Part 1: Building a Sales Org from Scratch

When you first arrive in the VP of Sales seat there is such a tremendous joy that overcomes you. All that work, obstacles overcome and hardship has paid off. You are at the top of the profession. Now there is a famous saying, “getting into Harvard is one thing…graduating is another.”

This is very true with the VP role. By day 1 you have to get your arms wrapped around the situation and what to do. The immensity of the challenge can’t really be explained but those who have been through it… know how hard it is. This is a 3 part series that I am writing to help guide you through the process.

Now there are different scenarios you face when arriving into the role. I myself have experienced joining and finding myself in the following scenarios:


  1. Bad sales culture with low attainment and high attrition

  2. CoFounder led sales motion lacking any systems or process

  3. An acquisition & having to integrate 2 different sales orgs into one


I’ve also had the fun experience of doing these leadership stops during 1) a global pandemic and 2) a recession. I’m not going to lie when I thought to myself, “what did I get myself into with this VP role?”

I highlight these reasons not to gain empathy but to shine the light on another point. The business world does not care what you are dealing with. These are just distractions on what needs to be done. Don’t get too wrapped up in these, know them and understand them, but focus on a process.

Now here is the good news. If you have gotten the VP job then you have a track record of success over an extended period of time. You more than likely have demonstrated an ability to assess a situation and think creatively on how to fix the problem.

So what is step 1? Focus on the first 30 days and get a sense of the following:

Assess the Team

The team you inherit is not always built in the mold of what is required. You need to assess your A, B and C players quickly. You can build a quick skillset matrix weighing your sellers on a scale of 1-5. See below for an example:

Can they source pipeline, can they pitch the product, can they execute a deal, what’s the overall performance and do they demonstrate leadership. This last part can simply be boiled down to can they take control of their situation and get it done.

Be quick to weigh the team members so you can start to make a decision on your roster quickly. Opening up job reqs, interviewing, hiring and ramping can take upwards of 120 days. If changes are needed you are already 3rd of the way through the year if you are beginning roster turnover on day 1. Let that sink in a little…. It is REALLY important to get the right people in seat.

Look at your Software Stack

What tools are available for the team to be successful? We all have a history of softwares we have used in the past and prefer over others. In a nutshell what you want to look at is the following:

  1. Do you have a CRM and how is it configured?

  2. Do you have email cadence systems?

  3. Do you have prospecting tools like LI Navigator, dialers, etc?

  4. Do you have data enrichment software?

  5. Do you have call intelligence software for coaching reps?

My guess is you’ll have some of these but they will either be configured incorrectly or used improperly. Now depending on the size of your org you may have resources that you can lean on to assist or you may have to roll your own sleeves up.

Either way you want to get your system stack lined up ASAP. This is ultimately how your sales team will executive to create and close revenue. You can also coach them to a process for creating a pipeline. My offense is called “the Bucket System” and it is centered around a structured process supported by technology.

Your KPI Data Set

This is a fancy way of saying “what will your board deck look like?” Do you have historical perspectives on lead and opp conversions? What about pipeline flow? Can you see what the key deals are? How are you going to forecast the next quarter? What does your dead loss analysis look like? You want to start getting the following reports set up:

  1. Rev conversion performance Lead to MQL to S1 to S2 to Closed Won

  2. Pipeline performance across new business, add on

  3. Which deals are the KEY ones and where are they at in the evaluation

  4. Your forecast and how you break that down

  5. Of the deals you lost, why did it happen?

All of these top points can be tied back to the systems you use and the resources that are using them. If you have the wrong people in place and the incorrect systems then your KPI data set will be a mess. Numbers will be all over the place and you won’t be able to make sense of the chaos.

Alternatively, if you set up daily meetings, shadow calls and actively assess what is happening then you can get your arms wrapped around the situation. You can also properly measure it with the right KPI data set.

Repeatable process in the sales pit is critical, for a refresher on the topic see HERE. Building a rhythm allows you to get a sense of your org. Reps can also understand what is expected and when. Remember, bad data in means bad data out.

Final Thoughts

Ok, so day 1-30 is in your rearview mirror - congrats! You’ve managed to get a sense of the people that work in your org, the systems used to execute and the measurement framework to weigh if things are working. This in itself is a small victory and should calm the nerves slightly.

Day 31-60 is when the rubber meets the road and you start influencing the revenue. Stay tuned for part 2 of this series next week.

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Part 2: Building a Sales Org from Scratch

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Measuring Rep Performance