From IC to CEO: Software Engineer Career Development (Interview with Max Rudman, CEO at Prodly)

Level-up your software engineer career development through other professionals’ stories: meet Max Rudman, CEO of Prodly, who went from IC to CEO over the years and has even founded a startup of his own. 

He shares interesting details about his career development and gives valuable advice to people interested in a similar path. 

This episode was written based on episode 84 of the Level-up Engineering podcast hosted by Karolina Toth.

This post includes:

• Max’s career development 
• Entrepreneurship
• Founding a startup
• Becoming a CEO
• Skills for software engineering career development
• Hard skills
• Soft skills
• Choosing between different opportunities 
• Is being CEO for everyone?
• Advice for aspiring managers
• Advice for aspiring founders
• Challenges of CEOs
• Legacy aims
• Product
• Culture
• Bonus advice
• About Max

How did you decide to go from IC to C-level roles and founding your own company?

Catching the entrepreneurial bug at a startup

In my second job out of college, I caught the “entrepreneurial bug”. I was working at a startup and was among the first engineers on the team. I found it absolutely exhilarating to work on the product and to find the product market fit. Everything was moving really fast: if we had an idea on Monday, we’d build it by the end of the week. 

I enjoyed this setup a lot. It reinforced my belief that I’m born for startups. In fact, I have never worked for big companies other than the three years I spent at Salesforce following SteelBrick’s acquisition. 

As we grew at this startup, I ended up running an engineering team for the very first time. I had doubts about my managerial skills - I wasn’t sure how to lead ICs to be honest. But because I’ve been there since the beginning, I ended up taking on those responsibilities, so my career progressed sort of naturally. 

Becoming a founder

Later on, I was determined to start my own company - I founded SteelBrick in 2005. How I came up with the name is a funny story. Having an online presence was a key component even back then, and I wanted to make sure we picked a domain name that’s still available. 

Being the engineer that I am, I took a very scientific approach, and I made a spreadsheet: I had a bunch of adjectives in one column and nouns in another, and I wrote a macro that put together every possible combination of them. Then I just pasted these names into the domain name checker to see what’s available. 

YellowBrick came out of that, and then some of my friends who ran an ad agency suggested SteelBrick to emphasize our strong, flexible technology. It was also important to pick a name that’s not too specific, because I wasn’t sure what the company would focus on at that point. 

Becoming a CEO

I joined Salesforce for a while during SteelBrick’s acquisition. I enjoyed the time I spent there, and the culture was also great. However, I always knew this wasn’t my final stop. You have to know what you’re good at and what your passions are and choose accordingly. Salesforce was a great temporary stop, but I always knew that I thrive in startups. That’s how I arrived at Prodly.

What are some of the skills that were essential for you to be successful in this transition from engineer to founder?

Hard skills

Being confident about the technology behind what we do was really important. I think there are generally two types of founders: product-focused and business-focused ones. Personally, I came from the product side with an engineering background, which helped me accomplish a lot of things, especially at the beginning. For the first years of SteelBrick, I bootstrapped it - I didn’t have any outside investment, and we actually got to over a million dollars of AR and 150 customers. I was able to do that because I could code and build anything in my product.

Soft skills

I improved my communication, listening and networking skills over time. Focusing on mindsets like perseverance and resilience were also big parts of this journey. The entrepreneurial roller coaster is filled with highs and lows, so emotional resilience is a must - that way, you can handle any situation.

Get out of your comfort zone

Being a founder requires you to go outside of your comfort zone. For technical people, I think sales and networking can be challenging, but these are the go-to activities that you’ll have to take on in a leadership role. You’ll also have to learn about sales and marketing, because early on, you’ll do everything by yourself, without any outsourcing. 

Doing things on your own means putting in many long work hours, but it can also be very effective. Sometimes, the most efficient team is a team of one - not the most productive one, but the most efficient indeed. There is zero miscommunication, zero overhead, and everyone is on the same page. 

How did you decide what opportunities to take and what opportunities to turn down throughout your journey?

Both in entrepreneurship and product management, you have to say no to a lot more things than you say yes to. How to decide between a yes and a no boils down to what you’re focusing on: what kind of customers you’re serving or what problems you’re trying to solve. Based on this, you can differentiate between opportunities and see what would make your solution stand out in the market. At the beginning of the founding journey, your resources are usually very limited, so you’ll have to be very picky about what you say yes to.

In your opinion, could any software engineer become the CEO of a company?

First of all, I don’t think all engineers aspire to be founders, CEOs or even managers - many ICs stay away from climbing the managerial ladder and aim to become architects instead. If you look into your skills and goals, you might realize you don’t enjoy working through other people’s problems that much, and you’re much more excited about solving technical challenges. You can probably learn the soft skills attributed to being a manager or a founder if you set your mind to it, but I’d encourage everyone to really think about what their true calling is first.

What advice would you give to ICs who want to become managers?

Think about your motives first. If you want to earn more money, there are lots of ways to do that without becoming a manager. Establish which software engineer career ladder you want to climb. You’re probably going to do great in a managerial role if…

• You genuinely enjoy working with people and solving their problems, 
• You have great communication skills
• And you find joy in getting everybody on the same page. 

Then the first step would be getting some managerial training. Nowadays, there are lots of resources available - you don’t necessarily need to go to a seminar for that. There are online courses and you can also get a mentor who can guide you through your journey. 

What is your advice for people aiming to become founders?

As you become a founder, the challenges you had as a manager just compound - now you have to deal with all kinds of people from many different areas of expertise, not just a team of engineers. You’ll face many challenges, both technical and people-related ones. You’ll also have to establish a base level knowledge in many fields at the beginning, such as marketing, sales, finance and HR, so you can lead people in those functions - especially if you don’t have leaders in these areas appointed yet. 

What kind of challenges do you face these days as a more experienced CEO?

I think there’s always room for improvement. The bigger the company gets and the more people report to you, leadership gets exponentially harder. It has to be a constant, ongoing learning experience - you’ll have to keep up with more and more challenges as the business grows. 

I like to keep up by reading a lot. There’s always a subject I can study more about, and there’s endless content and advice on the Internet about anything - both good and bad. That’s the challenge currently: you have to separate what’s trustworthy and what isn’t. 

What kind of legacy do you hope to leave behind?

In terms of products

Our mission is to make business software faster and easier to deploy, implement and maintain. We hope that software becomes a lot easier to use and a more joyous and productive experience for people maintaining business applications.

In terms of culture

We’re building an open, transparent and high performing culture. I’m especially proud of the transparency we’ve established: just recently, I had an experience where people brought a problem to me that we could openly talk out on a call. I was very pleased that they felt safe enough to go above their immediate manager and voice their displeasure directly to the CEO. 

When establishing transparency, you have to lead by example. Actions speak louder than words in this case - you can preach transparency and candid feedback for years, but if you punish people for speaking openly, that tells a whole different story. 

Bonus advice for your software engineer career development

It’s not a given that you have to go and work for 10-20 years at a company before becoming a founder or CEO. I sort of dabbled in entrepreneurship when I was going through college. At the end of the day, the most important thing is having the drive, the energy and the qualities to become one - the latter, you can learn. So most of all, whatever your goal is, you’ve got to want it. That’s it.

About Max

Max received his computer science degree from the University of Puget Sound. He founded his first startup, SteelBrick in 2005, which was acquired by Salesforce. After spending three years at Salesforce upon the acquisition, he became CEO of Prodly, a software solution that also streamlines Salesforce processes. Outside of work, he enjoys traveling, cooking and spending time with his family. 

Follow Max’s work at Prodly’s website or connect with him via LinkedIn.