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. GetBoost – The solution for buying likes on Instagram
    You can promote your Instagram post in a short time using our boosting services.
    These services will get you likes and generate buzz on the internet.
    It’s not worth investing in high-end photography or post-production that no one will ever be
    able to see. Give your post the kickoff and enjoy the results.
    We provide post boosting services that include buying Instagram
    likes from around the globe. If you are looking for quality results and a return on your
    investment, buy likes from a particular
    group of users.

    Now you have a good understanding of Instagram. You will be able to go viral by buying likes.
    Additionally, you’ll discover how to increase the engagement of users.

    We are always available to assist with any assistance we can to ensure that your content, posts, and
    pictures can be a powerful source of exposure and promotion.

  2. Howdy! This blog post could not be written any better!
    Reading through this article reminds me of my previous roommate!
    He always kept preaching about this. I am going to send this post to him.
    Fairly certain he’s going to have a great read. I appreciate you for sharing!

  3. Hello there! This is kind of off topic but I need
    some help from an established blog. Is it difficult to set up
    your own blog? I’m not very techincal but I can figure things out pretty fast.
    I’m thinking about making my own but I’m not sure where to begin.
    Do you have any ideas or suggestions? Many thanks

  4. I’m not sure why but this weblog is loading very slow for me.

    Is anyone else having this problem or is it a issue on my end?
    I’ll check back later on and see if the problem still exists.

  5. Hola! I’ve been following your blog for a while now and finally got the courage
    to go ahead and give you a shout out from Porter Texas! Just wanted to say keep up the excellent
    job!

  6. Oh my goodness! Incredible article dude! Many
    thanks, However I am experiencing issues with your RSS.
    I don’t understand the reason why I can’t join it. Is there
    anyone else getting the same RSS issues? Anybody who knows the solution will you kindly respond?
    Thanx!!

  7. Greetings from Ohio! I’m bored to tears at work so I decided to browse your website on my iphone during lunch break.
    I love the info you provide here and can’t wait to take a look when I get home.

    I’m amazed at how fast your blog loaded on my mobile ..
    I’m not even using WIFI, just 3G .. Anyhow, good blog!

  8. It’s genuinely very complex in this full of activity life to listen news on TV, so
    I only use web for that purpose, and take the most recent news.

  9. Have you ever thought about including a little
    bit more than just your articles? I mean, what you say is valuable and everything.

    But just imagine if you added some great visuals or video clips to give your
    posts more, “pop”! Your content is excellent but with pics and videos, this site could definitely be one of the very best in its field.

    Superb blog!

  10. Hi there to every , for the reason that I am genuinely keen of reading this webpage’s post to be updated regularly.
    It carries good information.

  11. Great blog here! Also your site loads up fast!
    What web host are you using? Can I get your affiliate
    link to your host? I wish my web site loaded up as quickly as yours lol

  12. Hello There. I discovered your weblog the use of msn. That is a
    very smartly written article. I’ll make sure to bookmark it
    and come back to read extra of your useful information. Thank you for
    the post. I will definitely comeback.

  13. I am really enjoying the theme/design of your site.
    Do you ever run into any internet browser compatibility issues?

    A couple of my blog visitors have complained about my site not operating correctly in Explorer but looks great in Safari.
    Do you have any recommendations to help fix this problem?

  14. I believe everything said made a bunch of sense.
    However, think about this, suppose you were to write
    a awesome headline? I am not suggesting your information is
    not good., but what if you added a post title that makes people want more?

    I mean Tips for Founders Sales: Lessons From Starting Two
    B2B Startups – Phil Strazzulla's Blog is a little vanilla.
    You should peek at Yahoo’s front page and note
    how they create article headlines to grab people interested.
    You might try adding a video or a related picture
    or two to get people interested about what you’ve got to
    say. In my opinion, it would bring your blog a little bit more interesting.

  15. Thank you for any other informative web site. Where else could I get that type of
    information written in such a perfect method? I have a
    undertaking that I’m just now working on, and I’ve been at the glance out for such info.

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

  17. 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
    website to come back later. Cheers

  18. I get pleasure from, result in I discovered exactly what I was taking a look for.
    You’ve ended my 4 day lengthy hunt! God Bless you man.
    Have a great day. Bye

  19. I’m extremely impressed together with your writing
    talents as well as with the format for your weblog. Is that this a paid
    theme or did you customize it yourself? Either way keep up
    the excellent high quality writing, it’s rare to peer a great weblog like this one today..

  20. Heya i’m for the first time here. I found this board and I find It truly helpful & it
    helped me out much. I hope to give something again and aid others such as
    you aided me.

  21. Its like you read my mind! You seem to know a lot about this,
    like you wrote the book in it or something. I think that you could do with a few pics to drive the message home a bit, but other than that, this is wonderful blog.
    An excellent read. I will definitely be back.

  22. That is very fascinating, You’re an excessively skilled blogger.
    I’ve joined your rss feed and sit up for searching for
    extra of your excellent post. Also, I have shared your website in my social networks

  23. 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 website to come back later.
    All the best

  24. Do you mind if I quote a couple of your articles as long as I provide credit and sources
    back to your site? My website is in the very same area of interest as yours and my users would really benefit
    from a lot of the information you provide here.
    Please let me know if this alright with you.
    Cheers!

  25. Amazing blog! Do you have any tips and hints for aspiring writers?

    I’m hoping to start my own blog soon but I’m a little lost on everything.
    Would you suggest starting with a free platform like WordPress or go for a paid option? There are so many choices out there that I’m totally overwhelmed ..
    Any ideas? Kudos!

  26. When I originally commented I clicked the “Notify me when new comments are added”
    checkbox and now each time a comment is added I
    get four emails with the same comment. Is there any way you can remove me from
    that service? Many thanks!

  27. Hi there just wanted to give you a quick heads up. The text
    in your content seem to be running off the screen in Internet explorer.

    I’m not sure if this is a format issue or something to do with web browser compatibility but I figured I’d post to let you know.
    The layout look great though! Hope you get the issue solved soon. Many thanks

  28. I’m not sure where you’re getting your information, but good topic.
    I needs to spend some time learning much more or understanding
    more. Thanks for great information I was looking for this information for my mission.

  29. I’m truly enjoying the design and layout of your site. It’s a very easy
    on the eyes which makes it much more enjoyable for me to come here and visit more often. Did you hire out a
    designer to create your theme? Great work!

  30. You are so awesome! I do not suppose I’ve truly read through anything
    like this before. So wonderful to discover another person with unique thoughts on this topic.
    Really.. many thanks for starting this up. This website is one thing that is required on the internet,
    someone with a little originality!

  31. I have learn several just right stuff here. Definitely
    price bookmarking for revisiting. I wonder how a lot effort you
    place to create this type of wonderful informative website.

  32. Woah! I’m really enjoying the template/theme of this blog.
    It’s simple, yet effective. A lot of times it’s
    very hard to get that “perfect balance” between usability
    and visual appeal. I must say that you’ve
    done a amazing job with this. Also, the blog loads extremely quick for me on Safari.
    Outstanding Blog!

  33. Have you ever thought about publishing an e-book or guest authoring on other
    blogs? I have a blog centered on the same ideas you discuss and would really
    like to have you share some stories/information. I
    know my subscribers would enjoy your work.
    If you are even remotely interested, feel free to shoot me an e mail.

  34. It’s a pity you don’t have a donate button! I’d without a doubt donate to this fantastic blog!

    I suppose for now i’ll settle for book-marking and adding your
    RSS feed to my Google account. I look forward to new updates and will talk about this website with my Facebook group.

    Chat soon!

  35. Just wish to say your article is as amazing. The clarity in your publish is
    simply great and i can assume you’re knowledgeable in this subject.
    Well along with your permission allow me to grab your
    RSS feed to stay up to date with approaching post.
    Thank you 1,000,000 and please keep up the gratifying work.

  36. Hello, I think your site might be having browser compatibility
    issues. When I look at your blog in Safari, 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, wonderful blog!

  37. Aw, this was a really good post. Spending some time and actual effort to create a great article… but what can I say… I hesitate a whole lot and
    don’t seem to get nearly anything done.

  38. you’re in reality a just right webmaster. The web
    site loading pace is incredible. It seems that you are doing any distinctive trick.
    Furthermore, The contents are masterwork. you’ve performed a great job on this
    subject!

Comments are closed.