How I got whooped my first 2 months of doing inbound sales

I am now a few months into a new startup sales role, and it is fair to say that it has been a humbling experience.

Mostly because the go-to-market (GTM) of my new startup is completely different. My previous startup had a GTM which claimed to be product-led growth but it really wasn’t. The product was a freemium one, so users hit limitations in the platform as they utilized it further. However, there was no system in the platform to capture intelligence about users who were hitting these caps and have them talk to sales about upgrading.

The way the sales team was fed leads was 1) through a heavy sales representative (SDR) driven outbound motion of emails, LinkedIn and phone calls and 2) a request demo form on the website.

Because of this, some leads had never actually used the product and just filled out a form due to an ad or article they had been served. 

Conversations as a result were a blank slate, and prospects eventually would find out about the freemium product, and go there if they were interested. Otherwise, they’d enter a sales guided motion of doing a proof-of-concept (POC) and eventually converting into an enterprise license which removed some of the freemium barriers around # seats, compute, etc.

It was a somewhat inefficient funnel, and after seeing how multiple startups do things, I believe it is critical to get a GTM funnel between product, marketing and sales working before even attempting to hire sales people.

That being said, when this funnel is set up correctly, it can lead to a nice inbound product / marketing to sales motion.

Inbound leads, especially from a free tool, are a different beast

With open source software led companies catching pace, the GTM motion can vary widely from company to company. My new company, for example, has adopted an open source first motion. Users start on open source, then may eventually become interested in the premium product, which contains additional feature and functionality benefits around security and scale.

From here, they enter the sales funnel as an inbound lead. Inbound leads are a totally different sales motion, as I’ve realized over the last couple of months. 

It seems fairly obvious, but an educated, inbound user knows what they want and needs a highly efficient and clear buying process.

I initially struggled with this, because I was used to a much more exploratory conversation from my previous sales role. In my last role, prospective buyers were very early in their journey, looking to get more information with no clear buying timelines, but interest in the technology and its associated technical / business outcomes.

When I moved to my new role being fed inbound leads, I got my ass kicked in probably my first 10-15 discovery calls with prospects. Buyers were very experienced in the free platform, and quickly wanted to understand what value they’d get from the premium version, and how they could go about purchasing it.

Get ready for crisping up your game if you are heading to an inbound sales role

Now 2 months into the role, I’ve finally figured out how to efficiently run the discovery to guided evaluation process as it relates to the product.

And the best way I could describe the journey from an open source to premium product sale is crisp and transactional. The buyer is educated most of the time, having used the free version of the product.

They understand at a high level what the differences are between the free and premium, and likely they’ve hit some scalability challenges which have led them to the premium product.

But your job as the salesperson is to qualify their 1) urgency and timing on scaling up and 2) their willingness to pay the minimum entry point for the premium product.

This prioritization ensures that you spend your time on the leads that will convert to a sale. Because at the end of the day, it’s a big barrier to overcome and your prospect really has to need your premium product.

Without a deep need or pain to upgrade to the premium platform, it’s likely the prospect will fall back on the free / open source platform, and waste your time.

I hate to say that any prospect is a waste of time. They all matter. But some will truly waste your time, and you will waste theirs.

Outbound versus inbound sales and key differences

There is a reason that companies separate out inside and outside sales teams. Typically, inside sales teams have a much faster path to closing deals with inbound, educated buyers that come in already 50% decided that they want to purchase a product.

Outbound sales on the other hand means that sales teams are generally working with potential buyers that will need a lot more education. These prospects generally have some or none of the portions of BANT (budget, authority, need, timeline).

Especially if you are selling for a startup, these buyers may have no idea what your product even does, or if they have a problem that you can solve. Or they may not even be buyers, but rather technical users who need to be guided through the buying process and how to go and secure the budget to purchase your software solution.

Sales cycles are longer in outside sales, ranging from months to over a year. Contrast that with inbound sales, where deals can be closed in 1-3 meetings (give or take).

Deal sizes may also be smaller with inbound sales, but that’s not always the case.

Figure out where your strengths lie and what you like doing

After 2 months of inbound sales, I’ve realized it’s not my strongest area and I don’t particularly love it.

But it has been a great learning experience in qualifying prospects’ need and urgency. With the compressed buying timelines, it has also taught me the importance of clear, next steps. Without these next steps from prospects, and buy-in on those next steps, the deal can easily stall out.

Unlike in outbound sales motions where there may be a bit more leniency around the timing of deals and building urgency, with inbound, the expectation is that each lead should be disqualified or converted to the next stage of the sales cycle relatively quickly.

After all, the prospect is coming in highly educated, so it’s important to guide them through the process to a buy or no buy, but not spending months and months doing it.

In my opinion, this leads to less creativity in inbound vs outbound sales. With inbound sales, there can be a relatively shortlist of questions to run through to decide if a customer needs the premium product features, or if the free will suffice.

However, with outbound sales, there is a lot of early discovery that has to happen (that likely takes more than one call) to identify if there is a pain or problem even worth solving. 

It’s less easy to create a laundry list of standard discovery questions, because the conversation can take many paths depending on the customer persona, their reason for contacting, their impression of what your product does, etc. There are a lot more unanswered questions in their minds versus for an inbound buyer.

Everything is a learning lesson, and successful companies need both inbound and outbound sales

For now, I will continue to crisp up my inbound sales game. If I had to summarize my learnings into 3 key pieces of advice, I would say:

1. Learn what happens if the prospect doesn’t upgrade to the premium version of your platform, to gauge their urgency to move (ex: will they miss a deadline, or have to use their clunky in-house product).

2. Challenge them if they feel like they aren’t ready to scale to the premium (within reason and with open-ended questions).

3. Sell the next meeting, and always set a follow up. Does it make sense to continue the conversation, and if yes, get something on the calendar. If it’s a no, close it out and revisit with them later.

The reality is that even if a company starts out inbound mostly, eventually they will need to go outbound to grow revenues past a certain point. 

If you plan on selling in startups, it’s beneficial to learn how to sell to both types of buyers (inbound vs outbound). 

There are lessons to be learned from performing inbound and outbound sales and I argue that experiencing both will make you a stronger salesperson, regardless what your preference is between the two.