CRO Will Anastas: Trusting and Training AI for Sales

By Neha Nirkondar

We recently had the opportunity to sit down with Will Anastas, a highly experienced Sales Executive. Will is currently Chief Revenue Officer at video optimization and analytics company Conviva. He also recently joined the Aviso Advisory Board. Below, you’ll find various video snippets and their transcriptions of our conversation with Mr. Anastas as he discusses various topics such as the value that AI can provide to sales teams and his advice to other CROs.

Aviso: What are you working on now & how did you get to where you are?

Will: I was in sales really since I stepped out of college, for the most part. I did a little stint in politics and then moved into the sales world. My first management opportunity was actually with Anheuser-Busch, the beer company. That’s really where I really got started in sales management. After that, I worked at a start-up in Boston called MediaMap, stayed there for about six years in sales management roles. Then went to Forrester where I got to experience a completely different dynamic because we weren’t selling a product per se, we were selling really analysts minds, for the most part. Selling human intellect to do an engagement is very different from selling a product. We did have a syndicated product that we sold, which is the research that we publish through our website. But primarily the customers that we were engaged with were looking for very bespoke consulting engagement with the analyst community. It was definitely a shift moving from a product, a tangible item, to something that was somewhat intangible in terms of advice.

When I went to Salesforce in late 2010, I literally thought the party was over. The company at that point had around 3,000 people, and had a really nice growth trajectory coming out of the downturn in 2008. They saw a flattening of their business for a year or so but then they were right back up and at it. That whole experience in Salesforce was incredibly transformative. You don’t typically go from a company that has 3,100 people in it when you arrive, and then you leave seven years later, and it’s 41,000 people. It was quite a dramatic change. I got to grow up in an environment that was constantly evolving and changing and adapting, and trying new things. What I loved about Salesforce is we could try different go-to-market strategies and see what worked. For me, it was just an amazing experience to have that type of autonomy to go and create new kinds of go-to-market models, but at the same time within a huge infrastructure that was being built around Salesforce and into the Salesforce economy. It was pretty amazing to live through. One thing I do remember is always interviewing, always hiring people. When I left my organization was about 350 people. So, it was a really, really large group. When I got there, it was 12. So, you just go through that kind of experience and it just changes your thinking and changes your mindset in terms of how to set up a sales organization. How do you optimize it? How do you use capacity modeling to understand exactly how to extract the revenue that you need in order to hit your number? It was just a phenomenal experience.

Aviso: Why did you join Aviso’s advisory board?

Will: To be quite honest, while I was at Salesforce, I worked with Trevor who, as you know, is the current CEO. Trevor really taught me a lot and I also taught Trevor some things as well. We both developed a huge mutual respect for each other as we went through that process. When I was approached about Aviso, I was like, “Wow, this is some pretty cool tech.” When I looked at it for the first time, I was really kind of blown away with a lot of the promise that we were looking for. Even when we were doing forecasting and pipeline modeling at Salesforce, we just didn’t have this type of advanced technology at our fingertips, and we had some really good tech at Salesforce. For me, it was really excitement about the AI component and excitement about all the visualizations I could use and to see the pipeline dynamics. Frankly, I needed a really high-end forecasting tool. That’s where the product really came together for me. Once I saw it, I was like, “Wow, I really wanna be a part of this.” I was thrilled to be asked and I’m just honored to be on the advisory board.

Aviso: What are you most excited about regarding the value of AI providing guidance to sales teams?

Will: My experience with AI really started when I was at Salesforce. I was part of a pilot team of leaders that were tapped on the shoulder to train Einstein, which is their AI application. We had a contest to see who would forecast better, Einstein or the human beings. Einstein won. That was like my aha moment that wow, artificial intelligence is pretty cool. I always had a hard time extrapolating out on November 1st what would happen on January 31st. Just that huge swath of time. Even though I had seven years of experience running this team and running this business, I was still off. Not by much, but enough that the AI component really, really did a better job than I did. That opened my eye to the power of AI once you train it and tune it properly, it can really be another marker for you as a leader to take a look at the number and say, “You know, this is what I think based on all of the historical contexts that I have running a sales team. Knowing all the personalities, knowing the sandbaggers, knowing the people who are inflating deals.”

Extrapolating that all and then using actual intelligence, and trends, and AI to kind of wash all that out and come up with a number. To me it’s a really great marker. When I’m asked to do a forecast that’s 60, 90 days out, my first stop is to look at what the AI component is saying, Aviso. And then at least I have a marker to start from and build off of. As this system gets tuned and trained it’s just gonna become more and more accurate. The other parts I love about it is just the simplicity of the nudges to the reps themselves. Like nudging them to do certain tasks. For instance, data quality and data hygiene has gone up exponentially for us. Because people are being nudged to do certain things that they would normally, that they’re supposed to do but they will just forget to do because they got too busy. For me on the data consumption side of the equation, I’m the one who has to make sense of all of that data that lives inside of Salesforce, in our instance. I have to make sure that that data is accurate in order to get the right outputs from Aviso.

It’s all intertwined and interconnected and I think any sales leader is definitely banging their chest saying, “Hey, we need to have clean data. We need clean data.” Because if you have clean data you can make better decisions. If you make better decisions, you’ll have a better business on your hands. For me, that’s been a transformative moment taking a journey with the early days of AI at Salesforce and now seeing what it’s become four years later is absolutely amazing to me.

Aviso: How does the current environment compare to previous downturns you have experienced?

Will: I’ve lived through a few. 2001 was certainly a shock event. We had the World Trade Centre and the disaster around 911 and how that impacted business. At the time the economy was getting frothy anyway due to the dot com boom and bubble. But you know, those are moments in time that just happened and you knew, while you’re in it, that things would get better, right?

So, there was some degree of certainty that this is just a normal economic cycle and these things happen and you know, people were saying just hang in there for a few years and things will get better. Same thing with 2008, right? I mean that destroyed the housing market and the banking sector took its licks on that one. But you knew that once you got the stimulus in the system and once all the governments pulled every lever, they could to get the economy going, you knew that that was something that was going to kind of solve itself. What’s unique about this is the uncertainty around it, right? I’ll be the first to admit when it first came down to me, I literally just got off a plane from London. By the end of the week, I was told not to come to work anymore. My kids were pulled out of school. The swiftness of the impact of COVID has been pretty amazing to watch. Now, I thought that Q2 would just be kind of like a lost quarter. We’re just gonna have to trudge through it and see what happens and hope for the best. What I’ve learned and I learned this pretty quickly in early May, was that the degree of uncertainty in this environment today is prolonged. And for us as CROs, it’s a really challenging time. We need to figure out exactly how we set ourselves up for the rest of the year. How do we do planning in 2021, in hopefully a post COVID world.

What happens if it’s not a post COVID world? What happens if we’re still in it in 2021? Right? Now, all indicators say that vaccines may be available and things may be coming down. But this thing is so unpredictable. That unpredictability is really what’s causing a tremendous amount of anxiety not only in the business community, but in society in general. Also the fact that it’s global in nature. I mean, my APAC team is feeling it as just like my immediate team is feeling it. There are no pockets of health at the moment, which is very, very different than really anything I’ve experienced. And I think for us, we just need to really kind of sharpen our game. Make sure you kind of tackle and maintain the fundamentals of sales.

Up your inspection of deals. Buying cycles have changed. Buying cycles have elongated. Buying decisions have gone up to the C-Suite as people hoard their cash. There’s a lot of interesting market dynamics going on right now that you didn’t necessarily see in those previous downturns. I think it’s fueled by the uncertainty of what’s going to happen in the future. I can’t predict what’s going to happen. I’m a glass half full person, just by nature. I’m hoping and praying that there’s a vaccine and that that vaccine comes by the end of the year and that we all get inoculated and we just go on about our regular lives in 2021. I hope we can see an economic rebound in 2021. But then again, I was also hoping for this to be a quarter event and just a little hit in March. It’s very difficult to predict the future on this one; that’s what’s causing a lot more anxiety than normal.

Aviso: What is your advice for CROs for driving growth in this new normal?

Will: It goes back to making sure that the fundamentals are sound inside of your sales organization. If you don’t have good fundamentals, you’re not gonna have an opportunity to build upon them. If you continue to think of innovative ways to connect with your customers, think of innovative ways to prospect. This environment has become very, very difficult. But it’s gonna take that innovation and as we think through different tactics on how to get people engaged, that’s really what’s gonna win. Just keep on iterating, keep on innovating, and seeing what works and like I’ve done a couple of pilot things in the past quarter just to see if they stick.

Some of them have and some of them have just not worked. Take the ones that have worked, and you rinse and repeat those over and over again and then you discard those that don’t. But that’s not the end of the journey. You’re always trying to innovate through this. Because, again, this is something we haven’t seen before.

You know potential customers also are in the same boat as you are. So, leading with empathy at this moment we’re all going through this shared collective global event is incredibly important. Those companies that are empathetic and flexible and listening to their customers, then those are the ones who are going to get paid back once this situation resolves. Those companies that are more strict on things and provide very little in flexibility, those brands are gonna get tarnished as we come out of this. Think of those innovative ways to help your customers through this because they’re going through the same pain that you are in a lot of ways and I think those are the companies that are going to win.

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