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A Chief Revenue Officer's learnings from $0 - $100M+ ARR

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With

Mark Kosoglow

B2B Sales



Imagine having your founder and CEO working weekends to develop leads and a calling list for the VP Sales in an early-stage B2B SaaS company.


That was Mark Kosoglow's experience when he first joined Manny Medina, the founder, and CEO at Outreach - the leading Sales Engagement Platform company in the industry.


I asked Mark about the reality of leading Sales at an early-stage B2B SaaS company, and if he could share a couple of lessons he would share. The importance of building pipeline was priority #1 and is something he is living with in his new role as the CRO at Catalyst Software. In fact, Mark said pipeline cures most ills of an early-stage B2B SaaS company.


When we double-clicked on pipeline, I asked Mark about the importance of identifying the Ideal Customer Profile early in the journey. Mark said this was critical to focus the outbound demand generation efforts early on, and to also build a buyer persona map to identify the different key members of the buying team, and create messaging that resonates with each buyer.


Mark requires Sales Development Representatives to conduct at least 50 activities per day, and add 15 new contacts into a cadence every day while ensuring there are no outstanding to-do activities at the end of every day.


What is the role of Account Executives in creating pipeline? Mark has a standard operating model which depends on the profile of the actual average contract value. But, as a rule, he uses the goal of 25 opportunities in the pipeline. Once that opportunity goal is hit the goal of outbound pipeline generation activities is reduced from 50 activities and 10 people sequenced per day to 50 activities and 10 people sequenced per week. Once the number of active deals in the pipeline reduces back to 15, then the activity goals increase back to 50 activities per day.


Cold calling is a lower value for Account Executives in the early stage but is a reality of the role until the active pipeline is to a point where 100% of an AEs time can be allocated to the highest value activity of turning opportunities into revenue.


Next, conversion becomes a top priority. One is a well-defined, stage-based deal management sales process, and second a strong deal review and management process to help the AE successfully move from opportunity to revenue. How a rep can "guide" the buyer through the buying process is a top priority in how sales management should be coaching an AE in the early days.


Mark does not believe stage-by-stage conversion is a priority early on, as there is not enough data to provide statistically valid feedback. However, at each stage of the Sales process there should be a primary "question" that should be answered such as:


- Do they have problems we can solve?

- Are the problems big enough to solve?

- Will the buyer agree "how to buy"?

- Will their investment be worth it?

- Will they buy?


A key to his success is encapsulated in the quote: "process makes you great, but documentation makes you legendary". This was discussed in the context of when to introduce a Sales Enablement function. Are there any signals that suggest when to invest in a Sales Enablement function? Mark highlighted that Sales Enablement is responsible for onboarding and not ongoing coaching or figuring out Sales Process, that is the Sales leader's role.


If you are considering a Sales leadership role at an early-stage B2B SaaS company, or are a founder/CEO looking to scale beyond founder-led sales, this conversation with Mark is a great listen!

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