5 Tips for Hiring Your Startup's First Sales Rep

Making your first sales hire as a startup founder can be daunting, especially if you’re new to sales or a first-time founder. The nature of a startup, with ever-changing dynamics, only adds to the challenge. Here are some tips to help you navigate the process of your first sales hire, ensuring you make an informed decision that sets your startup on the right path building a revenue team.

1. Assessing Your Readiness

Before diving into the hiring process, it’s crucial to evaluate whether your startup is ready for a sales hire. Without a clear understanding of the product’s value, target customer profiles, and market positioning, both your sales hire and your company are set up for a rough start. If you, as a founder, are still grappling with these fundamental aspects, it might be premature to bring on a sales hire. Leading the sales initiatives personally at the early stages can provide invaluable insights into your product’s market fit and customer profiles. If you have closed your initial sales and you do have a consistent message that’s resonating, with customers that are using the product and you know why, it may be a good time to engage your initial sales hire to take over.

2. What to Look For in Your First Sales Hire

Look for candidates with early-stage startup experience, up to you to judge what this means for you, but I suggest Seed to Series A/B. Be explicit about the job role and expectations in your job listing to attract the right talent. On soft skills, you want to probe for grit, proactive problem-solving, strong contributions, and drive.

3. Leverage Your Professional Network

If you’re a first-time founder with no sales background, it can be especially challenging to find the right person. Ask your network for help. If you’re venture-backed, lean heavily on your investors. If you’re not, tap into sales leaders at your previous companies. Leverage LinkedIn to search for sales reps who have been at startups you may want to model your company after. Look for early hires. Reach out cold to them with a connect request along with a message like this:

“NAME - I’m a founder and am impressed by your startup experience. We’re looking for our first sales hire and I’m wondering if you’re open to chat about your experience and how we can set our first hire up for success.”

Usually, people are happy to help and are eager to share their knowledge and experience. You can use a conversation like this for double value:

Pick their brain, and get a deep understanding of their experience at a startup; good, bad, ugly. Identify any insights you hadn’t thought through or anticipated to strengthen your job listing or search criteria.

If this candidate is amazing and you click, you may have just found your hire or a candidate to consider.

By the way, if you’re actively hiring I’m always happy to help founders find the right sales hire and happy to make introductions to folks in my network.

4. Setting Your Sales Hire Up For Success

Clearly define the expectations for the role. Utilize the job listing as a blueprint to “write them into the role”, meaning you should think deeply about the requirements, their day-to-day, and your expectations (e.g. 30, 60, 90 days). From there, you can test their alignment through pertinent questions during the interview.

Additionally, you should have a basic playbook prepared whether that’s in Docs, Notion, etc. The playbook should be a quick way for the sales rep to get up to speed on what the product is, what problems it solves, who has these problems, what are their responsibilities, most common use cases, most common pain points, competition, common objections + answers, etc. You can utilize a tool like OpTonal to automatically extract all of this information from your sales calls and use it to create a playbook like this one based on your actual conversations.

4. Interviewing Your Candidates

Sales interviews can be tricky and also a lot of fun. It’s a larger topic of its own but here’s the high level of what you may want to include:

a. Reference Checks: Seek references to gauge their past performance and work ethic. Even a quick chat with a former colleague or manager can provide invaluable insights.

b. Scenario-based Questions: Pose real-world scenarios related to your startup’s challenges. Their responses will shed light on their problem-solving capabilities and experience with similar hurdles in the past.

c. Mock Discovery Calls: Simulate a discovery call to evaluate their questioning techniques, objection handling, and ability to drive conversations towards identifying solutions. You’ve had many of these interactions so you can play the perfect prospect here! Give them some baseline info that’s realistic to what they’d actually encounter. Don’t overthink their product knowledge, they won’t have that yet.

d. Sales Process Evaluation: Have them outline their sales process from prospecting to close, revealing their strategic approach to sales and alignment with your approach.

e. Behavioral Questions: Incorporate questions to understand their resilience, teamwork, and how they handle rejection—key traits for any sales role.

Happy Hiring

Hiring the first salesperson is a significant step in your startup’s journey, congrats! While each topic mentioned above can be a separate blog, following these tips will guide you through a systematic and effective hiring process, ensuring you onboard a salesperson who is well-aligned with your startup’s goals and can drive your sales efforts towards success.