I suspect you are selling to a different buyer than your upmarket competitors that charge 10-20x more. They don’t just charge that much because their product is bigger and better – they probably have to charge that much because their cost of acquiring a customer is higher. In order to play ball in their end of the market they have to:
- Recruit and compensate enterprise sales reps (which clock in at $250k+ typically)
- Build extra functionality to meet enterprise needs (SSO, etc)
- Undergo costly audits and security routines to pass infosec and procurement reviews (SOC 2, etc)
This stuff costs money, and so it makes their products cost more. It’s also why you see enterprise-focused SaaS companies raising so much money – they spend more and make more per deal. Everything is bigger.
In your world, I suspect you have a few options:
- Figure out how to get yourself off the phone and offer a fully self-serve product. Do you really have to manually sell all your deals? At your price point, this will kill your company if so. Run screaming from this customer profile if they pay that rate and require a founder-level sales rep to close the deal.
- Push yourself upmarket and start pitching to more mature companies and/or buyers at those companies who have budget for at least 10-20x your current pricing. You can keep your higher-touch sales model (if a rep can sell ~$1M of ARR/year this can scale with non-founder hires). However, this likely will require some up front product and organizational investment to do right, or you won’t make it past the front door at these buyers.
The path to both of those is painful when you have an entrenched customer base and are dependent on the revenue they generate. My best advice would be to try and structure your offering into a “startup” and “enterprise” tier offering where conversations get elevated to enterprise after a certain level of EITHER usage or procurement baggage exists. Start having those enterprise conversations to understand the requirements.
Also, as a side note, I would not call 10-20x your price point “enterprise” – you are currently an $800/yr product, so 20x that would be $16k a year. That’s not enterprise software – it feels like something you’d see selling into smaller mid-market companies, and even at that price you’ll have a hard time with enterprise reps closing enough deals to make that $1M quota. Given that, and if you think this is a true ceiling on your price point, I am inclined to suggest that you try and remove the sales rep entirely, even on larger sales.