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!
I am regular reader, how are you everybody? This piece of writing posted
at this web page is really fastidious.
Ahaa, its good conversation concerning this post at this place at this weblog,
I have read all that, so at this time me also commenting
here.
I think that is among the such a lot important information for me.
And i am satisfied studying your article. But should
observation on few normal issues, The web site style is perfect, the
articles is in reality nice : D. Just right job, cheers
Attractive part of content. I just stumbled upon your website and in accession capital to say
that I acquire actually loved account your blog posts.
Anyway I will be subscribing on your feeds or even I achievement you get
admission to persistently quickly.
Nice post. I used to be checking constantly this blog and
I’m inspired! Very useful info specifically the
remaining phase 🙂 I maintain such info a lot.
I was seeking this certain information for a long time.
Thanks and good luck.
Thanks to my father who told me regarding this website,
this web site is actually awesome.
A fascinating discussion is worth comment. There’s no doubt that that you need to write more about this topic,
it may not be a taboo matter but usually folks don’t
discuss such topics. To the next! Kind regards!!
Hi there, its fastidious article regarding media print,
we all be familiar with media is a great source of data.
It is in reality a great and useful piece of information. I’m satisfied that you
shared this helpful information with us. Please keep us informed like
this. Thank you for sharing.
I was curious if you ever considered changing the layout of your blog?
Its very well written; I love what youve got to say. But maybe you could a little more in the way
of content so people could connect with it better. Youve got an awful lot of text for only having 1 or 2 pictures.
Maybe you could space it out better?
Everything is very open with a really clear
clarification of the challenges. It was really informative.
Your site is very useful. Many thanks for sharing!
Paragraph writing is also a excitement, if you be familiar with then you can write or else it is complex to write.
Hey I know this is off topic but I was wondering if you knew of
any widgets I could add to my blog that automatically tweet my newest twitter
updates. I’ve been looking for a plug-in like this
for quite some time and was hoping maybe you would have some experience
with something like this. Please let me know if you run into anything.
I truly enjoy reading your blog and I look forward to your new updates.
Currently it seems like BlogEngine is the best blogging platform available right now.
(from what I’ve read) Is that what you are using on your
blog?
Hi this is somewhat of off topic but I was wanting to know if blogs use WYSIWYG editors or if you have to manually code with HTML.
I’m starting a blog soon but have no coding skills so I
wanted to get advice from someone with experience.
Any help would be greatly appreciated!
It’s appropriate time to make a few plans for the future and it is time to be
happy. I have read this publish and if I may just I
wish to recommend you some fascinating things or suggestions.
Maybe you could write subsequent articles referring
to this article. I want to read even more issues about it!
Thank you for the auspicious writeup. It in fact was once a entertainment account it.
Look complex to far introduced agreeable from you! However, how can we keep
up a correspondence?
Hi! I understand this is somewhat off-topic however I needed to ask.
Does operating a well-established website like
yours take a lot of work? I’m brand new to writing a blog however I
do write in my journal daily. I’d like to start a blog
so I can share my own experience and thoughts online.
Please let me know if you have any kind of suggestions or tips for brand new aspiring blog owners.
Thankyou!
You are so cool! I do not think I’ve truly read through a
single thing like that before. So great to find another person with original thoughts on this topic.
Really.. thanks for starting this up. This site is one thing that’s needed
on the internet, someone with a bit of originality!
Generally I do not learn article on blogs, however I would like to say that
this write-up very forced me to check out and
do it! Your writing taste has been amazed me. Thank you,
very great post.
Hi there, just became aware of your blog through
Google, and found that it is really informative. I am going to watch
out for brussels. I will appreciate if you continue this {in future}.
A lot of people will be benefited from your writing. Cheers!
Spot on with this write-up, I actually believe this web site needs much more attention. I’ll probably be
back again to see more, thanks for the info!
Hey there, You’ve done an incredible job. I will certainly
digg it and personally suggest to my friends. I am sure they will be benefited from this web site.
Thanks for sharing your info. I really appreciate your efforts
and I will be waiting for your further write ups thank
you once again.
Hello, its pleasant paragraph regarding media print,
we all understand media is a fantastic source of information.
Sweet blog! I found it while searching on Yahoo News.
Do you have any tips on how to get listed in Yahoo News?
I’ve been trying for a while but I never seem to get there!
Many thanks
Hello all, here every person is sharing such know-how, so it’s pleasant to read this web site,
and I used to go to see this webpage daily.
Please let me know if you’re looking for a article author for
your site. You have some really good posts and I believe I
would be a good asset. If you ever want to take some of the load off, I’d absolutely love to write some material for your blog in exchange for a link
back to mine. Please send me an email if interested.
Many thanks!
of course like your web-site however you have to take a look at the spelling on several of your posts.
Many of them are rife with spelling problems
and I find it very bothersome to inform the truth on the
other hand I will definitely come again again.
Thank you for every other informative site. The place else could
I get that kind of info written in such a perfect way? I’ve a undertaking that I am simply now running on,
and I have been at the glance out for such info.
When some one searches for his required thing, so he/she wishes to be available that in detail, thus that thing is maintained over here.
We are a group of volunteers and starting a new scheme in our community.
Your website provided us with valuable info to work
on. You have done an impressive job and our entire community will be thankful to you.
Simply wish to say your article is as amazing. The clarity in your post is
simply excellent and i can assume you’re an expert on this subject.
Well with your permission allow me to grab your RSS feed to keep updated with forthcoming post.
Thanks a million and please continue the rewarding work.
Hey there, I think your website might be having browser compatibility issues.
When I look at your blog in Opera, 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!
Fabulous, what a weblog it is! This blog gives useful facts to us, keep it up.
Very nice post. I simply stumbled upon your blog and wished to say that I have really loved browsing your weblog posts.
After all I’ll be subscribing on your rss feed and I’m hoping
you write again soon!
If some one desires expert view on the topic of blogging afterward i propose him/her
to visit this blog, Keep up the good work.
Nice post. I was checking continuously this blog and I’m impressed!
Very helpful information particularly the last
part 🙂 I care for such info a lot. I was seeking this certain information for a long time.
Thank you and best of luck.
Hi there colleagues, how is everything, and what you
want to say regarding this post, in my view its genuinely remarkable in support of
me.
I would like to thank you for the efforts you’ve put in penning this blog.
I am hoping to view the same high-grade content by you later on as well.
In fact, your creative writing abilities has motivated me to get my own site now 😉
Hmm is anyone else experiencing problems with the images on this
blog loading? I’m trying to figure out if its a problem on my end or
if it’s the blog. Any feed-back would be greatly
appreciated.
What’s Happening i’m new to this, I stumbled upon this
I’ve discovered It positively useful and it has helped me out loads.
I’m hoping to give a contribution & aid different customers like its helped me.
Great job.
Nice post. I learn something new and challenging on websites
I stumbleupon every day. It will always
be useful to read content from other authors and use
a little something from their web sites.
Great website. Lots of helpful information here.
I’m sending it to some pals ans also sharing in delicious.
And of course, thank you on your effort!
Do you have a spam issue on this blog; I also am a blogger, and I was wondering your situation; many of us have created some nice practices
and we are looking to exchange techniques with other folks, please shoot me an e-mail if interested.
It’s an remarkable piece of writing designed for all the internet viewers;
they will take benefit from it I am sure.
I read this post completely concerning the comparison of most
recent and previous technologies, it’s amazing article.
Hey there! Quick question that’s completely
off topic. Do you know how to make your site mobile friendly?
My web site looks weird when browsing from my iphone. I’m trying to find a theme or plugin that might be able to correct this issue.
If you have any suggestions, please share. Cheers!
Way cool! Some extremely valid points! I appreciate you penning this write-up plus the rest of the site is
also very good.
Just wish to say your article is as amazing.
The clearness in your post is simply nice and i can assume you’re an expert on this subject.
Well with your permission let me to grab your feed to keep updated with forthcoming post.
Thanks a million and please continue the gratifying work.