Scaling Your Enterprise Team with Yotam Yemini

Scaling Your Enterprise Team with Yotam Yemini

March 8, 2021

Scaling Your Enterprise Sales Team with Yotam Yemini

A well-oiled sales machine is a key ingredient in driving rapid and sustainable revenue growth. However, founders often face challenges as they attempt to transition from founder-led sales and scale their sales team. To help entrepreneurs in our ecosystem prepare for this critical period, 645 hosted an intimate roundtable with Yotam Yemini to learn from his expertise on the subject and answer founder questions. Yotam is currently the COO of our portfolio company Oort, and previously joined Turbonomic as their first sales hire. At Turbonomic, he worked with the founders to help them scale from $0 to $80M of revenue, ultimately becoming VP Sales. He then joined Quantum Metric as their CRO, where he helped them grow 3,000% and achieve unicorn status in just a few years.

We have condensed key learnings from Yotam’s talk to make them available to all founders and operators out there. We hope these are helpful to anyone else seeking to build a world-class sales operation!

What should your first sales hire look like in terms of skills and experience?

The profile of your first sales hire will depend largely on the team that you already have in place. As a seasoned salesman, Yotam has found the most success in targeting relatively junior candidates as first hires, and working closely with them to get them productive. Usually these individuals have 2-3 years of work experience already, but are still early in their sales career. This means that they won't come in with preconceived notions and will be more open to adopting a new playbook.

Finding sources of talent can be one of the trickiest parts of the recruiting process. In fact, the best talent may not come from the places that you would first suspect. Yotam expressed his belief that experience selling into a similar decision maker is more important than experience selling a similar product. Knowing the buyer persona and what motivates them is an extremely valuable place from which to start. For example, if your company sells to the CIO, it’s better to hire a sales rep who previously sold to CIOs, even if it was for a very different product.

Yotam also quipped that he does not put much stock into sales achievements highlighted on a candidate's resume, because somehow he has “never seen a single sales candidate who did not beat their quota at their prior job.” More important than whether a candidate beats their quota is how they performed relative to their peers. To get to know your candidates better, Yotam highly recommends asking all candidates to take a quick 30-minute test like the Predictive Index early on in the interview process to gauge the two most important qualities in a sales candidate, attitude and aptitude.

Finally, if it works with your budget, Yotam prefers to hire multiple sales reps at one time. He is a big believer in the flexibility that this gives founders to run simultaneous experiments with their sales process, and he views the healthy competition that it can drum up between reps as an added bonus. Additionally, you may also consider hiring a product marketing person to help avoid a situation where sales reps are creating their own content. Pairing someone that has a product focus with your early sales reps can allow you to extract more insights from the calls and synthesize them for your product team.

How to integrate your first sales hire into your founder-led sales process

As a founder, you may not have a “sales bone” in your body, but what you do have is an understanding of the product that is likely unrivaled by anyone else in the organization. You’ve already spent time talking to early adopters to understand their pain points and how your product can help solve them. Passing these learnings on to your sales reps can help them get up to speed faster.

As an inexperienced new hire at Turbonomic, Yotam would join the founder Shmuel Kliger on his sales calls to learn how he pitched the business, how he answered certain questions, and how he moved the deal forward. They would then trade roles to have Yotam lead the next few calls and then have long internal debrief meetings to break down all the details. Practice makes perfect and going through this process is critically important for new hires. Once new sales hires have done 10-15 calls with close coaching, you can start transitioning them to taking calls on their own.

Founders often believe that, “If a sales rep learns to pitch like me, they will produce at my level,” but Yotam cautions that this is a dangerous assumption. He points out that there is an inherent level of customer trust that comes with the role of “founder,” and in that position you are far less likely to face the same objections that a sales rep will hear from potential customers. He recommends being very meticulous in tracking all sales conversations from the early days with customer intelligence software like Gong to capture and deliver insights from your customer interactions. This is critical for building the foundation of what will eventually become your company-wide sales playbook. The more reps you hire, the more they will need to rely on a documented playbook, rather than the founder’s experience.

How to measure sales rep effectiveness and when to put fuel on the fire

The first thing to do when building a sales team is come up with a territory plan; every productivity metric traces back to this. You should have an average deal size in mind and think about how many of those deals a salesperson would need to close to hit their quota. For example, to hit a $1M quota with a $100k average contract value, the rep will need 10 deals to close. Depending on the rep’s close rate, the size of their pipeline should be a multiple of the close target (3-5x is a good starting point if you aren’t sure). In this example, let’s say the rep’s close rate is 20%, their pipeline should have 5x the number of opportunities that you need to close, in this case 50 opportunities. Zooming out even further, a good rep will only be able to engage with approximately 5-10% of the targets they reach out to in a given quarter or year. Factoring in that math, a rep’s territory plan needs to begin with a 10x larger target to account for that drop off, so in this case 500 accounts. At the end of the day, sales productivity is simple math and knowing what good benchmarks look like.

Once you have the territory plan in place, you will name your stages of account engagement (i.e. prospecting, demo completed, visible opportunity, active trial, proposal sent, contract signed, post-sale value achieved, etc). From there, most of the rep’s time will be spent in the CRM system working on deals and moving them forward. On a monthly basis, you should look at a pie chart of how the rep’s target accounts are divided across all the different stages. When a rep first joins the company, the majority of their opportunities will be in the earliest stage. As time goes by, you’ll want to see the pie chart shrink in certain stages and grow in others as the rep should have fewer cold accounts and begin moving more prospective customers through the pipeline. In time, if all goes according to plan, you will see the number of deals closed start to grow. Territory progress based on account engagement is the most effective way to track rep productivity and sales predictability. See below an example breakdown of that.


Eventually, there will come a time when you need to hire a sales manager to oversee the reps on your team. In an ideal world, one of your early sales reps has demonstrated the aptitude and desire to step into this role and can be promoted from within. The actual timing of bringing on a dedicated sales manager should depend heavily on senior management's level of comfort leading the sales team. Yotam, with years of experience in this domain, mentioned that he will typically wait until the team grows to 8-10 reps before hiring a dedicated sales manager. For many others, this inflection point can occur much earlier (i.e. at a team size of 4-6 reps). Either way, the first sales manager should be expected to carry an individual quota and show that they can sell the company’s product before being put in charge of a team.

Critical tools for scaling your enterprise sales team

Finally, Yotam revealed some of the most invaluable tools for scaling up a quality sales team.

  • A Robust Deal Intelligence Platform - Quality transcription tools like Gong (mentioned above) is one of the best ways to assess and learn from your early sales efforts. Using a platform like this can help identify signals before it's too late, coach your team to be more efficient closers, and replicate what your best reps are doing to maximize the value of your pipeline. For some, the premium tier of Zoom may be sufficient, so long as you can record the call, transcribe the text and automatically log it into your CRM.
  • A Quality CRM - Although Yotam is partial to Salesforce, he recognizes that there are many quality options out there for startups. This is the best way to quantitatively understand sales productivity at any given moment in time and adjust your approach to optimize it. It’s critical to set up your CRM as a sales playbook, where the account and opportunity page layouts guide the sales rep through the critical parts of your sales process.
  • A CRM Booster - CRM’s are excellent at providing you a snapshot of your current pipeline status but typically fall short if you are looking for trends. Tools like InsightSquared can supercharge your CRM data and give you insights into historic and potential future performance. A tool like this works great once you have reached a critical mass of sales reps (typically 5-10), and at least a few quarters of data from which to start driving conclusions.
  • A Solution for Content Management - At the same time that a CRM booster becomes necessary, so too does a platform that will help with content management. Left to their own devices, sales reps may share outdated versions of critical documents including datasheets, whitepapers, slide decks and proposals. Tools like Highspot can help keep sales teams organized and ensure that the right collateral is going out at the right time, as well as give you insights about which of your prospective customers are actually reviewing the content you are sharing, and where they are focusing their attention within the content itself.

We hope these were useful learnings! Yotam also appeared on an interview series around scaling RevOps, which you can find the transcript of here. We encourage you to check that out as additional reading.