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. May I simply just say what a comfort to uncover someone who actually understands
    what they’re discussing over the internet. You definitely understand how
    to bring an issue to light and make it important. A lot more people have to read this and understand this side of the story.
    I can’t believe you are not more popular because you
    certainly possess the gift.

  2. Zu den häufig genannten Nachteilen gehört auch die aufwendige Reinigung der Roboter.

    Besonders ärgerlich ist es für einige Anwender, wenn sie
    den Roboter für die Reinigung erst auseinanderbauen müssen.
    Dazu gehört zum Beispiel das Befreien der Bürsten von Tierhaaren oder verstopfte Saugdüsen. Verfügt der Staubsaugerroboter über Konnektivitätsfunktionen, werden von einigen Kunden über damit zusammenhängende WLAN-Probleme im Test berichtet.
    Diese Probleme äußern sich häufig in Verbindungsabbrüchen.
    Hier stellt sich jedoch die Frage, ob die Probleme auf den Roboter selbst oder
    auf eine Inkompatibilität hierbei Router zurückzuführen sind.
    Die Käufer wünschen sich hier Geräte mit einem einfacheren Zugriff aufs Innenleben. Klar ist jedoch, dass sich bei kabellosen Verbindungen Probleme bei der Datenübertragung ergeben können. Einige Nutzer berichten im
    Zusammenhang hiermit WLAN auch von Problemen der Einrichtung des Geräts.
    Die WLAN-Verbindung ist im Test zwar sehr stabil
    und unterbrechungsfrei, sobald diese einmal
    eingerichtet ist. Die erstmalige Einrichtung stellt die Anwender jedoch vor Probleme.

  3. I’m no longer sure the place you are getting your info, however good
    topic. I needs to spend some time finding out much more or figuring out more.
    Thank you for wonderful information I was looking for this info for my mission.

  4. Hello, Neat post. There’s a problem along with your site
    in web explorer, may check this? IE still is the market chief and a big component of people will miss your excellent writing because of this problem.

  5. Hey this is kinda 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 experience so I wanted to get advice from someone with experience.

    Any help would be enormously appreciated!

  6. Thank you a lot for sharing this with all people you actually realize what you are talking approximately!

    Bookmarked. Please also consult with my web site =). We
    can have a hyperlink change agreement among
    us

  7. I just like the valuable information you supply in your
    articles. I’ll bookmark your weblog and test again here frequently.
    I am fairly certain I will learn lots of new stuff right right here!
    Best of luck for the following!

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

  9. Hello, Neat post. There’s a problem with your website in internet
    explorer, might check this? IE nonetheless
    is the marketplace chief and a big portion of other folks
    will miss your wonderful writing due to this problem.

  10. Thank you for any other fantastic post. Where else could anyone get that kind
    of information in such an ideal means of writing?
    I have a presentation subsequent week, and I’m on the look for such
    info.

  11. We are a group of volunteers and opening a new scheme in our community.
    Your site provided us with valuable information to work on. You have performed an impressive job and our whole neighborhood will be thankful to you.

  12. That is a really good tip particularly to those new to
    the blogosphere. Simple but very precise information… Appreciate your sharing this one.
    A must read post!

  13. Hmm is anyone else experiencing problems with the pictures on this blog loading?
    I’m trying to find out if its a problem on my end or if it’s the blog.
    Any feedback would be greatly appreciated.

  14. Hola! I’ve been reading your weblog for some time now and finally got the bravery to go ahead and give you a shout out from
    Porter Tx! Just wanted to say keep up the great work!

  15. That is a great tip particularly to those new to the blogosphere.

    Short but very accurate info… Many thanks for sharing this one.
    A must read article!

  16. I was recommended this web site by my cousin. I’m not sure whether this post is written by him as no one else know such detailed about my difficulty.
    You’re incredible! Thanks!

  17. Hi! This is my 1st comment here so I just wanted to give a quick shout out
    and tell you I genuinely enjoy reading your posts.
    Can you recommend any other blogs/websites/forums that go over the same subjects?
    Appreciate it!

  18. Very nice post. I simply stumbled upon your weblog and wanted to say that I’ve really enjoyed
    surfing around your weblog posts. In any case I’ll be subscribing to your feed
    and I hope you write again very soon!

  19. Link exchange is nothing else except it is only placing
    the other person’s weblog link on your page at suitable place and other person will also do similar in favor of you.

  20. Nice post. I learn something totally new and challenging on blogs I stumbleupon on a daily basis.
    It will always be exciting to read through articles from
    other writers and use something from other sites.

  21. Wow, amazing blog layout! How long have you been blogging for?
    you made blogging look easy. The overall look of your web site is
    excellent, as well as the content!

  22. Dazu schneiden Sie neben anderen das Fräse vorsichtig zwischen Mauer und Fensterrahmen lang.
    Denken Sie dabei daran, dass die Ankerpratzen aus Metall mit einer Metalltrennscheibe geschnitten werden müssen. Evtl.,
    wie stark Sie dem Mauerwerk zusetzen mussten, ist es nun isoliert betrachtet notwendig, eine glatte
    Fläche für den Einbau der neuen Fenster leistbar.
    Hängenbleiben: Den Spachtel trocknen lassen, bevor es weiter geht.

    Wie lange dieser aushärten muss, können Sie den Herstellerangaben entnehmen. Dies geht am einfachsten, wenn Sie eventuell entstandene Lücken mit Spachtelmasse ausgleichen.
    Die Schritte, die wir vorher angestellt haben, müssen nun in umgekehrter Reihenfolge wiederholt werden. Im Folgenden befestigen Sie das Dekompressionsdichtband
    außen am Fensterrahmen. Wir fangen hiermit Fensterrahmen an. Dazu
    müssen die Fensterflügel wie oben beschrieben entfernt
    werden. Mit „außen” sind die Kanten gemeint, die später
    Richtung Fenstersturz und Fensterlaibungen zeigen werden. Das
    Dekompressionsdichtband dehnt sich Richtung
    Wand aus und sorgt später für eine gute Abdichtung.
    Auch Fenster 3 fach Verglasung finden Sie bei uns.

  23. With havin so much content do you ever run into any problems of plagorism or copyright infringement?
    My blog has a lot of unique content I’ve either authored myself or outsourced but it looks like a lot of it is popping it up all over the internet without my authorization. Do you know any methods to help
    protect against content from being stolen? I’d definitely
    appreciate it.

  24. It’s a pity you don’t have a donate button! I’d without a
    doubt donate to this excellent blog! I suppose for
    now i’ll settle for bookmarking and adding your RSS feed to my Google
    account. I look forward to brand new updates and will talk about this site
    with my Facebook group. Talk soon!

  25. My coder is trying to persuade me to move to .net from PHP.

    I have always disliked the idea because of the costs.
    But he’s tryiong none the less. I’ve been using Movable-type on various websites for about a year and am concerned about switching to another platform.
    I have heard very good things about blogengine.net. Is there a way I can import all
    my wordpress posts into it? Any kind of help would be really
    appreciated!

  26. I’m not that much of a online reader to be honest but your blogs really nice, keep it up!
    I’ll go ahead and bookmark your site to come back later.

    Many thanks

Comments are closed.