How to build a team of future founders: Insights from Dover's founding engineer

John Holliman

CTO

April 30, 2022

5 min

  • I was one of the first 20 employees at my previous startup, Expanse (acquired by Palo Alto Networks last year). It was a phenomenal learning experience, but after more than 3 years at the company, I found myself itching for a role as an early member of the team at another small startup.

  • I went to MIT with Max and Anvisha, two of Dover's co-founders, and joined them while they were going through YC.

  • I ended up joining Dover as the first full-time employee and its Founding Engineer.

  • I was one of the first 20 employees at my previous startup, Expanse (acquired by Palo Alto Networks last year). It was a phenomenal learning experience, but after more than 3 years at the company, I found myself itching for a role as an early member of the team at another small startup.

  • I went to MIT with Max and Anvisha, two of Dover's co-founders, and joined them while they were going through YC.

  • I ended up joining Dover as the first full-time employee and its Founding Engineer.

Why I joined Dover as its first employee

A behind-the-scenes look into the first stage of a company

As an early employee, “you don't know what you don't know” about what it takes to build a business, but the good news is, you are placed directly in the middle of the action and quickly find out.

When I joined, I was grateful to have exposure to the many things that are abstracted away from an employee's experience as a team grows in size, like the origin of the desks you work on, or the actual name of the business being used. I remember scanning Bookface (internal messaging board for YC founders) for deals on office furniture in San Francisco with George, and recall when Max had to file a DBA application so we could refer to ourselves officially as "Dover" - a name George came up with on a trip to England after seeing it on a street sign.

Silliness aside, it was this view into what it actually takes to bring an operation to life that was exciting to me, and why I joined the team in the first place. There’s no better training for future founders than to see it all unfold firsthand, and I was thrilled to see the founders work through so much so quickly to get our company off the ground.

The problem space

The problem that Dover solves is pretty universally understood— recruiting is something every company goes through, and we've all had our fair share of experiences where the process could have been improved, as either the hiring manager, a member of the interview panel or the candidate.

I was excited about the prospect of making real change in the recruiting space, where inefficiencies and manual processes cause companies to lose out on great candidates, and vice versa.

I was also thrilled about the ability to improve our product as we dogfooded it ourselves — every time we hire someone (which we’ve done a lot of this year, considering our team was 10 people at the start but is now north of 60 people), we are able to see directly how our product can be improved to help our customers hire better.

The team (aka George, Max, and Anvisha)

I had gone to school with Max and Anvisha — and had always been impressed by (they were both active and leaders in various student organizations) and enjoyed spending time with them. When they pitched me about what they were working on while in YC, I was impressed and felt excited about making the leap to join them.

I didn't know George prior to my conversations with him about joining Dover, but after I spoke with him as well and got a better sense of the founders’ collective vision for the company, I felt that they were a group of whip-smart, thoughtful, and kind individuals who had bold goals about the recruiting space.  I couldn't wait to join them.

How we’ve improved since scaling our team to 60+ people

Our continued high level of trust, humility and transparency on the team

I wouldn't say it's unique that a company provides a high level of ownership to its employees, but it is absolutely unique that, while scaling to its current size, Dover continues to do so to the extent it does.

Here’s how we’ve done it:

  1. We are fortunate that we have more things to build than time to build them given the demand of our product — that means that any additional engineer on our team has the opportunity to carve out an area of ownership, whether that be the development, maintenance, and future enhancements to a major user-facing feature or a large backend improvement that will pay dividends over the months ahead in terms to development velocity and application performance. The engineers on our team are not only very technically adept, but are great at validating hypotheses through experimentation, rallying stakeholders to bring projects across the finish line, and building towards our ambitious product vision.

  2. Our interview process explicitly tests for: 1) product sense and the ability to communicate effectively, 2) curiosity and willingness to seek and accept help.

  3. The reason we do this in the interview process is that this is a pretty accurate reflection of life at Dover: you are trusted to take on large projects because you are a thoughtful and knowledgeable person, you are given the room to explore and articulate the resources you need to fill in the gaps. And, your team is there to quickly step in and work with you to get you across the finish line.

Our expanding product surface area

While we started out with our sourcing technology and automated outreach, we’ve expanded our product surface area to include scheduling automation, job pipeline performance tracking, inbound channel optimization (i.e. programmatic job board utilization and spend), referrals, automated job descriptions, and much, much more.

The engineering team is able to achieve this through tight and thorough collaboration with other stakeholders across the company — customer success, sales, marketing — as we continue to gather feedback from them and our customers and prioritize against our vision of making recruiting better together.

What I hope for

When I joined Dover, I was given the tools and visibility I needed to succeed as a founding engineer. I am grateful for that every day.

My goal is to continue to cultivate that environment for my teammates. I want to give them the resources and opportunities they need to be the early employees, leaders, or founders that they strive to be at Dover and beyond.

Given what we’ve built, the values we instill in ourselves and each other as a team, and the ambitious road we’re forging ahead on, I’m confident we can get there.

Why I joined Dover as its first employee

A behind-the-scenes look into the first stage of a company

As an early employee, “you don't know what you don't know” about what it takes to build a business, but the good news is, you are placed directly in the middle of the action and quickly find out.

When I joined, I was grateful to have exposure to the many things that are abstracted away from an employee's experience as a team grows in size, like the origin of the desks you work on, or the actual name of the business being used. I remember scanning Bookface (internal messaging board for YC founders) for deals on office furniture in San Francisco with George, and recall when Max had to file a DBA application so we could refer to ourselves officially as "Dover" - a name George came up with on a trip to England after seeing it on a street sign.

Silliness aside, it was this view into what it actually takes to bring an operation to life that was exciting to me, and why I joined the team in the first place. There’s no better training for future founders than to see it all unfold firsthand, and I was thrilled to see the founders work through so much so quickly to get our company off the ground.

The problem space

The problem that Dover solves is pretty universally understood— recruiting is something every company goes through, and we've all had our fair share of experiences where the process could have been improved, as either the hiring manager, a member of the interview panel or the candidate.

I was excited about the prospect of making real change in the recruiting space, where inefficiencies and manual processes cause companies to lose out on great candidates, and vice versa.

I was also thrilled about the ability to improve our product as we dogfooded it ourselves — every time we hire someone (which we’ve done a lot of this year, considering our team was 10 people at the start but is now north of 60 people), we are able to see directly how our product can be improved to help our customers hire better.

The team (aka George, Max, and Anvisha)

I had gone to school with Max and Anvisha — and had always been impressed by (they were both active and leaders in various student organizations) and enjoyed spending time with them. When they pitched me about what they were working on while in YC, I was impressed and felt excited about making the leap to join them.

I didn't know George prior to my conversations with him about joining Dover, but after I spoke with him as well and got a better sense of the founders’ collective vision for the company, I felt that they were a group of whip-smart, thoughtful, and kind individuals who had bold goals about the recruiting space.  I couldn't wait to join them.

How we’ve improved since scaling our team to 60+ people

Our continued high level of trust, humility and transparency on the team

I wouldn't say it's unique that a company provides a high level of ownership to its employees, but it is absolutely unique that, while scaling to its current size, Dover continues to do so to the extent it does.

Here’s how we’ve done it:

  1. We are fortunate that we have more things to build than time to build them given the demand of our product — that means that any additional engineer on our team has the opportunity to carve out an area of ownership, whether that be the development, maintenance, and future enhancements to a major user-facing feature or a large backend improvement that will pay dividends over the months ahead in terms to development velocity and application performance. The engineers on our team are not only very technically adept, but are great at validating hypotheses through experimentation, rallying stakeholders to bring projects across the finish line, and building towards our ambitious product vision.

  2. Our interview process explicitly tests for: 1) product sense and the ability to communicate effectively, 2) curiosity and willingness to seek and accept help.

  3. The reason we do this in the interview process is that this is a pretty accurate reflection of life at Dover: you are trusted to take on large projects because you are a thoughtful and knowledgeable person, you are given the room to explore and articulate the resources you need to fill in the gaps. And, your team is there to quickly step in and work with you to get you across the finish line.

Our expanding product surface area

While we started out with our sourcing technology and automated outreach, we’ve expanded our product surface area to include scheduling automation, job pipeline performance tracking, inbound channel optimization (i.e. programmatic job board utilization and spend), referrals, automated job descriptions, and much, much more.

The engineering team is able to achieve this through tight and thorough collaboration with other stakeholders across the company — customer success, sales, marketing — as we continue to gather feedback from them and our customers and prioritize against our vision of making recruiting better together.

What I hope for

When I joined Dover, I was given the tools and visibility I needed to succeed as a founding engineer. I am grateful for that every day.

My goal is to continue to cultivate that environment for my teammates. I want to give them the resources and opportunities they need to be the early employees, leaders, or founders that they strive to be at Dover and beyond.

Given what we’ve built, the values we instill in ourselves and each other as a team, and the ambitious road we’re forging ahead on, I’m confident we can get there.

Why I joined Dover as its first employee

A behind-the-scenes look into the first stage of a company

As an early employee, “you don't know what you don't know” about what it takes to build a business, but the good news is, you are placed directly in the middle of the action and quickly find out.

When I joined, I was grateful to have exposure to the many things that are abstracted away from an employee's experience as a team grows in size, like the origin of the desks you work on, or the actual name of the business being used. I remember scanning Bookface (internal messaging board for YC founders) for deals on office furniture in San Francisco with George, and recall when Max had to file a DBA application so we could refer to ourselves officially as "Dover" - a name George came up with on a trip to England after seeing it on a street sign.

Silliness aside, it was this view into what it actually takes to bring an operation to life that was exciting to me, and why I joined the team in the first place. There’s no better training for future founders than to see it all unfold firsthand, and I was thrilled to see the founders work through so much so quickly to get our company off the ground.

The problem space

The problem that Dover solves is pretty universally understood— recruiting is something every company goes through, and we've all had our fair share of experiences where the process could have been improved, as either the hiring manager, a member of the interview panel or the candidate.

I was excited about the prospect of making real change in the recruiting space, where inefficiencies and manual processes cause companies to lose out on great candidates, and vice versa.

I was also thrilled about the ability to improve our product as we dogfooded it ourselves — every time we hire someone (which we’ve done a lot of this year, considering our team was 10 people at the start but is now north of 60 people), we are able to see directly how our product can be improved to help our customers hire better.

The team (aka George, Max, and Anvisha)

I had gone to school with Max and Anvisha — and had always been impressed by (they were both active and leaders in various student organizations) and enjoyed spending time with them. When they pitched me about what they were working on while in YC, I was impressed and felt excited about making the leap to join them.

I didn't know George prior to my conversations with him about joining Dover, but after I spoke with him as well and got a better sense of the founders’ collective vision for the company, I felt that they were a group of whip-smart, thoughtful, and kind individuals who had bold goals about the recruiting space.  I couldn't wait to join them.

How we’ve improved since scaling our team to 60+ people

Our continued high level of trust, humility and transparency on the team

I wouldn't say it's unique that a company provides a high level of ownership to its employees, but it is absolutely unique that, while scaling to its current size, Dover continues to do so to the extent it does.

Here’s how we’ve done it:

  1. We are fortunate that we have more things to build than time to build them given the demand of our product — that means that any additional engineer on our team has the opportunity to carve out an area of ownership, whether that be the development, maintenance, and future enhancements to a major user-facing feature or a large backend improvement that will pay dividends over the months ahead in terms to development velocity and application performance. The engineers on our team are not only very technically adept, but are great at validating hypotheses through experimentation, rallying stakeholders to bring projects across the finish line, and building towards our ambitious product vision.

  2. Our interview process explicitly tests for: 1) product sense and the ability to communicate effectively, 2) curiosity and willingness to seek and accept help.

  3. The reason we do this in the interview process is that this is a pretty accurate reflection of life at Dover: you are trusted to take on large projects because you are a thoughtful and knowledgeable person, you are given the room to explore and articulate the resources you need to fill in the gaps. And, your team is there to quickly step in and work with you to get you across the finish line.

Our expanding product surface area

While we started out with our sourcing technology and automated outreach, we’ve expanded our product surface area to include scheduling automation, job pipeline performance tracking, inbound channel optimization (i.e. programmatic job board utilization and spend), referrals, automated job descriptions, and much, much more.

The engineering team is able to achieve this through tight and thorough collaboration with other stakeholders across the company — customer success, sales, marketing — as we continue to gather feedback from them and our customers and prioritize against our vision of making recruiting better together.

What I hope for

When I joined Dover, I was given the tools and visibility I needed to succeed as a founding engineer. I am grateful for that every day.

My goal is to continue to cultivate that environment for my teammates. I want to give them the resources and opportunities they need to be the early employees, leaders, or founders that they strive to be at Dover and beyond.

Given what we’ve built, the values we instill in ourselves and each other as a team, and the ambitious road we’re forging ahead on, I’m confident we can get there.

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