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!
Hi! I just wanted to ask if you ever have any issues with
hackers? My last blog (wordpress) was hacked and I ended up losing many months of hard work due to no back up.
Do you have any methods to stop hackers?
Woah! I’m really enjoying the template/theme of this site.
It’s simple, yet effective. A lot of times it’s very difficult
to get that “perfect balance” between superb usability and
appearance. I must say you’ve done a great
job with this. Additionally, the blog loads very fast for me
on Internet explorer. Superb Blog!
Wow! After all I got a weblog from where I know how to really get
valuable information regarding my study and knowledge.
Write more, thats all I have to say. Literally, it seems as though you relied on the video to
make your point. You obviously know what youre talking
about, why throw away your intelligence on just
posting videos to your weblog when you could be giving
us something enlightening to read?
Wow, this article is nice, my sister is analyzing such things, so I am going to let know her.
Every weekend i used to pay a quick visit this website, for the reason that
i wish for enjoyment, as this this web page conations actually fastidious funny
stuff too.
You’ve made some decent points there. I checked
on the internet for more info about the issue and found
most people will go along with your views on this site.
I have been surfing online more than 3 hours as of late, yet I by no means discovered any
fascinating article like yours. It’s beautiful value sufficient for
me. In my opinion, if all site owners and bloggers made just right content
as you probably did, the web might be much more helpful than ever
before.
Heya this is kinda of off topic but I was wondering if blogs use
WYSIWYG editors or if you have to manually code with HTML.
I’m starting a blog soon but have no coding expertise so I wanted to get guidance from someone with experience.
Any help would be enormously appreciated!
At this time I am going away to do my breakfast, afterward having my breakfast coming over again to read other news.
My partner and I stumbled over here by a different page and thought I might as well
check things out. I like what I see so now i am following you.
Look forward to looking at your web page again.
Howdy I am so happy I found your web site, I really found you by
accident, while I was looking on Digg for something else,
Anyways I am here now and would just like to say kudos for a incredible post
and a all round thrilling blog (I also love the theme/design), I don’t have time to read it all at the moment but I have book-marked it and also added in your RSS feeds, so
when I have time I will be back to read a lot more, Please do keep up the fantastic job.
After looking over a handful of the articles on your site,
I seriously appreciate your way of blogging.
I book marked it to my bookmark site list and will be checking back
in the near future. Please check out my web site too and tell me how you feel.
I have been surfing on-line greater than three hours as
of late, but I never found any fascinating article like yours.
It is lovely worth enough for me. Personally, if all website owners and bloggers
made excellent content material as you did, the internet shall
be much more useful than ever before.
Hello there I am so happy I found your web site, I really found you by mistake, while I was
looking on Aol for something else, Nonetheless I am here now and would just like to say cheers for a remarkable post and a all
round thrilling blog (I also love the theme/design),
I don’t have time to look over it all at the minute but I have book-marked it and also added in your RSS feeds, so when I have time I
will be back to read much more, Please do keep up
the superb b.
You really make it seem so easy with your presentation but I find this topic to be really something that I think I would never understand.
It seems too complicated and extremely broad for me.
I’m looking forward for your next post, I’ll try to get the hang
of it!
First off I want to say superb 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 have had a hard time clearing my thoughts in getting my
ideas out. I truly do enjoy writing but it just seems like the first 10 to
15 minutes are wasted simply just trying to figure out how to begin. Any suggestions
or hints? Cheers!
Hello I am so glad I found your weblog, I really found you by mistake, while I
was researching on Google for something else, Nonetheless I am here now and would just like to say thanks a lot for a incredible post
and a all round interesting blog (I also love the theme/design), I don’t have time to read it all at the minute
but I have bookmarked it and also added in your RSS feeds, so when I have time I
will be back to read much more, Please do keep up the
great b.
Nice respond in return of this issue with genuine arguments and describing all regarding that.
Quality articles is the key to attract the visitors to pay a quick visit
the site, that’s what this website is providing.
I’m now not positive the place you are getting your info, however great
topic. I must spend some time studying more or understanding more.
Thanks for fantastic info I was on the lookout for this information for my mission.
Today, I went to the beach with my kids. 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 placed 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 entirely off topic but I had to
tell someone!
Hi there just wanted to give you a quick heads up.
The words in your article seem to be running off the screen in Firefox.
I’m not sure if this is a formatting issue or something to do with web browser compatibility but I thought I’d post to let you know.
The design and style look great though! Hope you get the
problem resolved soon. Thanks
My developer is trying to persuade me to move to .net from PHP.
I have always disliked the idea because of
the expenses. But he’s tryiong none the less.
I’ve been using Movable-type on several websites for about a year
and am worried about switching to another platform. I have heard good things about blogengine.net.
Is there a way I can transfer all my wordpress posts into it?
Any kind of help would be greatly appreciated!
It’s an remarkable paragraph for all the web
users; they will take advantage from it I am sure.
Hi! 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?
Generally I don’t read post on blogs, however I would like to say that this write-up very compelled me
to take a look at and do so! Your writing style has been surprised
me. Thank you, very great post.
Quality articles is the key to attract the users to visit the web page,
that’s what this web page is providing.
What’s up, this weekend is fastidious in favor of me, since this moment i am reading this fantastic informative paragraph here
at my residence.
It’s remarkable for me to have a web site, which is useful for my experience.
thanks admin
Very good post. I am dealing with some of these issues as well..
Hi there to every single one, it’s truly a good for me to visit this website, it includes priceless
Information.
It’s really very complex in this full of activity life
to listen news on TV, so I simply use world wide web for that reason, and get the hottest news.
really interesting review. Moreover visit definitely the site to utilize slot deposit pulsa.
This page has received ranking right from slot via pulsa gambling cricket fans in Indonesia.
At this time there are generally loads of attractive promos in case people join at this moment.
I could not refrain from commenting. Very well written!
What a information of un-ambiguity and preserveness of precious know-how about unexpected
feelings.
Spot on with this write-up, I really believe this amazing site needs far more attention. I’ll probably be back again to
read through more, thanks for the info!
Nice blog here! Also your website loads up very
fast! What host are you using? Can I get your affiliate link
to your host? I wish my website loaded up as quickly as yours lol
We are a group of volunteers and starting a new scheme in our community.
Your site offered us with valuable info to work on. You’ve done
a formidable job and our whole community will be thankful to you.
Hi there to all, the contents present at this site are really
awesome for people knowledge, well, keep up the good work
fellows.
Hi there! Do you know if they make any plugins to help
with SEO? I’m trying to get my blog to rank for some targeted keywords but I’m not seeing very
good success. If you know of any please share. Kudos!
Excellent blog! Do you have any tips for aspiring writers?
I’m planning to start my own website soon but I’m
a little lost on everything. Would you suggest starting with a free platform like
Wordpress or go for a paid option? There are so many choices out there that I’m completely overwhelmed ..
Any suggestions? Thank you!
appealing review. Moreover visit the best site to achieve slot deposit
pulsa tanpa potongan. The amazing internet site has received endorsement using slot online
internet casino gamers in Negara sendiri. Generally there are usually many expected promos just in case you join at present.
You can definitely see your expertise in the work you write.
The arena hopes for even more passionate writers such as you who aren’t afraid to say how they believe.
All the time follow your heart.
This is my first time visit at here and i am genuinely pleassant to read everthing at
single place.
I always spent my half an hour to read this blog’s content daily along with a mug of
coffee.
Heya! I understand this is kind of off-topic however I had to ask.
Does building a well-established website like yours take
a large amount of work? I am completely new to running a blog but
I do write in my diary every day. I’d like to start a blog so I will be able to share my experience and
feelings online. Please let me know if you have any suggestions or tips for brand new aspiring blog owners.
Appreciate it!
Wow, incredible weblog structure! How long have you ever
been blogging for? you make running a blog look easy. The overall glance of your web site is magnificent, let alone
the content material!
It’s amazing to visit this web site and reading
the views of all friends on the topic of this paragraph, while I am also keen of getting
experience.
Can you tell us more about this? I’d want to find out more
details.