I asked 8 founders how they found their first customers and hires and how they scaled

Jess Li
7 min readAug 26, 2020

I spoke with 8 founders across sectors and stages to get their tactical advice on finding your first customers and hires and scaling your product.

How did you get your first paying customers?

Like a friends and family round for fundraising, I suggest finding first clients from friends and/or former business partners. When you are just starting, your product sucks (mostly). You cannot go to the market and sell it like a great product with a product-market fit. Personal connections can support your first sales. One important thing — it should be true sale (even if it is discounted). Never give your product for free.

  • B2B company in the process automation space

Strong influencer push using AspireIQ to help manage the influencer process.

  • B2C company in the retail space

Referral!

  • B2B2C company in the HR tech space

Our first paying customers were friends & family. Even though your friends & family may not fall directly within your target demographic, any and all feedback in the early days is important.

  • B2C company in the wellness space

Cold email! It was handwritten and close to the heart — compelling enough for the reader to see it and want to act on it!

  • B2B company in the sales automation space

We invited people to give us feedback on our product and they ended up becoming paying customers.

  • B2B company in the HR tech space

Our first paying customer was actually an inbound opportunity. Within two days of our announcement, I had a request through our website from a producer. She had been using a legacy broker previously and was disappointed in the service and reached out after reading about us on a popular logistics publication.

  • B2B company in the logistics space

Seeing a massive market opportunity in the cannabis industry, I wanted to just meet people in the space to see where the highest leverage areas were to help from a scalability perspective. I had a friend who already operated in the industry, and I asked him to introduce me to his industry partners, so he said the best way to mutually benefit would be for me to be his delivery driver to distribute products to his buyers at dispensary stores. I did that and built up my network of folks in the industry, and quickly I was driving all over the state for him to deliver his wholesale products. He said that this was probably his biggest pain point since he couldn’t rely on traditional 3rd-party logistics companies to able to ship his products, and hiring unknown drivers created a lot of risk for the company (like product or cash theft). He said he had a few other friends who were interested in shipping products with me since I was already going to many of these dispensary stores, and we’ve grown as a company through word of mouth ever since — one brand at a time.

  • B2B company in the cannabis logistics space

What is the hardest role to hire for and how did you hire for it?

It is so hard to scale sales without a first sales manager. You can’t hire the best people from the market because you don’t have proven sales traction, product-market fit, etc. Also, you have to fill the sales manager with the founder’s energy. Without it, they can’t sell anything. We are still looking for the right candidate!

  • B2B company in the process automation space

COO. As a small team and a lean company, our COO is essentially a co-founder and has her hands on everything. She originally was hired as our head of social content. But after working with her for a year and a half, I learned how immensely capable she is and most importantly, how much she cares about the company we are building. At this stage having someone in the trenches with you, who genuinely cares about your company and believes in what you are building is the most important quality. So I promoted her internally, rather than hiring someone externally for the role.

  • B2C company in the retail space

In general, any position that the founders don’t have a lot of experience doing themselves. This is an area where you don’t know what you don’t know. Consequently, hiring a person for this role is hard.

  • B2B2C company in the HR tech space

We spent many months looking for the perfect person to lead our growth marketing team. For a role like Head of Growth in the Bay Area, AngelList is a very appropriate place to start. However, the best candidates tend to be people that we search out via personal & investor networks.

  • B2C company in the wellness space

Developers easily — they are hard to find and very expensive! But it’s a price you need to pay to build a strong team from the early days.

  • B2B company in the sales automation space

Engineers — in Sydney there is a talent shortage! We offer really great equity.

  • B2B company in the HR tech space

Product and Engineering are the most challenging but for different reasons. For product, we were looking for a Head of Product and had over eighty candidates but most didn’t have the right mixture of marketplace and enterprise SaaS experience. We ended up finding someone who was an inbound candidate from the west coast. For engineering, there are so many engineering jobs out there that finding qualified engineers to join the team can sometimes be a challenge. The benefit we have is that we had fortunately just raised a lot of capital while other companies are going through layoffs.

  • B2B company in the logistics space

The hardest role to hire for was Director of Engineering. In fact, we’ve hired a few over time, but we currently don’t have one. I’m currently acting as the Director of Engineering, in addition to performing my CEO roles and responsibilities. This has been a pretty good setup so long as you have a good PM who can manage the day-to-day feature spec and development process at least for our stage of company (Series A). Salaries and equity compensation combined can account for up to $500K per year if you want an engineering director who can scale with the business as not just an individual contributor, but also a manager.

  • B2B company in the cannabis logistics space

When did you know you had something to scale?

When you can close the deals every countable period (week/month) and your optimistic pipeline predictions are consistently met or exceeded!

  • B2B company in the process automation space

Partnerships with big box retailers. Our products’ lower pricetag means we need large volume in order to scale, and as a bootstrapped company, large wholesale accounts is the most efficient and feasible way to get that large volume. Landing a wholesale partnership with a mass retailer showed us we had something to scale, and it also gave us more insight into the why. While exploring a partnership with retailers, we learned from them that our products are the only viable solution on the market to help them achieve their goals of reducing fashion footwear’s eco-footprint. And it is not only viable, but would have a dramatic effect.

  • B2C company in the retail space

Our first customer paid us to solve their problem. We started seeing themes when talking to customers. Our MVP was terrible and customers were willing to pay us to use it and give us feedback on how to make it better. There was a moment we realized that we could automate a lot of the boring stuff. This improved the customer experience and also reduced the amount of time needed to help customers.

  • B2B2C company in the HR tech space

It was pretty clear to us from the beginning that the market opportunity for personalized supplements was massive. For us, scaling was and still is a measured, gradual process. We didn’t flip a switch one day and go into “scaling mode” — it was a process of constant iteration on the product, growth marketing, and listening to customers.

  • B2C company in the wellness space

Once we did hundreds, not dozens, of user interviews! When people say “it’s not for me but I am sure X type of company or person would love this” that’s a red flag. At the very least, it’s not a positive signal. You need to see overwhelming want for what you are building because at least some of those will convert!

  • B2B company in the sales automation space

When we started getting referrals.

  • B2B company in the HR tech space

I knew we had product-market fit before starting the company. I had done a legacy version of this business when working at another company in the space and knew there was a need for better technology and a better product. We’re building scalable technology that is enabling shippers to move hundreds of shipments per day without having to spend all the time they normally would if they went with a legacy solution.

  • B2B company in the logistics space

We knew that there was something to scale when we kept running out of warehouse storage space every other month for customers (i.e. suppliers) that needed help distributing products. The market was also booming as recreational legalization of cannabis had just passed legislation in California and there was a plethora of investor capital flooding into the industry. People were creating brands left and right, and at that point, we knew we had to raise money and build a stable software product to scale our distribution business, and ultimately make it as easy as possible for new brands to launch in the cannabis space.

  • B2B company in the cannabis logistics space

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