Head of Platform & Infrastructure Engineering

Hi 👋🏾, I’m Abhik, Ashby’s Co-Founder and CTO. Ashby is growing fast, which means exponential growth across every product metric: jobs, applications, interviews, you name it. We’re not slowing down, and as a result, keeping Ashby performant and reliable is a company priority. We need your leadership to do that now and in the future.

We’ve already assembled a fantastic Platform & Infrastructure team of 11 engineers (all Senior+, >70% Staff), and they’ve done an excellent job handling our growth, but the management and leadership of Platform & Infrastructure have been diffused across our Engineering leaders. As we hit our next level of scale, it’s time for us to hire an Engineering leader responsible for performance and reliability, and for building out the team that ensures those. Hopefully, that’s you!

The Role

In this role, you will report directly to me, and your responsibilities will include:

• Building and maintaining a long-term vision and 6-month roadmap for Platform & Infrastructure.

• Growing the Platform & Infrastructure team. You’ll hire ICs, managers, and build out a headcount plan. This will include determining if more specialized roles need to be established (e.g., DB Admin).

• Building and maintaining an excellent relationship with Product Engineering. The ideal state is that Product Engineering can move incredibly fast independently without breaking performance or reliability, and Platform & Infrastructure doesn’t feel like they’re always cleaning up someone else’s “mess.” Today, there’s a great relationship, but there’s always room for improvement!

• Assessing and improving our monitoring and incident management process. Again, we’re doing relatively well here, but there’s always room to improve. For example, making uptime measurement easier and improving coordination with Support during incidents.

• Maintaining vendor relationships and negotiating pricing for our critical hosting and observability infrastructure, including AWS, ClickHouse, Datadog, and Braintrust. They have a meaningful impact on gross margin and need to be kept in check.

• You’ve managed managers. Managing other leaders is a very different ball game, and not everyone enjoys it or thrives in it. Within your first 6 months, you’ll most likely have to hire a manager underneath you.

• If you have experience managing developer experience and developer tools, building out a dedicated team for DevEx. If you don’t have experience here, DevEx will report into Product Engineering. Happy to discuss once we meet!

A big part of our secret sauce is how we run Engineering. We achieve incredible speed and quality by discarding many industry norms and being optimistic about Engineers. We consider what makes exceptional Engineers exceptional, then figure out how to hire them and build an environment that gives them the freedom and agency to be exceptional. You’ll be a key leader in ensuring that continues!

The Qualifications

We’re entrusting you with a company priority, so we want you to know how to scale products and build the great teams that do that. This means:

• You played an important role leading a company through a high-growth period (either as an IC Lead or Engineering Leader). You had to make high-quality decisions under pressure. That often meant striking a balance between short-term fixes to keep the product from falling over and long-term investments to ensure it didn’t happen again.

• You have experience hiring and building hiring processes, and enjoy it! You’ve designed interviews, interview loops, and led hiring strategy.

• You have a track record of excellent collaboration with other departments. You were a key contributor to company-level initiatives that involved Product Engineering, Product, Sales, or Support. Those departments felt heard and supported, yet positively challenged by you.

• You have a background in writing production software (far beyond scripts). Our Platform & Infrastructure team is exclusively made up of strong software engineers, not just folks who scale the systems software runs on. They can jump into any part of our app, understand the code, and modify the underlying logic. We expect you to have similar experience to grow and upskill the team.

• You are knowledgeable about platform and infrastructure technologies, networking, and hardware. You know how Kubernetes goes beyond a Container Orchestration Platform, how traffic flows between Load Balancers and Pods, and how the intricacies of the underlying hardware can cause Cloud abstractions to break, etc.

• You are a great communicator, particularly in writing. You’ll need to be able to go deep with Infrastructure Engineers in conversations while also communicating those concepts to folks like myself who have much less experience.

You should be comfortable managing a team spanning from the Americas West Coast to Europe. You’ll be able to hire managers to focus on specific time zones, but I expect you to have skips with some engineers (and you should want to, too!). To ensure a reasonable work schedule, we’re only hiring candidates who live in the PST-GMT time zone.

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 Shouldn’t Apply

• You’ve always been a line manager or never led a department within Engineering. You haven’t led the definition and evolution of culture and processes.

• You don’t enjoy coding or don’t find time to stay up-to-date on technology. We believe great leaders are folks who were great engineers themselves. That starts with loving the craft and never giving it up.

• You went into management because it was the only growth path available. We want folks who could have been Principal engineers (or were one!).

• You're happy with a team of engineers who are predominantly early-career or mid-career or don't thrive with ownership or autonomy. You believe that with enough guardrails, the team can get things done.

• To you, a Staff or Principal Engineer is someone who spends most of their time project managing or conducting architecture reviews. You don’t believe staff and principal engineers could lead by the example they set or the leverage they create through their work.

• You’re not optimistic or convinced that we can build a large engineering team that functions differently from the status quo. You think, at some size, common processes need to be implemented to ensure consistent delivery (e.g., sprint planning, product managers writing in-depth specifications). You might not say it out loud, but you think, at some size, compromises have to be made for the sake of hiring numbers or consistency.

Engineering Culture

Our engineering culture is motivated by Benji’s (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, including LLM-driven dev tooling.

• Putting effort into building a diverse team

Minimal Process & Lots of Ownership

The best engineers we’ve worked with delivered reliably magical outcomes. They often discovered problems, prioritized the right ones, 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 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, 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. ~34 hours of focus time, 2.5h of interviews, and 3.5 hours of meetings:

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. For example, our CI/CD takes ~10m, we deploy at least 15x a day, and our debugger 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).

• AI-powered tooling. We think of AI as a way to automate the mundane parts of building and maintaining high-quality software. We use a combination of third-party and internally built tools that, for instance, auto-triage customer issues, suggest fixes, prototype ideas, generate production-ready code, and conduct code reviews. Engineers have an unlimited token budget (but are not measured on it). We write in detail about our philosophy, current use of AI, and future plans for AI in Engineering here.

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, 30% of engineers and 50% of our engineering leaders at Ashby are from underrepresented groups. We actively maintain and improve these numbers by sourcing diverse candidates, providing generous paid family leave, banning leetcode interviews, providing guidance and coaching to candidates, and more.

Work-Life Balance: It’s A Marathon, Not a Sprint

The intensity of work at Ashby should feel like a marathon, not a sprint (nor speed-walking). We work with urgency and ambition to build excellent software, but we don’t need to prove out a new software category or product-market fit. That requires ingenuity and thoughtfulness, and that doesn’t happen with unrealistic deadlines or sleepless nights.

Our remote, low-meeting, high-ownership culture gives engineers (and to a similar degree, you) a lot of flexibility in how they structure their days and weeks. In practice, that means they keep their own hours, but there will be moments of intensity, like launching their feature at our annual user conference. We offer unlimited PTO, and they actually get to use it. Some of our most exceptional engineers take almost 30 days of vacation per year.

This way of working allows many of us on the team to be active parents, including Benji and me. I block off 1.5 hours every morning to spend with my daughter and drop her off at school. Mujda (Product Engineer) puts it best in an article about us: “I can say that Ashby is a great place to be a mom… No one bats an eye if I have to take my kid to a doctor’s appointment or have to work weird hours because childcare fell through.”

Interview Process

This is an important role that will lead our Platform & Infrastructure teams now and for the foreseeable future. The interview process reflects that in both challenge and length (5 rounds, ~6.5h):

1. Introduction call with me (30m, live)

2. A technical screen where we pair in our actual codebase (1h, live)

3. An interview to explore your past experience as a leader (1h, live)

4. Interview with Colin, our Head of EMEA Engineering (45m)

5. Final round where you meet various folks on the team and explore leadership and technical topics (3h)

I’ll have a strong read on whether we’re trending toward an offer by Round 3. Near the end of the process, we’ll do reference checks with a former manager, two direct reports, and a peer in Engineering. Depending on my bandwidth, we may start with an additional 30m screen with a recruiter.

This is also an important decision for you, so once you start interviewing, I’m always happy to have coffee chats in person or over Zoom to get to know each other.

Your First Six Months at Ashby

Your first three months at Ashby will be spent learning about Ashby Engineering and easing into leadership. While most of your onboarding will be driven by a 6-month plan you put together (and refine over time), you’ll also ship some product changes, features, and infra changes. What better way to learn how ICs work than to be one! Don’t worry if you’re not familiar with our technologies. The team is really helpful, and our dev environment is pretty awesome: it sets up in a single script, and you’ll be able to push your first product change on day one.

You and I will do 30-day, 60-day, 90-day, and 6-month reviews to calibrate on our unique culture and how you, I, and the team will work together.

Benefits

• Competitive salary and equity.

• 10-year exercise window for stock options. You shouldn’t feel pressure to purchase stock options if you leave Ashby —do it when you feel financially comfortable.

• Unlimited PTO.

• A minimum of 12 weeks of fully paid parental leave, covered by Ashby. For folks outside the US, it may be longer to be in line with regional requirements.

• Generous equipment, software, and office furniture budget. Get what you need to be happy and productive!

• $100/month education budget with more expensive items (like conferences) covered with manager approval.

• If you’re in the US, we offer top-tier health insurance for you and your dependents, with 100% of premiums covered by Ashby. In other countries, we provide high-quality supplemental health insurance for you and your dependents, also fully covered by us.

Ashby’s success hinges on hiring great people and creating an environment where we can be happy, feel challenged, and do our best work. We’re being deliberate about building that environment from the ground up. I hope that excites you enough to apply.

Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.

Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.