Having managed and hired sales teams that provide services and technology to the institutional investment community for my entire career (both at startups and growing companies), I can tell you that you are selling into a difficult market to crack, particularly if you are creating a brand new solution or category. Workflows are established, the clientele is extremely risk averse, and they are surprisingly slow to adopt innovation solutions. As I say, in this space, it is "evolution" not "revolution."
What does that mean when you are hiring a head of sales? You need to be extremely careful about hiring someone (especially a higher priced, senior sales manager) that is "established" or has great "pedigree" or has worked at one of the big dinosaurs for a long time -- particularly if you have not yet figured out an established, repeatable value proposition, a tested pricing model, or know how to fill your pipeline with real opportunities. From my experience, the ambiguity, lack of established marketing presence, and lack of real cash earning potential (due to long and unpredictable sales cycles) for the head of sales makes these hires very risky on both sides (at a very high cost). I've seen many a senior candidate that "looks great on paper" not work out because the realities of selling a new product into this space are more challenging than they are used to handling. They also become gun shy about trading on their reputation in their network to get traction for an untested product.
Unless you have cracked the code on your market fit and have shown that you are getting good traction with your positioning and pricing through closing deals on your own, then it might be a good time to hire the more senior manager, as their experience optimizing a pipeline can be extremely valuable. Otherwise, I strongly suggest hiring someone who is hungry, fearless, open to ambiguity (both in marketing messaging and earnings potential), and entrepreneurial to partner with you until you figure out the right model. If this is the stage you are in, you are less likely in need of efficient pipeline management and you more than likely need data points to establish a true sales model. That also means that right now, you are the head of sales and your hire is the sales rep that gets the meetings and does the deal execution.
Happy to connect offline if you would like to hear more specifics about some of my experiences. Good luck!