What I’ve learned from the transition to selling to larger companies — Harrison Rose

It’s the goal of many SaaS companies to begin selling their product or service to larger companies and enterprise. Of course, it’s not a quick and easy process to position your product, teams and company as a whole to move ‘upmarket’ and win some of this bigger business. Here’s what I’ve learned from the process of selling Paddle’s solution to larger companies.

As Chief Customer Officer and co-founder of a company that powers the checkouts of thousands of SaaS companies, I’ve been in the unique position of being able to oversee what prompts other companies to begin selling upmarket. Since Paddle was first founded 7 years ago, I’ve noticed that while companies have numerous ways of readying themselves to sell to bigger businesses, there are ultimately only 2 ways companies take the leap.

There are 2 key ways to move upmarket

SaaS companies take one of two paths to begin to sell to bigger business: reactively or proactively.

Companies who move upmarket reactively find that they have to step up to selling to enterprise-level businesses when they receive requests from bigger companies to use their product.

Those who make the move proactively, meanwhile, recognize that individuals are using their product in a professional capacity and prompt the move themselves, leveraging these professional consumers, or ‘prosumers’, to sell seats/licenses to teams and the business as a whole.

In Paddle’s case, we found that we’ve been pulled upmarket at various stages, with companies several times larger than our biggest client at the time showing interest in using our platform. It’s in a circumstance like this that SaaS companies are prompted to look at their processes and review their readiness for selling to bigger clients — often before they’d had a chance to entertain the ‘proactive’ route.

There are 3 areas that need adapting in your company

Through my own experience of moving upmarket and in overseeing the journeys of the companies we help to scale, it’s clear that there are 3 areas in which most companies need to make changes in order to serve larger customers. These are:

Product and positioning

It’s important to make sure your product is compatible for use within larger companies. A big step from a product perspective is thinking about how the product will be used differently by a team as opposed to individual use. For example, do you need to add features like collaboration and admin roles to enhance the experience of your product?

It’s also key to adapt the kind of products your company uses when moving upmarket. In my experience, it became more important than ever that the products our company uses all have single-server sign-on and integrate with the other tools we use.

Sales and Success teams

For starters, you’ll need a sales team if you didn’t already have one. A Sales team will support the process of selling to larger companies, while a Success team is important for onboarding your new customers, retaining them and upselling to them. In my experience, investing in Sales and Success is the key to winning and keeping big clients.

Billing

Larger customers want to pay in a different way to the smaller businesses you’re used to, both in terms of method of payment and billing model. Big companies are more likely to want to pay via wire transfer into a bank account that feels local to them over a payment network they’re used to, with the ability to raise a PO and renew licenses with ease. These are all things your company should enable — a Merchant of Record like Paddle is a great way to cater to these clients without the need to build out this infrastructure or internal expertise yourself.

As a company, you’re also going to want to review your billing model to make sure that you’re aligning the value your product is delivering with how the business is paying — and potentially for a variety of different customer types now, too.

At some point, you’ll also find that expansion within accounts is driving more revenue than initial acquisition and so, when choosing your billing provider, it’s important to make sure they have the ability to enable upselling and adapt for expansion so billing alterations don’t become a headache.

You need a single source of truth

The last thing you want to do is allow your infrastructure to be a blocker to your growth as a company. If you don’t have a financial source of truth and have taken a piecemeal approach to your billing and checkout, this will become increasingly difficult to manage as you begin selling upmarket with all that this entails — different billing models, different methods of payment and potentially selling to other countries, to name a few.

We all have limited time and resources when we’re scaling, so you’ve got to ask yourself: “what’s slowing me down and what tooling can help me achieve more?” A single source of truth like Paddle enables all financial transactions to take place on the same platform, with sales tax and compliance all taken care of.

Making changes to your current solution as you go can be painful and ultimately stunt your progression to selling to larger companies, so it’s hugely beneficial to have a single source of truth to be in the best position to sell upmarket.

About Harrison Rose

Co-founder & CCO @Paddle

Harrison Rose is the co-founder and Chief Customer Officer of Paddle.

Harrison began working in software at the age of 16 while still in school. At 18 he co-founded Paddle, leading the go-to-market and commercial efforts, with revenues tripling each year since launch which has made Paddle one of the fastest-growing software companies in the UK according to Deloitte Fast 50.