Chapter 1: Whale Hunting and your first 90 days as CRO
When it comes to the role of a Chief Revenue Officer, there is no grace period in my opinion. The clock starts right away and that’s because the revenue team is the most visible department with the most clearly defined goals in an early stage company. KPIs are ambiguous in almost every other department but that’s just not the case in the revenue team. If your CEO tells you that revenue is the collective responsibility of everyone in the company, smile and nod, but understand that the clock is ticking anyways. Everyone can measure revenue.
The second thing I think about when I take on a CRO role in an early stage company is knowing I have only so many days to change culture. Earlier in my career, I tried to make friends, time went by, then found out I couldn’t make the necessary changes anymore. Conversely, I also tried to make too many changes too quickly which resulted in friction. Trying to get the porridge just right takes practice.
With these thoughts in mind, I had a beautiful 90 day plan sketched out and ready to go prior to my first week. I put a lot of thought into my onboarding where I would win hearts and minds during my transition phase and execute my 90 day plan in parallel. However, one of my account executives, Stuart, informed the revenue team that we would be re-engaging with a key account (Company X) the following week.
Not only was Company X a key account, but it was also a Fortune 25 company. I learned that the founders of our company had been speaking to Company X for five years with no meaningful traction. This was arguably the most important account on our list and also a notoriously difficult company to partner with given their star status in the industry.
To be honest, I had no idea if we would be able to win this deal, since this was my first week on the job. But, I also knew that we had a chance to reset the relationship and change the narrative with Company X. A poor showing would close the door on any sales opportunity for one year (in my experience), maybe more. I called an internal meeting to discuss our strategy and to prepare for Company X which was in 7 days.
When we met as a team, I realized that we were not ready. The sales deck and our level of preparation was not at the required level to win over a Fortune 25 company. The materials and the sales process were still tied to a “founder led sales motion.”
As a quick sidebar for those not familiar with this term, a founder-led sales process is typically executed before the company “crosses the chasm”. In this stage, founders are targeting early adopters and figuring out what works with the objective of establishing product market fit. These early adopters are typically inclined to believe that change is necessary and are much more likely to lean into new technology since it aligns with their world view. Significant proof is not a hard requirement as the audience is predisposed to believe you. Excitement and credibility play key roles in the founder-led sale.
When a company begins to cross the chasm, the ideal customer profile (“ICP”) or the target audience shifts because you want to expand your total addressable market (“TAM”). As the TAM increases, the burden of proof also increases. Start-ups should move from a “vision based” sale focused on early adopters and towards a value based sale. The solution or product needs to deliver value or a return on investment (ROI) for the buyer because they will need a valid business case to justify the investment.
While I can’t publish the original sales deck, I can share that it was positioning our technology as transformative and aspirational. It’s actually what a lot of AI companies are doing right now, which I think is a risk, particularly in regulated markets like fintech, insurance, and healthcare. Most buyers in these industries, while interested in AI, aren't just buying the technology for the sake of technology. They want a solution that improves something tangibly and is easy to use. In fact, most long timers within regulated markets will tell you that the best technology doesn’t always win. If we were going to pitch Company X in 7 days, we would need to make a dramatic shift and reset all of our messaging and positioning.
The other thing I noticed during our planning meeting was that our preparation process for client meetings was not detailed enough. There wasn’t a checklist of things you do as part of the preparation process. As a result, the team wasn’t working off of the same set of information and assumptions. It just wasn’t clear to me that everyone in the meeting understood their role and responsibility. Finally, because roles and responsibilities weren’t clear, I noticed that our talk tracks were not dialed in either. For those sports lovers out there, you know it’s difficult to run a play on game day if you’ve never practiced it. I really wanted us to avoid the “show up and throw up” approach to sales. We had 7 days to make changes and we started meeting every day like it was a daily stand up to discuss progress and learnings.
There were good reasons to postpone this initial meeting with Company X but I ultimately saw this as an opportunity to accomplish multiple things at the same time:
Establish a new culture
Raise the bar
Lead from the front and show the team where we were going
Increase our speed and urgency
Help get me up the learning curve faster by experiencing things first hand
This was going to be a lot of work, but luckily my office wife at the time was the CMO. She was ready to step up the urgency and raise the bar across her team as well. Ideally, we would have used this as a teaching moment to get our people involved, coach them through the changes, and create buy-in as we changed our collateral and processes, but we just didn’t have the time. We decided to redo the deck together in real time, opting for speed versus collaboration. While others helped to be sure, the CMO and I were just trading edits constantly in the powerpoint.
In retrospect, it was risky to replace the deck given my lack of product knowledge but I was also fortunate to have experience with the technology we were selling. In the end, this was a sales pitch and not a product demonstration. We just needed to impress our contact enough so that they would involve other members of their team to advance the deal forward.
By Sunday night, we had rearchitected the sales deck to follow a new flow. For those of you who want to know, here was the rough outline of the new deck:
Vision statement
Company background
The Problem we are solving
The Solution (several slides)
ROI
Differentiation
Social Proof
How we work together
Next steps
I teach, sometimes successfully, that each slide should take up 2-3 minutes of talk time by the presenter. Also, the slides should be self explanatory in case the deck is passed onto someone else not in the meeting. Whether the deck is heard or read, it has to serve both purposes and rest comfortably within a reasonable time box when presented (less than 30 minutes for 8-12 slides). The other 30 minutes in a one hour meeting are reserved for introductions, Q&A (both directions), and next steps.
During our dry run Sunday night, we spent time assigning roles and responsibilities on the call. Our product was highly technical and none of our AE’s came from technical product companies. We decided that Stuart would be the Emcee for the session and help facilitate the meeting, including introductions and keeping us on track but the major content would be shared between myself and our sales engineer. Again, this wasn’t ideal, but given the importance of the meeting and the time crunch, we all agreed as a group that moving the deal forward was the most important objective.
Truthfully, I don’t remember that first meeting in great detail which means we didn’t do anything truly horrific. Our contact had enough curiosity to book another meeting with us and brought in additional members to update themselves on our new outlook. We had started to move our messaging from one of technical evangelism to one of value so that our buyer would begin to understand the problems we solve and the value they receive in return. This was probably the most important thing we accomplished in my opinion.
As for the team, I was able to learn a lot about our current state. I had a laundry list of things we needed to accomplish in the coming weeks:
Refinement and training on the sales deck
Practicing the new talk tracks
Understanding what questions to ask and when in a customer meeting
Roles and responsibilities in meetings
A formal checklist of items to prepare for client meetings
A common template for research notes
Product training
At the end of the day, the revenue team is a people business. Knowing what “good” looks like is not rocket science, but getting people trained on a new system takes time and effort. As an immediate follow up, I announced our first quarterly business review (“QBR”) as an excuse to meet one another, align on goals, and to practice all of our new processes together.
For Discussion
What did we do right?
What should we have done differently?
What do you want more of? And less of?
Next Chapter
In the next chapter, we skip ahead 6 weeks to the product demonstration. It’s another high leverage situation where we know the technical team is going to join the call to opine on our product. We are redoing the product demonstration during that six week period and preparing for a new set of personas to join the sales cycle.
In retrospect, we were actually more prepared this time around given the timeline and the new processes we installed and learned together. However, we still found ourselves in a predicament when over 30 people showed up on the demo when we were expecting six people. Long introductions, questions and general chaos ate into our call and we were left with 40 minutes to impress. Managing meetings, especially large ones, is so critical to keeping sales cycles manageable.
I look forward to posting the next abstract next week and discussing the importance of meeting management. Stay tuned and please do comment.
