥵 TA software didn’t help. As hiring managers, we know TA is a critical function, and as engineers, we know software can do better. So, we built and continue to build Ashby to give TA teams the highest standard of tooling. Software that’s intelligent and powerful. Software that provides insights into where they’re failing and automates or simplifies many of the tasks they’re underwater with. We want other functions and departments to be jealous of what TA teams can do with Ashby, and today they often are! Why You Should or Shouldn’t Apply Software engineers come in many flavors, not all of which fit our model. Here are some things to help you decide if this fits you and what you’re looking for: You’re not afraid to tackle any part of a technology stack. You do what’s necessary to successfully deliver a feature, whether writing frontend or choosing new infrastructure. We’ll provide a supportive environment to do it successfully (e.g., design system, SRE team). You’ve tackled projects with a lot of product and technical ambiguity, and you thrive at the intersection of the two. We’re not building a simple CRUD app, and many of the challenges we tackle require you to use your knowledge of our customers to build powerful abstractions and flexibility in the system to solve a class of problems. You know how to strike the right balance between speed and quality. Ashby wasn’t built quickly. We took four years to launch publicly because convincing customers to switch required a high-quality product. However, time isn’t infinite, especially for a startup, so we still move with urgency—we’ve built the equivalent of three or more VC-backed startups with a very small team. You are ambitious and always looking to improve your skills. For most engineers, this role will give you more freedom and responsibilities than you’ve experienced in the past. To thrive (and level up), you’ll need to be open to feedback (and we give lots of it). You’re an excellent collaborator and communicator. Ownership and freedom don’t mean you work in a vacuum. You’ll need to vet your decisions with the appropriate stakeholders, keep them up to date when necessary, and work with other engineers to get your projects across the finish line. Clear and concise communication helps a lot here! You seek to create leverage in your work. The nature of software is that you can often automate or abstract what would be tedious, time-consuming work. Your impatience usually leads to new abstractions, tools to allow Support to debug before Engineering, new lint rules to prevent common bugs, etc. Put another way, you shouldn’t apply if: To you, a tech lead, staff, or principal engineer is someone who spends most of their time project managing or doing architecture reviews. Our most tenured engineers spend most of their time building, and we often trust them with our most challenging problems. While they lead product and technical areas and help other engineers plan their most challenging work, it’s not a requirement, nor do engineers need their sign-off. You need company-driven process and structure to get your projects across the finish line. Sprint planning and well-defined project management processes are things you need or look to others to lead. You’d rather focus on the technical details and challenges. You only want to do exciting work. We’re building a team of kind, collaborative folks. Customer issues and investigations are distributed across the team, including our high-level ICs. You can get lost in the details. Once you start implementation, it can be hard to take a step back and think about the project as a whole. You like everything to be planned upfront. You haven’t led or taken ownership of projects before. You’re used to working with tech leads and taking on tasks distributed by them. You want to mentor earlier-career engineers. We rely on engineers owning their projects, so we need engineers with that experience. This requires the team to be reasonably tenured. More than 90% of the team would be considered Senior or above in the industry today, so mentorship opportunities are very limited. Engineering Culture Our engineering culture is motivated by Benji’s (my Co-founder and CEO) and my belief that a small, talented team, given the right environment, can build high-quality software fast (and work regular hours!). We do it through: Minimal process with ownership over decisions normally made by product and design Natural collaboration and deliberate communication Investing in tools and abstractions that give us leverage Putting effort into building a diverse team Minimal Process & Lots of Ownership The best engineers we’ve worked with delivered reliably magical outcomes. They took customer problems and relentlessly drove them to solutions that were not only successful but often brilliant and creative. While they did this with minimal oversight, stakeholders were never in the dark as to what was going on, and no setback was a surprise. Traditional product-development processes aren’t meant for the best engineers. Their purpose is to create consistent outcomes regardless of the engineer’s skill. But, consistency comes at the expense of an engineer’s time and freedom—both ingredients necessary to generate those magical outcomes. As a result, process stifles the best engineers and doesn’t give others the opportunity to practice the behaviors that made the best engineers the “best.” At Ashby, we want to build an environment that encourages every engineer to be their best. So, at Ashby, every Engineer runs their project. Product Managers (and Designers) build strategy, do customer research, and hand off problem briefs to Engineers. Engineers take on the rest: they research the problem, write product specs, build wireframes, and implement their solution end-to-end. We rely on engineers, not process, to push information outward to the relevant folks (e.g., Product Managers) and pull folks in to help (e.g., Designers, Infra). It’s a new level of ownership for many engineers, but we’d rather an engineer fail a bit and coach up their skills than use process as a crutch. Not everyone succeeds in our culture, but those who do thrive. Collaboration is Natural & Communication is Deliberate Our engineering team consists of lifelong learners who are talented but also humble and kind (meet them here!). These attributes create an environment where collaboration happens naturally. We combine this with research, prototyping, and written proposals to see around corners and get feedback from the team across time zones. Focus time is something that we hold sacred, and, with thoughtful and deliberate communication, engineers are in <2h meetings per week (I wrote about it here). To drive it home, here's a recent calendar of an engineer who has been with us for over 4 years: We also meet in person at least twice a year, once as a department and once as a company. You also have a small budget to meet up with folks in your city/region. Increase Leverage, not Team Size We built Ashby with the quality, breadth, and depth that many customers would expect from much larger teams over larger time scales. We’ve done this through investment in: Great developer tooling. Our CI/CD takes ~10m, and we deploy at least 15x a day. A debugger that works out of the box. Everyone on the team has contributed to our developer experience 💪🏾. Building blocks to create powerful and customizable products fast. At the core of Ashby is a set of common components (analytics modeling and query language, policy engine, workflow engine, design system) that we constantly improve. Each improvement to a common component cascades throughout our app (short video below). Here’s an impromptu quote from Arjun in our company Slack of what it’s like to build a feature at Ashby: And a demo of one of these building blocks: Put Effort into Diversity Diverse teams drive innovation and better outcomes. Having seen my mother and partner build their careers as minority women in non-diverse fields, I want to make sure Ashby creates opportunities for the next generation of engineers from underrepresented groups. Today, 21% of engineers at Ashby are from underrepresented groups. It’s not great, and we are taking conscious steps to improve, like sourcing diverse candidates, providing generous paid family leave, no leetcode interviews, and more. Interview Process At Ashby, our team and interview process want to help you show your best self. We’ll dive into past projects and simulate working together via pair programming, writing product and tech specs collaboratively, and talking through decisions. There are no leetcode or whiteboard exercises. Our interview process is three rounds: Introduction call with Hiring Manager (15 to 30m, live) A technical screen where we pair in our actual codebase (1h, live) Three non-coding interviews that focus on product thinking, technical design, and infrastructure (3h 15m, live can be split across multiple days) Depending on our leadership team’s bandwidth, we may start with an additional 30m screen with a recruiter. Your hiring manager will be your main point of contact and prep you for interviews. Each round will have written guidance so you know what to expect (you’ll need minimal preparation). You’ll meet 4 to 6 people in engineering (with 5-15 minutes in each interview to ask them questions). If we don’t give an offer, we’ll provide feedback! Your First Three Months at Ashby We want an exceptional onboarding experience for every new hire. At Ashby, your dev environment is set up with a single script, you push your first product change on day one, and you spend the rest of your time shipping product changes that give you a tour of our codebase and best practices.

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