Head of Engineering

Hi 👋🏾, I’m Abhik, Ashby’s Co-Founder and VP of Engineering. We’re looking for an Engineering leader who has done it all: You’ve built impressive products as an IC, you’ve built a bench of amazing Engineers, and you’ve established the cultural norms and processes of an entire Engineering department. Ashby’s success and ambition mean we’re doubling the Engineering team in the next year, and we need your experience and leadership to do it thoughtfully.

Our product and growth are exceptional. Ashby All-in-One is powerful, easy to use, and replaces several venture-backed companies' worth of products (often with a better experience). 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.

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 and then figure out how to hire them and build an environment that gives them the freedom and agency to actually be exceptional.

In other words, if engineers writing product specs, making product decisions, and not breaking down projects into individual tickets excites you, you’ve found the right place.

As Head of Engineering in the Americas, you’ll work closely with me and your counterpart in EMEA, Colin, to continue scaling our unique culture. You’ll manage our remote team of 20 engineers and 2 EMs, who cover a wide variety of specializations, from Product Engineers to Site Reliability Engineers to Design Engineers. Over the next year, you’ll grow that team to 40 engineers and 5-6 EMs.

I’ll share more details once we meet.

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 middle manager. You haven’t led the definition and evolution of the culture and processes of an entire Engineering department.

• You’ve never managed managers. Managing other leaders is a very different ball game, and not everyone enjoys it or thrives in it – the seniority of this role won’t let you explore that.

• 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 product 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 (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

You’ll be a critical part of figuring out how to scale these methods from 50 engineers to 100 and beyond.

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

This is an important role that will lead half of our Engineering team now and for the foreseeable future. The interview process reflects that both in challenge and length (~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. A deep dive into a past project with other Engineering Leaders (1h, live)

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

6. Interview with Benji, our CEO (45m, live)

7. Final round where you meet various folks on the team (90m)

Depending on my bandwidth, we may start with an additional 30m screen with a recruiter. Near the end of the process, we’ll do reference checks.

This is also an important decision for you, so 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 and features. What better way to learn how ICs work than to be one! Don’t worry if you don’t know 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.