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”

  2. With havin so much content do you ever run into any problems of plagorism or copyright infringement?
    My site has a lot of exclusive content I’ve either written myself
    or outsourced but it looks like a lot of it is popping it up all over the internet without my
    agreement. Do you know any solutions to help
    stop content from being ripped off? I’d genuinely appreciate it.

    Feel free to visit my blog post login poker pulsa

  3. My coder is trying to convince me to move to .net from PHP.

    I have always disliked the idea because of the expenses. But he’s tryiong none the
    less. I’ve been using Movable-type on a number of websites for about a year
    and am worried about switching to another platform.

    I have heard great things about blogengine.net. Is there a way I can transfer all my wordpress posts
    into it? Any kind of help would be greatly appreciated!

  4. Please let me know if you’re looking for a article author for your weblog.

    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
    content for your blog in exchange for a link back to mine.
    Please blast me an email if interested. Regards!

  6. An outstanding share! I’ve just forwarded this onto a
    colleague who had been conducting a little research on this.

    And he actually bought me breakfast simply because I
    discovered it for him… lol. So allow me to reword this….

    Thanks for the meal!! But yeah, thanks for spending time to talk about this topic here on your site.

    Also visit my page … joker123

  7. Good day I am so excited I found your blog, I really found you
    by error, while I was looking on Google for something
    else, Anyhow I am here now and would just like to say
    thanks a lot for a marvelous post and a all round exciting
    blog (I also love the theme/design), I don’t have time to read through it all at the minute but
    I have bookmarked it and also added your RSS feeds,
    so when I have time I will be back to read a lot
    more, Please do keep up the superb work.

  8. After exploring a few of the blog articles on your web site,
    I honestly appreciate your way of blogging. I book-marked it to
    my bookmark site list and will be checking back in the near future.

    Take a look at my website too and tell me what you think.

  9. My coder is trying to convince me to move to .net from PHP.
    I have always disliked the idea because of the expenses.
    But he’s tryiong none the less. I’ve been using
    Movable-type on numerous websites for about a year and am nervous about
    switching to another platform. I have heard good things about blogengine.net.
    Is there a way I can import all my wordpress content into it?

    Any kind of help would be really appreciated!

    My webpage … judi via pulsa

  10. Good day! I could have sworn I’ve been to this blog before but after looking at a few of the articles I realized it’s new to me.
    Nonetheless, I’m definitely pleased I stumbled
    upon it and I’ll be bookmarking it and checking back often!

  11. In fact no matter if someone doesn’t be aware of afterward its up to other visitors that they will assist, so here it happens.

    Look into my webpage – s128

  13. It’s the best time to make some plans for the longer term and it is
    time to be happy. I’ve read this publish and if
    I may I want to recommend you few interesting issues or tips.
    Maybe you could write subsequent articles regarding this article.

    I want to learn even more things approximately it!

    My webpage aduayamfilipina.com

  19. Hello, i think that i saw you visited my website
    so i came to “return the favor”.I am attempting
    to find things to enhance my site!I suppose its ok to use some of your
    ideas!!

  21. You really make it seem so easy with your presentation but I find this matter to be actually something that I think I would never understand.
    It seems too complex and very broad for me.
    I’m looking forward for your next post, I’ll try to get the hang of it!

  22. Attractive component to content. I simply stumbled upon your blog
    and in accession capital to assert that I get actually enjoyed account your weblog posts.
    Any way I will be subscribing for your feeds or even I achievement you get entry to constantly quickly.

  26. Hi there, I found your web site by way of Google while searching for a similar matter, your website came
    up, it appears great. I have bookmarked it in my google bookmarks.

    Hello there, simply become aware of your weblog thru Google, and found that it’s really informative.
    I’m gonna watch out for brussels. I will appreciate in case you continue this in future.

    Lots of people shall be benefited from your writing. Cheers!

  29. 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, very good blog!

  31. Just desire to say your article is as surprising.
    The clarity in your post is simply spectacular and i can assume you are an expert on this
    subject. Fine with your permission let me to grab your RSS feed to
    keep up to date with forthcoming post. Thanks a million and
    please carry on the gratifying work.

  32. Hello! I know this is kind of off topic but I was
    wondering if you knew where I could get a captcha plugin for my comment form?
    I’m using the same blog platform as yours and I’m having difficulty finding one?
    Thanks a lot!

  33. Heya just wanted to give you a quick heads up and let you know a few of the images
    aren’t loading correctly. I’m not sure why but I think its
    a linking issue. I’ve tried it in two different browsers and
    both show the same outcome.

  42. I seriously love your website.. Pleasant colors & theme.
    Did you make this amazing site yourself? Please reply back as I’m trying to
    create my very own site and want to know where you
    got this from or what the theme is called. Appreciate it!

  45. Hello just wanted to give you a quick heads up and let you
    know a few of the pictures aren’t loading correctly.
    I’m not sure why but I think its a linking issue.

    I’ve tried it in two different internet browsers and both show the same results.

    My site :: tanpa potongan

  46. I’ve been exploring for a little bit for any high-quality articles or blog posts on this kind of house .
    Exploring in Yahoo I at last stumbled upon this website.
    Studying this info So i am happy to convey that I’ve an incredibly good uncanny feeling I discovered
    just what I needed. I most certainly will make certain to don?t forget this web site and give it a glance regularly.

  50. Magnificent beat ! I would like to apprentice while you amend your web site, how could i subscribe for a blog website?
    The account helped me a acceptable deal. I had been a little bit acquainted of this
    your broadcast provided bright clear concept

    My site slotpulsa888.xyz

Comments are closed.