David Kahn, Head of Sales – Google Cloud, Nevada shares his insights to manage deal reviews and improve forecast accuracy with buyer sentiments.

David is a global sales leader with 20+ years of experience selling enterprise SaaS, PaaS, and IaaS solutions. He has a deep passion for delivering emerging and innovative cloud technology into the market.


BoostUp: In today’s selling environment, what are the common forecasting challenges for sales leaders? 

David: It comes down to hitting the number. It’s a coin-operated world, and you want to deliver accurately on your forecast. First and foremost, you want to achieve your numbers because it gives you far more leverage in the company when you meet your number or exceed it. Forecast accuracy is the next measure — Show command and control of your business. 

I’ve worked at both small start-ups and larger enterprises. The challenges generally remain the same, getting good visibility into the forecast for the month, quarter, or whatever period you are tracking. It’s challenging to know which deals are going to close even among the ones we already have visibility. Even more challenging is trying to forecast deals that aren’t even in the scope for that period.

Gauging the velocity of a deal is especially difficult when you’re at a start-up because it’s often the first time these types of deals are happening. There are customized components to such deals that need to be sorted out as well. All this creates a bit of an uncertain timeline that impacts forecasting accuracy.

BoostUp: Despite all the data and the technologies to support forecasting, why is it still leaning towards art rather than science?

David: It depends on the rep inputting data into the system. You try to standardize it as much as possible. While we get some basic information, most reps don’t use the CRM as their everyday source of truth. A lot of the information is inside their communication, calls, emails or somewhere else where it may not be accessible to a sales leader.

It requires you to sit down with the rep, hold daily standups and reviews to go over the deals. You do an assessment to understand why they feel the said deal is in a certain phase or is a certain amount before you can really put some sort of confidence level.

Often reps are dealing with multiple deals, and it’s hard to keep track of all of them. So my job as a sales leader is to challenge the opportunity, ask the difficult questions, look for confirmation, and in a variety of different ways to test the clients’ seriousness about closing those deals.

Then there are other intangibles. It’s that age-old question about marketing. You know that half of your marketing budget is wasted — you just don’t know which half. The same thing applies to sales deals, especially at the beginning of a quarter. The deals may all look good, but then you have to pay particular attention to all these intangibles. There are macro events happening to that company, within that industry and then it’s really you trying to read the tea leaves in terms of how engaged are the prospects, what sort of signs, nonverbal signs you’re picking up which will determine whether that deal closes and this becomes more urgent as the month or quarter moves on.

BoostUp: How do you prepare yourself for these conversations? 

David: l try to create consistency across all the reps. I apply the same level of scrutiny across all the different deals, asking the difficult questions about the discussion with their clients, about budgets, who is signing the deal, verifying the next steps and what needs to be done and then validate the timeline that they’re working on. You get to know and learn from experience how long it typically takes to get a deal done. But it’s consistency across the rep deals that adds more confidence to the forecast that I usually make.

BoostUp: How much time do you spend reviewing deals? 

David: It depends on where we are in the quarter. Typically, in Month #1, I’ll go through a broader view of the deals that are in play and try to do some sort of assessment for the deals to close? Then in Month #2, it’s much more focused on the deals that have crossed certain thresholds, certain milestones that we’ve set out in the first month. In Month #3, it’s an all hands on deck focused on the deals that we know have a real chance of closing, that have the buy-in, and has crossed all the final milestones.

BoostUp: Where do sales leaders like you still need help with deal reviews?

David: There are a couple of areas where we need support. Firstly, the data in the systems of record / CRM needs to be cleaner and updated. It needs to be easier to report on and in a way that allows us to act upon that information. Secondly, we need to capture other information about the buyer, about the company, about the deal, about the rep’s behavior that isn’t necessarily standard but still has a big impact on the deal and the timing of the deal. 

As a seasoned rep, you know that the level of engagement you’re having with the prospect is typically the leading indicator. If you’re seeing your buyers open, read your emails, respond, pick up the phone, reach out to you, then that’s good, especially if you have all the core information covered. But if you have all the core information— the budget, authority, timeline, etc. but if the engagement levels are low, that’s always very scary. That’s typically a good indicator of seriousness and timing but as the deal heightens it almost comes down to a little bit of hope and prayer which is never a comfortable feeling—Hope is not a strategy.

It is difficult to capture that information unless you as a leader are really sitting with the reps day in and day out. There is no systematic way. Without such insights, it’s challenging because it comes down to whether the rep wants to trust my gut or just believe in theirs. 

BoostUp: Any advice for sales leaders at growth-oriented start-ups?

David: Forecast and pipeline cure all ills. It’s a number game. You get to a certain volume, add critical mass into your pipeline, do the right things, and business will close for you. It’s just a question of how long it takes to get the momentum.

While every few years there is a breakthrough in sales where some new methodologies or technologies come up and they have a place for specific segments.

However, I do genuinely believe that having visibility into buyer behavior and sentiments will help elevate forecast accuracy. It can apply to all company sizes, all regions, all industries, and all types of sellers. 

Today, with machine learning and A.I technologies it’s possible to capture such intangibles to a much higher degree and leverage them to close deals. I think BoostUp.ai indeed is an excellent product to deliver on this need.