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

  2. Good post. I learn something new and challenging on sites I stumbleupon everyday.

    It’s always useful to read content from other authors and practice a
    little something from other sites.

  3. Today, I went to the beach front 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 totally off topic but
    I had to tell someone!

  4. You really make it appear so easy along with your presentation however I to find this topic to be actually something which I believe I’d by no means understand.
    It sort of feels too complicated and very huge for me.

    I’m looking ahead to your subsequent put up, I’ll attempt to get the
    dangle of it!

  5. Thank you for every other informative website. Where else may just I am getting that kind
    of info written in such an ideal manner? I have a venture that I am just now
    operating on, and I have been on the glance out for such info.

  7. I absolutely love your blog and find many of your post’s to be precisely what I’m
    looking for. Do you offer guest writers to write content in your case?
    I wouldn’t mind publishing a post or elaborating on some of the subjects you
    write about here. Again, awesome website!

  8. What’s up to all, how is everything, I think every one is getting more from this web site, and your views are fastidious designed for new users.

  12. 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 weblog when you could be giving us something enlightening to read?

  13. Hey there would you mind sharing which blog platform you’re using?

    I’m looking to start my own blog soon but I’m having
    a hard time selecting between BlogEngine/Wordpress/B2evolution and Drupal.
    The reason I ask is because your design seems different
    then most blogs and I’m looking for something completely unique.
    P.S Sorry for getting off-topic but I had to ask!

  14. An impressive share! I have just forwarded this onto a colleague who had
    been conducting a little homework on this.

    And he in fact bought me dinner simply because I stumbled upon it
    for him… lol. So allow me to reword this…. Thank YOU for the
    meal!! But yeah, thanks for spending time to discuss this matter here on your website.

  15. I am curious to find out what blog platform you have been working with?
    I’m having some small security problems with my latest website and I’d like
    to find something more risk-free. Do you have any recommendations?

  16. An outstanding share! I’ve just forwarded this onto a
    friend who had been doing a little homework on this. And he in fact bought me lunch because I discovered it for him…
    lol. So allow me to reword this…. Thanks for the meal!!
    But yeah, thanx for spending time to talk about this topic here
    on your web site.

  17. Nice post. I learn something totally new and challenging
    on websites I stumbleupon everyday. It’s always useful to read through articles from other
    writers and practice something from their sites.

  18. Hi there to every one, it’s really a pleasant for me to pay
    a quick visit this web page, it consists of priceless Information.

  22. Just desire to say your article is as surprising.
    The clarity in your post is simply nice and i can assume you
    are an expert on this subject. Fine with your permission allow me to grab
    your feed to keep updated with forthcoming post.
    Thanks a million and please keep up the enjoyable work.

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

  26. Hey there! I just wanted to ask if you ever have
    any problems with hackers? My last blog (wordpress)
    was hacked and I ended up losing months of hard work due to no backup.

    Do you have any solutions to prevent hackers?

  29. I simply could not depart your web site before suggesting that I extremely loved the standard info a person provide on your guests?

    Is gonna be back incessantly to investigate cross-check new posts

  31. Good day! I know this is kind of off topic but I was wondering which blog platform are you using for this website?

    I’m getting tired of WordPress because I’ve had problems
    with hackers and I’m looking at options for another platform.

    I would be great if you could point me in the direction of a good platform.

  32. With havin so much content do you ever run into any problems of plagorism or copyright infringement?
    My blog has a lot of completely unique content I’ve either created myself or outsourced but it appears a lot of it is popping it up all
    over the web without my agreement. Do you know any techniques to help protect
    against content from being stolen? I’d certainly appreciate it.

  35. We stumbled over here by a different page and thought I should check
    things out. I like what I see so i am just following you.
    Look forward to looking into your web page repeatedly.

  37. I was wondering if you ever thought of changing the
    structure of your site? 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 1
    or two images. Maybe you could space it out better?

  40. I know this site offers quality dependent articles or reviews and
    extra information, is there any other site which provides such information in quality?

  43. Howdy! I could have sworn I’ve been to this website before but after reading through some of the post I realized it’s new to me.
    Anyhow, I’m definitely glad I found it and I’ll be book-marking and checking back often!

  44. If you are going for most excellent contents like I do,
    only go to see this site daily for the reason that it provides feature contents,
    thanks

  45. Hi, i believe that i noticed you visited my website so i got here to go back the want?.I’m attempting to find issues to enhance
    my website!I assume its adequate to make use of a few of your ideas!!

  46. hey there and thank you for your info – I have certainly picked up something new from right here.
    I did however expertise some technical points using this site, as I experienced to reload the web site many times
    previous to I could get it to load properly. I had been wondering
    if your hosting is OK? Not that I’m complaining, but sluggish loading instances times will
    often affect your placement in google and could damage your high quality score
    if ads and marketing with Adwords. Well I’m adding this
    RSS to my e-mail and can look out for a lot more of your respective exciting content.
    Make sure you update this again very soon.

  48. My programmer is trying to convince 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 WordPress on a variety
    of 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 content into it?
    Any help would be greatly appreciated!

  49. Whats up very cool website!! Man .. Beautiful .. Amazing ..
    I will bookmark your web site and take the feeds also? I’m satisfied to seek out so many helpful information right here within the publish, we need develop extra strategies in this
    regard, thanks for sharing. . . . . .

Comments are closed.