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!
Very good article. I definitely love this website. Stick with it!
Pretty nice post. I just stumbled upon your weblog and wished to say that I’ve truly enjoyed browsing your
blog posts. In any case I will be subscribing to your rss feed and I hope you write again soon!
I am truly delighted to glance at this weblog posts which carries plenty of
helpful information, thanks for providing these statistics.
Hi, I do believe this is an excellent site.
I stumbledupon it 😉 I’m going to return once again since i have book
marked it. Money and freedom is the best way to change, may you be
rich and continue to help other people.
Heya i’m for the primary time here. I found this board and
I to find It truly helpful & it helped me out much. I’m hoping to present one
thing back and help others like you helped me.
What’s up, its good paragraph about media print, we all be
familiar with media is a great source of facts.
I’m not sure exactly why but this blog is loading incredibly slow for me.
Is anyone else having this issue or is it a issue
on my end? I’ll check back later on and see if the problem still exists.
fantastic issues altogether, you just won a new reader.
What might you recommend in regards to your publish that you made a
few days ago? Any positive?
With havin so much content and articles do you ever run into any issues of plagorism
or copyright violation? My site has a lot of unique content I’ve either created myself or outsourced but
it appears a lot of it is popping it up all over the internet without
my permission. Do you know any methods to help reduce content from
being ripped off? I’d truly appreciate it.
Thankfulness to my father who stated to me regarding this web site, this webpage is
actually awesome.
Hi there, I discovered your website by means of Google while looking
for a related topic, your site got here up, it
appears to be like good. I have bookmarked it in my google bookmarks.
Hello there, simply changed into alert to your blog
via Google, and located that it’s really informative.
I’m gonna be careful for brussels. I will be grateful if you
proceed this {in future}. Many folks will likely be benefited from your writing.
Cheers!
Hello there! I could have sworn I’ve been to this blog before but after reading through some of the post I realized it’s new to me.
Anyways, I’m definitely glad I found it and I’ll be
book-marking and checking back frequently!
Unquestionably consider that which you said. Your favourite reason appeared to be at the internet the simplest thing
to take note of. I say to you, I definitely get irked even as folks consider concerns that they plainly don’t
recognise about. You controlled to hit the nail upon the top and defined out the whole thing with no
need side-effects , people could take a signal.
Will probably be back to get more. Thank you
Hi! This is my first visit to your blog! We are a collection of volunteers and
starting a new initiative in a community in the same niche.
Your blog provided us beneficial information to work
on. You have done a outstanding job!
I’ve been surfing online more than three hours today, yet I never found any interesting article like yours.
It is pretty worth enough for me. Personally, if all webmasters and bloggers made good content as you did, the web will be a lot
more useful than ever before.
Great post.
Every weekend i used to go to see this web page, because i want enjoyment, since this this
website conations actually nice funny information too.
I really like what you guys tend to be up too. This kind of clever work and coverage!
Keep up the good works guys I’ve incorporated
you guys to my personal blogroll.
you are truly a excellent webmaster. The site loading pace is incredible.
It sort of feels that you are doing any distinctive trick.
Also, The contents are masterwork. you have done a great activity in this subject!
After looking at a handful of the articles on your web
page, I really appreciate your way of writing a
blog. I saved as a favorite it to my bookmark webpage list and will be checking back in the near future.
Please visit my website too and tell me what you
think.
Howdy very cool website!! Man .. Excellent .. Superb ..
I’ll bookmark your site and take the feeds
additionally? I am glad to find so many useful information here
in the publish, we need develop more strategies
in this regard, thanks for sharing. . . . .
.
I have been exploring for a little bit for any high quality articles
or blog posts on this kind of house . Exploring in Yahoo I
eventually stumbled upon this site. Studying
this info So i’m satisfied to convey that I have a very good uncanny feeling I
found out exactly what I needed. I so much for sure will make sure to
don?t disregard this website and give it a look on a constant basis.
Great blog here! Also your site loads up fast!
What web host are you using? Can I get your affiliate link to your host?
I wish my web site loaded up as fast as yours lol
For latest information you have to go to see world wide web and
on internet I found this web site as a most excellent site for newest updates.
You are so interesting! I do not suppose I’ve read anything like this before.
So wonderful to find somebody with some original thoughts on this topic.
Seriously.. thank you for starting this up.
This website is something that’s needed on the internet, someone with a little originality!
I visited multiple blogs but the audio feature for audio
songs current at this web site is actually fabulous.
What i do not realize is in truth how you are no longer actually much more neatly-preferred than you might be now.
You’re very intelligent. You already know thus
considerably relating to this topic, made me in my opinion believe
it from so many varied angles. Its like men and women aren’t interested
except it is something to accomplish with Woman gaga! Your personal stuffs outstanding.
All the time care for it up!
Джой порноказино порно периодически предлагает частично вернуть потраченные средства.
Cashback получают в основном опытные игроки.
Cashback реально получать раз в месяц.
Величина кешбэка указывается в специальной графе персонального кабинета.
I feel this is one of the so much significant
information for me. And i am glad studying your article.
However should remark on some normal issues, The site taste is
great, the articles is really nice : D. Good job,
cheers
Asking questions are genuinely nice thing if you are not understanding something
entirely, but this article presents fastidious understanding yet.
I was suggested this web site by my cousin. I’m not sure whether this post is written by him as no one else know such detailed about my problem.
You are amazing! Thanks!
Yesterday, while I was at work, my sister stole
my iPad and tested to see if it can survive a thirty 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!
I am curious to find out what blog platform you happen to be
using? I’m experiencing some small security issues with my latest blog and I would like to find something more risk-free.
Do you have any recommendations?
Asking questions are actually pleasant thing if you are not
understanding anything fully, except this piece of writing offers nice understanding yet.
Hi, i feel that i noticed you visited my weblog so i came to return the desire?.I’m attempting to find things to improve
my site!I guess its good enough to make use of some of your concepts!!
It’s an remarkable paragraph designed for all the web viewers; they will get advantage from it
I am sure.
This site truly has all the information and facts I wanted concerning this subject and didn’t know
who to ask.
Aw, this was a really good post. Finding the time
and actual effort to generate a good article… but what
can I say… I put things off a whole lot and never manage to get nearly anything done.
It’s an amazing piece of writing for all the web viewers; they
will take benefit from it I am sure.
Hello there, just became aware of your blog through Google, and found that it’s really informative.
I’m going to watch out for brussels. I will appreciate
if you continue this {in future}. Numerous people will be benefited
from your writing. Cheers!
constantly i used to read smaller content which also clear their motive,
and that is also happening with this paragraph which I am reading here.
This is really attention-grabbing, You are an overly skilled blogger.
I’ve joined your feed and sit up for in quest of more
of your great post. Also, I have shared your web site in my social
networks
What’s up mates, how is the whole thing, and what you desire to say
about this post, in my view its in fact amazing for me.
I simply could not go away your web site before suggesting that I extremely enjoyed the standard information an individual provide
to your guests? Is going to be back frequently in order to inspect new posts
Wonderful beat ! I wish to apprentice at the same time
as you amend your web site, how could i subscribe
for a blog site? The account aided me a appropriate deal.
I were tiny bit acquainted of this your broadcast offered bright
clear concept
Have you ever thought about creating an e-book or guest authoring on other websites?
I have a blog centered on the same information you discuss
and would really like to have you share some
stories/information. I know my audience would appreciate your work.
If you’re even remotely interested, feel free to shoot me an email.
Do you mind if I quote a few of your posts as long as I provide
credit and sources back to your webpage? My blog is in the very same niche as yours and
my users would truly benefit from a lot of the information you present here.
Please let me know if this alright with you. Cheers!
It’s appropriate time to make some plans for the longer term and it is time to be happy.
I’ve read this put up and if I may just I desire to counsel you some attention-grabbing
things or suggestions. Perhaps you could write subsequent articles referring to this
article. I wish to learn even more things approximately it!
I got this site from my buddy who told me on the topic of
this site and now this time I am browsing this web site and reading very informative articles at this time.
Hi there Dear, are you in fact visiting this web page regularly, if so afterward
you will definitely obtain fastidious experience.