In the wake of last week’s post, I received follow-up questions about how to approach making your first sales hire as a founder. I wrote down my thoughts on the topic a few years ago and figured it might be helpful to recirculate them in a #TBT post. It’s a bit longer than what I’ve been posting here, but I think it serves as a fairly comprehensive guide. This is a complex and meaningful step in growing your business — if you have any additional questions don’t hesitate to drop me a line!

A Founder’s Guide to the First Sales Hire

Congratulations, founders, you’re ready to make your first sales hire! It’s an exciting time, you are now ready to embark on the next stage of growth. As early-stage investors, we meet a lot of founders who are ready to make their first sales hire, but are unsure how to approach the process. It’s a surprisingly complicated decision and we thought we’d share some thoughts on the topic.

What does the business need right now?

Before even meeting with sales candidates, we think it’s incredibly important that founders assess the state of their business and answer three critical questions:

· What is our current sales growth trajectory?

· What is our ideal customer profile (ICP)?

· What are my personal strengths and weaknesses as an operator?

Answering these questions will help define the type of salesperson your company needs. Your sales traction, revenue growth, and ideal customer profile will dictate the types of salespeople best suited for the role. Your own personal background will refine the search, as you look to complement your own skillset. Taken together, these questions will help you zero in on the optimal ‘salesperson persona’ to take your business to the next level.

A ‘salesperson persona’ is an aggregate view of a candidate and comprised of many factors: their years of experience, the types of products they’ve sold, the types of customers they’ve sold to, their expertise in sales management and past roles in sales operations. In the following sections, we’ll help unpack each of these factors and add a few more basic skills that you should expect from a candidate.

We hope this piece will challenge you to thoughtfully consider the various salesperson profiles and skills, and help you find the right one for your business.

These skills are table stakes

Life at an early-stage startup means wearing many hats. In most sales organizations, there’s a lot of behind the scenes sales enablement work that needs to be done to support an efficient and effective sales process. The seller may get credit for the close, but getting that contract signed requires a series of collaborative efforts and coordination between sales, marketing, customer success, and product.

With this in mind, it’s essential that you find a candidate who’s both willing and able to execute these core functions:

● Be able to build a narrative & pitch — At larger companies, product marketing teams design the pitches, anecdotes, and rebuttals used by their sales team. Young companies typically don’t have those extensive resources and your candidate will need to shoulder that responsibility. We’d recommend setting up one of your interviews to be a mock pitch where the candidate has to design the sales pitch for your solution and handle objections on the fly.

● Create compelling content — Again, without a marketing team to create beautiful presentations, this responsibility should fall at least partially on your first sales hire. Make sure you’re comfortable with the candidate’s ability to build a sales deck that will visually represent the product and its value. Look for someone with high attention to detail.

● Be comfortable with calling cold leads — In mature companies, this responsibility either falls to the marketing team, a junior salesperson, or a sales development rep. In an interview, find out your candidate’s attitude towards this less glamorous role and his/her plans to generate new leads. Would they make cold calls, do an email drip campaign, or knock on doors?

● Build & refine a sales process — Your first salesperson will likely have to help refine your sales process design for bringing your product to market. You don’t want your first sales hire to simply take the sales process from their previous company and apply it to your business, just because it worked for them before. For homework, have candidates express what their sales process would look like for your solution. In the interview, have them justify their reasoning for that particular design.

● Interpret product feedback — This is so critical to the success of the company, yet it’s often overlooked when it comes to sales talent. Empathy is critical for a salesperson to be successful. This is especially true when closing your earliest customers who will help inform your product roadmap. Make sure your candidate has the ability to listen, absorb, and clearly articulate customer feedback. After facing rejection in the field, a less sophisticated salesperson will report the need to lower prices, while a top seller will deliver constructive feedback to a product manager and help determine how to better articulate the value proposition.

● Have Domain Expertise — This is typically top of mind for founders and while not essential, it can be highly accretive to a sales process. Salespeople with relevant domain expertise have empathy and understanding of their customer’s needs. They often know the native workflows, processes, and jargon, as well as other nuanced aspects of the customer’s day-to-day responsibilities that could only be known by someone who was in that seat before. This is not to suggest hiring for a rolodex, which has been shown statistically does not work.

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