SalesTechStar Interview with Scott Schnaars, Vice President of Americas at Cloudinary

Scott Schnaars, Vice President of Americas at Cloudinary talks about the various ways in which sales communication channels and trends have changed over the years while he highlights a few best practices that can help strengthen a sales team’s overall data and sales ops processes; catch the complete Q&A:

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Hi Scott, we’d love to hear about your journey through the years…tell us more about your role at Cloudinary?

I started selling as a kid going door to door to raise money for various causes. At University, I studied computer science and got into software sales by accident. Fortunately, my technical background made it easy for me to talk with IT people in the mid-90’s. I wasn’t a developer, but I knew enough to be dangerous and challenge people! My software sales journey – let’s call it a voyage – includes roles at Borland, a once very hot development tool and database software company; I was the third salesperson hired at the conferencing software company WebEx (acquired by Cisco) and also worked at Yahoo! for several years. That’s on top of the more recent roles I included in my biography.

At Cloudinary, I run new business sales, managing eight quota carriers and a team of Sales Development Reps (SDRs).

How have you seen sales evolve and salestech change the selling game over the years in the B2B marketplace?

The big difference in the selling game today compared to past years is that by the time I talk to buyers they’ve already acquired a lot of information in the form of reviews, referrals, case studies, articles, and analyst reports. This makes them really savvy, so it’s important that we salespeople reach out early to prospects and stay at least one step ahead of them.

Once they call us, they’ve likely made up their mind on the direction they want to take and are just looking for validation. That leads me to my next point about SDRs. With prospects educating themselves quite extensively using those online resources I mentioned before, it is important that sellers don’t overly rely on SDRs to build pipeline for themselves.  I encourage my team members to do their own prospecting, find out where people are in the buying process and what the pain points are and move things forward. My best sales reps are the ones who do their own prospecting and are confident about having conversations at the C-suite level.

Communication has changed quite a lot over the years as well. When I was starting out in the early 90s, we cut our teeth on cold-calling, and it was an invaluable way for getting used to rejection; and also finding ways to overcome objections. It was scary, but after you’ve made 1000 calls it’s no longer scary anymore. The main difference back then was that people used to pick up the phone when it rang, even if they knew it might be a salesperson. When was the last time you picked up the phone to an unrecognised number? It barely ever happens. Most prospects tend to ignore cold emails and other forms of messaging. So even though we have more communications channels than ever these days, making a meaningful connection requires a mix of personalization, education, and persistence.

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 A few best practices in B2B sales that you feel selling teams of today need to be paying more attention to?

I tend to stay clear of selling trends because buyers get wise to them pretty fast. Nobody likes that feeling of being “sold to” so I consistently just go back to the basics: is there some pain that we can solve? Is it a big enough pain to fix; does the person even want to fix it? You only discover the answers to these questions by asking smart questions, LISTENING, and being empathetic.

What are some precautions that you feel sales and revenue leaders should be taking when implementing new sales tools and especially when enriching their data and insights?

 First, companies should hire a sales ops person before they hire a sales leader.  Too many early-stage companies race out to hire a sales leader and then they will often bring in Salesforce; the marketing leader will bring in a system like Marketo, and the Customer Service leader might bring in Gainsight, but then no one really thinks about how to make all these systems work together. Over time even more systems accumulate. Maybe they’ll find a way to hobble them all together but it’s an organic process that eventually breaks down when the company reaches a certain size. Then the company might hire a new team or bring in consultants to rebuild everything from scratch and it gets really painful.

My takeaway is to lay the foundation properly early on. I’ve never regretted hiring a sales ops person too early.  Finance people think that it is a bad investment, but it is a “stitch in time saves 9” scenario.

 What are some best practices that you’d like to highlight that drive better data-driven marketing and sales strategies?

The B2B tech world that I’m in has been hugely influenced by Salesforce’s software and selling methodology, and that’s mostly been a good thing. However, I believe that every company needs to choreograph its own selling process. I’m currently having fun with doing just that for our own sales process at Cloudinary and using data and anecdotes to make the process more repeatable. For example, we have a really clear idea of what a first meeting should look like.

We have a well-defined slide deck, set of discovery questions, and the next steps. The second meeting is a little less clear: we currently show a demo – and I suspect that’s the right thing, but the format might need some tweaking. So I’m looking at using data to define what the goals and ideal outcomes of what our first 5 meetings should be. A key principle I believe in is “slowing down to speed up” by introducing a higher level of friction, early on, so that things go much faster on the back end of the process.

To get a good snapshot of our business, I look at a simple dashboard on a weekly basis that shows me meetings generated, opportunities created, deals closing this quarter, and deals closing next quarter amongst other data. This lets me quickly see the holes in a seller’s business and patch them in almost real time. I really like the sales enablement tools Gong and Chorus. These technologies are really helpful in coaching your team members and ensuring that they understand messaging.

The future of B2B sales…a few top thoughts and takeaways before we wrap up.

Over time, B2B sales will only get harder and more competitive. Today something like 60% of enterprise sellers don’t make their quota. I expect this number to continue going up as more companies raise and expectations get set higher and higher.

Three key takeaways: First, to be successful in sales, don’t rest on your laurels and expect SDRs to do all your prospecting for you. That’s the old way that worked better before customers got much more savvy and educated with online information and peer to peer referrals. Second, by all means start out with templates, but do orchestrate your own sales process and continually improve it through debriefing sessions with your team. Third, get a sales op person from the outset when you’re setting up your team, processes, and tools. It involves some up-front investment but will pay off big dividends in the long run.

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