Welcome to Season 3 of 10/10 GTM: The Podcast for Revenue Leaders!
Our guest for Episode 75 is Josh Solomon, VP Sales, Ask-AI. Before joining Ask-AI in 2023, Josh held leadership positions at Ada and BioConnect. He brings more than a decade of experience to the conversation.
In this episode, Ross and Josh discuss how you should be thinking about AI as a revenue leader. They explore the importance of zooming out, thinking medium term, and rebuilding your playbook with an AI-first approach.
Listen to the episode here, and get the key takeaways from our conversation below.
Zooming Out on the Future of AI
The key to success lies in what Josh calls “zooming out” rather than honing in. The idea is simple: AI is disruptive. And as it continues to advance, older technologies will inevitably fade away.
So what does this mean for B2B revenue leaders? Change is coming — fast.
As Josh puts it, “AI will create a future where the cost of intelligence and the ease of deployment will be so low that differentiation will be impossible.”
He expects this shift to create intense price and feature pressure across markets. In that world, the teams that win won’t do so based on their product, per se, but on the unique experience they deliver.
“My thesis here is that you need to win on experience,” Josh says. “Ask yourself: What are the (technological) moats you can build? But more importantly, how do those show up to your customer and shape their experience working with your business?”
And that starts now. “You need to figure out how to drive a better customer experience,” Josh continues. “What does that mean? Today, this quarter, or this year — how do you think about the actions that you can take as a leader to close that gap?”
From first touch to tech support, today’s SaaS playbooks often make it hard to create a standout experience — too many teams, too many touchpoints, too many tools. So the real question becomes: how will you differentiate?
Thinking Medium Term
Before investing in shiny new AI-powered tools, take a step back and get clear on the business problem you’re trying to solve. Once you’ve nailed that down, then you can start thinking through the right steps (and the right tools) to solve it.
Take prospecting, for example. You might assume an AI SDR will solve your pipeline problem, so you rush to implement one. But if you haven’t identified why prospecting is broken in the first place — bad targeting? messaging? Handoffs? — then AI won’t fix it. It’ll just automate the mess.
“What is your medium-term vision?” asks Josh. “The inherent benefit of AI is the speed, quality, and depth of the products you can build, if applied correctly. That opens the door to rethink how sales and CS work. Can they run on the same platform? And if so, what’s the performance, risk, and cost benefit of aligning those teams around shared tooling?”
Once you have that clarity, you can identify where AI fits. But getting it right requires medium-term thinking. As Josh puts it, “If you take a medium-term lens, you’ll be able to drive 80% of your AI use cases out of two or three tools across all of GTM and CX.”
Some of the low-hanging fruit associated with AI includes making reps’ lives easier by giving them access to verified knowledge that helps them perform better and work faster. Another opportunity is what Josh calls “batch mode” which is when you ask AI to do things like “Tell me everything about our accounts,” or “Show me a backend report.” This shift doesn’t just impact day-to-day tasks. It also changes how leaders think about insights and how reps approach their work.
Rebuilding Your Playbook with an AI-First Approach
By taking an AI-first approach to rebuilding your playbook, you can rethink what your field teams do day-to-day, and what core skills are now essential for success. With rep interactions becoming AI-assisted and most “Tier 1” work on the path to automation, companies have the option to higher lower-cost, junior level reps to do mid-level work and/or fewer high-level reps operating at scale.
“I’m going to hire really smart, capable people in international markets and give them low-cost AI tooling to help them perform,” explains Josh. “One of our customers just opened an offshore team and they gave them basic AI tooling. Within three months, that team was outperforming their US team because they had access to the knowledge and they had the ability to do basic copywriting.”
According to Josh, this shift will create new roles and ratios that change how customers are served. He believes there will be more consulting roles, more technical sellers, more full funnel or multi-stage roles (such as one rep handling sales or onboarding), and new compensation plans. And for leaders, this represents an opportunity to rethink how to upscale and enable their teams. Because the biggest gap in AI adoption isn't technology, it’s enablement.
“There’s a knowledge gap,” says Josh. “When reps can’t find the deal updates or information they need, it creates inefficiencies. Most of that knowledge already exists, but it’s buried in Slack threads, support tickets, PRDs, and other unstructured sources. AI is incredibly good at surfacing that information. Even starting with something simple, like making this data accessible through AI so teams can do their jobs better — that’s a clear level-one win.”
Ultimately, SaaS isn’t dead, but the SaaS world is changing fast. Powered by AI, revenue leaders can increase efficiency, improve the customer experience, and reimagine how their teams operate and deliver value.
About Josh
Josh got his start in sales at FutureShop, learning the art of commission selling while still in college. That early role led him into the startup world, where he grew with a company serving major clients like Meta and global data centers. Nearly a decade later, with a plethora of AI-led experience under his belt, Josh joined Ask-AI where he serves as the VP of Sales.
To learn more or connect directly, follow Josh on LinkedIn
