In the third edition of our flagship interview series “Wintage Club Conversations”, we were delighted to welcome Andrew Johnston, Head of Sales at Superhuman. Andrew has over 15 years of experience in sales and business development, having held leadership roles at companies such as Twilio, Scale AI, and now Superhuman. His transition from the entertainment industry to tech sales is uniquely insightful.

Andrew’s journey into sales was, in his words, “a natural evolution”. Driven by his people-oriented nature and love for sealing deals, Andrew rose through the ranks at companies like SendGrid and Twilio. Although starting his career in the entertainment industry, he eventually transitioned into tech sales.

"I've always been oriented towards business and the people aspect," Andrew shared. "I love the thrill of the win and the chase."

Be deliberate when building & scaling

Leaders need to take a conscious approach to establishing a high-performing sales team, especially in the enterprise space. Andrew had this to say on being deliberate about growth, "I've learned that, especially in enterprise sales, one of the old sayings—'go slow to move fast' is apt. It really is important that you get not only the right hires but also the right process in place," he noted, "Moving too quickly and hiring, in some cases, maybe the wrong people put me in a position to have to backtrack and slow down deals later on. This is something you don't want to do given that these cycles are already long in nature."

Below are all the considerations you need to keep in mind when scaling your enterprise sales teams:

• Making the right hires: Hiring decisions should align with company goals and should take into account the position requirements.

• Putting the right processes in place: CRM systems, sales automation tools, and communication platforms should be interconnected and geared toward efficiency.

• Qualifying opportunities: Establish a robust process for qualifying sales opportunities to ensure the team focuses on high-potential leads.

• Reimagining the buyer’s journey: It’s important to take a structured and tailored approach to guide your prospects from initial contact to deal closure. Adopt a step-by-step approach with effective communication, ensuring you address objections, and negotiate terms to close the deal.

It’s well past time to jump on the GenAI train

Enterprise sales teams are swiftly adopting generative AI as organizations race to leverage its potential for maintaining a competitive edge.

As GenAI catches on across functions, Andrew believes that sales teams not adopting these tools will quickly fall behind. "If you are not looking at how to adopt Gen AI tools into your stack, whether it's a feature functionality of a tool that you already use or it's a new first-of-its-breed tool that is Gen AI first, I think you're going to get behind very quickly," he warned.

Andrew gave the example of using ChatGPT or a tool like Superhuman that embeds AI. "If you are a sales team and you're competing and you're not using things like ChatGPT or you're not using a tool like Superhuman that embeds AI, you're going to be slower to respond, you're going to move slower inside of deals, and if that's a competitive situation, you might not get the customer first or you might have a more responsive competitor."

Moreover, recent multimodal solutions capable of handling various data types (text, images, videos), are expected to further increase the features and applications of GenAI in sales and other business functions. With that, smaller language models or SLMs are also gaining traction due to their ability to provide high-quality, precise outputs with less data.

With tech stacks, less is more

Using too many tools in a single pipeline, be it in sales or something else, does more harm than good. Andrew’s team at Superhuman uses around 8 to 10 tools, which he acknowledges is excessive. This creates a challenge, particularly the lack of integration and communication between tools. Andrew pondered on possible practical options for consolidation:

"[We’re] seeing, in certain cases, the large orchestration layers like the Gongs of the world who are now starting to consolidate. They're building more feature functionality. So, Outreach, Gong, Clari, they're all getting more competitive with each other so they can be kind of a single point platform for things like sales forecasting, call intelligence, sales engagement platform.”

Andrew also identifies a rising “appetite” to lessen the number of tools used, but make their use cases more in-depth. More tools don’t always mean more productivity:

"I think the problem that comes with more tools is that they don't often speak well to each other. So, if you have seven or eight tools across the sales cycle, does the one top of the funnel speak to the one at the bottom of the funnel, and is the data and sentiment shared across all those tools so that you can pull down information?"

Moving onwards & upwards

Looking ahead, Andrew talked about two main goals for Superhuman's sales organization in 2024: driving more ARR through expansion and increasing Net Revenue Retention (NRR) across the business. Moving upmarket and landing larger mid-market and enterprise deals is a priority tied closely to increasing NRR.

Andrew explained: "As you move upmarket, as you land larger mid-market deals, as you land enterprise corporations, you’ll find that those corporations typically have a longer stay with a company…They don't switch tools as often. They make deeper buying decisions."

Superhuman is also assessing its tool stack to ensure it supports the complexities that come with selling to mid-market and enterprise organizations. From infosec to pricing and packaging, having the right tools becomes key.

The future: shorter enterprise sales cycles

As sales teams adopt more advanced technology and tools, Andrew is hopeful that enterprise sales cycles can be shortened from 12 months down to what we've seen in mid-market. With the right systems in place, sellers can focus more on the product and drive ROI for customers.

He told us "Maybe, and I'm hopeful, that enterprise will go from 12 months down to closer to what we've seen in mid-market because they can move so much faster because we've got supporting tools that help us get through those processes quicker and serve those customers better."

Leaders like Andrew Johnston have welcomed GenAI and advanced tools to increase output and better serve customers. With deliberation in hiring and process, the right tools, and a focus on moving upmarket, enterprise sales teams are able to position themselves for success in 2024 and beyond.

Check out the full video of our conversation with Andrew Johnston below.