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. Hi there! I know this is kinda off topic but I was wondering which blog platform are you using for this site?
    I’m getting fed up 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.

  3. When I initially left a comment I appear to have
    clicked the -Notify me when new comments are added- checkbox and now every time a comment is added I receive four
    emails with the exact same comment. Is there a way you are able to remove
    me from that service? Thanks!

  5. Hello! I simply wish to offer you a big thumbs up for your great
    info you have here on this post. I’ll be coming back to your website for more soon.

  6. I’ll immediately snatch your rss feed as I can not to find your
    email subscription link or newsletter service.
    Do you’ve any? Please permit me recognise in order that I could subscribe.
    Thanks.

  7. We’re a gaggle of volunteers and starting a new scheme in our
    community. Your site provided us with useful information to work on. You have done a formidable process and our entire neighborhood will be thankful to you.

  8. What’s up to all, it’s truly a fastidious for me to pay a quick visit this web site, it includes priceless Information.

  12. Wonderful website you have here but I was wondering if you knew
    of any community forums that cover the same topics talked about in this article?
    I’d really like to be a part of community where I can get responses from other
    knowledgeable people that share the same interest. If you
    have any suggestions, please let me know. Thanks a lot!

  13. Thanks for a marvelous posting! I quite enjoyed reading it, you could be a great author.

    I will make sure to bookmark your blog and will come back at some point.
    I want to encourage one to continue your great job, have
    a nice holiday weekend!

  14. I’m gone to say to my little brother, that he should also pay a visit this weblog on regular basis to obtain updated from most up-to-date
    news update.

  17. With havin so much written content do you ever run into any problems of plagorism or copyright infringement?
    My blog has a lot of exclusive content I’ve either authored myself or outsourced but it appears a lot of it
    is popping it up all over the web without my permission. Do you know any solutions to help protect against content from being
    ripped off? I’d definitely appreciate it.

  19. Nice post. I learn something new and challenging on sites I stumbleupon on a
    daily basis. It’s always helpful to read through content from other
    writers and use something from other web sites.

  20. Hi there i am kavin, its my first occasion to commenting anywhere, when i read
    this piece of writing i thought i could also make comment
    due to this sensible article.

  22. Wow, amazing blog layout! How long have you
    been blogging for? you make blogging look easy. The overall look of
    your website is magnificent, let alone the content!

  25. I have to thank you for the efforts you’ve put in writing this website.
    I am hoping to check out the same high-grade blog posts from you later
    on as well. In truth, your creative writing abilities has encouraged me to get my
    own site now 😉

  26. Woah! I’m really loving the template/theme of this website.

    It’s simple, yet effective. A lot of times it’s tough to get that “perfect balance” between usability and visual appearance.
    I must say that you’ve done a very good job with this.
    Also, the blog loads extremely fast for me on Firefox.
    Superb Blog!

  28. Appreciating the commitment you put into your blog and in depth information you offer.
    It’s awesome to come across a blog every once in a while that isn’t the same outdated rehashed material.
    Great read! I’ve bookmarked your site and I’m including your RSS
    feeds to my Google account.

  29. Have you ever considered creating an e-book or guest authoring on other sites?
    I have a blog based on the same ideas you discuss and
    would really like to have you share some stories/information. I know
    my viewers would value your work. If you are even remotely interested, feel free
    to shoot me an email.

  30. You really make it seem really easy with your presentation however I in finding
    this topic to be really one thing which I think I would
    by no means understand. It sort of feels too complex
    and extremely huge for me. I’m taking a look ahead to your subsequent post, I will attempt to get the dangle of it!

  32. Every weekend i used to pay a quick visit this website, for the reason that i want enjoyment, since
    this this web page conations actually nice funny stuff too.

  34. A motivating discussion is definitely worth comment.

    I believe that you ought to publish more about this
    issue, it might not be a taboo subject but usually folks don’t discuss such issues.
    To the next! Many thanks!!

  37. I am not sure where you are getting your info, but good
    topic. I needs to spend some time learning much more
    or understanding more. Thanks for fantastic info I was looking
    for this info for my mission.

  39. Hey there, You’ve done a great job. I’ll certainly digg it
    and personally suggest to my friends. I’m confident they will be benefited from this website.

  41. Good day! I could have sworn I’ve visited this web site before but after
    looking at a few of the posts I realized it’s new to me.
    Anyhow, I’m definitely pleased I discovered it and I’ll be
    bookmarking it and checking back often!

  45. Its such as you read my thoughts! You seem to know so much
    approximately this, such as you wrote the ebook in it
    or something. I feel that you just could do with some p.c.
    to drive the message home a bit, but other than that, this is wonderful blog.
    An excellent read. I’ll definitely be back.

  46. Do you have a spam problem on this blog; I also am a blogger,
    and I was wondering your situation; many of us have created some nice procedures and we are looking to exchange techniques with other folks, please shoot
    me an email if interested.

  47. I like the helpful info you provide in your articles.
    I will bookmark your weblog and check again here regularly.
    I’m quite sure I will learn plenty of new stuff right here!

    Good luck for the next!

  48. I know this web page presents quality based articles and additional information, is
    there any other web site which presents these things in quality?

  49. Hi, I think your blog might be having browser compatibility issues.
    When I look at your blog in Chrome, 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, superb blog!

Comments are closed.