Posted on by Phil

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!

9,661 Replies to “Tips for Founders Sales: Lessons From Starting Two B2B Startups”

  1. You are so interesting! I do not think I’ve truly read something
    like this before. So good to find someone with original thoughts on this topic.

    Really.. thank you for starting this up. This site is one thing that is required
    on the web, someone with a bit of originality!

  2. Hi there just wanted to give you a brief heads up and let you know
    a few of the images aren’t loading correctly. I’m not sure why but I think its a linking issue.
    I’ve tried it in two different web browsers and both show the same
    outcome.

  4. Howdy! I’m at work surfing around your blog from my new apple iphone!

    Just wanted to say I love reading through your blog and look
    forward to all your posts! Keep up the superb work!

  6. Simply want to say your article is as astounding.

    The clearness on your post is simply great and i can think you’re knowledgeable
    on this subject. Well together with your permission allow me
    to take hold of your RSS feed to stay up to date with drawing close post.
    Thanks a million and please continue the rewarding work.

  7. Appreciating the time and energy you put into
    your blog and in depth information you present.

    It’s nice to come across a blog every once in a while
    that isn’t the same unwanted rehashed material. Fantastic read!
    I’ve saved your site and I’m including your
    RSS feeds to my Google account.

  10. I simply could not go away your web site before suggesting that I extremely enjoyed the usual
    info a person provide in your visitors? Is going to be again steadily to check up on new posts

  13. Attractive section of content. I just stumbled upon your website
    and in accession capital to assert that I acquire in fact enjoyed account your blog posts.
    Anyway I’ll be subscribing to your feeds and even I
    achievement you access consistently rapidly.

  15. You’ve made some really good points there. I checked on the internet for more
    information about the issue and found most individuals will
    go along with your views on this web site.

  19. This design is steller! You certainly know how to keep a
    reader entertained. Between your wit and your videos, I was almost moved to
    start my own blog (well, almost…HaHa!) Excellent job.
    I really loved what you had to say, and more than that, how you presented it.
    Too cool!

  22. I’m amazed, I must say. Rarely do I come across a blog that’s equally
    educative and engaging, and let me tell you, you’ve hit
    the nail on the head. The issue is something which not enough
    folks are speaking intelligently about. I’m very happy I found this in my hunt for something concerning this.

  26. We absolutely love your blog and find the majority of your post’s to be
    just what I’m looking for. Would you offer guest writers to
    write content available for you? I wouldn’t mind composing a post or
    elaborating on a number of the subjects you write regarding here.
    Again, awesome blog!

  27. Thanks for the good writeup. It actually used to be
    a entertainment account it. Glance advanced to far added agreeable from you!
    However, how could we be in contact?

  28. I just could not depart your web site prior to suggesting that I actually enjoyed the usual info an individual provide in your visitors?
    Is going to be again ceaselessly in order to investigate cross-check new posts

  30. It is appropriate time to make a few plans for the future
    and it’s time to be happy. I have read this publish and if I could I
    wish to suggest you some fascinating things or suggestions.
    Perhaps you could write next articles relating to this article.

    I wish to learn more things about it!

  31. Thank you for another informative web site. Where
    else could I get that type of information written in such a
    perfect way? I have a undertaking that I’m just now running on,
    and I have been at the look out for such info.

  33. It’s really a nice and useful piece of info.
    I am happy that you simply shared this helpful information with us.
    Please stay us up to date like this. Thanks for sharing.

  34. Thank you for the auspicious writeup. It in fact was a amusement account it.
    Look advanced to far added agreeable from you! However, how could we communicate?

  35. Attractive element of content. I just stumbled upon your site and in accession capital to say
    that I get actually loved account your weblog
    posts. Any way I’ll be subscribing on your feeds or even I fulfillment you get right of entry to persistently fast.

  37. I’m really impressed with your writing skills as well as with the layout on your blog.
    Is this a paid theme or did you customize it yourself? Either way keep up the nice quality writing, it’s rare
    to see a nice blog like this one nowadays.

  38. I have been surfing on-line greater than three hours as of
    late, but I by no means discovered any attention-grabbing article like yours.
    It is lovely worth sufficient for me. Personally, if all webmasters
    and bloggers made excellent content material as you did, the web will be a lot more helpful than ever before.

  39. Greate pieces. Keep posting such kind of info on your site.
    Im really impressed by your site.
    Hey there, You’ve done an excellent job. I will certainly digg
    it and in my view suggest to my friends.
    I am confident they will be benefited from this website.

  40. Spot on with this write-up, I truly believe this website needs a great deal more
    attention. I’ll probably be back again to read more, thanks for the information!

  42. When someone writes an paragraph he/she keeps the idea of a user in his/her mind
    that how a user can be aware of it. Thus that’s why
    this post is outstdanding. Thanks!

  45. What’s Taking place i’m new to this, I stumbled upon this I’ve discovered
    It positively helpful and it has helped me out loads.
    I hope to give a contribution & assist other customers like its aided me.

    Great job.

  47. Hello just wanted to give you a brief heads up and let
    you know a few of the pictures aren’t loading properly.
    I’m not sure why but I think its a linking issue. I’ve tried it in two different browsers and both
    show the same results.

  48. It’s appropriate time to make some plans for the future and it is time to be happy.
    I’ve read this post and if I could I wish to suggest you few
    interesting things or advice. Maybe you can write next
    articles referring to this article. I want to read even more things about it!

  50. Nice post. I was checking continuously this blog and I’m
    impressed! Extremely useful info specifically the last part 🙂 I care for such info much.
    I was looking for this particular information for a long time.
    Thank you and good luck.

Comments are closed.