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Onboarding your first Sales Hire as an Entrepreneur




In today’s blogpost I would like to introduce my partner for Zero to 100, Stephanie (Schatz) Friedman. Stephanie has been an executive in 3 successful startups and was most recently the SVP of Sales and Customer Success at Xamarin which has since been acquired by Microsoft.

Stephanie joined Xamarin as its first non-engineering hire in 2012 and built the organization from Zero to $50M ARR and 100 sales people.

An interview about that experience is included below, and I look forward to hearing her share more of her experience and insights next week in our inaugural Zero to 100 event.


D: When you joined Xamarin, what did those first weeks look like?

S: In the early days I played the role of a “trailblazer” salesperson as you describe it. I was figuring out who we were selling to, what our message was – basically figuring out our repeatable sales motion.

In parallel I designed our lead to cash process, implemented salesforce and marketo, and a whole list of other sales support software tools together with the founding team. After a couple of months I made my first hire: an amazing mobile developer who joined as our first customer success engineer.

We started out inbound only, with fairly small deal sizes and short sales cycles – basically a typical high-velocity sales model. Over time we added a midmarket and corporate team as well as a channel team.

Later on we added an inside Enterprise team and eventually that inside Enterprise team evolved to a more a traditional Enterprise field team.

After about 4 years SMB, Enterprise and Partners represented each about ⅓ of my revenue.

Fast forward 3.5 years I had a team of about 100 sales people and we were approaching $50M of run rate sales – and then we were acquired by Microsoft for about 10x revenue.

Evolution of Xamarin Sales Team Structure
Evolution of Xamarin Sales Team Structure

D: Great experience. So what kind of content can our audience expect from you?

S: Over the years I have tried to become more and more intentional about how I build and run a sales team. My goal is to share a strategic view on how to build and manage a high performing sales team, in combination with very hands-on and tactical ideas as well as lessons learned.

D: That sounds great. Give us an example!

S: Yes, absolutely. Founders often ask me: I have hired my first sales person, he / she is going to show up on Monday – what do I do ?

While sales onboarding is a complex topic there are a handful of very specific things that have worked well for me and my teams.

In general, before you start hiring sales people it is paramount that the founders have started to successfully sell the product. Your CEO or one of your founders should be your best salesperson. Once you have hired your head of sales or first sales person it is important to teach them as much as possible of what the CEO and founders know. That means you need to extract everything that works well with regards to selling from the founders. There are several things to do here, but one of the best ways for new sales hires to learn is to do joint customer calls – so do as many of them in the first weeks as possible.

Here are some best practices:

  1. Keep in mind the best time to learn and teach a new sales hire is not on – but before and after the call. (In general I am very big on call prep, as well as debriefing calls).
  2. Schedule a brief call prep session during which you define the objective and the agenda for the call, and explain as much as possible your reasoning and your strategy around it. In my experience it is very helpful for a sales organizations to have a very simple rule: No call without an agenda, no call without preparation.
  3. The document that I like to use to prepare for calls and also take notes during the calls is called the “Blacksheet”. I like to use this for all mid-sized and larger accounts, for an SMB team the note taking functionality of Salesforce often works just fine. We often just used a simple google doc for the Blacksheet and attached it to the account in Salesforce; it would have all the basic information about the account at the top, and then ongoing notes from every customer call.*

For every customer call I recommend you have the following sections:

    1. Attendees
    2. Objective of the call
    3. Agenda of the call
    4. To dos
    5. Notes from the call
    6. Follow up email:
      1. I have always liked for the rep to draft his/her follow up email right in the Blacksheet, using the list of to dos from the call. As a rule this email should always go out on the same day, ideally right after the call.
      2. Very important: Avoid the subject line “follow-up”. Nobody wants to be “followed-up on.” Always find a subject line that is of value to the customer, even if it’s an account that you have been managing for a long time. Make sure to create value at every interaction.
  1. Blacksheets and brief call prep sessions are the best tool to make sure everybody is on top of their game during the call and all attendees have the relevant information. It’s very important to make sure you create an atmosphere during call prep where the new sales hire feels comfortable asking every question they have.**
  2. I usually recommend to do a series of “mock” calls first, in a relaxed environment. One evening just order pizza and start impersonating some easy and some more difficult customers – this can actually be a lot of fun.
  3. The first series of actual joint customer calls are best done by the founders so your new hire has time to listen and learn. After a while it is time to switch, and your new hire will start leading the calls. I have found it best for the founder to then actually sit back and be in listen-only mode, even though this might require some disciplined restraint on their behalf – it’s the only way for your new hire to actually get a chance to practice. Even though it is very tempting to tackle the most important / most urgent accounts first ideally let them do some practice calls with smaller or less important accounts to start with.
  4. Take the time to dissect every call right afterwards. It is sometimes hard to allocate that time in a fast moving startup, but a debrief can often be done in less that 5 minutes and I have seen it pay back in spades.
  5. There is a method to customer call debriefing that I really like – three simple questions:
    1. What went well?
      • This is the moment to praise your new sales hire for everything they have done well, and also make sure they notice and internalize the things that you and other call participants did that worked well.
    2. What didn’t go well?
      • This should be discussed in a friendly and relaxed way – as a team, trying to improve together. Try to make your team comfortable, for example by mentioning things you said that you would phrase differently if you could go back. One of my mantras is “Better everyday” which gives everybody the space to learn and improve constantly.
    3. What can we blueprint? (positive and negative).
      • This one is very important. You won’t find a blueprint on every call – but once or twice a week someone will do something awesome (or terrible), and blueprinting it means “We will do this from now on on every call” or “We will never make this mistake again”. Obviously overtime these blueprints need to become a part of your sales training material.David: this idea of Blueprinting is key to the sub-phase “Find Repeatable Sales Motion” that we will talk about in detail in the Zero to 100 curriculum. We are looking to document a sales playbook that can be used to train new sales reps, and these blueprints will become a part of that playbook. 
  6. Depending on the seniority level of the hire it might make sense to jointly write / review important emails during the first weeks before they go out to the customer; not in a spirit of micromanagement, but rather giving your new team members time to find the “voice” of the new company they now work for.
  7. Lastly, before you bring any new sales hires on board I strongly suggest you have them pass a writing test. Written communication with your customers is highly important, and attention to detail here really matters.


D: Fantastic – I am looking forward to our first live event of “Zero to 100” on September 11th in San Francisco!


*Another important reason for blacksheets is handover of accounts, which has to happen in a fast growing startup on quite a regular basis as you add new sales people and therefore have to redesign territories.

**The process of preparing for customer calls and debriefing afterwards is at least as important as the document itself.