Step-by-Step Guide for Being the First Salesperson at Your Startup

If you’re reading this, you should have already found your product market fit. If you haven’t, get it done and come back when you’re ready.

This guide assumes that you know where your prospects are (your potential customers that you can find on Linkedin who would be interested in your product, or people you’re being introduced to from your existing customers, or investors), and you are able to schedule initial calls with them.

1. Setting up the first meeting

Right after you setup the meeting and send the calendar invite, make sure to tell the following to the person you’re scheduling the meeting with: “Can you please send me the email addresses of your team members and manager, so I can add them to the call and make sure we answer their questions as well?”. This small thing can save you a ton of time. First, it ensures that you get more stakeholders on the call —and when you do that, you can reach out to anyone of them if someone goes quiet. You also get to understand who wants what, who is the decision maker, and if this is something they could actually be purchasing, and actually need.

Important tip: sometimes it makes sense to send a questionnaire to your prospect before jumping on the first call. This will: 
1. Show that they put some time in responding to your questionnaire and are actually interested in fixing their problem.
2. Help you understand how much they could be spending with your company. For example, when I was working at Sauce Labs, we sent a questionnaire out prior to getting the call scheduled, this questionnaire asked how many tests they were running, how often (daily, weekly), how many tests they were planning on running within 6 months, and in how many browsers. This gave us a VERY good idea of how much they’d end up spending with us, and if we should actually be spending our time with them (or just point them to our self-serve option). This simple tip saves everyone a lot of time, gives you an idea of what they could end up buying, and shows commitment from their side.

2. Always add an agenda on the calendar invite

The agenda can be something as simple as:

- Intros
- Review project goals (of your prospect)
- Demo (of your product)
- Q&A
- Next steps

3. Once everyone is on the call

a) Introduce yourself and everyone that’s on the call with you from your team.

b) Ask for introductions on their end (and take notes on who they are).

c) Say: the agenda for the next hour is to review your project objectives/how you’ve been doing things, then we will show you how we can help you, answer your questions, and then we will take a couple of minutes at the end of the call to discuss next steps — does that work for everyone, and is there anything else you’d like to add to the agenda?

I learned how to run a sales call from an excellent sales training leader back at MongoDB, Ian Spandow. The purpose of following these steps is so they know who they’re talking to, you know who you’re talking to, and they understand what you are going to accomplish in the next hour (or 30 min). This way, nobody is in the dark and wondering what is happening. Make sure to take notes!

4. Qualifying questions

First, create an Evernote file for each new prospect, copy/paste the questions below, and take notes on all answers for each company you speak with:

  • Tell us about your project, why are you looking into____, what’s driving the need for_____?
  • How are you currently _____
  • What do you like about your current _____ (system, database, software, etc). This is a good question which typically leads them to “Well, I actually hate XYZ about them” and you will get very useful information from asking this).
  • Can you help me understand how that is impacting your daily work?
  • In an ideal world, how would you like this to be done?
  • What is important to you that we help you accomplish in order for you to work with us? (you need to get answers from everyone on the call on this question, this is very important because there are different things that are important for each person)
  • Are you currently looking at any other alternatives? (This is another very important question that will help you later on, when you know who your competition is, and if at the end of the process they are telling you that they’re going to your competition because they’re cheaper, you will be able to tell them “Sure they’re cheaper, but we have XYZ, which you said were very important to you, is that still the case or have your requirements changed?”)
  • Do you already have a budget allocated for this project? (I know this is a tough question for y’all technical people, so you can ask this on the second call if you’d like)
  • When would you like to get this started? Are there key milestones or dates we should be aware of?
  • In addition to yourself, who else is involved in the purchasing decision? Can you help me understand how that process is, so I can align resources accordingly?

You need to take notes on every interaction that you have with your prospect, and also note anything important that they say — via email for example. This will help you remember key things that can be easily forgotten.

5. The demo

There’s no need to start your demo by showing them how much money you raised by Andreessen Horowitz, and that Walmart is one of your 20,000 customers. Nobody really cares about that (and honestly they are all rolling their eyes in their heads, praying that you go by these slides as fast as possible, just like you would). What they care about is that you solve a pain point they currently have. By now you know what is important to each person on the call, so you would start by setting up the problem that they’re going through: “Mike, as you mentioned you wake up every Monday morning dreading the 15 useless meetings that you have that day” and then you’d say “with our software, we magically compress 15 meetings into 1” and then “Cary, you mentioned that getting your team to be more efficient would be a dream come true, with our product, Walmart Labs has increased their engineers’ efficiency by 4x! (yes, here’s where you start to drop your customers’ names — through examples on how you improved their lives)

Don’t start blabbing about features that nobody on the call cares about, if some features are critical to mention, feel free to touch on them, but don’t start listing the 20 different things you can do, while they only care about 3 things.

6. At the end of the call
Always review next steps: “As a next step, would next Tuesday or Wed afternoon work for us to do a deeper dive with the broader team, and make sure we answer their questions?”

If their office is within driving distance from you, here’s a wonderful chance to go meet them in person for this second meeting. Believe me, this will help you in many levels. Face time is huge! Say something like “Since we’re so close to you guys, why don’t we stop by your office and put faces to the names while we do the technical deep dive?”. Here you also want to make sure that you get as many people in the meeting as possible, and you need to ask for it, otherwise you’ll end up meeting with just one or two people. “Can you please add the rest of the team, as well as the CTO / Director of Technology to the meeting, so we can make sure we answer their questions as well?”

Sales Pro tip — if you ended the call earlier than the allocated time, you should say “Thank you all for your time today, I’m glad that we managed to give you 10 minutes of your day back”. This gives them a warm, happy feeling about you not wasting their time, and ends the call on a good note.

7. If they go quiet/stop answering:

Don’t take silence personally! Everyone is super busy, and it’s 100% ok to follow up a few times! If they don’t respond to a couple of your follow up emails after that first demo (and, again, you know that you can solve their problem), send an email saying:

Hi ____,

While I’ve tried to reach you, I haven’t heard back from you and that tells me one of three things:

  1. You’ve already chosen another ______ for this and if that’s the case please let me know so can I stop bothering you.
  2. You’re still interested but haven’t had the time to get back to me yet.
  3. You’ve fallen and can’t get up and in that case please let me know and I’ll call 911 for you…

Please let me know which one it is because I’m starting to worry…

Thanks in advance and I look forward to hearing back from you.


— — 
This email gets 90% of the people to respond, it’s magical. And they typically answer something like “Haha, it’s actually #2, another project took priority until March, can you please touch base in early April?”. Then you assign yourself a task to check in with them in April.

Another option is:
“Have you given up on this project?”. This simple question also gets people to answer you by telling you what is going on.

Lastly, you can also text them, aren’t we all getting more and more comfortable communicating via text anyway? 98% of people read the texts they get, and 1/3 of them feel like they must respond within 10 minutes! What a lovely secret weapon that’s not so secret, but yet nobody really does it!

8. Closing the customer
For the prospects that are continuing to work with you, make sure to always schedule “next steps” at the end of every interaction. If your product requires that they try it for 2 weeks or a month, make sure that you help them get onboarded properly (if needed), and that you check in with them every week or every few days to see how things are going. Also, you want to make sure that everyone that needs to try your product within that group is actually participating in the trial, and seeing the results that they want. Here you typically find someone that is stuck, and you get them unstuck. You want to make sure that all stakeholders are onboard, happy, and seeing results with your product. Triple Bonus Point to you if your product is so sticky that once they are using it, it’s nearly impossible to live without — this alone can make your sales cycle very short, and can make your closing rate much higher than a typical startup.

From there on, it’s a matter of closing your customer. If they want a discount, you can always give something, but you always need to get something in return, that’s why it’s called negotiation, you give, they give. It can be anything such as “if we were able to extend you a 13% discount, would you be able to sign it by the end of the week?”, or “if you can sign a 3 year agreement, we will lock you in at a 27% discount for the 3 years”. And negotiation doesn’t always have to be monetary, you can always negotiate on: number of licenses, time of contract, buying more in the future, giving them professional services, giving them additional features (or taking features away), and so forth.

If you take a step back and take a broad look at this article, you’ll notice that it’s all about them, we are focusing on their needs, what is important to them, and most importantly, it’s focused on constantly asking questions, truly listening and being present to what they are saying (something rare now a days). Don’t go into meetings just waiting for the opportunity to say how awesome your product is, when you do that, you never hear what they actually need, and the customer feels like you’re wasting their time and disrespecting them by not listening. Bonus stat: did you know that when people are talking about themselves, it triggers the same pleasure sensation in the brain as food?! 😋 It’s never about you, it’s about them. When you make your customer successful, your company will thrive and grow exponentially.

Happy selling!
Please share this article (or clap clap) with anyone that may need sales tips.
Thank you Lecole Cole for reading drafts of this article.

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