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 think this is among the most vital information for me. And i am glad reading your article.

    But should remark on few general things, The web site style is ideal, the articles is
    really great : D. Good job, cheers

  2. Link exchange is nothing else except it is just placing the other person’s weblog link on your page at suitable place and other person will also do similar for you.

  3. Wonderful goods from you, man. I’ve remember your stuff prior to and you’re simply extremely wonderful.
    I actually like what you have bought here, certainly like what you’re saying and the way wherein you say it.
    You make it enjoyable and you still take care of to stay it smart.
    I can not wait to learn far more from you.
    This is really a terrific web site.

  6. I do accept as true with all of the concepts you’ve offered on your post.
    They are really convincing and can certainly work. Still, the posts are too quick for beginners.

    May you please lengthen them a little from subsequent time?
    Thank you for the post.

  7. I have been browsing online greater than three hours as of late, yet I never found any attention-grabbing article like
    yours. It is pretty worth sufficient for me. In my opinion, if all
    site owners and bloggers made excellent content material as you did, the internet will be much more helpful than ever before.

  8. Thanks for ones marvelous posting! I really enjoyed reading it, you
    are a great author. I will make certain to bookmark your blog and may come back in the future.
    I want to encourage you to definitely continue your great writing,
    have a nice weekend!

  9. Article writing is also a excitement, if you be acquainted with afterward you can write if not it is complicated to write.

  13. Its like you read my mind! You seem to know so much about this, like
    you wrote the book in it or something. I think that you can do with some pics to drive the message home a little bit, but other than that, this is excellent blog.
    A great read. I’ll definitely be back.

  14. Hi there! Someone in my Myspace 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! Wonderful blog and terrific design and style.

  15. Heya i am for the first time here. I came across
    this board and I in finding It really useful & it helped me out
    much. I’m hoping to give one thing back and aid others like you helped
    me.

  16. Hello, i think that i saw you visited my weblog so i came
    to “return the favor”.I’m attempting to find things to improve my web site!I suppose its ok to
    use some of your ideas!!

  21. Fantastic beat ! I would like to apprentice at the same
    time as you amend your website, how could i subscribe for
    a blog site? The account helped me a acceptable deal. I
    have been a little bit familiar of this your broadcast provided vivid transparent concept

  22. Dass Haare beim Gesamterscheinungsbild eine wichtige Von Bedeutung, haben Frauen längst verstanden. Ist die Frisur
    typgerecht und top gesund und munter, fallen kleine Schwächen in Hinblick auf Outfit weit weniger ins Gewicht.
    Die Frisur prägt den Look – und setzt genau die
    Akzente, die ihrer Trägerin wichtig sind.

    Die Klassiker unter den Damenfrisuren: Bob und Co.

    Die Wahl der richtigen Damenfrisur ist daher viel wichtiger als die Entscheidung für oder gegen ein bestimmtes Paar Schuhe,
    wie etwa. Mittellange Damenhaarschnitte sind erfreulicherweise wieder oft zu sehen. Man trägt auch wieder kürzer –
    endlich! Sehr begrüßenswert ist in diesem Zug
    die Rückkehr des Bob – einem echten Frisurenklassiker,
    den es in unzähligen Varianten gibt. Und der übrigens fast jeder
    Frau gut zu Gesicht steht! Jung, frech und trendig ist auch der
    Long Bob – und zudem eine tolle Alternative für Frauen, die sich
    gerne von ihrer Langhaarmähne verabschieden möchten, aber nicht so recht wissen, wie.

  25. I just couldn’t depart your web site before suggesting that I
    really enjoyed the standard information a person supply for your guests?
    Is gonna be back incessantly to check out new posts

  28. Nur fünfzehn Minuten auf Schusters Rappen vom Ortszentrum entfernt, findet sich Cala Agulla, eine malerische Bucht
    die in der Hochsaison – im Juli und im August –
    a fortiori von Familien und in der Vor- und Nachsaison, von jungen Leuten bevölkert wird.
    Dennoch gilt, dass die äußeren Strandgebiete der Cala
    Agulla eher ruhig sind und zum Entspannen einladen, der mittlere Teil dagegen als beliebte Partyzone bekannt
    ist. Wer seine Zeit in Cala Ratjada neben anderen das Familie verbringt und auf der Suche nach familienfreundlichen Stränden ist, allen grund haben die Cala
    Son Moll und die Cala Gat einmal genauer anschauen. Beide Strände sind eingebettet
    in eine unvergleichlich schöne Landschaft und bieten auf den fuß der Stadt
    viel Ruhe und Platz ums Strandleben zu genießen. Auch
    die Cala Mesquida, ein bei Surfern sehr beliebter Strand
    befindet sich in der Nähe von Cala Ratjada.
    Wer den Strand besuchen möchte, sollte allerdings über ein Auto verfügen.

  29. An interesting discussion is worth comment.

    I think that you need to write more on this subject matter, it might not be a taboo matter but usually people do not speak about these issues.

    To the next! All the best!!

  31. Der Skibus hält direkt vorm Haus. Hier findet Ihr die passenden Pensionen,
    Ferienhäuser & Skihotels. Die Preise gelten pro
    Kopf und pro Woche. Mitten zentral von Stumm im Zillertal befindet sich unser Appartementhaus Kaltenbach-Stumm mit gut
    ausgestatteten Ferienwohnungen. Wir Unterricht geben unseren aktuellen Angeboten weitere
    tolle Skireisen für Euren Skiurlaub im Zillertal. Nicht das
    Richtige für Euch? Also lasst die Seele baumeln, denn die Sauna mit Ruheraum kann kostenfrei
    genutzt werden. Die Preise gelten pro Kopf und pro Woche.

    Die komfortablen Appartements für 4-9 Personen sind großzügig und gemütlich eingerichtet.

    Der Skibus hält ca. Gerne! Ob Gruppenreise, Ski-Kurzurlaub oder einfach nur günstige Skireisen: wir haben die passenden freien Unterkünfte im
    Zillertal und den restlichen Alpen für Euren Winterurlaub im
    Programm. Die Aufenthalte sind inkl. 2,5 km vom Zentrum von Mayrhofen entfernt.
    Skipass buchbar – auch die Kurztripps! Mit unseren Appartements
    wird Eure Skireise zum reinsten Wellness-Urlaub.
    Auf Schusters Rappen sind Gasthöfe, Restaurants, Geschäfte und der Supermarkt bequem zu erreichen. Wollt Ihr noch etwas?
    50 m vom Haus entfernt.

  34. You really make it seem really easy together with your
    presentation however I in finding this matter to be really something which I believe I would
    never understand. It kind of feels too complicated and very huge for
    me. I’m looking ahead for your subsequent publish, I will attempt to
    get the hang of it!

  37. What’s Happening i’m new to this, I stumbled upon this I’ve found It positively
    useful and it has aided me out loads. I’m hoping to give a contribution &
    assist different customers like its aided me.
    Great job.

  39. I am not positive where you are getting your info, however great topic.
    I needs to spend some time learning much more or understanding more.
    Thanks for great info I used to be looking for this information for my mission.

  40. What i don’t understood is in reality how you’re no longer actually a
    lot more neatly-liked than you may be right now.
    You are very intelligent. You recognize therefore considerably in relation to this matter, produced me personally consider it from so many varied angles.

    Its like men and women are not fascinated except it is one thing to do with Woman gaga!
    Your individual stuffs nice. At all times maintain it up!

  41. Wer im Urlaub oder im Büro nicht nur Fotos sehen möchte, die der
    Saugroboter während seiner Arbeit macht, sondern dieses Gerät
    auch mit allen seinen Funktionen steuern möchte,
    für den ist ein Saugroboter mit einer App-Fernsteuerung genau das richtige.
    Im Gegensatz zur klassischen Fernbedienung, über die heutzutage
    praktisch jeder Saugroboter verfügt, sind Geräte mit einer App-Fernsteuerung erst im
    Kommen. So sind sie z.B. Allerdings sind solche Geräte meist erheblich vielseitiger als ihre klassischen Konkurrenten ohne App-Fernsteuerung.

    Lage, den Wohnraum mit einer integrierten Kamera mit Bewegungssensor zu überwachen, sie können Mails mit
    Fotos an den Besitzer schicken und gezielt in Wohnräumen nachschauen,
    ob das Licht (oder z.B. Insgesamt können Saugroboter auch
    völlig ohne Licht arbeiten. Zu beachten ist aber: Staubsaugerroboter mit Kamera-Navigation finden sich in abgedunkelten Räumen nicht mehr zurecht, ihre Navigation versagt hier völlig.
    Dagegen funktioniert die Steuerung über virtuelle Wände bzw.

    Leuchttürme auch in völlig dunklen Räumen hervorragend, da hier mit unsichtbaren Infrarotstrahlen gearbeitet
    wird.

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

  43. 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. Personally, if all web owners and bloggers made good content as
    you did, the web will be a lot more useful than ever before.

  44. I love your blog.. very nice colors & theme.
    Did you design this website yourself or did you hire someone to
    do it for you? Plz answer back as I’m looking to construct my own blog and would like to find out where u got this from.
    appreciate it

  45. Excellent items from you, man. I have bear in mind your stuff previous to and you’re just
    extremely excellent. I really like what you have obtained right
    here, really like what you are stating and the way in which in which you say
    it. You’re making it entertaining and you still care for to keep it smart.
    I cant wait to learn far more from you. That is actually a wonderful web site.

  47. Attractive section of content. I just stumbled upon your weblog and in accession capital to assert that I acquire actually enjoyed account your blog posts.
    Anyway I’ll be subscribing to your augment and even I achievement you access
    consistently quickly.

  49. Hmm it looks like your website ate my first comment (it was extremely
    long) so I guess I’ll just sum it up what I submitted and say, I’m thoroughly enjoying your blog.
    I as well am an aspiring blog blogger but I’m still new to everything.
    Do you have any suggestions for first-time blog writers?
    I’d definitely appreciate it.

Comments are closed.