How AI is Changing Enterprise Sales
Orchestra.inc x The Signal
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Hey y’all!
Last week was an amazing week for humanity. Whether you like Elon or not, he’s booked some massive wins for Team Human lately.
I’m excited to share the first post in a series of GTM technologies that I’ve been exploring. Read more about my thought process behind sponsored deep dive posts. (And, please share your feedback on this concept!)
If you want to sponsor a deep dive post, reach out to me (“Season 1”—8 posts—are already booked. But, if people like this concept, I’ll open up “Season 2” in January.)
Today’s sponsored deep dive post is brought to you by Orchestra.inc!
Thank you to Amos, Co-founder & CEO of Orchestra.inc, for supporting this idea before anyone else had said ‘yes’. 🙏 You’re the man.
Every time I talk with Amos, I leave the conversation feeling energized and inspired. My assumptions get challenged. And he helps me see how AI can be applied to GTM in new ways.
If you’re a revenue leader at a Series A+ company with enterprise sellers, and want to learn how Orchestra.inc can help you leverage the power of AI, reply to this email, or send me a message on LinkedIn, and I’ll connect you with Amos directly! I guarantee you’ll enjoy the conversation and learn a ton from chatting with him.
Alright, let’s get into it.
How AI is Changing Enterprise Sales
The enterprise sales playbook is being rewritten by AI in real time—turning guesswork and gut-feeling into data-driven decision-making.
I see a lot of talk about AI use cases in enterprise sales. But, it’s usually pretty basic stuff like call summaries, research into 10Ks, or other one-off workflows.
In today’s post, we'll explore how AI is reshaping enterprise sales, diving into real applications and looking at how these new tools are transforming the role of modern enterprise sellers and the impact AI will have over time. This isn’t about the future. This is happening right now.
AI Applications: Low vs. High ACV
One way I’ve been thinking about how to apply the many AI applications (it can be overwhelming) is by looking at a company’s average deal size.
Automation and things like AI SDRs? Probably best suited for high-velocity sales motions.
But what about in true enterprise sales orgs? Where a rep isn’t doing mass outreach, and may only have a small number of named accounts.
Segmenting use cases by ACV helps show the different applications. For example:
Low ACV Deals (<$20K):
AI leans towards full automation
Focus on engineering campaigns at scale
Sales roles shift towards "GTM engineers"
More similar to marketing than traditional sales
High ACV Deals (>$20K):
AI tools provide deep research — enabling true “value-selling”
Emphasis on relationship building and multi-threading
AI augments rather than replaces human interaction
In-person interactions become more important
Sales reps become strategic thinkers
The Shift from Reactive to Proactive Selling
In the enterprise space, we're witnessing a fundamental change in how sales reps approach their accounts:
→ The Old Way: Reps reactively chose accounts based on limited information and gut feeling.
→ The New Way: AI-powered tools allow reps to be proactive, using real-time data and events.
Let me give a concrete example. Navan (formerly TripActions) has one of the most impressive enterprise sales teams I’ve ever encountered. And they’re using Orchestra.inc’s AI to power this new way of doing sales.
Instead of a rep manually researching 100 accounts in their book of business, one by one, they now have AI agents scouring the internet for relevant signals every day, across all of their accounts and contacts. And the AI is able to find really rich data, in real-time, to help them be a more consultative seller. Helpful data points like:
Quarterly earnings calls specifically mentioning increased travel budgets
Press releases about expanding to new offices
Job postings indicating company growth
Etc.
This goldmine of information allows reps to prioritize their outreach based on actual buying signals rather than guesswork (or the alternative: mass volume aka spray-and-pray).
And the research done for one company (in this case, Navan), is not relevant for many other companies, even direct competitors. To me, this is when you know you’re using “rich” data, instead of generic, out-of-the-box data that most B2B datasets include.
The new bottleneck of go-to-market is creativity.
And AI agents (like the ones Orchestra.inc is building) can help you unlock this—and the data required to run creative experiments—in a way that was never possible before AI.
The Importance of Transparency in AI Tools — Especially in the Enterprise
Your enterprise accounts are your highest potential source of revenue, so it’s incredibly important to avoid the risk of AI hallucinating or misstating information.
AI is powerful and will change the way sales is done (for the better). But, I’m bearish on the "black box" approach to AI (like “Lead Scoring”), for three reasons:
Trust Issues: Reps are less likely to use tools they don't understand.
Actionability: A high lead score is useless without context for relevance. (eg: I can’t add someone to my “Excellent” sequence.)
Continuous Improvement: Transparent systems allow for human input and refinement. If reps don’t understand/trust something coming from a blackbox, they won’t use it; and if they don’t use it, it won’t improve.
Amos, Co-founder & CEO of Orchestra.inc shared an example of this that really resonated with me:
Think about the Spotify algorithm analogy: a listener can get stuck in a loop of the same songs from a black box AI that perpetuates existing patterns without room for creative exploration of new songs.
This feedback loop is dangerous.
Similarly, a sales AI may send a customer lots of leads from the automotive industry. Because that’s what their CRM data says is “good.” But, over time, what would be better is if the AI could run creative experiments to send leads from other industries that end up revealing a new industry for the company to expand into.
Without the human insights and input, this wouldn’t happen.
The blackbox algorithm holds you back from experimenting and finding these new markets, messages, and other components of an ever-changing go-to-market motion.
The Evolution of the Enterprise Sales Rep
As AI takes over routine tasks, the role of the enterprise sales rep will continue to evolve. Enterprise reps are becoming:
Data Analysts: Interpreting complex data sets to identify opportunities.
Strategic Thinkers: Adapting approaches based on AI-generated insights.
Relationship Builders: Focusing on high-touch, personalized interactions. Multi-threading. Finding warm paths into accounts. Meeting customers in person. Etc.
Creative Problem Solvers: Using AI insights to craft unique solutions.
Many people have come to the same conclusion of what an AI-powered sales tool will look like: some sort of magically generated list of accounts/contacts, labeled/scored, and stack-ranked for a rep to call down the list like a mouse mindlessly racing through a maze to find the cheese.
This isn’t the future I want.
This product vision is overly deterministic. It leaves out the ability to be nuanced based on the unique strengths of each seller.
It lacks creativity.
The Future of AI in Enterprise Sales
Looking ahead, there are a bunch of unanswered questions that I’m tracking closely:
Will AI make sales approaches more homogeneous or allow for greater differentiation?
How will the balance between AI-driven insights and human creativity be struck?
What new skills will sales reps need to thrive in this AI-augmented landscape?
What infrastructure will run the AI-enabled enterprise sales motion?
One thing is clear: the most successful sales organizations will be those that leverage the power of AI while maintaining the human touch that is crucial in high-stakes, complex sales environments.
As we navigate these new waters, it's important to remember that AI in sales isn't about replacing human intelligence—it's about augmenting it. The key is to use AI as a tool that empowers sales reps to be more strategic, more informed, and ultimately more successful in building meaningful relationships with customers.
In the end, the impact of AI on your sales process isn't uniform—it's as unique as your business and your customers. AI is not going to replace enterprise sales reps any time soon. But, I do think the reps/teams who figure out how to incorporate AI into their daily workflows will start to be the sellers who make president’s club in the years to come.
•••
Let me know how you’re seeing AI being used in enterprise sales orgs today.
PS: If you want to learn more about Orchestra.inc, reply to this email and I’ll introduce you to Amos directly.
See you next time!
-Brendan
🫡