How fast-growing startups overcome forecasting challenges

Stepping into a Series B or C round we see companies start to hit a stride to go down the path of rapid growth which really comes from a couple of things— you’ve found a way to predictable revenue, and you have a fantastic sales leader in order to project and present the profile of revenue capture that you’re pursuing. So what do these leaders managing sales teams, building and growing these revenue engines use as tools and techniques that help them see the blind spots, understand better what’s in their current mix and help them make the right decisions?

In this virtual fireside chat, Matthew Gray – Sales Leader at New Relic and Chris Pham – Head of Sales at Deal Path share the challenges they face as revenue leaders in the path to growth and the tools & techniques they use to overcome the challenges.

Matt: In my experience running sales organizations across different stages from small organizations with thirty to forty employees all the way to working with companies that are large-scale with hundreds of thousands of employees, the one thing I find, it all comes down to challenges that the sales leaders face. Whenever I look at the different aspects of this role, being on the front lines of bringing revenue into an organization whether you’re selling Saas, hardware cloud-based assets, services, etc. we all run into similar challenges and those challenges are pretty primitive but they’re increasingly difficult to understand with the enormous amounts of information that we’re all inundated with. Our discussion today is about the challenges that sales & sales leaders face and to look into those aspects.

As Sales leaders, we have responsibilities for forecasts, deal inspections, activities, rep productivity, and also measure what’s important for the executives — whether it’s new logos, expanding installs or retaining the install base. So Chris, when you look at the things that are top of mind for you, what are the challenges you face today as the leader of sales at Deal Path?

Chris: We have a large booking number that I’m going after directly. But like you mentioned I think forecasting has been a real struggle for us here at Deal Path and is probably the number one thing we’re trying to work on and do better. There are months where we beat our forecast by three times, and there are months where we’re delivering 40 to 50% off our forecast number, and that varies widely.

So, being able to understand the market segment that you’re in and being able to coach reps to execute deals in the right way is important. I guess that falls under the point of deal inspection as well. It begins with forecasting the deal, understanding what’s going on, also coach the reps, and then turn that all around to an accurate forecast.

And I think all that is a big challenge as a series A company. You might empathize with folks who have some market traction and a good ideal target profile and who are still out there testing that thesis and refining that thesis. It creates a bit of chaos as everybody understands, ‘Hey, we have these segments. How do we treat them differently? How are they qualified differently? And how are we pacing these deal out internally.’ Also, you have an enterprise team that needs to be managed very differently than the commercial sales team, so forecasting accuracy gets tough when adding that in the mix as well.

Matt: We are all trying to grow companies but if you look at the reasons why 75% of venture-backed start-ups fail there are a lot of different attributes including lack of focus and lack of quality revenue. These are things that pop up very often but are areas companies can work on with better tools. We find bad hiring or running out of money is always a problem, but the lack of sales is the number one indicator. Many a time you have signals that you have hit the wrong market or got the wrong team. When I look at what you’re doing right now and think about the pressure that’s on you today, your charter, goals and the responsibilities that you outline, where do you need help the most?

Chris: I need proactive insights into my deals. I need to know when they are at risk. I need to know what I can do about that. Especially when I have to hire a bunch of reps, onboard them, make them productive and manage the forecast across these several different reps with less than five-year experience. I need to keep profits at a high level and also coach my reps actually to execute with the prospects consistently. Then based on the returns of the opportunities that they are bringing to the table, during forecasting, I have to be able to see where the risk is so I can triage on what’s urgent and what’s important in the course of my day.

As a VP of Sales, you have a lot of things on your plate. Not only are you managing the rest of the executive team and leadership team, but you’re also managing your own business, your forecast, and your people, and you’re managing the deals themselves. There’s a lot of moving parts here. So one of the things that I need help is to know which deals to spend my time on.

Matt: That’s good feedback because these things are indeed quite common. As VP Sales you’re trying to scale, you are doing ten jobs at once, and you are being pressed on by the board and by the executives to deliver and so just having stale data or bad data doesn’t cut it.

While these are not excuses but when you look at these things where do you breakthrough? Where do you see that moment of clarity when you have stepped through, you’re able to succeed in your role and also help your team get over the line?

Chris: There are the big wins that you can count on — to sign a deal, get a logo overline, but I think the real win is when you get pressure tested account executives that you can count on, that they trust and believe in your systems and tools. I think that’s where I’ve seen the breakthrough happen.

When we have a string of wins, account executives understand how to win, and they understand how to win within your system, and so those folks require or should get more investment. They’re the ones who learn the system, learn how to use it well, and have been able to reproduce the results. The output of that, the symptoms of that is you’ll see more consistent closing opportunities, better negotiating without your help, deals that come to you that are real both in engagement and in the terms that have been already been agreed upon.

So you know all that work, you keep on hammering away at it because better notes, better qualification, better closing, better output happens with a couple of reps that breakthrough themselves and then it is not much you have to handle by yourself because of these breakthroughs.

Matt: In your day to day, where does it start to break down? Where are your biggest challenges in getting that data right and getting those things into the right hands at the right time?

Chris: I think every sales leader will agree that salesforce can be a challenge. Keeping salesforce up to date, looking at all the notes in salesforce, trying to keep up with everything that’s happening in your business can feel like an impossible task sometimes.

All of these notes, activities, and all these meetings that are happening across the whole week and just being able to keep track and tabs on where is this deal? What’s the most important thing that’s happening right now today? How can I support this part of the deal getting over the line? All this isn’t always clearly evident. So I think that you can get into a little bit of paralysis just looking at the data that is accumulated and with the proliferation of tools as well for your sales teams, a lot of BI & analytics tools, coaching tools, automation tools, etc. Yes, there’s a lot of areas where all the data is collected, and analysis is done, but how do you as a leader genuinely understand what is the most important information to grasp. That is difficult. 

That’s where it breaks down for me. I find myself looking at a lot of old notes trying to get them updated, analyze it, and take action on it, but by then the process is just too slow.

Matt: When you look at conducting deal reviews you mentioned a couple of things that are important that I want to dig in—How do you manage your pipeline and the reps that you cover? How do you uncover red flags? How do you save deals? How do you bring deals forward and based on everything you just mentioned how do you do all this stuff?

Chris: A lot of the deal review is done one-on-one where we will cover the top deals for a rep while applying a healthy sense of skepticism to the deals. Part of it is the art of reading your rep and how confident are they in the answers that you’re qualifying for. So much of it is, do they have happy ears, or are they looking at a deal in a way that is unrealistic?

For instance, at DealPath, we are working on qualifying for an outcome. Often our prospects might think it is a good idea to adopt technology, but they don’t understand the impact it might have, and they might not be explicit about that. So when deals come in without that outcome, and our reps aren’t forcing our prospects to think about it then that makes the deal unqualified. We can get decently far along without the deal being qualified, and that’s one thing, I’m asking a lot about my reps deals in the pipeline. And what I’m seeing is maybe four out of five deals are unqualified because it is more focused on process as opposed to the specific outcome that our deals are generating. So at the end of the day, I’m doing deal reviews in a one-on-one covering the top deals and then asking the qualification questions. Where I need help is that often it is not enough because your reps are going to tell you one thing. They are great at selling themselves and you, and they might hear things in a certain way that’s not always the truth.

Matt: You bring up some interesting points here. When you’ve got issues with stale data, how do you manage to know what is good and what is not? And what is the help you need when you don’t have the bandwidth to keep up?”

Chris: The quality of notes can be a hit or miss based on the reps or may be based on the week and how they’re executing their week.

So here BoostUp helps me get the call insights based on the opportunities that I’m looking at. I want to hear a tone myself. I want to hear what the gib-gab was on that call myself and triangulate that with what my rep is telling me at the same time. It can often be one thing they interpret on what happened versus what actually happened on that call. So that’s one of those things that’s been helpful to have with BoostUp. 

From a forecast accuracy standpoint being able to teach the reps what is the qualification and what is qualified? And have a healthy sense of skepticism and taking reps through a few examples of when that hasn’t worked out. That’s how we’re managing it today and I find especially newer reps have happy ears all-time. Most sales leaders can empathize with that.

Matt: In an ideal world, what would you have? What does nirvana look like? If you were to open up your forecasting tool, what would you rather have in front of you?

Chris: My nirvana is that the forecasting tool can self-coach the account executive on what is doable or not doable. That would allow them to inspect their own deals before it gets to me. I think the big portion of tools need to be able to empower the end-user to get value out of it themselves right and so for me, that’s the step one and then by the time the deal gets to me then we can inspect the most critical part of the deal that hasn’t yet been derisked.

Matt: That’s good insight because you basically want to be able to get to the good stuff in the deal and understand it is forecasted accurately.

One of the things you mentioned, Chris, was a lack of centralized tools, lack of clear stage identification, lack of clear inspection until it gets to you. Those are things that seem like common challenges because if people want to get to a Series C funding they need to have this resolved and have a good understanding and handle on where their money comes from, how much it costs to make money and then really how long it takes to get it and what their philosophy of that pipeline looks like. You can make a predictable pipeline start to grow and then begin to hire more headcount.

Today what we have available is entirely unacceptable, and we know there needs to be a better alternative. In the things that we’ve talked about we’ve got an exciting intersection between what we need and what we have right now. That’s where BoostUp comes in to play to build out a way of looking at all this unstructured data and turn that into actionable insight to provide forecasting intelligence.

So what’s your experience with forecast intelligence tools? What are some of the things that you would say were pains earlier and can now say you don’t have that problem and that you really can rely on a capability like BoostUp to sort through that information and provide you with the best visibility into your data?

Chris: What I like about BoostUp is that it enables my coaching from the viewpoint of opportunity management and forecast management. There are other tools out there that enable you to do coaching but from a different angle. I think BoostUp is the right angle for Head of Sales / VP Sales because, at the end of the day, that’s a big problem that we are talking about. To be able to deliver on your forecast, predictably grow revenue, that’s the angle and basis of how you’re interacting with Reps.

With BoostUp, you’re able to see what are your big deals and which ones are at risk, what has changed in the deal and potentially what needs to change. You can see a lot more deal velocity, what’s happened recently and you can also pull out the actual information— the emails, listen to the calls itself if you want and also get a read from the algorithm as to why this deal might be at risk.

So I’m able to look at my ninety-day pipeline and make sure that the deals that I think are good are truly good. Any of the big deals that we’re looking at may not be risky from the Rep’s point of time, but from BoostUp I can see that maybe they actually are and I should do more analysis there.

Matt: When I look inside of salesforce for instance, and I think about my contacts and how they relate to opportunities and the activities that support moving the opportunity from a pipeline to a best case, to commit and then to close one deal, it’s all around the activities which are very hard to track. It’s very easy for the Rep to say that they had a meeting, but it’s very difficult to look at an opportunity to think about what’s my interaction momentum, what’s my momentum in terms of the sentiment? That’s incredibly difficult for a Rep to give you a subjective answer because if they didn’t cover pricing, if they haven’t covered the objections, if they haven’t gotten to a decision-maker who has the authority, it’s very difficult for you to know that forecast is accurate because you uncover those things at close stage and that’s when it’s too late to say that this is a committed deal. It’s a best-case deal, and we got to requalify it to get a commit again.

When you look at the context to understand, does your champion have the sentiment that is supporting you get this deal done? Did you have the decision-maker on the phone? Those are things that the sales leader who is two levels above the Rep does not have time to go through. They don’t have the bandwidth and while getting to look at your sales teams activity is a great thing but that again is structured and unstructured data, which make it very difficult to weave through all the different pieces of data, the messages, phone calls, presentations, emails, and the salesforce data to get a good understanding of the deal.

Now that’s what BoostUp does. BoostUp brings in all these data from the most common platforms — Zoom video conferencing, Gmail, Outlook, Phone calls, Salesforce action, etc — to be able to measure things, to really weave all that data together, to summarize the data, to look at deal behavior, seller behavior, the things around the prospect conversations, forecast risk indicators, deal summaries, and specific risk indicators. These are things that we want to be able to uncover as sales leaders to have better forecast accuracy.

So when you look at the impact BoostUp has had for you, Chris, what do you see? What are the measurable differences you have noticed?

Chris: We closed at least one deal directly because of BoostUp. Just recently we misheard something on a call and were able to take a look via BoostUp and remedy it in the next meeting.

Overall BoostUp helps you save time and stop wasting time on deals that are early and unqualified, spend more time with the deals that are qualified and to get context. As a Head of Sales / VP of Sales you’re switching contexts all the time, all day and what BoostUp allows you to do is within only a few minutes really understand the context of what’s happening in this deal, what needs to happen next so you can do a review. 

One of the interesting use cases of BoostUp was when we recently separated from one of our reps and were transferring his pipeline across the organization. I found myself going to BoostUp first to figure out what actually is going on with all these deals. Without BoostUp, you would never know. You would transfer over, look at the notes, get a feel of what happened based on a couple of emails that get transferred over. But with BoostUp I could understand — Hey, these are the good ones. I can listen to the exact sentiment. I understand the exact sentiment. I can go to the call. I can directly hear what’s happening, and within a few minutes, I have it all in one place. I understand which opportunity needs to go where to be best prosecuted moving forward. So it helps directly with the transfer of pipeline and to be able to make that decision quickly without wasting a bunch of time.

Matt: Excellent! Thank you, Chris. I appreciate you taking the time to discuss this in the middle of your busy and hectic revenue-generating role.

For our audience, hopefully, there have been some excellent insights here for you to understand how to do more with the time you have. You can visit BoostUp.ai to learn more about the platform or reach out at demo@boostup.ai to understand how this platform can help you.