Tips for Founders Sales: Lessons From Starting Two B2B Startups

Thus far I’ve founded two bootstrapped B2B startups, and led sales on both. One is off to the races, profitable, and growing. We even hired a general manager so that I can free myself up to work on other projects. The other is slightly more nascent, and just barely at ramen profitability.

It’s really hard to get started with founder led selling. I’m a (slight) introvert, and had basically no sales experience before starting my first business. While I have a business mind, and an MBA in addition to my programming skills, it was still very challenging for me to get started.

I used to view sales as this dark art that I could never master. I’m not “salesy.” I’m much more of a steak than sizzle person. I’m too honest. I don’t look, talk or act like the various stereotypes of a sales person. And so, I thought it was basically unattainable for me to be successful with sales for the first year of my first business.

I’m proud to say that through a lot of struggle and learning, I’ve actually become a decent sales person. For whatever I lacked in initial extroversion and unblended confidence, I make up for in understanding of strategy and product. I’m even fairly confident I could hit quota for any post product/market fit b2b SaaS startup out there.

What I’ve learned about b2b founder sales

It’s been nearly five years now since I started the first business. As a result, I get introduced to other founders every month or two who are starting to sell their products and want advice. Coming out of these conversations, I find myself repeating the same themes.

So, in no particular order, here’s my advice when starting to do B2B sales at your startup:

Find a sales mentor who’s done pre-product/market fit selling before. It’s essential that someone has done the selling at the earliest stages of a company’s lifecycle. Even someone who led sales at a Series A company won’t have the proper mindset or experience to help you through this. Ideally, it’s another founder who’s been through it, and actually done the selling vs the strategy behind sales. Another bonus is if they’ve sold to the exact customer persona you’re trying to reach.
Network with account executives who sell into a similar persona. Ask them to walk you through their entire sales process, from initial outreach to demo. Give them your sales pitch, and listen to their feedback. You’ll get good practice demo’ing, and some advice. However, you should realize that most sales reps selling a post product/market fit product will have very little understanding of why someone buys their product, that’s really up to you to figure out.
Record your first 50 demos and listen to them each within 24 hours of the pitch. You will start to make small adjustments in messaging, in how long you answer questions, etc. Be your own coach and try to look objectively at your pitch.
Ask for demos for software you are thinking about buying. Think about what the sales reps do well, and what they don’t do well. Mainly do this because you will realize 90% of sales reps are pretty mediocre. They don’t show up on time. They ramble. They don’t do any research. They are too aggressive. You can be 10x better than they are as a sales person, even if you’ve never sold before. And, you’ll have to be to get started without a brand, and a product that is probably half complete.
Ask sales people you admire what books and blogs they read. My recommendations: FirstRound Review’s articles, this book on founding sales, and the Challenger Sale are good places to start. There is also a hilarious instagram account you will start empathizing with.
Spend as much time in person with your prospects as possible. That means demos, as well as conferences, dinners, coffee, whatever you can. This will allow you to build trust, and learn a lot faster about your customer than doing calls or even video calls. Working out of one of their offices side by side is a great way to hear how they talk, what they care about, etc. This is great for product development, and even better for sales.
Sales calls will probably become the most important way you will get feedback on your product in the next 6-18 months. Keep track of the themes you hear, and start to think about how you can build those into your offering / start charging for them. Record the closed/lost reasons for no-sale in a structured way so you can see what % fell out of the funnel due to pricing, competitors, etc.
Sales can be a grind. I used to get nervous before calls, and found that creating a routine pre-demo really helped – jumping jacks, review the script, and believe that the product I’m offering will help the person on the other end of the phone. You also need to let go of any ego or expectations of being treated like a human being. Most people view sales people as a nuisance. You will get let down a lot by your prospects every single day, but that makes the wins so much sweeter. Plus, it’s a thing that happens to everyone, not just you.
It’s going to take you a few months to make your first sales (assuming your product is >$1k/yr). Don’t get discouraged. Don’t think “we need to change the pitch/outreach/etc.” If you’ve been thoughtful about your process from the get-go, just keep building your pipeline.
Celebrate the wins. I’m so bad at this and have some sort of Catholic guilt about it. When someone says “yes” – celebrate. When someone signs the contract – celebrate. When someone goes live – celebrate. High five your co-founder. Get a beer after work. Tell your significant other. Enjoy the moment and pat yourself on your back.

There are a million nuances to sales. My first business was straight B2B SaaS where we were selling HR a product to help with their recruiting. Getting headspace was tough. Getting budget was tough. Getting them to think about their job in a new way was tough.

In my new business, I’m selling to marketing. It’s a completely different buyer that has more budget and is more likely to experiment with new products. I also have an advantage in that I’m putting reviews of their software online, which means they care a lot more than if I was selling them a tool they can ignore. This allows me to cut through the noise more effectively. Of course, it comes with many other challenges, and some I haven’t even run into yet.

I hope you enjoy your journey to becoming an A+ sales person, which is a very attainable goal for any founder. My journey has helped me build win new business, think deeper about product, and kickstarted my personal branding efforts.

Good luck, and feel free to connect if I can be helpful in your journey!