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So You Joined a Startup as the First Sales Hire… Now What?

First Sale Rep At A Startup
Career Development

Joining an early stage SaaS startup can be exciting, but it can also be daunting. The founders often have lofty goals, minimal structure or direction, and the company is just beginning to build out its sales motion.

If you’re the first sales rep at a startup — or one of them — you’ll be responsible for helping the founders acquire the company’s first customers, establish a system to sales, and achieve wins in an initial niche market.

That’s why I built this guide, to help you improve your game in the short-term and set you up for success in the future.

So without further ado, here are 3 DOs and 3 DON’Ts for your first 30 days at a startup.

DO: Learn Your Product, Fast

The more product knowledge you have, the more confidence you’ll be able to instill in your executives and customers.

As soon as you join, the clock is ticking to start selling and hitting your revenue targets. So, it’s important to get up to speed as fast as possible. The key is to find hacks to speed up your product training.

For example:

  1. Use a voice memos app to record a live demo with a customer. Transcribe it, and voila! You’ve got a script to study.

Block an hour per day to commit the talk track to memory, and then find a friend or family member to practice on. This regimen does wonders!

  1. Write a complete job description of the buyer personas you’re targeting: their responsibilities, stakeholders, and measures of success.

This exercise is one of the fastest ways to learn your ideal customer profile.

  1. Don’t let “perfect” be the enemy of “good enough.” Jump into customer interactions, even if you don’t feel 100% ready. You can offer up a question on a discovery call, or take the lead in part of a demo to cement your learning.

In a startup, everything is going to feel new all the time. Get used to it.

DO: Prospect, It’s Never Too Early

If your startup is like most, up to now the founders have relied on their personal networks to acquire early customers. While this might have landed them a few early adopters, the sales strategy needs to evolve quickly to target prospects who have the business pain your product relieves.

As one of the first hires, it’s often up to you to ensure the sales strategy does evolve.

Here are some tips:

  1. Write down a definition for your company’s Ideal Customer Profile (ICP). This is going to be a list of 5–7 criteria that signify how acute the business pain is on the part of your prospect.

If your founders are saying, “Our ideal customer is everyone,” that’s a red flag. Remind them that, while a narrow ICP may feel like it limits your growth potential, it actually focuses your business on exactly the right customers.

Trust me, he who tries to sell to everyone, sells to no one.

  1. Build a Target Accounts List with 50–100 rows of customers who meet your Ideal Customer Profile. Create a column for each demand signifier, and then score your accounts based on how many criteria they meet.

Use LinkedIn for outwardly available customer data, and to save time, hire an overseas freelancer to do the data entry for you.

DO: Focus on Social Media

Unless your founders are social selling mavens, your company’s presence across social media channels is probably lacking.

As you begin prospecting, your solution needs to be visible on any platform your potential customers interact with.

You can’t control what the founders do, and chances are they don’t have time anyway. However, they’re still the face of the brand, so ghostwrite a short LinkedIn article or blog post for your CEO.

This is a great way to master the value proposition, and to help drive leads to your landing page.

RELATED: How to Use LinkedIn to Build High-Value Relationships

Remember, you don’t have to be an SEO wizard (or an English major) to write half-decent content. If your buyer personas are active on Twitter, create a company account and start interacting with prospects and thought leaders in your niche market.

You can do this in just 15 minutes a day.

DON’T: Forgo 1:1s With Your Manager

As with most startups, your team is probably small, relationships are likely informal, and you’re probably working directly alongside your CEO. Nevertheless, it’s crucial to carve out time to meet one on one with your manager.

1:1s are crucial to connect on pressing sales priorities and develop a strong relationship.

Before you go home on your first day, create a calendar invite for recurring, weekly 1:1s, and share it with your manager.

This sets the expectation that you value the meeting and take it seriously.

Include an agenda in your invite with, at minimum, three items:

  • Two-way feedback
  • Pipeline review
  • What you’re focused on this week

DON’T: Overlook Data Hygiene in Your CRM

As the first sales hire, you’ll be owning sales operations in addition to sales. This means you’re in charge of implementing the technologies necessary to be efficient and effective in hitting your sales goals.

Implement a system of good data-hygiene as soon as you can. The longer you take to implement a CRM, the harder it will become, and the more work you’ll have to do in the meantime.

Here are some tips to follow during the first 30 days:

  1. Insist that the company implement a CRM, ideally Salesforce. Most likely, the team has been tracking pilots and open opportunities outside of a CRM, and while that may have worked when the team was just starting, it won’t scale well.
  2. Schedule a meeting to review everything in the pipeline, and get as much of that data as you can into Salesforce. The most important thing is to make sure all sales activity is logged going forward.
  3. Define your sales stages to signify how far a deal is from the finish line, and how likely it is to close. Although your sales process will evolve over time, the CRM needs to reflect what the sales process currently looks like.

These six stages are a good starting point: Lead > First Contact > Demo > Proposal > Negotiation > Closed Won/Lost

Start-up Sales Process

  1. Set up some basic reporting on what you currently think you should be tracking. For example, you may track “projected sales revenue by quarter” to share with your executives and “opportunities by lead source” to understand where your leads are coming from.

DON’T: Try to Do Everything at Once

The first step on the road to a repeatable, scalable sales process is prioritization, often on a daily basis.

Write a 30:60:90 day plan with 3–5 objectives. This isn’t a dissertation, so don’t overthink it. Just create one slide or a simple spreadsheet that has the information in one place.

Here are some examples of the kinds of objectives you may include:

  • Lead my first demo with a prospect
  • Identify 100 potential customers that have the distinct business problem we solve
  • Set up our Salesforce instance

RELATED: Data Governance: Salesforce Objects in a Lead-to-Cash Process

For each objective, include “actions” (showing how you’ll get there) and “results” (how you’ll measure success). In a 1:1, share the plan and get your CEO’s feedback.

Don’t beat yourself up if you feel overwhelmed. You’re only human, and you can’t do everything at once. This is why prioritization is so important.

Key Takeaways

Ask any early sales hire at a startup and they’ll tell you getting started can feel daunting, but while it may be daunting it doesn’t have to be overwhelming.

Keep these takeaways in mind:

Know your product, but remember that you don’t need to know it perfectly to get in front of customers.

He who tries to sell to everyone, sells to no one, so stay focused and identify an ICP.

The best time to start prospecting was yesterday. The second best time is right now.

Now that you have a roadmap for your first 30 days, you’re ready to put your company, and your career, on a path towards success. So, go make it happen!

Davey is a sales leader, early-stage GTM expert, and Head of Sales at Matik.io, a software that automates the generation of repetitive data-driven presentations, so reps can spend more time selling and less time on tedious tasks. Prior to Matik, Davey was the first salesperson in the West at WeWork, which grew from zero to >$1B in revenue in 5 years. When he’s not leading a team of awesome sellers, Davey is an avid lap-swimmer, R&B listener, and Jewish deli connoisseur.