My bootstrapped company sells highly complex B2B SaaS to SMBs/SMEs. Here are some lessons/advice:

- Not all SMBs/SEMs are same. You have to still define more narrowly your Ideal Customer Profile or ICP. For example, for us, the price point averages 12-20k USD/Year. This prices out startups or people who are just getting started. We look for SMBs that are established and already doing what we sell in some capacity.

- Pricing is very hard to get right and you have to constantly evolve. We started with $199/Month plans and now sell min. $12k/Year (with some extreme exceptions). Dont worry about getting it right once. Keep evolving with time and customer demand.

- Competition is important to be aware of but don't go nuts trying to keep up with them. Most likely, they will outpace you at everything with more funding, bigger teams etc. Just focus on what u can do best. In a crowded B2B market, competition won't kill you necessarily. Everyone can get a piece of the pie. Focus on your share.

- SMBs size can vary and technically a 2 person company is an SMB and a 100 person company is also an SMB. So the sales cycle will vary depending on the size of your customer.

- In the early days (less than say ~50 customers in B2B), you the founder(s) are the sales person. You cannot hire a sales team magically on Day 1 and expect them to sell a complex product that you understand the best. Won't work. If you are not willing to sell it yourself, forget about it.

- To do it yourself, you will have to figure out how to do outbound (you find potential leads) and inbound(leads finding you).

For inbound, it has to your website obviously. Content is king. No other way around it. It will take time though. No AI shortcuts. Challenges is that most B2B SaaS space iks now heavily crowded with incumbents with years of SEO and inbound marketing. But don't give up and start with a niche. Don't go too wide. Go narrow.

- For outbound, you have think about where your leads may hang out. May be linkedin with industry search is a low hanging fruit ? May be tools like apollo.io or more expensive ones like zoominfo. Note that zoominfo is terrible for SMB leads in my experience.

- Even after you have sold enough and have a decent number of customers yourself, don't build a sales team unless you have a repeatable pattern. In other words, you can effectively write down your exact sales process from a new lead all the way to closing the deal.

- Once you are ready to hire sales people, try to hire an Account Executive (AE) first or a really smart SDR (sales dev. rep) who can quickly become an AE (Less than 9-12 months). SDR usually are hunters. They go and find leads for you. Mostly outbound but could do inbound if you have incoming leads as well. AEs usually own the fully cycle including prospecting and demo/close etc. AEs will need your help as a founder/more technical person for complex tech questions and usually those are done by sales engineers at larger orgs. FOr small startups, it will again just be the founder(s). At least for me, it still is.

- Reward them handsomely with commission structure along with a decent base. Usually the whole package is called OTE (On Target Earnings which includes base + commissions and usually should be split 70-30 for SDRs and 50-50 for AEs).

So many more things to say. Been doing this for 9+ years now. Reach out if you want to ask anything. Happy to share my experience. Heck, I have decided to put this in a blog post with more details to come.