The Top 10 Things I’ve Learned Selling SaaS into the Enterprise

Last month I hit two years at mParticle and had some time to reflect on how far the business has come, and all the things I’ve learned along the way. The learnings are from my perspective as the first business hire, pre-revenue. I hope you find them useful.

1. Early customers for a top-down enterprise SaaS company are really tough to land, and most big companies only buy things that other big companies have bought. This means that high-growth startups are the best initial target customers for a top-down SaaS company. High-growth startups have budget, constantly have new problems given their growth, and often have an accelerated procurement process compared to older organizations. When you land high-growth startups, older enterprises will notice, as they often fear getting disrupted by younger competitors punching dents in their business.
2. It’s hard to qualify opportunities, pre-market fit. The definition of a qualified opportunity is that the pain you’re solving for this particular person is a pain you’ve solved for a previous person or customer. In retrospect, I wasted a lot of time on unqualified opportunities because I didn’t know what qualified opportunities looked like. I can see how many companies fail at this stage because they spent too much time chasing the wrong opportunities. Becoming disciplined around qualifying and sticking to a checklist is hugely important when you’re still figuring out PMF.
3. When things get hard, it helps to have founders who have done it before. You can point me to every blog post that says the odds of repeat founders having future success are no greater than first-time founders, but it sure does make it easier for early employees to take the punches. In the back of early employees’ minds is the notion, “this founding team has been through the trenches and came out on top.” It can be an incredibly important unspoken cultural dynamic during the tougher days early on.
4. Prospects are reluctant to say no, even if they’re not interested. If you’re fortunate enough to have good investors and a solid network, you’ll get people to take first meetings. Prospects who don’t want to work with you often won’t give you honest feedback because they feel bad saying no. It’s important that you get feedback if people don’t move forward — learning exactly what they didn’t want, and potentially what they do want. Failing to do proper discovery and understanding of a “no” is failing to learn what you need to build for PMF.
5. Early sellers at SaaS companies need to moonlight as PMs. It becomes your job to do one of two things: (1) drive revenue through sales or (2) articulate what has to be built in order to drive revenue through sales. Don’t wave your hands in the air because no one is buying, without prescribing what needs to be built so you can be successful. Early stage B2B is about closing the gap between what you have built and what the market wants in order to accelerate revenue. The first $100K MRR is just as much about market research as it is about closing business.
6. When the team is under 15 people, everyone sits together and cross- functional work is the norm. For salespeople, take advantage of learning from this immersion; it’s a rare time when you can absorb from technical functions and accelerate your learnings in areas that might be weak. At big companies, you’ll sit on the sales floor and won’t be exposed to other functions in the same way. I value that I sat next to our lead Android engineer for my first two years at the company — it helped me learn a lot about our technology, and ultimately made me better connect with some of our engineering customers. Take advantage of sitting in the weeds of your product. It will show in your meetings when you engage technical stakeholders on the other side of the table.
7. Decks are your enemy, unless they’re used as a discovery tool. Don’t fall in love with presentations. Get comfortable asking questions and always be mindful that the right ratio of speaking to listening is probably around 25% to 75%. Your job is to determine very quickly if the pain you’re learning about can be solved with your tool. If you spent every first meeting latched to a deck, your ratio of speaking to listening would be wildly off.
8. Customer success is everyone’s job. People will come in and manage this (in our case we have an excellent team), but it’s everyone’s job. Sales, engineering, marketing — these can all be functions that only the specific teams worry about. Customer success needs to be the most important thing that everyone on the team internalizes. High-growth SaaS startups that stumble often fall harder if they churn customers, versus failing to generate revenue in line with expectations. Even if you’re not selling services as a line item in a contract, you don’t have the right to be absent when it comes to customer success. We’ve experienced almost no churn as a result of our CEO ensuring that everyone feels responsible for the success of our customers.
9. Selling SaaS is a lot more fulfilling than selling advertising. When someone buys SaaS, they buy a solution to a problem that is often very painful. When someone buys advertising, they are tasked with spending $ more than they are with solving a pain point. When you check in with customers and realize that they’re either more efficient or making more $ as a direct result of using your tool, it can be incredibly rewarding. I never felt that selling media.
10. Discovery never ends. When a deal closes or implementation ends, don’t convince yourself that discovery is over. The relationship is solidified, but it’s crucial that your discovery never ends, because customers will keep having new problems. Some you’ll be well positioned to solve — and odds are that most of your customers and prospects will share these problems. Use current customers to help inform your roadmap, and make sure you’re matching their pace of innovation with your own tools. When I look at companies like Salesforce or Oracle, it’s easy for me to understand how they have 100’s of product lines. Besides pure execution, they have continued discovery, even after their initial products were successful…and they just kept building.