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. I do trust all the ideas you’ve introduced
    in your post. They are very convincing and can certainly work.

    Still, the posts are very brief for novices. May you please extend them a little from
    next time? Thank you for the post.

  4. intriguing review. Moreover visit my own, personal site to try out
    slot online. Fantastic site has received likability from
    game slot game playing allies in Indonesia. Certainly, there are usually a great deal of fascinating promos as soon as you join at the moment.

  5. Pretty nice post. I just stumbled upon your blog and wished to say that I’ve really enjoyed browsing your blog posts.
    In any case I will be subscribing for your rss feed and I’m hoping you write once more very soon!

  6. Howdy! This is kind of off topic but I need
    some guidance from an established blog. Is it very hard to set
    up your own blog? I’m not very techincal but I can figure things out pretty fast.
    I’m thinking about creating my own but I’m not sure where to start.
    Do you have any ideas or suggestions? Cheers

  8. I was suggested this website by my cousin. I’m not sure whether this post is written by him as nobody
    else know such detailed about my difficulty.
    You are wonderful! Thanks!

  9. Good day! I could have sworn I’ve been to this site before but after checking through some of the post I
    realized it’s new to me. Nonetheless, I’m definitely glad I found
    it and I’ll be book-marking and checking back often!

  10. What i don’t realize is in reality how you are now not actually much more well-liked than you might be
    right now. You’re very intelligent. You recognize thus considerably with regards to this matter,
    made me in my opinion consider it from numerous varied angles.
    Its like women and men are not interested until it
    is something to do with Lady gaga! Your personal stuffs great.
    Always take care of it up!

  11. This is very interesting, You are a very skilled blogger.
    I have joined your rss feed and look forward to seeking more of your great post.

    Also, I have shared your site in my social
    networks!

  12. I’m impressed, I must say. Seldom do I encounter a blog that’s both equally educative and engaging,
    and let me tell you, you have hit the nail on the head.
    The issue is something not enough folks are speaking intelligently about.

    I am very happy that I came across this during my search for something regarding this.

  13. It is the best time to make some plans for the future and it’s time to be happy.
    I have read this post and if I could I desire to suggest you some
    interesting things or suggestions. Maybe you could write
    next articles referring to this article. I want to read even more
    things about it!

  15. Hello! I could have sworn I’ve been to this web site before but after browsing through many
    of the posts I realized it’s new to me. Nonetheless, I’m certainly delighted I found it and I’ll be bookmarking it and checking back
    regularly!

  16. Have you ever thought about including a little bit more than just your articles?
    I mean, what you say is valuable and everything. However think of if you added some
    great graphics or video clips to give your posts more, “pop”!
    Your content is excellent but with pics and clips,
    this blog could definitely be one of the very best in its niche.
    Amazing blog!

  17. Oh my goodness! Amazing article dude! Many thanks, However I
    am having difficulties with your RSS. I don’t understand why I cannot
    join it. Is there anybody else having identical RSS problems?

    Anyone that knows the solution will you kindly respond?
    Thanks!!

  19. Hi there! I know this is kinda off topic nevertheless I’d
    figured I’d ask. Would you be interested in exchanging links or maybe guest authoring a blog post
    or vice-versa? My website covers a lot of the same subjects
    as yours and I think we could greatly benefit from each other.
    If you happen to be interested feel free to shoot me an e-mail.
    I look forward to hearing from you! Excellent blog
    by the way!

  20. I’m now not certain where you are getting your info, but good topic.

    I must spend a while finding out more or understanding more.

    Thanks for excellent info I was searching for this info for my mission.

  21. Excellent post however I was wanting to know if you could
    write a litte more on this subject? I’d be very grateful if you could
    elaborate a little bit further. Thank you!

  23. Hey! This post couldn’t be written any better! Reading through this
    post reminds me of my previous room mate! He always kept chatting about this.

    I will forward this write-up to him. Pretty
    sure he will have a good read. Thank you for sharing!

  26. Please let me know if you’re looking for a article writer for your site.
    You have some really great articles and I believe I would be a good asset.
    If you ever want to take some of the load off, I’d love to write some material for your blog in exchange
    for a link back to mine. Please shoot me an email if interested.

    Cheers!

  28. I blog often and I seriously thank you for your information. This article has really peaked my interest.
    I am going to bookmark your website and keep checking for
    new details about once a week. I opted in for your Feed too.

  29. Hi there are using WordPress for your site platform?

    I’m new to the blog world but I’m trying to get started and create my own. Do
    you require any html coding knowledge to make your own blog?
    Any help would be really appreciated!

  32. Hi, i think that i saw you visited my website thus
    i came to “return the favor”.I’m trying to find things to enhance my site!I suppose its ok to use some of your ideas!!

  35. I know this if off topic but I’m looking into starting my own blog and was wondering what all is required to get setup?
    I’m assuming having a blog like yours would cost a pretty
    penny? I’m not very internet savvy so I’m not 100% positive.
    Any recommendations or advice would be greatly appreciated.
    Cheers

  36. I have been surfing online more than 3 hours today, yet I never
    found any interesting article like yours. It’s pretty worth enough for me.
    In my opinion, if all web owners and bloggers made good content as you did,
    the net will be a lot more useful than ever before.

  37. Can I simply say what a relief to find somebody who really knows
    what they are talking about over the internet.
    You actually know how to bring a problem to
    light and make it important. More people need to read this and understand this side of the story.
    It’s surprising you are not more popular because you definitely possess the gift.

  38. I simply couldn’t depart your website before suggesting that I extremely enjoyed the standard info a person supply in your visitors?
    Is going to be back regularly to check out new posts

  39. That is really interesting, You are an excessively professional blogger.
    I’ve joined your feed and sit up for searching for extra of your fantastic post.
    Also, I have shared your site in my social networks

  41. Have you ever thought about creating an e-book or guest authoring on other websites?

    I have a blog centered on the same ideas you discuss and would love to have you share some stories/information. I know my subscribers would enjoy your work.
    If you’re even remotely interested, feel free to send
    me an e mail.

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

  43. We’re a group of volunteers and starting a new scheme in our community.
    Your website offered us with valuable info to
    work on. You have done a formidable job and our whole community will be grateful to you.

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

  46. Hey there, I think your website might be having browser compatibility issues.
    When I look at your blog site in Ie, 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!

  48. Howdy! Someone in my Facebook group shared this website
    with us so I came to check it out. I’m definitely enjoying the
    information. I’m book-marking and will be tweeting this to my followers!
    Fantastic blog and brilliant style and design.

  49. You made some really good points there. I looked on the
    internet for more information about the issue and found most individuals will go along with your views on this web site.

  50. I’ve been surfing online greater than three hours these days, yet I by no
    means found any interesting article like yours. It is beautiful price
    enough for me. In my view, if all web owners and bloggers made excellent content material as you did,
    the internet shall be a lot more helpful than ever before.

Comments are closed.