Get to know: Will Conway, CEO of Pathwire

On the lighter side of things we ask Will Conway, CEO of Pathwire, about what makes him tick.

What would you describe as your most memorable achievement?

The most memorable achievement in my career so far was when the original staff of 25 Mailgun employees got a check when we sold the majority of the stake of the company to Thoma Bravo. After years of hard work to get the company off the ground, it was nice to be able to reward the team responsible for our success so far.

What first made you think of a career in technology?

I had always wanted to go to law school, but I worked at a small business intelligence company in college so tech was on my radar. Following college when I was looking for opportunities to stay in the San Antonio area, Rackspace kept popping up. At the time, Josh Odom, who would later become the CTO of Pathwire, was a good friend of mine and kept talking about the cloud and what he was doing there. Even once I entered tech, I always had the intention of going back to law school. After a while though, tech proved to be a lot more exciting and engaging than what a career in law would have provided me with.

What style of management philosophy do you employ with your current position?

Hire great people, get out of their way. We need true specialists who can scale and people who are fantastic at reinventing themselves. Josh and I used to be involved in everything, but as we grew, it became impossible. A few years ago, we realized we were only able to experience so much success because of the strong team we had.

One of our core values is ownership – team members must care too much to let things fail. This does not mean no one is allowed to make an error. In the event mistakes are made, we close the feedback loop and people become more autonomous over time.

What do you think is the current hot technology talking point?

To me, right now, the hottest technology talking point is the transition from Web-based marketing due to increasing privacy regulations such as GDPR, CCPA and the new Virginia Consumer Data Privacy Act (CDPA).

Organizations are finding it harder to chase the customer now than they have in the past.

Luckily, email is still the number one used communication and has one of the highest levels of ROI. Email has never been owned by anyone – it has always been regulated by a third party. Despite the fact that the advertising components of email are relatively new, email service providers are still ultimately in charge of handling compliance regulations. Because email is established, there is more opportunity for organizations to chase the customer. Every point of engagement is an opportunity to ‘wow’ the customer.

How do you deal with stress and unwind outside the office?

Anytime I am not spending time with my work family, I am spending time with my real family. Brazilian Jiu Jitzu also helps me forget about the stresses of work. After all, it’s hard to worry about your company when you are worrying about being choked and rolling around on the mat. I also try to read a lot whenever I can.

If you could go back and change one career decision what would it be?

I do not have a lot of regrets when it comes to my career. The only one that I can identify is I might not have waited as long as I did to get into entrepreneurship. A lot of my career was spent in sales, and I learned a lot in the process of building out significant sales teams. As a salesperson, you get used to putting it all on the line, month after month, quarter after quarter, to deliver results.

Entrepreneurship lifestyle isn’t that different — if you can find the right people to build your team with. One reason for the success of Pathwire was that we learned how to give hard problems to smart people who are humble enough to bring them back for inspection or outside eyes. This has allowed us to ‘divide and conquer’ while still ensuring speed doesn’t come at the expense of feedback. One person really doesn’t need to know all the things about all the things; you need to play people to their strengths and apply the feedback loop. It is probably the only way I would have gotten here.

What do you currently identify as the major areas of investment in your industry?

For Pathwire specifically, we are heavily focused on investing in the best-of-breed technologies for every stage of the lifecycle of email. We have found that it’s a lot more difficult to get an increase in ROI when we only use one mechanism. An organization’s email capabilities affects everyone on the team – from the sysadmins in charge of incorporating the API to trigger emails like password resets to simple notifications, to marketers in charge of capturing email addresses, building the templates and crafting the campaigns. Once you send the message, companies are lacking the insight into whether their messages are hitting the right folder in the inbox or delivered when they’ll be most likely to receive engagement. It’s crucial for businesses to not only be in control of email open and engagement rates, but every major point of conversion in the email’s life cycle, which is something you only find at Pathwire.

What are the region-specific challenges when implementing new technologies in North America?

When implementing new technologies in North America, you have to keep in mind compliance laws within the varying states and across the globe. GDPR, CCPA and now the CDPA present a bit of a conundrum for companies. Even if you are not operating out of the specific region, your customers might be, which presents some challenges.

For companies just starting out, scaling systems can be a double-edged sword. Leaders have to know when to make the points of evolution and not simply invest in go-to-market strategies. Understand the balance of when it is okay to use industry standard solutions to grow your business, or if it is time to bring in a third-party vendor such as Salesforce to take you to the next level. This can be a challenge because if you wait too long, you can stunt your growth. If you invest too early, you are taking on more of an expense.

What changes to your job role have you seen in the last year and how do you see these developing in the next 12 months?

At the beginning of COVID-19, there was a lot of information flying around on what was and was not okay with operating during the pandemic. One of my biggest challenges was cutting through the noise to create a feeling of solidarity within the company. After all, we were all going through this journey together. Once everyone grasped the reality of the virus, the biggest challenge was just feeling like we could communicate effectively without our traditional office visits, but by moving things to a purely remote format, everyone in every office was on the same level, and we implemented a weekly townhall that really brought us together.

On an operational front, the pandemic allowed myself and the other leaders in the company the opportunity to see how amazing our employees perform despite not having a normal office structure. The entire experience turned out to be validating. For an overwhelming amount of people, they do better when they are given the space. For those who have struggled with remote work, we were able to help identify areas of weakness and coach them.

Looking ahead, we have learned the importance of each team member having clear goals and providing them with the tools they need to thrive. Whether that be not asking everyone to go back to an office setting or identifying the people who need an extra boost to reach leadership, the next 12 months will be focused on continuing to evolve and learn from our circumstances, so regardless of what the next 12 months brings it will only make us more resilient.

What advice would you offer somebody aspiring to obtain a C-level position in your industry?

Don’t be afraid to take some risks. In order to climb the ladder, you have to go all in on your skillset and be comfortable with evolving yourself. Evaluate what you can bring to the table to decide whether you should aim to obtain a C-level position within an existing company or start your own, because they are two completely different skill sets.

There are people who are excellent at growing within a company, but that didn’t feel like the right fit for me. I knew that I had to take the big risk and break out on my own. Luckily, I deposited myself at the right place, at the right time, with the right people and became comfortable learning new things on the fly. Anyone who has that appetite – starting your own business will be the most satisfying way to do it. It will cost a lot, so make sure it’s something not just you, but the people around you, are willing to pay. If so, find the smartest people you know and start the process of failing forward until it works. If you choose the other route and decide to work within an existing company, learn your speciality and run with it.