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!
Today, I went to the beach front with my children. I found
a sea shell and gave it to my 4 year old daughter and said “You can hear the ocean if you put this to your ear.”
She put the shell to her ear and screamed. There was a hermit
crab inside and it pinched her ear. She never wants
to go back! LoL I know this is totally off topic but I had to tell someone!
Heya! I just wanted to ask if you ever have any problems with hackers?
My last blog (wordpress) was hacked and I ended up losing many
months of hard work due to no data backup.
Do you have any methods to stop hackers?
Hi there to every , as I am in fact keen of reading this webpage’s post to be updated daily.
It contains nice data.
Hi there I am so excited I found your website, I really found you by error, while I was searching on Aol for something else, Nonetheless I am here now and would just like to say thanks
for a remarkable post and a all round interesting blog (I also love the theme/design), I don’t have time to look over it all at the moment
but I have book-marked it and also added your RSS feeds,
so when I have time I will be back to read much more, Please do keep up the fantastic jo.
This is my first time go to see at here
and i am actually impressed to read all at single place.
Very quickly this site will be famous among all blogging users, due to
it’s fastidious articles
I do not know if it’s just me or if everybody else experiencing problems with your blog.
It appears as though some of the text on your posts are running off the screen. Can somebody else please provide feedback and let me know if
this is happening to them too? This might be a problem
with my web browser because I’ve had this happen before.
Cheers
This post will help the internet users for building up new weblog or even a blog from start to end.
I am regular reader, how are you everybody? This post posted at this site is genuinely good.
Awesome article.
My brother suggested I might like this web
site. He was totally right. This post truly made my day. You can not imagine simply how much time I had spent
for this info! Thanks!
With havin so much written content do you ever run into
any issues of plagorism or copyright infringement?
My website has a lot of completely unique 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 permission. Do you know
any ways to help stop content from being ripped off?
I’d really appreciate it.
Hi there to every body, it’s my first go to see of this webpage; this web site contains awesome and truly fine information in favor of readers.
Hey there! This post couldn’t be written any better! Reading this post reminds me
of my old room mate! He always kept talking about this. I will forward this
page to him. Fairly certain he will have a good read. Many thanks for sharing!
Just want to say your article is as surprising. The clarity to your post is just spectacular and i could
assume you’re an expert in this subject. Fine together with your
permission allow me to seize your RSS feed to stay up to date
with coming near near post. Thanks 1,000,000
and please continue the gratifying work.
Hello to all, as I am genuinely keen of reading this
web site’s post to be updated on a regular basis. It carries nice information.
Write more, thats all I have to say. Literally, it seems as though you relied on the video
to make your point. You clearly know what youre talking about,
why throw away your intelligence on just posting videos to your
site when you could be giving us something informative to read?
It’s going to be ending of mine day, except before ending
I am reading this impressive post to improve my know-how.
You are so interesting! I do not suppose I’ve read anything like that before.
So nice to discover somebody with a few unique thoughts on this subject.
Really.. thanks for starting this up. This website is one thing that is required on the web,
someone with some originality!
I constantly spent my half an hour to read this blog’s content
all the time along with a mug of coffee.
Stop by my page: slot joker baru
I every time used to study piece of writing in news papers but now as
I am a user of internet so from now I am using net for
articles, thanks to web.
Now I am ready to do my breakfast, once having my breakfast coming again to read additional news.
This is my first time go to see at here and i am really happy
to read everthing at one place.
Hi there! Do you know if they make any plugins to assist with SEO?
I’m trying to get my blog to rank for some targeted keywords but I’m not seeing very
good results. If you know of any please share. Cheers!
Good post. I will be experiencing many of these issues
as well..
This information is priceless. Where can I find out more?
Have you ever considered about adding a little bit more than just your articles?
I mean, what you say is valuable and everything. Nevertheless imagine if you added some great images or video clips
to give your posts more, “pop”! Your content is
excellent but with images and clips, this site could definitely be one of the best in its niche.
Good blog!
Hi it’s me, I am also visiting this site on a regular basis, this web page is truly nice and
the visitors are truly sharing pleasant thoughts.
Saved as a favorite, I love your web site!
Everything is very open with a clear clarification of the challenges.
It was truly informative. Your site is useful. Thanks for sharing!
Genuinely no matter if someone doesn’t be aware of then its up to other viewers that they will help, so here
it occurs.
Every weekend i used to visit this website, as i wish for enjoyment, for the reason that this this web page conations in fact fastidious funny data too.
You’re so cool! I do not believe I have read through something like this before.
So great to discover someone with some unique thoughts on this issue.
Seriously.. thanks for starting this up. This web site is one
thing that’s needed on the web, someone with some originality!
I know this if off topic but I’m looking into starting my own blog
and was curious 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 smart so I’m not 100% sure.
Any recommendations or advice would be greatly appreciated.
Thanks
Hello everyone, it’s my first pay a quick visit at this web page,
and piece of writing is really fruitful for me, keep up posting these content.
I don’t even know the way I finished up here, but I believed
this publish was once good. I don’t understand
who you’re however definitely you’re going to a well-known blogger should you aren’t already.
Cheers!
I will right away take hold of your rss feed as I can not find your email subscription link or e-newsletter service.
Do you have any? Please permit me understand in order that I may just subscribe.
Thanks.
I’m impressed, I have to admit. Seldom do I come across a blog that’s both equally educative and engaging, and without a doubt, you’ve hit the nail on the
head. The problem is something that too few folks are
speaking intelligently about. I’m very happy I stumbled across this in my search for something concerning this.
Hi, Neat post. There’s a problem together with your web site in web explorer,
might check this? IE still is the marketplace chief and a big
component of people will leave out your great writing because
of this problem.
First off I would like to say great blog! I had a quick question in which I’d like to ask if you don’t
mind. I was interested to know how you center yourself and clear your head prior to writing.
I’ve had difficulty clearing my thoughts in getting
my ideas out there. I truly do enjoy writing however it just seems like the
first 10 to 15 minutes are wasted simply just trying to figure out how to begin. Any recommendations
or hints? Kudos!
This is my first time pay a visit at here and i am
genuinely pleassant to read everthing at alone place.
Please let me know if you’re looking for a article author
for your weblog. You have some really good articles and I think I would be
a good asset. If you ever want to take some of the load off,
I’d love to write some articles for your blog in exchange for a link back to mine.
Please shoot me an email if interested. Thanks!
I am really loving the theme/design of your web site.
Do you ever run into any browser compatibility problems?
A couple of my blog audience have complained about my site not working correctly in Explorer but
looks great in Firefox. Do you have any ideas to help fix this problem?
I loved as much as you will receive carried out right here.
The sketch is tasteful, your authored material stylish.
nonetheless, you command get bought an impatience over that you wish be
delivering the following. unwell unquestionably come further formerly again as exactly the same nearly a lot often inside
case you shield this hike.
Hi there I am so glad I found your web site, I really found
you by accident, while I was researching on Askjeeve for something
else, Regardless I am here now and would just like
to say thanks a lot for a tremendous 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 moment but
I have book-marked it and also added your RSS feeds, so when I
have time I will be back to read much more, Please do keep up
the fantastic job.
First of all I want to say terrific blog! I had a quick question that I’d
like to ask if you don’t mind. I was interested to know how you center yourself and
clear your mind before writing. I’ve had difficulty clearing my mind
in getting my ideas out. I do take pleasure in writing however it just seems like the first 10
to 15 minutes are generally wasted simply just trying to figure
out how to begin. Any ideas or tips? Appreciate it!
I don’t even know the way I finished up right here, however I believed this post was once great.
I don’t realize who you’re however certainly you’re going to a famous
blogger in the event you aren’t already. Cheers!
Hi would you mind letting me know which webhost you’re using?
I’ve loaded your blog in 3 different internet browsers and I must say this
blog loads a lot faster then most. Can you recommend a good hosting provider at
a fair price? Thanks a lot, I appreciate it!
Hey there! Do you know if they make any plugins to safeguard against hackers?
I’m kinda paranoid about losing everything I’ve worked
hard on. Any tips?
It’s really a great and helpful piece of info.
I’m happy that you shared this useful info with us.
Please stay us up to date like this. Thanks for sharing.