What a year of B2B sales taught me as a bootstrapped founder

My co-founder and I have been running our SaaS for quite a while now. While there are things that are fundamentally the same from day 1, we did a lot of pivots, especially when we started looking for and getting to know our potential clients. I’d like to share with y’all what we learned in our first year of doing sales.

1. Develop close relationships with clients

This might sound obvious, but hear me out. There are many profitable startups in the low-end B2B space, but they’re very hard to pull off and cost a lot of money. We decided to make the switch to a high-touch process, and from our experience, this switch made it easier to build strong relationships with our customers. We did video calls, sent personalized emails, and even built tailored versions of our product. As a result, our customers got to know us and felt our commitment to the company. We also got to charge more per customer lol.

This approach can quickly spiral into what some people call the “agency trap”, where you can lose focus and build a series of super-customized solutions that you eventually just bill people by the hour instead. I personally think it’s not that bad, but just keep this in mind.

2. Finding the right ICP 

Doing cold outreach to individuals would need a lot of effort and time, so I had to be picky about which type of people I chose to invest my time in. In order to find my ICP, I had established the following criteria:

• Who would benefit from our service?

• Do they have a high willingness to pay?

• Are they realistically open to becoming our customer?

It took lots of iteration cycles and testing unpaid clients for us to find out who’s a good customer. We still run small-scale experiments even to this day to continuously improve our product-market fit. One tip I would recommend is to iterate your offer. Try to be as generous as you can, especially when you’re just starting out. 

3. How to get leads

I found cold emails to be great for B2B because:

• It’s highly scalable

• It’s a fairly “democratic” form of outreach

• There’s no platform risk

People’s inboxes are saturated, but I found that I have better reply rates when I reach out to people who already show intent. Finding these people is fairly easy on LinkedIn. LinkedIn also has a high level of trust, so people are much more receptive. Just put yourself out there, and you’ll be able to at least find a few potential customers to talk with and refine your offering.

4. How to do calls

At first, the idea of calls made me nervous. Over time, I realized the best way for me to connect with my prospects is just to be real, talking knowledgeably and honestly about my product. 

Ask questions! One trick I do whenever I have a call with someone new is that I ask the prospect about their business, industry, and ICP. It’s quite interesting to talk with so many different entrepreneurially-minded people from all kinds of verticals.

Use an online calendar where people can book calls at pre-approved slots (e.g Calendly). This removes a lot of back-and-forth to find a date that works. I also tried AI transcription tools, but they never really worked for me, so now I just use an A4 paper and jot down some notes. After the call, I enter the data manually on our sales CRM. 

5. Sales is a real-world feedback loop.

Over the last few months, I’ve developed quite a thick skin and learned to see rejection just as a data point and not take it personally. What motivates me the most to keep doing sales is that I’ve come to appreciate how powerful it is to get direct feedback from the market through personal interaction. This is the fastest business optimization loop that I know of. Just talking with people and trying to solve their problems so they give you money.

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PS: I started moving over to X/Twitter. I'll post more there in the future. Feel free to follow along if you're curious about me building in public.

https://x.com/Matt___Bauer