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. significant review. As well visit each of our site which can be played game slot online.
    This particular url has received magnificence from slot
    pulsa tanpa potongan gaming folks in Negara sendiri.
    Presently there tend to be loads of beautiful promos when you finally join at this moment.

  3. essential review. Likewise visit desired site that is certainly played out agen slot deposit pulsa.
    This phenomenal site has received endorsement through judi slot online game playing gamers in Negara sendiri.

    Now there tend to be many astounding promos because you join at that point.

  5. amazing review. Also visit our site to achieve situs slot
    online. This incredible website has received qualifications right from slot machine
    game games avid gamers in Negara sendiri. Right now there are usually a lot of intriguing promos if however
    , you join at the moment.

  8. Hi there, just became alert to your blog through Google, and found that it is
    really informative. I am gonna watch out for brussels.
    I’ll be grateful if you continue this in future.
    Numerous people will be benefited from your
    writing. Cheers!

  9. With havin so much written content do you ever run into any issues of plagorism or
    copyright infringement? My website has a lot of unique content I’ve either created myself or outsourced but it seems a lot of
    it is popping it up all over the web without my permission. Do you know any
    solutions to help reduce content from being ripped off?

    I’d certainly appreciate it.

  11. necessary review. Also visit this site to appreciate slot pulsa online.
    This kind of web page has received popularity having agen slot pulsa playing customers in Dalam negeri.
    Truth be told there will be a lot of interesting promos if however , you join at that point.

  12. appealing review. In a very similar trend visit an site to examine slot Joker388.
    This great web site has received i. d. by Joker123 login gambling house persons in Negara sendiri.
    In that respect there are actually quite a few amazing promos
    should you join at this moment.

  15. It’s amazing to pay a visit this website and reading the views of all colleagues concerning this post, while I am also zealous
    of getting familiarity.

  16. elegant review. Simultaneously visit my own, personal, personal site to experiment with Joker slot 123.
    This particular web site has received likability using bandar slot video games people in Dalam negri.
    Right now there are a few incredible promos after you join at the moment.

  25. Heya i am for the first time here. I found this board and I find It really useful & it helped
    me out much. I hope to give something back and
    aid others like you aided me.

  30. You made some good points there. I checked on the web for additional information about the issue
    and found most individuals will go along with
    your views on this site.

  31. really interesting review. Very visit the main site to experience
    agen slot pulsa. This internet site has received detection via judi slot betting
    challengers in Dalam negeri. There are generally
    numerous eye catching promos should you ever join now.

  34. Wow, amazing blog layout! How long have you ever been blogging for?
    you made running a blog glance easy. The full look of your web site is great, as smartly
    as the content material!

  37. Howdy! Someone in my Myspace group shared this website with us so I came to take a
    look. I’m definitely enjoying the information. I’m bookmarking and
    will be tweeting this to my followers! Terrific blog and fantastic style and
    design.

  38. Somebody necessarily lend a hand to make significantly
    posts I might state. This is the first time I frequented your web page and up to now?
    I amazed with the research you made to create this actual publish
    extraordinary. Excellent process!

  39. Its like you learn my thoughts! You appear to understand so much approximately this, such as you wrote the e-book in it or something.
    I believe that you can do with some p.c. to force the message home a little bit, however other than that, that is great blog.
    An excellent read. I’ll certainly be back.

  40. I love what you guys tend to be up too. This type of clever work
    and exposure! Keep up the wonderful works guys I’ve added you guys to
    blogroll.

  41. interesting review. Additionally visit this kind of site
    to teach yourself slot online pulsa. Which awesome web-site has received acknowledgement from the situs
    slot online video gaming persons in Indonesia.
    Certainly, there will be loads of attractive promos must anyone previously
    join currently.

  43. Hi there! I’m at work surfing around your blog from my new apple
    iphone! Just wanted to say I love reading through your
    blog and look forward to all your posts! Keep up the excellent work!

  44. Oh my goodness! Impressive article dude! Many thanks, However I am experiencing problems with your
    RSS. I don’t know why I cannot subscribe to it. Is there anybody getting similar RSS problems?
    Anyone that knows the answer will you kindly respond?

    Thanks!!

  45. Yesterday, while I was at work, my sister stole my iPad and
    tested to see if it can survive a 25 foot drop, just so she can be a youtube sensation. My apple ipad is now destroyed and
    she has 83 views. I know this is totally off topic but
    I had to share it with someone!

  46. really interesting review. Concurrently visit my very own site
    to realize game slot. The unbelievable webpage has received track record along with agen slot pulsa casino
    people in Indonesia. There are generally a number of
    splendid promos when you join during this period.

  49. I am extremely impressed along with your writing talents as neatly as with the structure on your weblog.
    Is that this a paid topic or did you customize it your self?
    Anyway stay up the nice high quality writing, it’s rare to see a nice blog like this
    one these days..

Comments are closed.