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Being the First Seller at Your Startup

In May 2021 I took a big leap and became the first seller at Pulley, an equity management solution for hyper-growth startups. This role is the definition of “wearing many hats'' – I’m an account executive, a customer advocate, an engineering advisor, and a process builder. 

While the role comes with challenges, it’s also a great opportunity to pick up new skills, make good money, and be a key team member of a growing startup. 

The chance to build a great culture

As the first member of the sales organization, I see this opportunity as a springboard for the rest of my career. We’re tackling new challenges in the market and offering innovative solutions for our customers. You just can’t find this chance for advancement at a larger startup or enterprise company. 

Perhaps one of the biggest benefits of joining Pulley at the ground level is that I get to help set the culture and tone of the organization as we grow. In the past, I’ve worked at companies where people behaved as if we were still in middle school; only some people were allowed to sit at the in-crowd table at lunch.

Fortunately, I've also worked at companies that were very collaborative, where people got along and helped each other close sales deals. This is how I want to influence my company culture today. Working in a collaborative environment can make a big difference in the quality of work the sales team produces. 

Even if I’m not responsible for a particular task or problem, I want to be available and encourage colleagues to reach out to me whenever they need help. This is one way I contribute to the success of the business as the first seller.

For example, my main role is new logo acquisition. To increase my chances of success, I also reach out to law firms so they can recommend their clients to our services. I speak to these firms five days a week because, even though they won’t buy directly from Pulley, it’s important to familiarize them with our product. They’re usually blown away with what we can do and are excited to get started.

Tackling big challenges

Of course, being the first seller comes with plenty of challenges. It’s really a double-edged sword. There were no processes in place when I joined so it was important that I really understood our core value proposition as a company. 

You should focus on really nailing how you sell the bread and butter products that you offer. Otherwise, you’ll end up chasing too many opportunities that don’t fit the ideal customer profile for your services. 

For example, over the last year, we’ve done very well with attracting the attention of new startups. We’re also getting noticed by larger and later-stage startups. The problem is – we didn’t have the processes, features, and resources needed to sell to them (we do now!). We had to create the personas and playbooks on the fly and iterate after every conversation. As a first seller, be realistic about which leads are worth pursuing.

At larger enterprise companies like Salesforce, every process is outlined, documented, and detailed. But as a startup seller, I must use my best effort plus quite a lot of trial and error to close deals. Jump into your prospect discussions with the knowledge you have and continue to refine your processes from there. 

Bringing a new product to market requires a lot of interaction with prospects, customers, partners, and colleagues. The good thing is that as the company continues to develop more functionality, I’m intrinsically involved in that process and I feel more comfortable driving price increases for future deals. 

Serving as the voice of the customer 

In my role, I must balance the needs of the customers with the reality that we can't build a custom solution for everyone. When they ask for features to be added to the platform, I need to determine if this is a feature they actually need to use our software successfully, whether we can deliver on their request, or if I simply need to teach them a new workflow within our product that gets them what they need. 

Sometimes there is no workaround in our tool that supports their particular need. That’s when it’s time to pull in the product and engineering teams and figure out a solution. Luckily, we’re a small tight-knit team and I can speak directly with the founder about a feature build. 

That’s another great learning opportunity for me because I’ve never worked with a founder before who has a technical background and can really understand what goes into building new functionality. 

I find that there are usually themes in what the customers are asking for and I can fill out a standard template for the product team to review. The template consists of three questions: 

  1. What is the feature request? 
  2. How many customers are affected by this request? 
  3. What problem will this feature solve?

Feature development at a startup is very fluid. There are larger features on our roadmap, with scheduled engineering sprints, but other requests can be prioritized if there’s a clear need to build something that will make our customers successful and close new business. 

My advice for joining a startup as one of the first sellers 

My number one piece of advice is to prepare for uncertainty. You must be adaptable to changing situations and new challenges. There are no historical records for sales to reference. You won’t know if February is usually a slow month for sales, for example, because you’re the one setting those benchmarks. 

Things can change fast. Your priorities can shift month to month, or even weekly. One day your focus is on inbound leads and the next, you’re working on outbound prospecting to law firms as a way to establish partnerships. 

The worst mindset a first seller can have is – “that isn’t in my job description.” 

Early-stage startups are perfect for people who want the excitement that comes with uncertainty. You’ll need to get your hands dirty because you won’t have a team of sales engineers and customer success managers to support you. Instead, become your own subject matter expert and learn to fill in your own knowledge gaps. 

A first seller gets to work with a team of innovators to tackle and solve problems together. There’s trial and error, big wins, and strategy changes. It’s a wild ride – but you’ll learn more than you ever could at an enterprise company.

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