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. Oh my goodness! Amazing article dude! Many thanks, However I am having issues
    with your RSS. I don’t understand the reason why I can’t join it.
    Is there anyone else having identical RSS issues? Anyone who knows the solution can you kindly respond?
    Thanx!!

  2. I will right away clutch your rss feed as I can’t in finding your
    email subscription hyperlink or newsletter service.
    Do you have any? Kindly permit me recognise so that I could subscribe.
    Thanks.

  3. We stumbled over here coming from a different website and thought I may as well check
    things out. I like what I see so now i’m following you.
    Look forward to going over your web page for a second time.

  4. Normally I do not learn article on blogs, however I wish to say that this
    write-up very compelled me to take a look at and do it!
    Your writing style has been amazed me. Thanks, very
    great post.

  5. Heya i am for the first time here. I found this board and I find It
    really useful & it helped me out a lot. I hope to give something back and help others
    like you aided me.

  6. whoah this blog is wonderful i love studying your articles.
    Stay up the good work! You realize, many persons are
    searching round for this information, you could help them greatly.

  7. Hey There. I found your blog using msn. This is an extremely well written article.
    I will make sure to bookmark it and come back to read more of
    your useful information. Thanks for the post. I will definitely return.

  9. Thank you for the auspicious writeup. It actually used to be a
    enjoyment account it. Look complicated to far brought agreeable
    from you! By the way, how could we communicate?

  11. I do believe all of the ideas you’ve offered in your post.
    They are really convincing and will definitely work.
    Still, the posts are very quick for newbies. May just you
    please lengthen them a bit from subsequent time?
    Thanks for the post.

  12. Hi there, i read your blog occasionally and i own a similar one and i was just wondering if you get a
    lot of spam comments? If so how do you stop it, any plugin or
    anything you can advise? I get so much lately it’s driving me insane so any
    support is very much appreciated.

  13. Hello exceptional website! Does running a blog like
    this require a great deal of work? I’ve very little knowledge of coding but I had been hoping to start my own blog in the near future.

    Anyway, should you have any recommendations or tips for new blog
    owners please share. I know this is off subject nevertheless I simply had to ask.

    Thanks!

  15. hey there and thank you for your information – I have certainly picked up anything new from right here.
    I did however expertise a few technical issues using this web site, since I experienced to reload the website lots of times previous to I could get
    it to load correctly. I had been wondering if your web hosting is
    OK? Not that I am complaining, but sluggish loading instances
    times will sometimes affect your placement in google and could damage your
    high quality score if ads and marketing with Adwords.
    Anyway I’m adding this RSS to my email and could
    look out for a lot more of your respective interesting content.
    Make sure you update this again very soon.

  17. Good day I am so happy I found your website, I really found you by error,
    while I was searching on Digg for something else, Regardless I
    am here now and would just like to say many thanks for a remarkable
    post and a all round thrilling blog (I also love the
    theme/design), I don’t have time to look over it all at
    the moment but I have book-marked it and also included your RSS
    feeds, so when I have time I will be back to read more, Please do keep up the great jo.

  18. Write more, thats all I have to say. Literally, it
    seems as though you relied on the video to make your
    point. You definitely know what youre talking about, why
    throw away your intelligence on just posting videos to your blog when you could be
    giving us something enlightening to read?

  21. Great post however I was wanting to know if you
    could write a litte more on this topic? I’d be very thankful if you could elaborate a little
    bit further. Thanks!

  25. Undeniably imagine that which you said. Your favourite justification appeared to be at the net the easiest factor to bear in mind of.
    I say to you, I certainly get annoyed even as other folks consider concerns
    that they plainly don’t recognise about. You managed to hit the nail upon the
    highest and outlined out the whole thing without having side-effects , people could take a signal.
    Will likely be back to get more. Thanks

  26. May I simply say what a relief to discover an individual who really understands what they are discussing over the internet.
    You actually know how to bring an issue to light and make it important.

    More and more people should read this and understand this side of the story.
    I was surprised you aren’t more popular given that
    you certainly possess the gift.

  27. Hey are using WordPress for your site platform?
    I’m new to the blog world but I’m trying to get started
    and create my own. Do you require any html coding expertise to make your own blog?
    Any help would be greatly appreciated!

  28. This is really fascinating, You’re a very professional blogger.

    I have joined your rss feed and stay up for in the hunt for extra of your
    fantastic post. Also, I have shared your website in my social networks

  29. Woah! I’m really loving the template/theme of this site. It’s simple, yet effective.
    A lot of times it’s tough to get that “perfect balance” between superb usability and appearance.

    I must say you’ve done a great job with this.
    In addition, the blog loads very fast for me on Safari.

    Excellent Blog!

  33. I used to be suggested this web site via my cousin. I am
    not sure whether or not this submit is written by way of him as no one else recognise such specific approximately my problem.
    You are amazing! Thanks!

  34. Hello, i think that i saw you visited my weblog so i came
    to “return the favor”.I am trying to find things
    to improve my web site!I suppose its ok to use some of your ideas!!

  35. really interesting review. On top of that visit my very own site to be aware of slot
    pulsa tanpa potongan. Often the amazing site has received recognition from slot pulsa online casino people in Dalam negeri.
    Presently there will be many intriguing promos as you join right
    now.

  38. Its such as you read my thoughts! You appear to know a lot approximately this, like you wrote the ebook in it or something.

    I believe that you just can do with a few p.c. to force the message home a little bit,
    but other than that, this is excellent blog. A fantastic read.

    I will certainly be back.

  39. Howdy! Do you know if they make any plugins to assist with SEO?

    I’m trying to get my blog to rank for some targeted keywords but I’m
    not seeing very good success. If you know of any
    please share. Kudos!

  42. important review. Too visit my site to get down judi slot.
    This page has received popularity originating from game slot online video gaming
    colleagues in Negara sendiri. Generally there tend to be
    lots of beautiful promos in the event you join currently.

  44. Greetings! I’ve been following your site for a long time now and finally got the courage to go ahead and give you a shout out from
    Austin Tx! Just wanted to mention keep up the excellent job!

  45. interesting review. In addition to that visit the
    actual site which can be gamed situs slot online.

    This site has received my partner and i. d. from the comfort of
    slot via pulsa game playing contacts in Indonesia.
    Right now there will be lots of ideal promos cleaning
    soap join presently.

Comments are closed.