Whether he’s building the latest and greatest version of Adlib or biking a grueling mountain trail, Peter Duff has a dogged determination to “keep on pedaling.” At just 15 years old, he built a user interface designed to simplify DOS for the layperson, and his career in technology didn’t stop there. With no well-worn path guiding the way, he cofounded Adlib Software and built it into the thriving organization that it is today.

I sat down with Peter to chat business, leadership, and how he went from a maxed-out entrepreneur to the leader of a thriving software company.

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How did your childhood shape you into the leader you are today?

I’ve always had an entrepreneurial streak. I had a paper route as a kid, and I ran my own grass-cutting operation too. As a teen, I started to think more seriously about launching my own business. I always loved writing code. When we were in the early days of personal computing—when I was about 15—I built a user interface that people could operate instead of DOS command prompts. The business didn’t go far, but the seed was planted.

Can you tell us about the early days of Adlib?

A business partner and I had a small software consultancy for several years and found ourselves out of work. To drum up new business, I went through the phone book and started calling local software consulting companies to see who was looking for outsourced development work. This is a great story, actually. Scott Mackey’s father ended up hiring us to pitch a Visual Basic job when we hadn’t even seen the language. As scrappy 20-somethings, we learned the program literally overnight and ended up helping them win the business.

A year later, our two firms joined to become Adlib. We consulted for two years while building out our own software product in the proverbial basement and maxing out credit cards to do so. By 2001, we stopped consulting, commercialized our business, and focused solely on building content transformation software.

How has your vision for Adlib evolved since its inception?

The big picture was always to apply automation to processes involving documents, and we initially thought that would mean building end-user type software. The more we engaged with our early customers, the more we realized we needed to change our strategy. With highly regulated industries in mind, we incorporated more sophisticated functionalities into the existing software. Eventually we won over a handful of big pharma companies, and that helped turn the tide.

We’ve remained committed to solving business issues around unstructured content, but what Adlib may become over time is evolving. Even today, we believe our focus on automating content intelligence and contract analytics positions us to enter a market leveraging AI capabilities. Adapting to the constantly changing landscape is exciting for all of us.

In 2019, you stepped down as Adlib CEO to focus on a more product-centric role. What precipitated your decision? How has it been?

I’ve always enjoyed striking a balance between being able to engage with executives while also being able to talk to programmers about code. As CEO, I naturally spent more time on the former. As we redirected the product and organization to embrace AI, I found myself eager to drive the product forward. I have also spent a lot of time helping Adlib become a cloud and SaaS company. By prioritizing a very specific area within contract analytics, we could start to develop that expertise more deeply and build out the product. I couldn’t have had this impact on the software as CEO.

You mentioned Adlib’s focus on contract analytics. Why contract analytics, and why now?

Large corporations are saddled with trying to make sense of massive collections of documents. This is a heavy manual lift, and they often have to hire teams to fish through mountains of agreements by hand. Contracts in particular have the potential to cause problems when data can’t be discovered efficiently. This issue is pervasive across different verticals, and, since we already had so much relevant experience, we jumped at the chance to expand our offering to meet this need.

Contracts are particularly challenging, because there are nuances between each one, even those with very consistent themes. By making pertinent information accessible in an automated way, companies can concentrate on compliance and assess risk more efficiently.

What is your proudest accomplishment at Adlib?

I’m proudest of the people that have come through Adlib. By giving our employees a place to be creative and solve problems, we’ve fostered a dynamic culture that I’m honoured to be a part of. We also have some very loyal customers who have been with us for years, even decades. These enduring relationships, with our employees and clients, are grounded in trust and respect, which is why they work. I’m very proud of that.

Adlib has been recognized as a great place to work for the third year in a row. What makes a great company culture?

I think openness is at the heart of people loving to work here. When we hire new employees, we welcome them thoughtfully into the organization by sharing our vision for the future, our strategy for accomplishing our goals, and even the mistakes we’ve made. We also look for people who bring a unique set of experiences that perhaps we haven’t seen before. Openness also extends to sharing ideas and trying new ways of doing things. We want people to consider their roles at Adlib as far more than a job.

How do you maintain that rapport as the company gets larger?

As a start, I like to know everyone’s name and the names of their spouses and how many children they have. I genuinely care about our employees and make sure that’s evident in all my interactions with them, whether in meetings or chatting in the lunchroom. The close connection people have with each other pervades throughout the company, not just between them and me. I want people to feel like they’re part of a family, even as we grow.

How has the pandemic shifted your approach to business and life?

Before the pandemic, work life very much centered around our head office. When Covid-19 hit, we had to adapt to new ways of doing business. So, we did an experiment and had the entire organization work from home on a Friday. By Wednesday of the following week, we transitioned to a fully remote work environment. We modified our regular touchpoints from monthly town halls to weekly and shortened them up. We changed weekly team meetings in some instances to shorter, daily interactions.

We have a lot of empathy for what the team is going through. People are struggling with childcare, stress, and so much uncertainty. We’ve adopted flexible work hours to help ease the burden and have generally done everything we can to make people feel supported during these unprecedented times.

I heard you’re an avid mountain biker. What lessons have you learned from the trail that you can apply to business?

Great question. When riding long distance races that are particularly grueling, I remind myself that—despite how I may feel, and the challenges I must endure—I just need to keep moving. The same holds true having been in this business for nearly 20 years.

The other similarity is more conceptual. There’s an element of risk associated with mountain biking: One rides close to an edge or faces literal and physical obstacles. Rather than succumbing to fear, you need to relentlessly pursue your goal. Success in mountain biking, and in business, means being able to tolerate risk and not focusing on all the things that could go wrong.

Now more than ever, we can all take these lessons to heart. Thanks for taking the time, Peter.