Welcome to Season 3 of 10/10 GTM: The Podcast for Revenue Leaders!
Our guest for Episode 50 is Andrew Johnston, Head of Sales at Superhuman. Before joining Superhuman, he held leadership roles at companies like Scale AI and Twilio. With over a decade of experience, Andrew brings valuable insights and expertise to the conversation.
In this episode, Ross and Andrew discuss strategies for moving upmarket, fostering creativity in sales, and building a culture of trust and transparency.
Listen to the episode here, and get the key takeaways from our conversation below.
Strategies for moving upmarket
“When you move into enterprise, you have to make sure everyone’s on board,” says Andrew. “This begins with how you structure the sales organization. Do you have the right focus and expectations? People have to know that it’s going to take a while to get to the desired outcome. So once you get into a larger deal or opportunity, bring in folks from the broader company to help you sell.”
This approach allows the entire organization to operate as a cohesive team, working toward the same goal. By involving people from different functions early in the sales process, there’s a sense of shared ownership and collaboration. Everyone is moving in the same direction, which not only helps win the deal but also creates outcomes that benefit the company and all stakeholders involved. When departments outside of sales are motivated to contribute to the selling process, the collective effort drives momentum and builds a culture focused on achieving bigger wins.
“We have a company that is our largest sold deal to date. One of our lead engineers actually built out a sales deck to pitch a new set of features for the technical team at this end customer. I was like, ‘I don’t even have to do my job,’” explains Andrew. “When you get to the point where the engineer is doing that selling for you and is so passionate about winning the deal, you’ve done the right thing because the way you’ve fundamentally shifted the focus of the organization to outcomes.”
Reaching this point starts with making sure that all departments, from engineering to marketing, experience the challenges of moving upmarket. This happens through open communication, cross-functional meetings, and giving every team visibility into the demands of enterprise sales. When all teams are invested in the process, they see the importance of their role, creating a unified push toward long-term success.
Fostering creativity in sales
Creativity in sales often starts at the top. To be an effective leader, it’s important to lead by example — showing rather than just telling. This means showing versus telling.
“It starts with the CEO, VPs, and CROs,” says Andrew. “If the people from the top aren’t getting into the deals, I don’t care how big your company is, you’re not really doing your job. In my opinion, one of the core things every organization needs to do is make everyone a seller — especially everyone in leadership so they can set an example of what successful selling looks like.”
At Superhuman, even the Head of Finance has a quota. 'We’ve built our sales plan for the year, and when we’re in contract negotiations with vendors, he suggests they check out Superhuman. This creates a natural opportunity for us to close more deals,'” says Andrew.
Aside from taking a top-down approach, another great way to foster creativity is in the actual negotiation process. “One of the funnest parts of sales is figuring out how to create a contract or structure that incentivizes the customer and creates the right business outcome for the company,” explains Andrew.
So, how can reps approach this creatively? Here are a few ideas:
- Offer strategic discounts: Instead of blanket discounts, customize them to specific actions or commitments. For instance, provide a discount if the customer agrees to a longer contract term, refers a new client, or purchases additional products.
- Bundle services: Create value by bundling services or products that complement each other. This can make the offer more appealing without needing to drastically reduce the price.
- Customer-run competitions: Create competitions where customers can win rewards based on their usage of the product or their success with your solution. For instance, offer incentives for customers who reach specific performance goals or milestones, driving both engagement and retention while showcasing the value of your offering.
"We try to identify power users and champions within organizations, and that’s our biggest linchpin," Andrew continues. "Every company has its own way of finding these linchpins. I had a customer who was selling us on their product. I gave this sales leader a specific discount for his team, then I posted on LinkedIn and said, 'Anyone who uses this product with a domain from this company gets an additional discount,' leveraging my network. We’ve done things like that to be creative."
Building a culture of trust and transparency
To build a culture of trust and transparency, start every one-on-one or small group meeting with a zero-to-10 ranking from each person. “The only ranking you can’t say is seven,” says Andrew. “You can be anywhere from one through six, or eight, nine, or 10, but you cannot be a seven — it’s just a blah answer. The idea behind this is that if you’re not a 10, we want to know what’s contributing to that. And we get a lot of rich answers — everything from tough projects or deals to personal challenges that are creating stress or holding someone back. This creates compassion and helps us understand where people are at and what their blockers are.”
Doing this enables Andrew’s team to have open communication and also helps the team proactively address challenges before they escalate. It allows the leadership team to provide the right support and resources, ultimately driving better engagement, productivity, and well-being across the organization.
In terms of driving transparency, this starts with the leaders being open and communicative about their thoughts, challenges, and direction. "I err on the side of being an oversharer," says Andrew. "A lot of traditional sales leaders advise against it, but I’ve found that when you openly share what you're thinking, where the organization is headed, and what's both painful and joyful, the team becomes more compassionate and engaged."
At Superhuman, this transparency extends to what they call "Non-blocking feedback." Team members are encouraged to challenge each other directly, but without halting progress. "It’s about speaking your piece, accepting feedback, and moving forward. It empowers people to act like a GM, make decisions, and understand where others stand," Andrew explains.
By encouraging the team to take ownership, Andrew fosters a culture of autonomy and confidence. "When someone asks for guidance, I often tell them to create the solution first — write the email or build the plan — and then I’ll review it. Most of the time, they have the right answer, and this process boosts their confidence and trust in themselves, allowing them to move faster and more independently."
About Andrew
Andrew is a proven sales lead with experience building and managing sales teams in developer-focused AI, infrastructure, and SaaS products. In addition to his work in sales, he’s also an active angel investor and advisor, having invested in companies such as Rutter API, Endgame.io, Momentum.io, and Unwrap AI. Outside of work, Andrew stays active as an instrument-rated private pilot and a half-Ironman triathlete.
