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. Heya this is somewhat of off topic but I was wanting to know if blogs use WYSIWYG editors or if you have to
    manually code with HTML. I’m starting a blog soon but have no coding know-how so I wanted to get
    advice from someone with experience. Any help would be greatly appreciated!

  2. Hello, I think your site might be having browser compatibility issues.
    When I look at your blog site in Opera, it looks fine but when opening in Internet
    Explorer, it has some overlapping. I just wanted
    to give you a quick heads up! Other then that, great blog!

  8. 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 waste your intelligence on just posting videos to your site when you could be giving us something informative to read?

  9. I’m no longer sure where you are getting your info, however good topic.
    I needs to spend some time finding out much more or figuring out
    more. Thanks for fantastic info I was searching for this info for my mission.

  12. I’m not certain the place you are getting your information, but good topic.
    I must spend a while learning more or understanding more. Thank you for great information I was searching for this info for my mission.

  13. of course like your web-site however you need to test the
    spelling on quite a few of your posts. Many of them are rife with spelling problems and I find it very
    troublesome to tell the truth then again I will definitely come back again.

  15. Howdy! This is my first visit to your blog!
    We are a group of volunteers and starting a new initiative in a community in the same niche.
    Your blog provided us beneficial information to work on. You have done a extraordinary job!

  16. Great work! This is the type of info that should be shared across the net.
    Shame on the search engines for now not positioning this submit upper!
    Come on over and seek advice from my website . Thank you =)

  17. First off I would like to say superb blog! I had a quick question that I’d like to ask if you don’t mind.

    I was interested to find out how you center yourself and clear your thoughts before writing.
    I have had trouble clearing my thoughts in getting my thoughts
    out there. I do enjoy writing but it just seems like the first 10 to 15 minutes are lost simply just trying to figure out how to begin.
    Any recommendations or hints? Kudos!

  20. Great post. I used to be checking constantly this weblog and I
    am impressed! Very useful information specifically the
    last part 🙂 I maintain such information a lot.
    I used to be looking for this particular information for a very long time.
    Thank you and good luck.

  22. Hey there! I simply want to offer you a big thumbs
    up for the great information you have got here on this post.
    I will be returning to your website for more soon.

  25. Today, I went to the beach with my kids. I found a sea shell and gave it to my 4 year old daughter and said “You can hear the ocean if you put this to your ear.” She put the shell to her ear and screamed.
    There was a hermit crab inside and it pinched her ear.

    She never wants to go back! LoL I know this is entirely off topic but I had to tell someone!

  26. I have been surfing online more than 3 hours as of late, but I never discovered
    any fascinating article like yours. It’s pretty worth sufficient for me.

    In my view, if all webmasters and bloggers made excellent content as you
    did, the web might be a lot more helpful than ever before.

  27. I was curious if you ever thought of changing the layout of
    your website? Its very well written; I love what youve got to say.

    But maybe you could a little more in the way of content so people could connect with it better.
    Youve got an awful lot of text for only having
    one or 2 images. Maybe you could space it out better?

  29. Fantastic beat ! I wish to apprentice while you amend your web site, how could i subscribe
    for a blog site? The account aided me a appropriate deal.
    I were a little bit acquainted of this your broadcast provided shiny
    clear concept

  30. Wow, fantastic weblog layout! How lengthy have you been running a blog for?
    you make blogging glance easy. The full glance of your web site
    is wonderful, as well as the content!

  33. Link exchange is nothing else except it is just placing the
    other person’s website link on your page at appropriate place
    and other person will also do same in favor of you.

  35. With havin so much content do you ever run into any problems of plagorism or copyright infringement?
    My website has a lot of exclusive content I’ve either authored myself or outsourced but it looks like a
    lot of it is popping it up all over the web without my permission. Do you know any techniques to help prevent content from being
    stolen? I’d genuinely appreciate it.

  36. First off I want to say awesome blog! I had a quick question which
    I’d like to ask if you don’t mind. I was interested to find out how you center yourself
    and clear your mind before writing. I have had a difficult time clearing my thoughts in getting
    my thoughts out. I truly do take pleasure in writing however it just
    seems like the first 10 to 15 minutes tend to be wasted just trying to figure out how to begin. Any ideas or hints?
    Thanks!

  37. Currently it sounds like Movable Type is the best blogging platform out there right now.
    (from what I’ve read) Is that what you’re using
    on your blog?

  39. Howdy! Do you know if they make any plugins to safeguard against hackers?
    I’m kinda paranoid about losing everything I’ve worked hard on. Any tips?

  40. May I simply say what a comfort to find an individual who
    truly understands what they’re discussing over the internet.

    You actually realize how to bring an issue to light and make it
    important. More and more people should check this out and understand this side of your story.
    I was surprised you are not more popular since you definitely possess the gift.

  42. Please let me know if you’re looking for a article writer for your blog.
    You have some really great posts and I believe I would be a good asset.
    If you ever want to take some of the load off, I’d absolutely love to write some material for your blog in exchange for a link back to mine.
    Please shoot me an e-mail if interested. Thanks!

  43. Howdy this is somewhat of off topic but I was wondering if blogs use
    WYSIWYG editors or if you have to manually code with HTML.

    I’m starting a blog soon but have no coding knowledge so I wanted
    to get guidance from someone with experience. Any help would be greatly appreciated!

  50. Hi there! I could have sworn I’ve visited this blog before but after looking at many of the posts I realized it’s
    new to me. Anyways, I’m definitely pleased I came across it and I’ll
    be bookmarking it and checking back frequently!

Comments are closed.