Ashley Mai, Enterprise Customer Success Manager at Parkable

A cocktail waitress from Houston who wound up working in Customer Success for a really cool New Zealand tech company. Recently we caught up with Ashley Mai, Customer Success Manager at Parkable, to learn more about her journey into working in tech. Ashley shares some deeper insight into her career path into Customer Success, some of the common misconceptions as well as why she loves working at Parkable. Thanks for sharing your story, Ashley.

Firstly, how would you explain to a five year old what it is you do?

I have a big group of friends. It’s my job to get them excited, help them through their challenges and guide them to success, kind of like a coach!

And for the adults, what does that translate to in regards to your day-to-day?

Everyday looks different in a tech start-up world. A lot of communication and liaising happens for me throughout the day as I represent both our company and all of our enterprise customers.

Depending on the day, my tasks include project management, implementing success programs for new customers, creating reports to present to executives, troubleshooting, software training, relationship sales and feeding our development team information on how customers are using the software so they can strategize ways on how to enhance the product.

Sometimes I’m outside in the parking lot with our field team installing hardware. A lot of ‘uh oh’ and ‘how do we fix that?!’ is also said a lot in my day to day.

What are some of the common misconceptions about working in Customer Success?

Some people think customer success and customer support are the same thing.

Although customer success managers and customer support managers compliment each other, customer success is a wider discipline as it strongly leans towards proactive, rather than reactive.

CSM’s deal with things including change-management onboarding, tracking engagement to accelerate product adoption, delivering metrics that are important to our customers, and ensuring their goals stay aligned with the product ongoing.

It requires clear product knowledge for the purpose of driving customers to achieve the best ROI results throughout the partnership and unlock more opportunities for the business to scale.

Tell us a little bit more about your career journey and ultimately about how you ended up working at Parkable?

I got my degree at University of Houston, where I was born and raised. During my internships and going to college, I was also juggling two other jobs as a cocktail waitress and a bartender all around Houston.

Before that, I was a manager at a fast-food restaurant chain, and before that, I helped my parents at both of their restaurants during my teenage years. My extensive background in hospitality helped me land a job with Uber Eats.

I visited Seattle after graduating, where we met a friend named Remo. He took us around his office at Amazon, and it validated my curiosity to work in tech.

Not because of the ridiculous amenities, but because I felt overwhelmingly inspired to be present and in the same space where people worked hard to change the world. Everything about the office was futuristic.

I wanted to be part of something like that. I wanted to work closely with pioneers and the game changers and learn from them.

I saw Uber Eats was advertising a sales role in Houston afterwards and I submitted my CV. I got a call from a San Francisco area code during my shift that night and sprinted to the bathroom to take the interview.

Toilets were flushing and the loud hand dryers were going off during the call. It was a strange experience, but I nailed the initial interview and we had a good laugh about it afterwards.

About two months later, I landed third on the global sales leaderboard at Uber. I think at this stage, we were in about fifty cities by then, so business was scaling super fast.

I met a cool chick from the Chicago team on a Zoom meeting, where she asked if I wanted to spontaneously move to New Zealand with her as she heard Eats was launching soon.

We landed a meeting with the NZ team and pitched them. Soon after, I purchased a one-way ticket and I was gone.

After launching thirteen areas in two different countries, my time with Uber came to an end, as the New Zealand office was absorbed by the Sydney office.

I found another opportunity right after at Sharedspace, a Kiwi platform that connects people to spaces and worked there for several months with a small team. Things didn’t work out as they didn’t have the capacity to keep me and support my visa.

It had been four months since I’d been out of a job as I wasn’t allowed to work unless a company sponsored me.

It’s risky for a company to hire an expat, and it’s heaps of admin as they have to prove that no other citizen is qualified to fill the role.

After about sixty interviews, and hearing a million no’s, I thought my time in NZ was over and my (already extended) visa was running out of time.

On the very brink of my decision of packing my bags, Parkable found my LinkedIn and called me. I had a chat with their recruiter and she got me a meeting with the CEO later that week.

After meeting with the executive team, they offered me an opportunity I was hoping for as it was everything I wanted to be a part of - tech, the sharing economy, working with a small team/start-up!

I think I gave a good squeal on the phone when they called me with their answer. No shame.

I’ve been with Parkable for over a year now and absolutely loving it! We have an awesome team and I feel very lucky to be surrounded by a group of amazing people.

Can you share some more insight into what that transition was like?

When I was in Houston working for Uber, it was such early days that our office didn’t even have monitors or stationary. You were given a laptop and that was it. I was trained by one of the very first sales reps on the original San Francisco team and learned a lot from him.

We had three days of real training and then you were thrown in the deep end, so it was up to you to close, close, close. Those who didn’t make it got cut, sad to say, so the role was super competitive, but the incentives were worth it.

I loved working with the Houston team, we all were so passionate about food - there was a heated debate about the new trending food item, restaurant, or bar almost everyday.

When I moved to NZ, I didn’t know what to expect. I only (barely) knew one person. I didn’t understand people’s accents.

I knew I wasn’t crazy for hearing the word ‘jandals’ instead of wearing ‘sandals’. Kiwis are some of the nicest people I’ve ever met. The vibe here is a lot more chill, and a ‘no worries’ type of mentality.

The people on the Uber team in Australia and New Zealand were so friendly, it felt like I knew them for years.

We all meshed so well, and they became my best friends. We had catered lunches everyday and you can tell that Uber Eats was growing out of it’s start-up infancy stages.

We had more processes put in place, we found better ways of doing things, but still had all the freedom to try, learn, succeed and fail as the sky was the limit. That’s one thing I loved about working there.

You had all the resources, and if you found a process that you can prove works, you can playbook it and share it amongst other Uber employees around the globe.

What is it specifically that you like about working Parkable relative to your past jobs?

100% the culture. It’s so important to find a group of people who share the same values, goals, interests, who are like-minded.

It’s hard finding a good team, let alone finding a great boss to drive the boat, whilst the rest of the team are helping to make the boat go faster.

I think culture is vital to any company, especially in a start-up world because things move fast and if you don’t set those missions and values at the early start, you lose perception of the end goal and the ultimate WHY.

CV’s can be quite lifeless. Have you done anything unique in the past to get the attention of an employer or seen others that have been creative in this regard?

I saw that one of the most popular advertising agencies in Houston was looking for an intern. I knew it was going to be competitive, so I started doing more research on the company.

I sent them an email, which was basically my entire cover letter, convincing them on why they should hire me through GIFs. There were about ten GIFs in the email I think. Attached to that email was my CV.

About ten minutes later, the CEO replied back and asked his EA to try and get me into the office the next week.

Parkable continues to evolve. What kind of candidates do you think Parkable is looking for in terms of experience, attitude and character?

Someone who can think on their feet, and someone who isn’t scared to try new things outside of their role. A great leader who is coachable, someone who is always down to help others, and most importantly, knows how to have fun!