C-suite career advice: Randall Ward, Appfire

How important are specific certifications? “We look to hire those with strong character and hands-on experience. That real experience wins over education, because we can teach certifications, but we can’t teach character and resilience.”

Headshot of Randall Ward, CEO & Co-founder at Appfire

Name: Randall Ward

Company: Appfire

Job Title: CEO and Co-Founder

Location: Burlington, Massachusetts

Randall Ward is Co-Founder and CEO of Appfire. He has spent the past 25 years building and scaling software companies, from early-stage through IPO and acquisition. He helped architect MIT’s OpenCourseWare platform and held a technology advisory role for LFM/SDM, one of MIT Sloan School of Management’s most prestigious programs. Ward is an investor and advisor to emerging enterprise software companies, and he is actively involved with investments in virtual workspaces, AI advancements in healthcare, and software automation. 

What was the most valuable piece of career advice that you received? There have been a few big pieces of advice that I often reflect on as my career progresses. Ken Olsen, the CEO of Digital Equipment Corporation, once said that ‘if you ever have an opportunity to build a great business and scale worldwide, make it matter and leave an impact.’ This sentiment has stuck with me in my career. It’s a key driver behind Appfire joining Pledge 1% in 2015 and giving one percent of product, profit, equity, and employee time to support global communities. I’ve also been told to sleep on big decisions before diving in and seeing them through, especially if it’s a major pivot that could impact long-term viability. I’ve never regretted following that advice. 

What was the worst piece of business advice that you received? One piece of bad advice stands out to me. A former advisor once said that I should pick the quicker route to exit and cash in the business, rather than put the best interest of the customer and team at centre. Looking at what we’ve accomplished on this route, I’m glad we didn’t follow that advice.

What advice would you give to someone starting their career in IT/tech? It’s vital that people new to IT/tech spend more time listening and absorbing and learning than they do showing off their newly acquired skill sets. Experience counts for a lot, and rapidly acquired capabilities will rarely (if ever) make up for the value of someone with experience. Listen. Learn. And then contribute. 

Also, for those who are launching a new business, a partner can go a long way. It’s so important to make sure you’re in complete alignment with them when it comes to character and values.  

Identifying strong mentorship is key, too, and I still connect with several of these people today. I’ve found that I make better decisions with the benefit of their counsel. Selecting a mentor is all about being brave enough to ask. Don’t take one no as a no from everyone. Likemindedness will ultimately help new tech professionals find that attraction, so it’s helpful to join more tight-knit, specialised communities or participate in a local ‘lean coffee.’

Did you always want to work in IT/tech? I was around enterprise computers at the age most kids had their first TRS-80. I wrote my first bulletin board software at 15 and it's still being used as critical State Government infrastructure today. I’ve always wanted to work with my hands and help people. Being in close proximity to software and hardware platforms at such an early age was a springboard into IT and I feel fortunate that I get to wake up and do that every day.

What was your first job in IT/tech? My first tech job was working for the government straight out of university. Specifically, I worked at a military installation in the middle of the desert. Military work as a civilian was not the best career path for me, and not nearly as fun as a G.I. Joe cartoon, but I did work with pretty advanced technology, which made for epic stories at the bar. That role taught me the importance of persistence, and I learned that I’m not always right.

What are some common misconceptions about working in IT/tech? One common misconception is that you must follow a managerial track up the ladder to grow your skills and advance your career. In fact, it can be every bit as rewarding to operate as an individual contributor.

What tips would you give to someone aiming for a c-level position? I’d first remind them that c-level activities can be less rewarding than the work they’ve done in the past. We don’t operate the day-to-day activities from the c-suite. Instead, by the time you’ve reached this level, you’re moving farther away from daily business operations to focus on more strategic priorities and vision planning. You can give directions, but your teams are the ones taking action.

A good c-level contributor creates clear paths of communication across teams and identifies focused workstreams that achieve corporate goals.

What are your career ambitions and have you reached them yet? My biggest career ambition is to make sure Appfire leaves a positive impact on the world and a template for other businesses to follow. While we’ve taken giant steps towards this goal, for example with the Pledge 1% initiative, we have some work yet to do. I wake up each day just as excited as the day before, even with (or especially because of) the challenges ahead.

Do you have a good work life balance in your current role? I do. Leaning back to mentorship, I have three former CEO mentors with whom I’m very close, and they’ve all given me great advice in this area: In addition to healthy boundaries, it’s important to set good expectations at home to communicate the peaks and valleys of your work schedule and responsibilities. It can also be helpful to build litmus tests so we can identify if we’re giving too much to work and not enough to life. I like to set a limit on the number of days I’ll travel for business. I also restrict where I keep work technology in my house. The home office is where work happens, and I don’t allow it to take place anywhere else. Slack is the only work app I allow on my phone. The key is to be disciplined about those boundaries.

What, if anything, would you change about the route your career path has taken? I would have spent more time studying the business models of previous companies I’ve worked for. I’ve worked under CEOs that have made impressive transformational changes to those organisations. There would have been so much to learn had I spent more time thinking about the business, rather than solely focusing on the products I was creating. I’ve come to realise the inner workings of the business itself are more fascinating than the tactical work.

Which would you recommend: A coding bootcamp or a computer science degree? Either path can bring you to success. If you need to learn how to learn, then a university education can be incredibly valuable. If you already know how to learn, then a coding bootcamp will go a long way towards a successful tech career.

How important are specific certifications? I’m a strong believer in building blocks. It’s a common misconception that to be successful in tech you need the best certifications outright, but I disagree. We look to hire those with strong character and hands-on experience. That real experience wins over education, because we can teach certifications, but we can’t teach character and resilience.

What are the three skills or abilities you look for in prospective candidates? I always like to see practical experience from prospective candidates, where they’ve already built a customer-centric product at some point in their career. I also want them to be able to walk me through their history — what brought them to where they are today? I want to hear about the hard decisions and challenges they’ve faced. Are they willing to be vulnerable and go into detail about those challenges, or will they shy away? What they are passionate about outside of work is also nearly as important to me as their priorities at work. I like to hear about past volunteer experience because it helps me see their passions and interests more clearly.

What would put you off a candidate? I always want to meet candidates who have done their homework. If I meet someone who does not understand our business, that may put me off. Great candidates come with a positive attitude, and I also want them to come with questions and excitement about Appfire. Hearing their likes and dislikes about their last job can show their character in how they talk about their previous role. How did they view their experience, and what did they learn from their challenges? 

What are the most common mistakes made by candidates in an interview? How can those mistakes be avoided? When I’m speaking with a candidate, I like to ask for their life story from birth to now. If they skim over the details and skip to career talking points, I’ll want them to slow it down. It’s important for me to look for candidates that have an integrated life: they care about their family and friends, and participate in volunteer work – this is where character is formed.

Do you think it is better to have technical or business skills – or a mix of both? A mix of both technical and business skills is better nowadays. You can’t be a leader in technology without understanding key aspects of how such technologies impact business, especially as AI changes and elevates more technical job functions. Great technology professionals will be able to put their unique skill sets to use as technology continues to progress and impact the way we work.