Never Take No For An Answer: How Aspire’s Head of Startup Experience Is Empowering Startups in SEA

Written by
Content Team
Last Modified on
March 28, 2024

Yan Kessler, Aspire’s Head of Startup Experience, is a tireless leader who is as relentless as he is energetic一key traits for a role that supercharges startups to reach their full potential. Prior to joining Aspire, Yan spent years working with the region’s largest insurance companies where he launched several ventures and led sales functions in countries such as Thailand, Indonesia and Vietnam.

His adeptness in sales, however, did not happen overnight.

He got his start in regional sales when he caught the attention of a high-level insurance MNC executive who saw him working alone in the office on Christmas and the rest was history. His unparalleled work ethic and hunger to hit ambitious targets continues to this day as he now heads both Sales and Business and Development (BD) at Aspire. 

Fun fact: As Aspire’s first sole salesperson at the time, he would make continuous calls with a wide range of customers to gain valuable on-the-ground user insights.

In this interview, we caught up with Yan to find out how he juggles being a new dad with his demanding schedule, why he doesn’t believe in the sales adage “always be closing” and what are some of the most inspiring startups he has worked with over the years.

Can you briefly share your background prior to joining Aspire?

I started working in sales and BD in the US for a beverage company for almost a year and went back to Europe where I did my MBA. That was how I started working for an insurance company. After 2 or 3 years in the insurance company, I finished my MBA and wanted to grow within the business but I didn’t really have any opportunity within the business to go abroad. 

One day, I was still working in the office on Christmas day. One of the bosses at Allianz who was visiting saw me and asked, “What are you still doing at 4 in the office?” I explained to him that I’m driven and I need to close more business before the end of the year. He said, “Just share with me your CV. Tell me what you want to do. If you are bored, I will get you a job”. 

Within 2 weeks, I was sent abroad by an insurance company to launch their new venture in Thailand. I built this for 2 years and then I duplicated the model in Indonesia where I’ve done a joint venture with one of the biggest insurance companies in Indonesia. I pretty much did the same in Vietnam and Myanmar.

It seems like you’ve been all over Southeast Asia! 

To give you an idea of how extensively I traveled, I had a passport which was called a high travel passport一it is a fifty page passport. I was changing my passport every 14 to 15 months because it was just full. I was travelling every single week to at least one country. After 4 to 5 years, I got super tired of it. My wife as well. 

What about the startup culture appealed to you the most?

I would say it’s the ability to do whatever you want. This was what I was doing before as well because I was sent from the UK to Thailand where I was the first employee where I was able to do pretty much what I wanted and I really liked that. 

But for a startup, I was really looking for high-scale growth. In my previous role, we went from zero to one which was like a steady growth一like 5% to 10% per month which is not bad. I wanted an environment where we can grow from 15% to 20% to 50% month on month and work with younger people. Compared to my previous industry, a lot of new guys in startups are very young and come from top universities一you can really be challenged on a daily basis. 

The key word here seems to be “pumped”. Is that a key quality you look for in your sales team?

Definitely! I manage two teams一the BD and Sales team. The BD team is responsible for finding new leads. The Sales team needs to negotiate and close those leads. It is a completely different type of skill set. In terms of BD, they really need to be pumped because for those guys, they come in in the morning and everyday they call and hit like 300 random people to try to convince them to have a meeting with them. To be able to do that, they need to be really pumped, energetic and never take no for an answer. 

Compared to the Sales guys, they need to be listeners. I will always tell them that “you have two ears and one mouth” so you need to listen way more than what you talk. And if you’re able to do that and ask the right questions, I think you would excel. 

What does a typical day in your role look like? Any go-to coffee/ Spotify playlist to get you through the day?

Mornings for me are super hectic. As a new dad, I would wake up at 5am every day to take care of my daughter. Then, I usually start work at around 8:30 to 9 when I can. 

First thing I do is I look at numbers. I would then prioritize my day. I’m a big fan of post-its so I would write what I need to get done by the end of the day. 

I look at my emails once a day because the rest of the time, I would block my day to conduct weekly training for the Sales and BD team, attend meetings with various teams and be on back-to-back client calls.

How was the experience like being the first sales person on the team and conducting the training?

When I first joined the lending team as the Head of Regional Sales, I was conducting the weekly and biweekly training on how to sell, how to create a pitch, and how to generate renewals一 basically how to train anyone about any sales or BD techniques.

When I transitioned to Head of Startup Experience, the first thing I did was look at more than 500 clients who have not made a deposit yet and in two weeks, I’ve called every single client. I was doing back-to-back calls per day just to get an understanding on who our client is, why they are not making a deposit, and how we can improve. To really get a solid understanding of why people were not using our account. That has helped me a lot to get full ground visibility of what’s going on. 

The job that most of the guys don’t want to do, I’ve done it myself so that helps me a lot in terms of training. When a new joiner comes in, there’s a sales or commercial package where they go through all the decks. Thanks to Wingman, they have some recorded videos that they need to look at and then every day for two weeks, there’s a call that’s been set up with them and they have to pitch in front of the sales guy. This roleplay exercise makes sure that they can answer any question and we can really see that they are using the right pitch. 

On top of that, I am doing bi-weekly training with the team on different sales techniques where I share a lot of articles, podcasts and books about how to improve your BD technique, how to pitch on LinkedIn and so on. ‘

In your years as Head of Startup Experience, what’s the greatest thing about your job?

Closing business. I’m super pumped to hit targets. I think it’s the greatest thing you can have, especially when your team is performing and hitting their targets. That’s the highlight. It means, team-wise, you’ve done a great job. 

Which startups have inspired you the most? Why do you think they stand out?

I’m a big fan of startups who are useful and create value. One of them is H3 Dynamics, which makes hydrogen drones with the goal of creating hydrogen planes. I think this is interesting as it’s a whole new market and something that is needed. 

There is a startup in Thailand that I like called Yindii. Think Foodpanda but for food waste. For example, if hotels still have food, they will sell it at a very high discount or for free for people who are on the streets and don’t have enough to eat. For a startup like this, they did quite well during the pandemic. 

Ula in Indonesia is also an inspiring startup一they are an e-commerce platform that helps small business owners get working cash and inventory.

In your opinion, how does Aspire empower startups?

In a number of ways. First, we make it easy for them to manage all their finances using one platform. There’s the early stage and growth stage type of clients. For the early stage, it’s a no-brainer for the founders as they can really do everything using one platform. Everything is transparent and upfront and it’s 100% digital. 

For them, they don’t have time to focus on how to manage their finances. They need an easy and trustable solution to manage the entire financial needs which is what we provide一including the kickstart plan that help companies to incorporate in Singapore. In the growth stage, it’s mostly about products that we have that’s unique. 

One of them is the expense management solution that helps growing startups to manage their entire expenses using one platform and everything is directly synced to one platform. In terms of reconciliation, it’s saving them a lot of time. So some of the CFOs tell us that they’ve been saving over 4 hours per month by using our platform.

In a sales team, rejections are part and parcel of the job. What are some effective ways to ensure your team remains motivated? 

I think just to learn something from every single call that you have. What’s great about Aspire is we get to talk to companies that we don’t know about and would love to know about. In every call, I’m trying to be as curious as possible to understand the market. If I’m able to understand the market, I’m more willing to help them out一either through us or through referrals. This is really what I’m trying to teach the team. Not every sale needs to be a win. 

There used to be this saying called “ABC: Always Be Closing”. This is something that I hate because I prefer to focus on the sales that matter instead of closing every single sale. To keep the team motivated, I always try to teach them something new and remind them “in every call you need to learn something and add value to the client”. If the objective of the call is just to close, it is going to be a nightmare. If your objective is to actually learn something about the client, his industry and even his story, then it’s amazing. 

Currently you’re rapidly scaling your team. What does it take to be an Aspire sales professional? What are the key qualities/skills you look out for?

I think it’s great because we’re really talking to a wide range of diverse clients一not only the ones that are based in Singapore. The highest quality that I'm looking at is curiosity, coachability and prior success. If you have someone who is not a super strong sales person yet, but if he is willing to learn and is exceptionally curious, you don’t need to sell. You just need to ask the right questions. The person in front of you will tell you all their pain points. 

How do you destress after a long day? Any interests/hobbies outside of work?

Prior to my baby and now it’s different [laughs]. Just having my daughter in my arms helps me destress. I’m also a super sporty guy. I used to do 6-7 activities per week before my daughter一 which is not the case anymore.

I’m also super interested in people. I love to read books people would usually find boring like how the brain works, how different cultures work, how to manipulate people. These kinds of things usually link to your brain and how you decide to make choices in your life. Besides reading, I listen to podcasts when I can, which is whenever I have my baby in my arms and need to walk her around. 

It’s interesting that you mention books. What’s a book every salesperson should read?

For me, one of the best books in terms of sales is called Never Split The Difference by Chris Voss. He used to be the head negotiator at the CIA. He explains different selling and negotiation techniques that really work in everyday life. It’s also a book that is easy to read, especially for non sales people. Usually, sales books are quite boring but he explains the story of his life with cool examples. It’s definitely a book I’ll recommend everyone in my team to read because I’ve learned a lot and I think everyone can learn from it, even those outside of sales. It gives very simple sales techniques that helps you to do everything一even how to negotiate your salary. 

If you weren’t Head of Startup Experience, what would you rather do instead?

I am convinced that I’m in this world to make a great impact in people’s lives. When I was doing insurance and even now at Aspire, I would tell myself this. We are helping entrepreneurs to do things that would not be possible a few years back because startups did not exist. 

If I’m no longer at Aspire, I would work in an NGO and try to create an impact in this world as I am really passionate about people. 

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